Phytochemical and Pharmacological Study of the Eysenhardtia Genus

Review Phytochemical and Pharmacological Study of the Eysenhardtia Genus

Abraham Garcia-Campoy 1 , Efrén Garcia 2 and Alethia Muñiz-Ramirez 3,*

1 Laboratorio de Investigación de Productos Naturales, Escuela Superior de Ingeniería Química e Industrias extractivas Instituto Politécnico Nacional, Av. Instituto Politécnico Nacional S/N, Unidad Profesional Adolfo López Mateos, Ciudad de Mexico CP 07708, Mexico; [email protected] 2 Laboratorio de Química Supramolecular y Nanociencias, Instituto Politécnico Nacional, Acueducto S/N, Barrio la laguna Ticomán, Ciudad de Mexico CP 07340, Mexico; [email protected] 3 CONACYT-IPICYT/CIIDZA, Camino a la Presa de San José 2055, Col. Lomas 4 Sección, San Luis Potosí S.L.P CP 78216, Mexico * Correspondence: [email protected]

Received: 29 July 2020; Accepted: 18 August 2020; Published: 31 August 2020

Abstract: The participation of natural products in health care has been remarkable, and today they continue to play a key role in the discovery and development of new treatments. Phytochemical studies together with pharmacological tests have managed to integrate bioactive agents as an alternative solution to reduce or regulate the problems caused by diseases. The Eysenhardtia genus is a family of plants that are rich in secondary metabolites, which have shown potential activity in the control and mitigation of urinary disorders, diabetes, oxidative stress, protein glycosylation, microbial infections, inﬂammation, pain or discomfort, muscle contractions, cytotoxicity, or as a cellular or neuronal signaling modulator. These conditions generally appear in comorbid diseases, which motivated the bibliographic review associated with the plant. This document presents the beneﬁcial actions produced by Eysenhardtia extracts and/or bioactives to inhibit, control, or reduce the complications or discomfort of degenerative diseases and thus generate new therapeutic alternatives.

Keywords: Eysenhardtia; phytochemical; pharmacological

1. Introduction The relationship between humanity and medicinal plants goes back to ancient times. The oldest records found correspond to the Sumerians, approximately 5000 years ago [1]. The growth and development of civilizations have been closely linked to the use and exploitation of the healing properties of medicinal plants [2]. The process of recognition and use of herbalism in the preparation of remedies, infusions, or concoctions for the treatment of disease has been carried out by trial and error [3]. There are countries with a long tradition of using herbal medicine such as China, India, Japan, Pakistan, and Mexico. Ethnopharmacological studies have contributed to the amplification of knowledge and the discovery of new drugs or effective bioactive compounds for the control of diseases [4]. Mexico has a history of using ethnomedicine, whose origins go back to pre-Hispanic cultures where archaeological ﬁndings have shown its anthropological inﬂuence and impact on Mexican culture [5]. One of the plants with antecedents is Eysenhardtia polystachya (EP), dating back to the era of New Spain where Nicolas B. Monardes (1565) relates the use of a tree to treat kidney and urinary diseases; he describes that they drank a blue-colored infusion which was obtained by placing thin slices of a wood (bark) into water for a period of time [6]. Furthermore, in the Florentine Codex, Fray Bernardino de Sahagún refers to the use of “Coatli” for fever or retention of urine [7]. In the following centuries (XVI and XVII), it was taken to Europe where it was known as Lignum

Plants 2020, 9, 1124; doi:10.3390/plants9091124 www.mdpi.com/journal/plants Plants 2020, 9, 1124 2 of 33 nephriticum [8,9]. Later, it continued to be consumed in a traditional way by Mexicans for the control of urinary, contraceptive [10], antidiarrheal, and antiseptic disorders, as well as for the control of diabetes [11,12]. In recent decades, the Eysenhardtia genus has attracted attention due to its medicinal properties. This triggered a series of phytochemical and pharmacological studies linked to the identification of health benefits. Among the actions determined are its diuretic [13], antidiabetic, antiglycation [14], antioxidant [15], anti-inflammatory [16], and antimicrobial [17] potential. It also has cytotoxic properties [8], is cardioprotective, and inhibits neurodegeneration and modulators of cell signaling [15]. This article presents a bibliographic review focused on the diverse activities that have been attributed to the Eysenhardtia genus, which is made up of fourteen species [18].

2. Taxonomic Classiﬁcation Kingdom: Plantae Phyllum: Tracheophyta Class: Magnoliopsida Orden: Fabales Family: Fabaceae Species: E. adenostylis, E. platycarpa, E. punctata, E. subcoriacea, E. cobriformis, E. reticulata, E. orthocarpa, E. polystachya, E. texana, E. angustifolia, E. spinosa, E. peninsularis, E. parvifolia, E. schizocalyx. Common names in Mexico: Cuate (Jal.), Coatillo (Pue.), Coatl (l. náhuatl), Cohuatli, Cuatle (Oax.), Lanaé (l. chontalpa, Oax.), Palo cuate, Rosilla (Sin.), Palo dulce (Sin., Mex., Hgo., Pue., Mich.), Palo azul (Mex), Taray (N.L., Dgo.), Tlapahuaxpatli; Ursa (l. otomí, Hgo.), Vara dulce, Varaduz (Dgo.). Common names in English: Kidneywood, Mexican Kidneywood [19–21].

2.1. Description of the Eysenhardtia Genus The Eysenhardtia genus is a deciduous tree or shrub 3 to 9 m high with a diameter of 15 to 35 cm [20]. It has a crown and alternate, compound, pinnate leaves, elliptical leaﬂets, and aromatic resins. Its wood is branched brown [19]. The bark is rough and scaly with a dark coloration on the outside and reddish-brown on the inside [20]. It shows inﬂorescences in spiky clusters lobed with white corolla. Its fruit is shown in a curved pod that houses a thin seed susceptible to water, and it is a hermaphroditePlants 2020, 9, x FOR (Figure PEER 1REVIEW)[17]. 3 of 27

Figure 1. Eysenhardtia genus.

2.2. Geographical Distribution of the Eysenhardtia Genus It is found throughout Mexico, mainly in the states of Colima, Chiapas, Chihuahua, Coahuila, Mexico City, Durango, Guanajuato, Guerrero, Hidalgo, Jalisco, State of Mexico, Morelos, Oaxaca, Puebla, Querétaro, San Luis Potosí, Sinaloa, Sonora, Tamaulipas, Tlaxcala, Veracruz, and Zacatecas. It has also been found in the southeastern United States (Figure 2) [22,23].

Figure 2. Geographical distribution of Eysenhardtia [22,23].

3. Secondary Metabolites Isolated from the Eysenhardtia Genus The Eysenhardtia genus has shown to be an excellent source of secondary metabolites with flavonoids, flavones, isoflavones, flavonones, phenolic compounds, chalcones, dihydrochalcones, coumarins, pterocarpan, sugars, and fatty acids, among others, in its composition. Table 1 shows the phytochemical compounds identified from the different parts (leaves, branches, heartwood, and bark) of the genus.

Plants 2020, 9, x FOR PEER REVIEW 3 of 27

Plants 2020, 9, 1124 3 of 33 Figure 1. Eysenhardtia genus.

2.2.2.2. GeographicalGeographical DistributionDistribution of of the the Eysenhardtia Eysenhardtia Genus Genus ItIt is is found found throughoutthroughout Mexico,Mexico, mainly in in the the states states of of Colima, Colima, Chiapas, Chiapas, Chihuahua, Chihuahua, Coahuila, Coahuila, MexicoMexico City,City, Durango,Durango, Guanajuato,Guanajuato, Guerrero, Hidalg Hidalgo,o, Jalisco, Jalisco, State State of of Mexico, Mexico, Morelos, Morelos, Oaxaca, Oaxaca, Puebla,Puebla, Quer Querétaro,étaro, San San Luis Luis Potos Potosí,í, Sinaloa, Sinaloa, Sonora, Sonora, Tamaulipas, Tamaulipas, Tlaxcala, Tlaxcala, Veracruz, Veracruz, and Zacatecas. and ItZacatecas. has also been It has found also been in the found southeastern in the sout Unitedheastern States United (Figure States2)[22 (Figure,23]. 2) [22,23].

Figure 2. Geographical distribution of Eysenhardtia [22,23]. Figure 2. Geographical distribution of Eysenhardtia [22,23].

3.3. SecondarySecondary MetabolitesMetabolites Isolated Isolated from from the theEysenhardtia EysenhardtiaGenus Genus TheThe EysenhardtiaEysenhardtia genusgenus hashas shown to be an excellent excellent source source of of secondary secondary metabolites metabolites with with flavonoids,flavonoids, flavones,flavones, isoflavones,isoflavones, flavonones, flavonones, ph phenolicenolic compounds, compounds, chalcones, chalcones, dihydrochalcones, dihydrochalcones, coumarins,coumarins, pterocarpan, pterocarpan, sugars, sugars, and and fatty fatty acids, acids, among among others, others, in in its its composition. composition. Table Table1 shows 1 shows the phytochemicalthe phytochemical compounds compounds identified identified from thefrom diff therente different parts (leaves, parts (leaves, branches, branches, heartwood, heartwood, and bark) ofand the bark) genus. of the genus.

Plants 2020, 9, x FOR PEER REVIEW 4 of 43

Table 1. Phytochemical compounds identified in the species Eysenhardtia.

Phenolic Compounds

Plants 2020, 9, 1124 4 of 33 Part Used Referenc Number Compound Structure Species (Type of e(s) Extract) Plants 2020, 9, x FOR PEER REVIEW Table 1. Phytochemical compounds identiﬁed in the species Eysenhardtia. 5 of 43

Phenolic Compounds Part Used (Type Number Compound Structure Species Reference(s) Plants 2020, 9, x FOR PEER REVIEW of Extract) 5 of 43

coatline B (3′-C-β-glucopyranosyl-α,2′,4′,3,4- Wood 2 E. polystachya [13] coatlinepentahydroxydihydrochalcone) A (3′-C-βcoatline-glucopyranosyl- A (3 -C-β-glucopyranosyl-α,2 ′,4′,4- (aqueous)Wood Plants 20201 , 9, x FOR PEER REVIEW1 0 E.E. polystachya polystachya Wood (aqueous)[13]5 of [4313 ] tetrahydroxydihydrochalcone)α,20,40,4-tetrahydroxydihydrochalcone) (aqueous)

coatline B (3′-C-β-glucopyranosyl-α,2′,4′,3,4- Wood 2 E. polystachya [13] pentahydroxydihydrochalcone) (aqueous)

coatline B (3′-C-βcoatline-glucopyranosyl- B (3 -C-β-glucopyranosyl-α,2′,4′,3,4- α, Wood 2 2 0 E.E. polystachya polystachya Wood (aqueous)[13] [13] pentahydroxydihydrochalcone)20,40,3,4-pentahydroxydihydrochalcone) (aqueous)

Wood 3 matlaline E. polystachya [7] (aqueous)

Wood 3 3 matlaline matlaline E.E. polystachyapolystachya Wood (aqueous)[7] [7] (aqueous)

Wood 3 matlaline E. polystachya [7] (aqueous)

Wood 4 4 octa-acetyl coatlineocta-acetyl A coatline A E.E. polystachyapolystachya Wood (aqueous)[13] [13] (aqueous)

Wood 4 octa-acetyl coatline A E. polystachya [13] (aqueous)

Plants 2020, 9, x FOR PEER REVIEW 6 of 43

Wood Plants 20205 , 9, x FOR PEERPlants REVIEW2020, 9, 1124 nona-acetyl coatline B E. polystachya [13]6 of 43 5 of 33 (aqueous)

Table 1. Cont. Plants 2020, 9, x FOR PEER REVIEW 6 of 43 Phenolic Compounds Part Used (Type Number Compound Structure Species Wood Reference(s) 5 nona-acetyl coatline B E. polystachya of Extract) [13] (aqueous)

WoodWood 65 5 nona-acetyldihydrocoatlinenona-acetyl coatlinenona-acetyl B B coatline B E.E. polystachyapolystachya Wood (aqueous)[13][13] [13] (aqueous)(aqueous)

Wood 6 6 nona-acetyldihydrocoatlinenona-acetyldihydrocoatline B B E.E. polystachyapolystachya Wood (aqueous)[13] [13] (aqueous) Heartwood (methanol) Wood 6 nona-acetyldihydrocoatline B E. polystachya [13] (aqueous) Plants 2020, 9, x FOR PEER REVIEW Heartwood 7 of 43 (methanol) 7 3,4-dimethoxy-8,9-methylenedioxypterocarpan7 3,4-dimethoxy-8,9-methylenedioxypterocarpan E. polystachya Bark [8,24] [8,24] Bark (CHCl3-MeOH) Heartwood (methanol) (CHCl3- MeOH) O O Heartwood O HeartwoodHeartwood 87 3,4-dimethoxy-8,9-methylenedioxypterocarpan8 dehydrorotenonedehydrorotenone E.E. polystachyapolystachya (methanol)Bark [8,24][24] [24] (methanol)(methanol)

O OMe OMe 7 3,4-dimethoxy-8,9-methylenedioxypterocarpan E. polystachya (CHClBark 3- [8,24] MeOH)

(CHCl3- MeOH)

Heartwood 9 angustlegor-retoside E. polystachya [24] (Methanol)

Bark

10 (3S)-7-hydroxy-2′,3′,4′,5′,8-pentamethoxyisoflavan E. polystachya [8]

(CHCl3- MeOH)

Plants 2020, 9, x FOR PEER REVIEW 7 of 43

O O O Heartwood 8 dehydrorotenone E. polystachya [24] (methanol)

O OMe O O OMeO Heartwood 8 dehydrorotenone E. polystachya [24] Plants 2020, 9, 1124 (methanol) 6 of 33

O OMe Table 1. Cont. OMe

Phenolic Compounds PartHeartwood Used (Type 9 Numberangustlegor-retoside Compound StructureE. Speciespolystachya [24]Reference(s) (Methanol)of Extract)

HeartwoodHeartwood 9 9 angustlegor-retosideangustlegor-retoside E.E. polystachyapolystachya [24] [24] (Methanol)(Methanol)

Plants 2020, 9, x FOR PEER REVIEW 8 of 43

Bark

Bark Plants 202010 , 9, x FOR PEER (3REVIEWS)-7-hydroxy-210 (3′,3S′)-7-hydroxy-2,4′,5′,8-pentamethoxyisoflavan,3 ,4 ,5 ,8-pentamethoxyisoﬂavan E.E. polystachyapolystachya [8] 8 of 43[8 ] 0 0 0 0 (CHCl -MeOH) Bark3 (CHClBark 3- MeOH)

11 (3S)-3′,7-dihydroxy-2′,4′,5′,8-tetramethoxyisoflavan E. polystachya [8] 10 (3S)-7-hydroxy-2′,3′,4′,5′,8-pentamethoxyisoflavan E. polystachya [8] (CHCl3- (CHClBark 3- MeOH) MeOH) Bark 11 (3S)-3′11,7-dihydroxy-2(3S)-3′,40′,7-dihydroxy-2,5′,8-tetramethoxyisoflavan0,40,50,8-tetramethoxyisoﬂavan E.E. polystachyapolystachya [8] [8] (CHCl3-MeOH) (CHCl3- MeOH)

Bark

Bark 12 (3S)-212′,3′,4′,5′,8-pentamethoxy-7-(3S)-20,30,40,50,8-pentamethoxy-7-O-acetylisoflavanO -acetylisoﬂavan E.E. polystachyapolystachya [8] [8] (CHCl3-MeOH) (CHCl3- Bark MeOH)

12 (3S)-2′,3′,4′,5′,8-pentamethoxy-7-O-acetylisoflavan E. polystachya [8]

(CHCl3- MeOH)

Bark

13 (3S)-2′,4′,5′,8-tetramethoxy-3′,7-O-diacetylisoflavan E. polystachya [8]

(CHCl3- Bark MeOH)

13 (3S)-2′,4′,5′,8-tetramethoxy-3′,7-O-diacetylisoflavan E. polystachya [8]

(CHCl3- MeOH)

Plants 2020, 9, x FOR PEER REVIEW 8 of 43

Bark

11 (3S)-3′,7-dihydroxy-2′,4′,5′,8-tetramethoxyisoflavan E. polystachya [8]

(CHCl3- MeOH)

Plants 2020, 9, x FOR PEER REVIEW Bark 9 of 43

12 Plants(32020S)-2,′,39,′,4 1124′,5′,8-pentamethoxy-7-O-acetylisoflavan E. polystachya [8] 7 of 33

(CHCl3- MeOH) Table 1. Cont. Bark

Phenolic Compounds 14 isoduartin (2′,7-dihydroxy-3′,4′,8-trimethoxyisoflavan) E. polystachya [8] Part Used (Type Number Compound Structure Species (CHCl3- Reference(s) Plants 2020, 9, x FOR PEER REVIEW of Extract) 9 of 43 MeOH)

Bark

(3S)-2 ,4 ,5 ,8-tetramethoxy-3 ,7- Bark Plants 202013 , 9, x FOR PEER (3REVIEWS)-2′13,4′ ,5′,8-tetramethoxy-3′0,7-0O-diacetylisoflavan0 0 E.E. polystachyapolystachya [8]9 of 43[8 ] O-diacetylisoﬂavan (CHClBark3-MeOH) (CHCl3- MeOH) 14 isoduartin (2′,7-dihydroxy-3′,4′,8-trimethoxyisoflavan) E. polystachya [8] Bark (CHCl3- Bark MeOH) 15 cuneatin (7-hydroxy-2′-methoxy-4′,5′-(methylendioxy)isoflavone) E. polystachya [8] isoduartin Bark 14 isoduartin14 (2′,7-dihydroxy-3′,4′,8-trimethoxyisoflavan) E.E. polystachyapolystachya (CHCl3- [8] [8] (20,7-dihydroxy-30,40,8-trimethoxyisoﬂavan) (CHCl3-MeOH) (CHClMeOH)3- MeOH)

cuneatin (7-hydroxy-2 -methoxy-4 ,5 - BarkBark 15 0 0 0 E. polystachya [8] (methylendioxy)isoﬂavone) (CHCl3-MeOH) 15 cuneatin (7-hydroxy-2′-methoxy-4′,5′-(methylendioxy)isoflavone) E. polystachya [8] Bark (CHCl3- Bark Plants 2020, 9, x FOR PEER REVIEW MeOH)Bark 10 of 43 (CHCl -MeOH) 16 7-hydroxy-216 ′,47-hydroxy-2′,5′-trimethoxyisoflavone,4 ,5 -trimethoxyisoﬂavone E.E. polystachyapolystachya 3 [8] [8] 15 cuneatin (7-hydroxy-2′-methoxy-4′,5′-(methylendioxy)isoflavone)0 0 0 E. polystachya (CHClHeartwood3- [8] MeOH) (CHCl(Aqueous)3-

HeartwoodMeOH) (Aqueous)Bark

Bark 17 (α-R17)-α,3,4,2′,4′(-pentahydroxydihydrochalconeα-R)-α,3,4,20,40-pentahydroxydihydrochalcone E.E. polystachyapolystachya Bark [25] [25] (CHCl3-MeOH) (CHCl3- MeOH)

16 7-hydroxy-2′,4′,5′-trimethoxyisoflavone E. polystachya (CHCl3- [8] Bark MeOH) Heartwood (Aqueous) 16 7-hydroxy-2′,4′,5′-trimethoxyisoflavone E. polystachya (CHCl3- [8] MeOH)Bark Heartwood (αR)-3′-C-β-D-xylopyranosyl-α,3,4,2′,4′- 18 E. polystachya (Aqueous) [25] pentahydroxydihydrochalcone (CHCl3-

MeOH)

Bark

(αR)-3′-O-β-D-xylopyranosyl-α,3,4,2′,4′- 19 E. polystachya [25] pentahydroxydihydrochalcone (CHCl3- MeOH)

Plants 2020, 9, x FOR PEER REVIEW 10 of 43

Plants 2020, 9, x FOR PEER REVIEW Bark 10 of 43

17 (α-R)-α,3,4,2′,4′-pentahydroxydihydrochalcone E. polystachya [25] (CHCl3- MeOH) Bark

17 Plants 2020,(9α,- 1124R)-α,3,4,2′,4′-pentahydroxydihydrochalcone E. polystachya [25] 8 of 33 (CHCl3- MeOH) Table 1. Cont. Bark

(αR)-3′-C-β-D-xylopyranosyl-α,3,4,2′,4′- Phenolic Compounds 18 E. polystachya [25] pentahydroxydihydrochalcone Part Used (Type Number Compound Structure Species (CHCl3- Reference(s) of Extract) MeOH) Bark

Plants 2020, 9, x FOR PEER REVIEW (αR)-3′-C-(βα-D-xylopyranosyl-R)-3 -C-β-D-xylopyranosyl-α,3,4,2′,4′- α,3,4,2 ,4 - Bark 11 of 43 18 18 0 0 0 E. polystachya [25] [25] pentahydroxydihydrochalconepentahydroxydihydrochalcone (CHCl3-MeOH) (CHCl3-

MeOH) Bark Plants 2020, 9, x FOR PEER REVIEW 11 of 43 (αR)-3 -O-β-D-xylopyranosyl-α,3,4,2 ,4 - Bark 19 (αR)-3′-O-β-D-xylopyranosyl-0 α,3,4,2′,4′- 0 0 E. polystachya [25] 19 pentahydroxydihydrochalcone E. polystachya (CHCl3-MeOH) [25] pentahydroxydihydrochalcone Aerial parts (CHCl3- 20 4′,5,7-trihydroxy-8-methyl-6-(3-methyl-[2-butenyl])-(2S)-flavanone E. texana (CH2Cl2- [26,27] MeOH) BarkMeOH)

(αR)-3′-O-β-D-xylopyranosyl-α,3,4,2′,4′- 19 E. polystachya Aerial parts [25] pentahydroxydihydrochalcone40,5,7-trihydroxy-8-methyl-6-(3-methyl- Aerial parts 20 4′,5,7-trihydroxy-8-methyl-6-(3-methyl-[2-butenyl])-(220 S)-flavanone E.E. texanatexana (CHCl(CH23Cl- 2- [26,27] [26,27] [2-butenyl])-(2S)-ﬂavanone (CH2Cl2-MeOH) MeOH)MeOH)

Aerial parts 40,5,7-trihydroxy-6-methyl-8-(3-methyl- Aerial parts 21 4′,5,7-trihydroxy-6-methyl-8-(3-methyl-[2-butenyl])-(221 S)-flavanone E.E. texanatexana (CH2Cl2- [26,27] [26,27] [2-butenyl])-(2S)-ﬂavanone (CH Cl -MeOH) MeOH)2 2

Aerial parts

21 4′,5,7-trihydroxy-6-methyl-8-(3-methyl-[2-butenyl])-(2S)-flavanone E. texana (CH2Cl2- [26,27] MeOH)

Plants 2020, 9, x FOR PEER REVIEW 12 of 43

Plants 2020, 9, x FOR PEERPlants REVIEW2020, 9, 1124 12 of 43 9 of 33

Table 1. Cont. Plants 2020, 9, x FOR PEER REVIEW 12 of 43 Aerial parts Phenolic Compounds 22 4′,5-dihydroxy-7-methoxy-6-(3-methyl-[2-butenyl])-(2S)-flavanone E. texana (CH2Cl2- [26,27] Part Used (Type Number Compound Structure Species MeOH) Reference(s) of Extract) Aerial parts 22 4′,5-dihydroxy-7-methoxy-6-(3-methyl-[2-butenyl])-(2S)-flavanone E. texana (CH2Cl2- [26,27]

MeOH)

Aerial parts 40,5-dihydroxy-7-methoxy-6-(3-methyl- Aerial parts 22 4′,5-dihydroxy-7-methoxy-6-(3-methyl-[2-butenyl])-(222 S)-flavanone E.E. texanatexana (CH2Cl2- [26,27] [26,27] [2-butenyl])-(2S)-ﬂavanone (CH Cl -MeOH) MeOH)2 2

Heartwood 23 7-hydroxy-4′-methoxyisoflavone E. polystachya [28,29] (Aqueous)

HeartwoodHeartwood 23 23 7-hydroxy-4′-methoxyisoflavone7-hydroxy-40-methoxyisoﬂavone E.E. polystachyapolystachya [28,29] [28,29] (Aqueous)(Aqueous)

Heartwood 23 7-hydroxy-4′-methoxyisoflavone E. polystachya [28,29] (Aqueous)

LeavesLeaves Plants 202024 , 9, x FOR PEER REVIEW24 4′-O-methyl-8-prenylnaringenin4 -O-methyl-8-prenylnaringenin E.E. platycarpaplatycarpa [30]13 of 43[30 ] 0 (Methanolic)(Methanolic)

Leaves 24 4′-O-methyl-8-prenylnaringenin E. platycarpa [30] (Methanolic)

5,40,1”-trihydroxy-6,7-(3”,3”- BranchesBranches 25 5,4′,1′′-trihydroxy-6,7-(325 ′′,3′′-dimethylchroman)flavone E.E. platycarpaplatycarpa Leaves [30] [30] 24 4′-O-methyl-8-prenylnaringenindimethylchroman)ﬂavone E. platycarpa (Methanolic)(Methanolic) [30] (Methanolic)

Branches and 26 (2S)-4′-O-methyl-6-methyl-8-prenylnaringenin E. platycarpa leaves [30] (Methanolic)

Branches and 27 5,7-dihydroxy-6-methyl-8-prenylflavanone E. platycarpa leaves [30] (Methanolic)

Plants 2020, 9, x FOR PEER REVIEW 13 of 43

Branches 25 5,4′,1′′-trihydroxy-6,7-(3′′,3′′-dimethylchroman)flavone E. platycarpa [30] (Methanolic)

Branches 25 Plants5,4′,12020′′-trihydroxy-6,7-(3, 9, 1124 ′′,3′′-dimethylchroman)flavone E. platycarpa [30] 10 of 33 (Methanolic)

Table 1. Cont.

Phenolic Compounds BranchesPart Used and (Type Number Compound Structure Species Reference(s) 26 (2S)-4′-O-methyl-6-methyl-8-prenylnaringenin E. platycarpa ofleaves Extract) [30] (Methanolic)

BranchesBranches and and 26 (2S)-426′-O-methyl-6-methyl-8-prenylnaringenin(2S)-40-O-methyl-6-methyl-8-prenylnaringenin E.E. platycarpaplatycarpa leavesleaves [30] [30] Plants 2020, 9, x FOR PEER REVIEW (Methanolic)(Methanolic) 14 of 43

Plants 2020, 9, x FOR PEER REVIEW 14 of 43 BranchesBranches and and 27 5,7-dihydroxy-6-methyl-8-prenylflavanone27 5,7-dihydroxy-6-methyl-8-prenylﬂavanone E.E. platycarpaplatycarpa leavesleaves [30] [30] (Methanolic)(Methanolic) Branches and 28 5,7-dihydroxy-8-methyl-6-prenylflavanone E. platycarpa leaves [30] Branches(Methanolic) and 27 5,7-dihydroxy-6-methyl-8-prenylflavanone E. platycarpa leaves [30] Branches(Methanolic)Branches and and

28 5,7-dihydroxy-8-methyl-6-prenylflavanone28 5,7-dihydroxy-8-methyl-6-prenylﬂavanone E.E. platycarpaplatycarpa leavesleaves [30] [30] (Methanolic)(Methanolic)

BranchesBranches 29 29 5,7-dihydroxy-6-prenylflavanone5,7-dihydroxy-6-prenylﬂavanone E.E. platycarpaplatycarpa [30] [30] (Methanolic)(Methanolic)

Branches 29 5,7-dihydroxy-6-prenylflavanone E. platycarpa [30] (Methanolic)

Leaves 30 5-hydroxy-7-methoxy-8-prenylflavanone E. platycarpa [30] (Methanolic)

Plants 2020, 9, x FOR PEER REVIEW 14 of 43

Branches and 28 5,7-dihydroxy-8-methyl-6-prenylflavanone E. platycarpa leaves [30] (Methanolic)

Plants 2020, 9, 1124 Branches 11 of 33 29 5,7-dihydroxy-6-prenylflavanone E. platycarpa [30] (Methanolic)

Table 1. Cont. Plants 2020, 9, x FOR PEER REVIEW 15 of 43 Phenolic Compounds Part Used (Type Number Compound Structure Species Reference(s) of Extract) Plants 2020, 9, x FOR PEER REVIEW 15 of 43

Branches 31 5,7-dihydroxy-8-prenylflavanone E. platycarpa LeavesLeaves [30] Plants 202030 , 9, x FOR PEER REVIEW5-hydroxy-7-methoxy-8-prenylflavanone30 5-hydroxy-7-methoxy-8-prenylﬂavanone E.E. platycarpaplatycarpa (Methanolic) [30]15 of 43[30 ] (Methanolic)(Methanolic)

Branches 31 5,7-dihydroxy-8-prenylflavanone E. platycarpa [30] (Methanolic)

BranchesBranches 31 31 5,7-dihydroxy-8-prenylflavanone5,7-dihydroxy-8-prenylﬂavanone E.E. platycarpaplatycarpa [30] [30] (Methanolic)(Methanolic) Bark subcoriacin (3-(2′-hydroxy-4′,5′-methylendioxyphenyl)-6-(3′′- 32 E. subcoriacea [31,32] hydroxymethyl-4′′-hydroxybut-2′′-enyl)-7-hydroxycoumarin) (Methanolic) Bark subcoriacin (3-(2 -hydroxy-4 ,5 - subcoriacin (3-(2′-hydroxy-4′,5′-methylendioxyphenyl)-6-(30 0 ′′0 - Bark 32 32 methylendioxyphenyl)-6-(3”-hydroxymethyl-4” E. subcoriacea [31,32] [31,32] hydroxymethyl-4′′-hydroxybut-2′′-enyl)-7-hydroxycoumarin) (Methanolic) -hydroxybut-2”-enyl)-7-hydroxycoumarin) (Methanolic) Bark subcoriacin (3-(2′-hydroxy-4′,5′-methylendioxyphenyl)-6-(3′′- 32 E. subcoriacea [31,32]

hydroxymethyl-4′′-hydroxybut-2′′-enyl)-7-hydroxycoumarin) Bark (Methanolic) E.E. platycarpa,platycarpa, Bark 33 33 (+)-cathechin (+)-cathechin [30,31,33][30 ,31,33] E.E. subcoriaceasubcoriacea (Methanolic) (Methanolic) Bark

E. platycarpa, 33 (+)-cathechin [30,31,33] E. subcoriacea

(Methanolic)Bark

E. platycarpa, 33 (+)-cathechin [30,31,33] E. subcoriacea (Methanolic)

Plants 2020, 9, x FOR PEER REVIEW 16 of 43

Plants 2020, 9, x FOR PEER REVIEW 16 of 43 Plants 2020, 9, 1124 12 of 33 Bark E. platycarpa, 34 (−)-epicatechin [30,31,33] Table 1. Cont. E. subcoriacea Plants 2020, 9, x FOR PEER REVIEW 16 of 43 (Methanolic) Phenolic Compounds Bark E. platycarpa, Part Used (Type 34 Number(−)-epicatechin Compound Structure Species [30,31,33]Reference(s) E. subcoriacea of Extract) (Methanolic) Bark E.E. platycarpa,platycarpa, Bark 34 34 (−)-epicatechin( )-epicatechin [30,31,33][30 ,31,33] − E.E. subcoriaceasubcoriacea (Methanolic)Bark E. platycarpa, (Methanolic) 35 (+)-afzelechin [30,31,33] E. subcoriacea (Methanolic) Bark

E. platycarpa, Bark 35 35 (+)-afzelechin (+)-afzelechin [30,31,33][30 ,31,33] E.E. subcoriaceasubcoriacea (Methanolic) (Methanolic) Bark

E. platycarpa, 35 (+)-afzelechin [30,31,33] E. subcoriacea Bark (Methanolic) E.E. platycarpa,platycarpa, Bark Plants 202036 , 9, x FOR PEER REVIEW36 eriodictyol eriodictyol [30,31,33]17 of[30 43,31 ,33] E.E. subcoriaceasubcoriacea (Methanolic) (Methanolic) Bark

E. platycarpa, 36 eriodictyol [30,31,33] E. subcoriacea Bark (Methanolic) E. platycarpa, BarkBark 37 (+)-catechin-3-37 (O-+)-catechin-3-β-D-galactopyranosideO-β-D-galactopyranoside [30,31,33][30 ,31,33] E. subcoriacea E.E. subcoriaceaplatycarpa, (Methanolic) 36 eriodictyol [30,31,33] E. subcoriacea (Methanolic)

(Methanolic)

Bark E. platycarpa, 38 quercetin-3-O-β-D-galactopyranoside [30,31,33] E. subcoriacea (Methanolic)

Bark

39 2′,4′-dihydroxychalcone-6′-O-β-D-glucopyranoside E. polystachya [34] (Water/MeOH )

Plants 2020, 9, x FOR PEER REVIEW 17 of 43

Plants 2020, 9, x FOR PEER REVIEW 17 of 43 Bark E. platycarpa, 37 (+)-catechin-3-O-β-D-galactopyranoside [30,31,33] E. subcoriacea (Methanolic) Bark E. platycarpa, 37 Plants 2020(+)-catechin-3-, 9, 1124 O-β-D-galactopyranoside [30,31,33] 13 of 33 E. subcoriacea (Methanolic) Table 1. Cont.

Phenolic Compounds Bark Part Used (Type Number Compound StructureE. Speciesplatycarpa, Reference(s) 38 quercetin-3-O-β-D-galactopyranoside of Extract) [30,31,33] E. subcoriacea (Methanolic) Bark E. platycarpa, Bark 38 38quercetin-3-O-quercetin-3-β-D-galactopyranosideO-β-D-galactopyranoside [30,31,33][30 ,31,33] E.E. subcoriaceasubcoriacea (Methanolic) (Methanolic)

Plants 2020, 9, x FOR PEER REVIEW 18 of 43

Bark

Bark 39 2′,4′-dihydroxychalcone-639 2 ,4 -dihydroxychalcone-6′-O-β-D-glucopyranoside-O-β-D-glucopyranoside E.E. polystachyapolystachya [34] [34] Plants 2020, 9, x FOR PEER REVIEW 0 0 0 (Water/MeOH) 18 of 43 (Water/MeOH Bark ) α,3,2′,4′-tetrahydroxy-4-methoxy-dihydrochalcone-3′-C-β- 3940 2′,4′-dihydroxychalcone-6′-O-β-D-glucopyranoside E. polystachya [34] glucopyranosy-6′-O-β-D-glucopyranoside (Water/MeOH Bark) α,3,2 ,4 -tetrahydroxy-4-methoxy- α,3,2′,4′-tetrahydroxy-4-methoxy-dihydrochalcone-30 0 ′-C-β- Bark 40 40 dihydrochalcone-3 -C-β-glucopyranosy- E.E. polystachyapolystachya [34] [34] glucopyranosy-6′-O-β-D-glucopyranoside0 (Water/MeOH) 60-O-β-D-glucopyranoside (Water/MeOH )

Bark 7-hydroxy-5,8 -dimethoxy-6 α-L- 7-hydroxy-5,8′-dimethoxy-6′-L-rhamnopyranosyl-8-(3-phenyl-0 0 Bark 41 41 rhamnopyranosyl-8-(3-phenyl-transacryloyl)- E.E. polystachyapolystachya [34] [34] transacryloyl)-1-benzopyran-2-one (Water/MeOH) 1-benzopyran-2-one (Water/MeOH Bark)

7-hydroxy-5,8′-dimethoxy-6′-L-rhamnopyranosyl-8-(3-phenyl- 41 E. polystachya [34] transacryloyl)-1-benzopyran-2-one (Water/MeOH )

Bark

6′,7-dihydroxy-5,8-dimethoxy-8(3-phenyl-trans-acryloyl)-1- 42 E. polystachya [34] benzopyran-2-one (Water/MeOH Bark)

6′,7-dihydroxy-5,8-dimethoxy-8(3-phenyl-trans-acryloyl)-1- 42 E. polystachya [34] benzopyran-2-one (Water/MeOH )

Plants 2020, 9, x FOR PEER REVIEW 18 of 43

Bark

α,3,2′,4′-tetrahydroxy-4-methoxy-dihydrochalcone-3′-C-β- 40 E. polystachya [34] glucopyranosy-6′-O-β-D-glucopyranoside (Water/MeOH )

Bark

7-hydroxy-5,8′-dimethoxy-6′-L-rhamnopyranosyl-8-(3-phenyl- 41 E. polystachya [34] Plants 2020, 9, x FOR PEERPlants REVIEW2020, 9transacryloyl)-1-benzopyran-2-one , 1124 19 of 43 14 of 33 (Water/MeOH ) Table 1. Cont.

Phenolic Compounds Plants 2020, 9, x FOR PEER REVIEW 19 of 43 PartBark Used (Type Number Compound Structure Species Reference(s) of Extract) 43 9-hydroxy-3,8-dimethoxy-4-prenylpterocarpan E. polystachya Bark [34] (Water/MeOH Plants 2020, 9, x FOR PEER REVIEW 19 of 43 6′,7-dihydroxy-5,8-dimethoxy-8(3-phenyl-trans-acryloyl)-1-6 ,7-dihydroxy-5,8-dimethoxy-8(3-phenyl-trans- )Bark 42 42 0 E.E. polystachyapolystachya Bark [34] [34] benzopyran-2-oneacryloyl)-1-benzopyran-2-one (Water/MeOH) (Water/MeOH 43 9-hydroxy-3,8-dimethoxy-4-prenylpterocarpan E. polystachya ) [34] (Water/MeOH Bark)

BarkBark 43 9-hydroxy-3,8-dimethoxy-4-prenylpterocarpan43 9-hydroxy-3,8-dimethoxy-4-prenylpterocarpan E.E. polystachyapolystachya [34] [34] (Water/MeOH) (Water/MeOH 44 5,4′-dihydroxy-7,2′-dimethoxyl-isoflavone E. polystachya [34] ) (Water/MeOH Bark)

Bark 44 5,444′-dihydroxy-7,25,4 -dihydroxy-7,2′-dimethoxyl-isoflavone-dimethoxyl-isoﬂavone E.E. polystachyapolystachya [34] [34] 0 0 (Water/MeOH) (Water/MeOH Bark)

44 5,4′-dihydroxy-7,2′-dimethoxyl-isoflavone E. polystachya Bark [34] (Water/MeOH α,4,4 -trihydroxy-dihydrochalcone-2 - Bark 45 α,4,4′-trihydroxy-dihydrochalcone-245 0 ′-O-β-D-glucopyranoside 0 E.E. polystachyapolystachya ) [34] [34] O-β-D-glucopyranoside (Water/MeOH) (Water/MeOH Bark)

45 α,4,4′-trihydroxy-dihydrochalcone-2′-O-β-D-glucopyranoside E. polystachya [34] (Water/MeOH Bark)

45 α,4,4′-trihydroxy-dihydrochalcone-2′-O-β-D-glucopyranoside E. polystachya [34] (Water/MeOH )

Plants 2020, 9, x FOR PEER REVIEW 20 of 43

Plants 2020, 9, x FOR PEER REVIEW Bark 20 of 43

46 (3R)-5,7-2′,4′-tetrahydroxyl-3′-methoxyl-isoflavanone E. polystachya [34] Plants 2020, 9, 1124 15 of 33 (Water/MeOH Bark) Plants 2020, 9, x FOR PEER REVIEW Table 1. Cont. 20 of 43

46 (3R)-5,7-2′,4′-tetrahydroxyl-3′-methoxyl-isoflavanone Phenolic Compounds E. polystachya [34] (Water/MeOHPart Used (Type Number Compound Structure Species Reference(s) of) Extract) Bark

(3R)-5,7-2 ,4 -tetrahydroxyl-3 - Bark 46 (3R)-5,7-246′,4′-tetrahydroxyl-3′-methoxyl-isoflavanone0 0 0 E.E. polystachyapolystachya [34] [34] 47 flemichapparin C (9-methoxy-2,3-methylenedioxycoumestan)methoxyl-isoﬂavanone E. polystachya (Water/MeOH) [34] (Water/MeOH Bark)

ﬂemichapparin C Bark 47 flemichapparin47 C (9-methoxy-2,3-methylenedioxycoumestan) E.E. polystachyapolystachya [34] [34] Plants 2020, 9, x FOR PEER REVIEW (9-methoxy-2,3-methylenedioxycoumestan) (Water/MeOH) 21 of 43 (Water/MeOH ) Bark Plants 2020, 9, x FOR PEER REVIEW Bark 21 of 43 Bark 4748 flemichapparin48 neohesperidin-dihydrochalcone C (9-methoxy-2,3-methylenedioxycoumestan)neohesperidin-dihydrochalcone E.E. polystachyapolystachya [34] [34] (Water/MeOH) 49 hesperetin dihydrochalcone glucoside E. polystachya (Water/MeOH [34] ) (Water/MeOHBark)

Bark) 48 neohesperidin-dihydrochalcone E. polystachya [34] Bark 49 hesperetin49 dihydrochalconehesperetin dihydrochalcone glucoside glucoside E. polystachya (Water/MeOH [34] [34] (Water/MeOH) (Water/MeOH)

Bark) Bark 48 neohesperidin-dihydrochalcone E. polystachya [34] Bark 50 50 aspalathin aspalathin E.E. polystachyapolystachya (Water/MeOH [34] [34] (Water/MeOH) ) (Water/MeOH

Bark)

50 aspalathin E. polystachya [34]

(Water/MeOH )

Bark

51 sandwicensin E. polystachya [34] (Water/MeOH Bark)

51 sandwicensin E. polystachya [34] (Water/MeOH )

Plants 2020, 9, x FOR PEER REVIEW 21 of 43

Bark

49 hesperetin dihydrochalcone glucoside E. polystachya [34] (Water/MeOH

)

Bark

50 Plants 2020, 9, 1124 aspalathin E. polystachya [34] 16 of 33 (Water/MeOH

Table 1. Cont. )

Phenolic Compounds Part Used (Type Number Compound Structure Species Reference(s) Plants 2020, 9, x FOR PEER REVIEW of Extract) 22 of 43

Bark

Bark 51 51 sandwicensinsandwicensin E.E. polystachyapolystachya [34] [34] Plants 2020, 9, x FOR PEER REVIEW (Water/MeOH) 22 of 43 (Water/MeOHBark ) 2′-O-α-L-rhamnopyranosyl- α,6′-dihydroxy-4′-acetyl-4- 52 E. polystachya [35] methoxydihydrochalcone (Water/MeOH Bark)

2′-O-α-L-rhamnopyranosyl-2 -O-α-L-rhamnopyranosyl- α,6′-dihydroxy-4′-acetyl-4-α,6 -dihydroxy- Bark 52 52 0 0 E.E. polystachyapolystachya [35] [35] methoxydihydrochalcone40-acetyl-4-methoxydihydrochalcone (Water/MeOH) (Water/MeOH )

Bark Plants 2020, 9, x FOR PEER REVIEW 22 of 43 Bark 53 53 6′methoxy-sieboldin6 methoxy-sieboldin E.E. polystachyapolystachya [35] [35] 0 (Water/MeOH) (Water/MeOH

Bark)

53 6′methoxy-sieboldin E. polystachya Bark [35] (Water/MeOH 2′-O-α-L-rhamnopyranosyl-2 -O-β-D-glucopyranosyl-4 α,6′-dihydroxy-4′-acetyl-4--methoxy-4- Bark 52 54 0 0 E.E. polystachyapolystachya [35] [35] methoxydihydrochalconehydroxy-3-isoprenyldihydrochalcone (Water) /MeOH) (Water/MeOH Bark)

2′-O-β-D-glucopyranosyl-4′-methoxy-4-hydroxy-3- 54 E. polystachya [35] isoprenyldihydrochalcone (Water/MeOH Bark)

2′-O-β-D-glucopyranosyl-4′-methoxy-4-hydroxy-3- 54 E. polystachya [35] isoprenyldihydrochalcone Bark (Water/MeOH 53 6′methoxy-sieboldin E. polystachya ) [35]

(Water/MeOH

)

Bark

2′-O-β-D-glucopyranosyl-4′-methoxy-4-hydroxy-3- 54 E. polystachya [35] isoprenyldihydrochalcone (Water/MeOH )

Plants 2020, 9, x FOR PEER REVIEW 23 of 43

Plants 2020, 9, x FOR PEER REVIEW 23 of 43 Plants 2020, 9, 1124 Bark 17 of 33

55 2′,4′,6′-trihydroxy-4,5-dimethoxy-3-isoprenyldihydrochalcone E. polystachya [35] Table 1. Cont. Plants 2020, 9, x FOR PEER REVIEW (Water/MeOH 23 of 43 Bark Phenolic Compounds ) Part Used (Type 55 2′,4′,6′-trihydroxy-4,5-dimethoxy-3-isoprenyldihydrochalconeNumber Compound StructureE. Speciespolystachya [35]Reference(s) of Extract) (Water/MeOH Bark ) 2 ,4 ,6 -trihydroxy-4,5-dimethoxy- Bark 55 2′,4′,6′-trihydroxy-4,5-dimethoxy-3-isoprenyldihydrochalcone55 0 0 0 E.E. polystachyapolystachya [35] [35] 3-isoprenyldihydrochalcone (WaterBark/ MeOH) (Water/MeOH 3′-C-β-glucopyranosyl-α, 2′,4′,6′-trihydroxy-4- ) 56 E. polystachya [35] methoxydihydrochalcone (Water/MeOH Bark )

3′-C-β-glucopyranosyl-α3, 2-C-′,4′β,6-glucopyranosyl-′-trihydroxy-4- α, Bark 56 56 0 E.E. polystachyapolystachya [35] [35] methoxydihydrochalcone20,40,60-trihydroxy-4-methoxydihydrochalcone (Water/MeOH) (Water/MeOH Bark)

3′-C-β-glucopyranosyl-α, 2′,4′,6′-trihydroxy-4- 56 E. polystachya [35] methoxydihydrochalcone (Water/MeOHBark ) 3′-C-β-glucopyranosyl-α3, 2-C-′,4-trihydroxy-4β-glucopyranosyl-′,6′- α, Bark Plants 202057 , 9, x FOR PEER REVIEW57 0 E.E. polystachyapolystachya [35]24 of 43[35 ] dimethoxydihydrochalcone20,4-trihydroxy-40,60-dimethoxydihydrochalcone (Water/MeOH) (Water/MeOH Bark )

3′-C-β-glucopyranosyl-α, 2′,4-trihydroxy-4′,6′- 57 E. polystachya [35] dimethoxydihydrochalcone Bark (Water/MeOH Bark )Bark 58 3-hydroxyphloretin-458 3-hydroxyphloretin-4′-O-β-D-glucopyranoside0-O-β-D-glucopyranoside E.E. polystachyapolystachya [35] [35] 3′-C-β-glucopyranosyl-α, 2′,4-trihydroxy-4′,6′- (Water/MeOH) 57 E. polystachya (Water/MeOH [35] dimethoxydihydrochalcone (Water/MeOH) )

Bark

59 3,4′-dihydroxy-2,4,6-trimethoxydihydrochalcone E. polystachya [35] (Water/MeOH )

Bark

60 2′,4′,4-trihydroxy-3′-methoxydihydrochalcone E. polystachya [35] (Water/MeOH )

Plants 2020, 9, x FOR PEER REVIEW 24 of 43

Plants 2020, 9, x FOR PEER REVIEW Bark 24 of 43

58 3-hydroxyphloretin-4′-O-β-D-glucopyranoside E. polystachya [35] (Water/MeOH Bark)

58 Plants3-hydroxyphloretin-42020, 9, 1124 ′-O-β-D-glucopyranoside E. polystachya [35] 18 of 33 (Water/MeOH ) Table 1. Cont. Bark Phenolic Compounds 59 3,4′-dihydroxy-2,4,6-trimethoxydihydrochalcone E. polystachya Part Used (Type [35] Number Compound Structure Species Reference(s) (Water/MeOHof Extract) Bark)

Bark 59 3,4′-dihydroxy-2,4,6-trimethoxydihydrochalcone59 3,4 -dihydroxy-2,4,6-trimethoxydihydrochalcone E.E. polystachyapolystachya [35] [35] 0 (Water/MeOH) Plants 2020, 9, x FOR PEER REVIEW (Water/MeOH 25 of 43 ) Bark

Plants 2020, 9, x FOR PEER REVIEW Bark 25 of 43 60 2′,4′60,4-trihydroxy-32 ,4 ,4-trihydroxy-3′-methoxydihydrochalcone-methoxydihydrochalcone E.E. polystachyapolystachya [35] [35] 0 0 0 (Water/MeOH) (Water/MeOHBark Bark) 61 2′,4′,6′,4-tetrahydroxy-3,5-diisoprenyldihydrochalcone E. polystachya [35]

60 2′,4′,4-trihydroxy-3′-methoxydihydrochalcone E. polystachya (Water/MeOHBark [35] (Water/MeOH) 20,40,60,4-tetrahydroxy-3,5- Bark 61 2′,4′,6′,4-tetrahydroxy-3,5-diisoprenyldihydrochalcone61 E. polystachya ) [35] [35] diisoprenyldihydrochalcone (Water/MeOH) (Water/MeOH )

Bark

3 -C-β-glucopyranosyl-α,2 ,4 ,3,4- Bark 62 3′-C-β-glucopyranosyl-62 α,2′,4′,3,4-pentahydroxydihydroxychalcone0 0 0 E. polystachya [35] [35] pentahydroxydihydroxychalcone (Water/MeOH) (Water/MeOHBark )

62 3′-C-β-glucopyranosyl-α,2′,4′,3,4-pentahydroxydihydroxychalcone E. polystachya [35] (Water/MeOH )

Bark

63 3′-O-β-D-glucopyranosyl-α,4,2′,4′,6′-pentahydroxydihydrochalcone E. polystachya [36]

(Water/MeOHBark )

63 3′-O-β-D-glucopyranosyl-α,4,2′,4′,6′-pentahydroxydihydrochalcone E. polystachya [36] (Water/MeOH )

Plants 2020, 9, x FOR PEER REVIEW 25 of 43

Bark

61 2′,4′,6′,4-tetrahydroxy-3,5-diisoprenyldihydrochalcone E. polystachya [35] (Water/MeOH )

Bark

62 Plants3′-C-β2020-glucopyranosyl-, 9, 1124 α,2′,4′,3,4-pentahydroxydihydroxychalcone E. polystachya [35] 19 of 33

Plants 2020, 9, x FOR PEER REVIEW (Water/MeOH 26 of 43 ) Table 1. Cont.

Phenolic Compounds Plants 2020, 9, x FOR PEER REVIEW Part Used (Type 26 of 43 Number CompoundSterols and terpenoids Structure Species Reference(s) of Extract)

Bark

3 -O-β-D-glucopyranosyl-α,4,2 ,4 ,6Sterols- and terpenoids Bark 63 3′-O-β-D-glucopyranosyl-63 α0 ,4,2′,4′,6′-pentahydroxydihydrochalcone0 0 0 E. polystachya [36] [36] pentahydroxydihydrochalcone (Water/MeOH) (Water/MeOH )

Branches 64 oleanolic acid Sterols and terpenoids E. platycarpa [30] (Methanolic)

BranchesBranches 64 64 oleanolic acidoleanolic acid E.E. platycarpa platycarpa [30] [30] (Methanolic)(Methanolic)

BranchesBranches 65 65 β-sitosterol β-sitosterol E. platycarpa [30] [30] (methanolic)(methanolic)

Branches 65 β-sitosterol E. platycarpa [30] (methanolic)

Plants 2020, 9, x FOR PEER REVIEW 27 of 43

Plants 2020, 9, x FOR PlantsPEER REVIEW2020, 9, 1124 27 of 43 20 of 33

Table 1. Cont. Plants 2020, 9, x FOR PEER REVIEW Branches 27 of 43 66 β-sitosteryl β-D-glucopyranoside E. platycarpa [30] Sterols and terpenoids (Methanolic) Part Used (Type Number Compound Structure Species Reference(s) of Extract) Branches 66 β-sitosteryl β-D-glucopyranoside E. platycarpa [30] (Methanolic)

BranchesBranches 66 66β-sitosteryl β-D-glucopyranosideβ-sitosteryl β-D-glucopyranoside E.E. platycarpaplatycarpa [30] [30] (Methanolic)(Methanolic)

Branches 67 β-sitosteryl palmitate E. platycarpa [30] (Methanolic)

BranchesBranches 67 67 β-sitosteryl palmitateβ-sitosteryl palmitate E.E. platycarpa platycarpa [30] [30] (Methanolic)(Methanolic)

Branches 67 β-sitosteryl palmitate E. platycarpa [30] (Methanolic)Bark

Bark 68 68 stigmasterol stigmasterol E. polystachyapolystachya [8] [8] (CHCl3-MeOH) (CHCl3- Bark MeOH)

68 stigmasterol E. polystachya [8]

(CHCl3- Bark MeOH)

68 stigmasterol E. polystachya [8]

(CHCl3- MeOH)

Plants 2020, 9, x FOR PEER REVIEW 28 of 43

Plants 2020, 9, x FOR PEERPlants REVIEW2020, 9, 1124 28 of 43 21 of 33

Table 1. Cont. Branches 69 3-O-acetyl-11α,12α-epoxy-oleanan-28,13β-olide E. platycarpa [30,33] Plants 2020, 9, x FOR PEER REVIEW (Methanolic) 28 of 43 Sterols and terpenoids Part Used (Type Number Compound Structure Species Reference(s) Branchesof Extract) 69 3-O-acetyl-11α,12α-epoxy-oleanan-28,13β-olide E. platycarpa [30,33] (Methanolic)

BranchesBranches 69 3-O-acetyl-1169 α,123-Oα-acetyl-11-epoxy-oleanan-28,13α,12α-epoxy-oleanan-28,13β-olide β-olide E.E. platycarpaplatycarpa [30,33] [30,33] (Methanolic)(Methanolic)

Branches 70 lupeol E. platycarpa [30] (Methanolic)

BranchesBranches 70 70 lupeol lupeol E.E. platycarpaplatycarpa [30] [30] (Methanolic)(Methanolic)

Branches 70 lupeol E. platycarpa [30] (Methanolic)

BranchesBranches 71 71 betulinic acid betulinic acid E. platycarpa [30] [30] (Methanolic)(Methanolic)

Branches 71 betulinic acid E. platycarpa [30] (Methanolic)

Plants 2020, 9, x FOR PEER REVIEW 29 of 43

Plants 2020, 9, x FOR PEER REVIEW 29 of 43 Branches and 72 3-O-acetyloleanolic acid E. platycarpa leaves [30] (Methanolic)

Plants 2020, 9, 1124 Branches and 22 of 33 72 3-O-acetyloleanolic acid E. platycarpa leaves [30] (Methanolic) Table 1. Cont. Plants 2020, 9, x FOR PEER REVIEW 29 of 43

Fatty acidsSterols and terpenoids Part Used (Type Number Compound Structure Species Reference(s) of Extract)

Plants 2020, 9, x FOR PEER REVIEW 30 of 43

Fatty acids BranchesBranches(Ethanolic)Branches and and and 72 72 3-O-acetyloleanolic3-O-acetyloleanolic acid acid E.E. platycarpaplatycarpa leavesleavesleaves [30] [30] (Methanolic)(Methanolic) 73 stearic acid E. polystachya [12]

(Ethanolic) Plants 2020, 9, x FOR PEER REVIEW Fatty acids Branches and 30 of 43 Branches and Branchesleaves and leaves 73 73 stearic acid stearic acid E.E. polystachya polystachya (Ethanolic)leaves [12] [12] 75 palmitic acid E. polystachya (Ethanolic) [12] Fatty acids Branches(Ethanolic) and Branches(Ethanolic) and 74 74 arachidic acidarachidic acid E.E. polystachya polystachya leaves [12] [12] leaves (Ethanolic)

BranchesBranches and and 75 palmitic acid E. polystachya leaves [12] leaves (Ethanolic) Branches and 75 palmitic acid E. polystachya Branches and [12] 74 arachidic acid E. polystachya leaves [12] leaves Branches and 73 stearic acid E. polystachya [12] (Ethanolic)leaves Branches and 76 76 linoleic acid linoleic acid E.E. polystachya polystachya leaves [12] [12] (Ethanolic) (Ethanolic) (Ethanolic)

Branches and Branchesleaves and 74 arachidic acid E. polystachya [12] 76 linoleic acid E. polystachya leaves [12]

Hydroxybenzene (Ethanolic)

Hydroxybenzene

Plants 2020, 9, x FOR PEER REVIEW 31 of 43

Branches and leaves 77 syringol E. polystachya [12]

(Ethanolic) Plants 2020, 9, x FOR PEER REVIEW 31 of 43

Plants 2020, 9, 1124 23 of 33

Branches and Branches and Plants 2020, 9, x FOR PEER REVIEW Table 1. Cont. leaves 31 of 43 leaves 77 syringol E. polystachya [12] 78 catechol Hydroxybenzene E. polystachya [12] Part Used (Type Number Compound Structure Species (Ethanolic) Reference(s) (Ethanolic)of Extract) Plants 2020, 9, x FOR PEER REVIEW Branches and 32 of 43 leaves Branches and 77 77 syringol syringol E.E. polystachya polystachya leaves [12] [12] (Ethanolic)

BranchesBranches(Ethanolic) andand Cyclohexane leavesleaves Branches and Plants 2020, 9, x FOR PEER REVIEW 32 of 43 8078 78 D-pinitolcatechol catechol E.E.E. polystachya polystachyapolystachya leaves [12][12] [12] (Ethanolic) (Ethanolic)(Ethanolic) Cyclohexane Branches and Branchesleaves and Plants 2020, 9, x FOR PEER REVIEW leaves 32 of 43 78 catechol E. polystachya BranchesBranches [12] 79 79 3-O-methyl-myo-inositol3-O-methyl-myo-inositol E.E. platycarpa platycarpa [30] [30] 80 D-pinitol E. polystachya (Methanolic)(Methanolic) [12]

Cyclohexane Branches(Ethanolic) and (Ethanolic)leaves Branches and 81 lactic acid E. polystachya [12] Branchesleaves and 80 80 D-pinitol D-pinitol E.E. polystachya polystachya leaves [12] [12] (Ethanolic)(Ethanolic) Cyclohexane (Ethanolic) Branches and Branches 79 3-O-methyl-myo-inositol E. platycarpa Branchesleaves and [30] (Methanolic) 81 81 lactic acid lactic acid E.E. polystachya polystachya leaves [12] [12] (Ethanolic) Branches and (Ethanolic)leaves BranchesBranches and and 82 82 2-furoic acid 2-furoic acid E.E. polystachyapolystachya leaves [12] [12] Branchesleaves 79 3-O-methyl-myo-inositol E. platycarpa (Ethanolic) [30] 81 lactic acid E. polystachya (Methanolic) [12] (Ethanolic)

(Ethanolic) Branches and leaves 82 2-furoic acid E. polystachya [12]

(Ethanolic)

Plants 2020, 9, x FOR PEER REVIEW 33 of 43

Plants 2020, 9, x FOR PEER REVIEW Branches and 33 of 43 leaves 83 succinic acid E. polystachya [12]

Plants 2020, 9, 1124 (Ethanolic) 24 of 33 Branches and Plants 2020, 9, x FOR PEER REVIEW 34 of 43 leaves Plants 2020, 9, x FOR PEER REVIEW 33 of 43 83 succinic acid Table 1. Cont. E. polystachya [12]

Cyclohexane (Ethanolic) BranchesPart Used and (Type Plants 2020, 9, x FOR PEER REVIEWNumber Compound Structure Species 34Reference(s) of 43 Branchesofleaves Extract) and 86 N,N-diethyl carbamate E. polystachya leaves [12] 84 fumaric acid E. polystachya Branches and [12] 83 83 succinic acid succinic acid E.E. polystachya polystachya leaves [12] [12] (Ethanolic)(Ethanolic) Branches and Branches(Ethanolic) and Branchesleaves and 8684 84 N,N-diethylfumaric carbamate acid fumaric acid E.E. polystachya polystachya leaves [12] [12] (Ethanolic)

(Ethanolic) Carbohydrates or saccharides Branches and Plants 2020, 9, x FOR PEER REVIEW BranchesBranchesleaves and and 34 of 43 leaves 85 85 sinapic acid sinapic acid E.E. polystachya polystachya leaves [12] [12] 84 fumaric acid E. polystachya (Ethanolic) [12] (Ethanolic)

Carbohydrates or saccharides Branches(Ethanolic) and Branchesleaves and leavesleaves 85 sinapic acid E. polystachya Branches and [12] 8687 86 N,N-diethylD-erythrose carbamateN,N-diethyl carbamate E.E. polystachya polystachya leaves [12] [12] (Ethanolic) (Ethanolic) (Ethanolic) Carbohydrates or saccharides Branches and Branchesleavesleaves and 87 85 87 D-erythrosesinapic acid D-erythrose E.E. polystachya polystachya leaves [12][12] [12] (Ethanolic) (Ethanolic)(Ethanolic) Carbohydrates or saccharides Branches and Branchesleaves and 88 88 D-mannose D-mannose E.E. polystachya polystachya leaves [12] [12] (Ethanolic)

(Ethanolic) Branches and Branches and leaves leaves 88 D-mannose E. polystachya [12] 87 D-erythrose E. polystachya [12]

(Ethanolic) (Ethanolic)

Branches and leaves 88 D-mannose E. polystachya [12]

(Ethanolic)

Plants 2020, 9, x FOR PEER REVIEW 35 of 43

89 D-arabinose E. polystachya Branches and [12] Plants 2020, 9, x FOR PEER REVIEW leaves 35 of 43

Plants 2020, 9, 1124 25 of 33 (Ethanolic) 89 D-arabinose E. polystachya Branches and [12] Table 1. Cont. leaves Plants 2020, 9, x FOR PEER REVIEW 35 of 43 Carbohydrates or saccharides Part Used (Type Number Compound Structure Species Reference(s) 90 xilose E. polystachya Branches(Ethanolic)of Extract) and [12] leaves 89 D-arabinose E. polystachya BranchesBranches and and [12] 89 D-arabinose E. polystachya leavesleaves [12] (Ethanolic) (Ethanolic) 90 xilose E. polystachya Branches and [12] (Ethanolic)Branches and leaves 90 xilose E. polystachya leaves [12] (Ethanolic)

OH OH (Ethanolic) 91 trehalose E. polystachya Branches and [12] OH leaves 90 xilose E. polystachya Branches and [12] O OH Branchesleaves and 91 trehalose E. polystachya leaves [12] O O HO (Ethanolic)(Ethanolic)

OH OH 91 trehalose HO OH E. polystachya Branches and [12] OH (Ethanolic) OH leaves

O OH

O O HO (Ethanolic)

HO OH OH OH 91 trehalose OH E. polystachya Branches and [12] OH leaves

O OH

O O HO (Ethanolic)

HO OH

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4. Pharmacological Activities The pharmacological activities were described chronologically in order to encapsulate the research carried out on Eysenhardtia gender through the years.

4.1. Urinary Disorders As previously mentioned, the plant was analyzed for its beneficial effects on kidney or urinary tract problems. In 1998 carried out a study to test the diuretic and antilytic effect of the aqueous extract of Eysenhardtia polystachya bark in rats [37]. The model animals were induced with urolithiasis by implanting a zinc disk in the bladder. As a result, they observed a significant reduction in the weight of the uroliths after the administration of the aqueous extract of E. polystachya in the affected animals compared to the control group. Diuretic action was also verified by identifying an increase in the volume of urine [37], as well as favoring the retention of potassium [38]. In the year 2000, the compounds responsible for the antiurolithiatic (antilithiatic) and diuretic activity were identified, which correspond to 7-hydroxy-20,40,50-trimethoxyisoflavone (16) and 7-hydroxy-40-methoxyisoflavone (23) [28,39]. Later, in 2002, the effect of isoflavones isolated from the bark of Eysenhardtia polystachya on the formation of oxalate and calcium phosphate (COM) stones in urine was analyzed and reported in a preclinical trial. From this study, it was found that the phenolics compounds reported were able to inhibit the formation and growth of COM, consequently reducing the appearance of kidney stones and suggesting the use of isoflavones as a preventive treatment [29].

4.2. Antimicrobial Activity The inappropriate use of treatments and the ability of microorganisms to adapt have led them to develop tolerance to various antimicrobial drugs; this has prompted the continued search for new drugs that offer other options, possible sources thereof being plants. In the case of the genus Eysenhardtia, the first report found on antimicrobial activity was published in 1997, in which an antimicrobial scan was performed using minimal inhibitory concentration (MIC) tests. The microorganisms used were Sarcina lutea, Proteus vulgaris, Staphylococcus aureus, Escherichia coli, and Candida albicans. The information obtained showed that the E. polystachya methanol extract had an effect on inhibiting the different strains studied; this inhibitory action was shown to have potential against Gram positive and Gram negative bacteria [40]. In 1998, the antimicrobial action of the compounds (3S)-7-hydroxy-20,30,40,50,8-pentamethoxyisoflavan (10), (3S)-30,7-dihydroxy-20,40,50,8-tetramethoxyisoflavan (11), stigmasterol (68), isoduartin (14), cuneatin (15), 7-hydroxy-20,40,50-trimethoxyisoflavone (16) and 3,4-dimethoxy-8,9-methylenedioxypterocarpan (7), isolated from the bark E. polystachya was analyzed for each of it. The results showed that they had no action against Escherichia coli, Pseudomonas aeroginosa, Streptococcus aureus, Bacillus subtilis, Shigella smiled, and Candida albicans at a concentration of 200 µg/mL [8]. In 1999, the compounds (α-hydroxydihydrochalcones, (αR)-α,3,4,20,40-pentahydroxydihydrochalcone (17), (αR)-30-C-β-D-xylopyranosyl-α,3,4,20,40-pentahydroxydihydrochalcone (18), (αR)-30-O-β-D- xylopyranosyl-α,3,4,20,40-pentahydroxydihydrochalcone (19) and coatline B [(αR)-30-C-β- D-glucopyranosyl-α, 20,3,40,4-pentahydroxydihydrochalcone]) (2) isolated from the bark of E. polystachya. They did not show activity against Escherichia coli, Pseudomonas aeroginosa, Streptococcus aureus, Bacillus subtilis, Shigella smiled, and Candida albicans [25]. Likewise, in 1999 were evaluated the compounds 40,5,7-trihydroxy- 8-methyl-6-(3-methyl-[2-butenyl])-(2S)-flavanone (20), 40,5,7-trihydroxy-6-methyl-8-(3-methyl- [2-butenyl])- (2S)-flavanone (21) and 40,5-dihydroxy-7-methoxy-6-(3-methyl-[2-butenyl])-(2S)-flavanone (22), from the aerial zone of Eysenhardtia texana Kunth from an extract of methanol and dichloromethane. The flavonones were active in inhibiting the growth of Staphylococcus aureus, and one of them also reduced the proliferation of Candida albicans [26,27]. Plants 2020, 9, 1124 27 of 33

Subsequently, the antimicrobial action of the methanol extracts of E. polystachya and E texana were studied to mitigate nine strains of bacteria and a yeast linked to urinary infections; the species evaluated were Escherichia coli, Proteus mirabilis, Proteus vulgaris, Klebsiella pneumoniae, Enterobacter aerogenes, Pseudomonas aeruginosa, Serratia marcescens, Staphylococcus aureus, Staphylococcus epidermidis, and Candida albicans. The results showed that E. texana had limited antibacterial activity; in contrast, E. polystachya showed a broad-spectrum antimicrobial eﬀect against the microorganisms evaluated. The authors suggest its use as a possible alternative for the inhibition of Gram positive and Gram negative bacteria, since it exists there is a shortlist of appropriate drugs to inhibit these families of microorganisms [18]. In 2012, the antibacterial potential of 47 plants in oral infections was researched by analyzing ethanolic and aqueous extracts. E. polystachya, showed a reduction in the proliferation of Streptococcus mutans and Porphyromonas gingivalis [41]. Subsequently, the ethanol extract from the leaves and branches of E. polystachya was analyzed using the MTT test, as well as the lowest inhibitory concentration (MIC). The data showed activity for Escherichia coli (MIC = 1.56 µg/mL), Staphylococcus aureus (MIC = 0.78 µg/mL), and multi-resistant organisms (MIC > 100 µg/mL) [12].

4.3. Antidiabetic Activity Diabetes is a chronic degenerative disease related to hyperglycemia. Excess glucose in the blood causes health problems related to the generation of reactive oxidant species, the glycation of proteins, lipoperoxidation, difficulty in recognizing, sensitivity, and secretion of insulin, among others; this results in a diabetic pathology. In 1998, the hypoglycemic capacity of 28 plants was evaluated; among the species analyzed was E. polystachya, which was considered an appropriate candidate to regulate glycemic levels in a pre-clinical study [11]. Subsequently, the antihyperglycemic activity of the methanolic extracts of the leaves (LEP), branches (BEP), and bark (REP) of Eysenhardtia platycarpa was studied in diabetic rats induced with streptozotocin, as well as in healthy animals. It was observed that the REP extract did not exhibit antihyperglycemic action compared to LEP and BEP. Additionally, the effect of 3-O-acetyloleanolic (72) acid (isolated from BEP) was observed in reducing blood glucose levels in diabetic rats. In 2007, a study was published evaluating the antioxidant activity of the methanol extracts of E. platycarpa, E. puntacta, and E. subcoriacea in a murine pancreatic model. The tests showed that these species were protected from the damage induced by 2,2-azo-bis(2-amidinopropane)dihydrochloride (AAPH). Furthermore, some bioactives, (3-O-acetyl-11α,12α-epoxy-oleanan-28,13β-olide (69), (+)-catechin (33), and (+)-catechin-3-O-β-D-galactopyranoside (37)) isolated from the branches of E. platycarpa, showed radical scavenging capacity 2,2-diphenyl-1-picrylhydrazyl (DPPH), increase the concentration of pancreatic glutathione (GSH), the activity of glutathione peroxidase (GSHPx) and catalase (CAT), as well as regulating the gain in levels of glucose in diabetic rats induced with streptozotocin after five days of administration [33]. In 2008, the antioxidant activity of secondary metabolites identified in the aerial zone of E. subcoriacea was reported. Among the bioactive drugs described are 3-(20-hydroxy-40,50-methylendioxyphenyl)- 6-(30’-hydroxymethyl-40’-hydroxybut-20’-enyl)-7-hydroxycoumarin (32), (+)-catechin (33), (-)-epicatechin (34), (+)-afzelechin (35), eriodictyol (36), (+)-catechin 3-O-β-D-galactopyranoside (37), and quercetin 3-O-β-D-galactopyranoside (38), all of which countered the presence and development of free radicals (DPPH and AAPH) and can be used to suppress diabetic pathology [31]. In 2010, the antihyperglycemic and antioxidant effect of subcoriacin (3-aryl-6prenylcoumarin), a secondary metabolite from E subcoriacea, was researched. The administration of the bioactive compound to streptozotocin-induced diabetic rats for five days showed a reduction in blood glucose levels, increased activity of the enzymes (glutathione peroxidase (GSHPx), superoxide dismutase (SOD) Plants 2020, 9, 1124 28 of 33 and catalase (CAT)) of the endogenous system. For this reason, the protective action of Subcoriacin against pancreatic damage induced by free radicals under a diabetic condition [32] was suggested. In 2014, the antioxidant, antidiabetic and antiglycation properties of the aqueous-methanolic extract of Eysenhardtia polystachya were analyzed. The ability to decrease and/or eliminate free radicals DPPH, ABTS, was noted, as well as the reactive oxygen species (RO , O ,H O , OH, ONOO , 2 − 2 2 2 − − NO , HOCl, 1O ), and the ability to absorb oxygen radicals (ORAC) by donating electrons (H+). − 2 The ability to sequester metals for the formation of chelates and decreased lipoperoxidation was also examined. At the same time, the activity to inhibit fluorescent AGEs, glycation of hemoglobin, and methylglyoxal products was determined. As for in vivo tests with strepzotocin-induced diabetic murine models, a decrease was observed in blood glucose levels, triglycerides (TG), total cholesterol (TC), thiobarbituric acid reactives substances (TBARS), and low-density lipoprotein (LDL). At the same time, an increase in serum insulin, body weight, and liver biomarkers were induced. Consequently, the methanolic-aqueous extract of EP demonstrated the ability to interact at the different points evaluated, exercising beneficial actions in the control of disorders associated with diabetes based on the presence of phenolic compounds [14]. In 2016, were analyzed six compounds (20,40-dihydroxychalcone-60-O-β-D-glucopyranoside (39), α,3,20,40-tetrahydroxy-4-methoxy-dihydrochalcone-30-C-β-glucopyranosi-60-O-β-D-glucopyranoside (40), 7-hydroxy-5,80-dimethoxy-60α-L-rhamnopyranosyl-8-(3-phenyl-transacryloyl)-1-benzopyran-2-one (41), 607-dihydroxy-5,8-dimethoxy-8(3-phenyl-trans-acryloyl)-1-benzopyran-2-one (42), 9-hydroxy-3,8- dimethoxy-4-prenylterocarpan (43), and α,4,40-trihydroxy-dihydrochalcone-20-O-β-D-glucopyranoside (45)) from the aqueous-methanol extract of the bark of Eysenhardtia polystachya, for their possible antioxidant potential, in streptozotocin-induced diabetic mice. The first five flavonoids showed favorable effects on the regulation and protection of hepatic and cellular biomarkers associated with disorders caused by oxidative stress in diabetes [34]. Furthermore, the inhibition capacity of 11 dihydrochalcones from the methanolic extract of the E. polystachya bark in the formation of advanced glycation end products (AGEs) was studied in their multiple stages (early, intermediate, and final). Protein glycation corresponds to the interaction of proteins with excess sugars in the body; this hyperglycemic condition occurs during diabetes. The tests carried out were in vitro, and it was concluded that each of the isolated bioactives were capable of inhibiting and protecting from the formation and accumulation of AGEs. The biocomposites analyzed were: (60methoxy-sieboldin (53), 20-O-α-L-rhamnopyranosyl-α,60,dihydroxy-40acetyl-4-methoxy-dihydrochalcone (52), 20-O-β-D- glucopyranosyl-40-methoxy-4-hydroxy-3-isoprenyl-dihydrochalcone (54), 20,40,60trihydroxy-4,5- dimethoxy-3-isoprenyl-dihydrochalcone (55), 30-C-β-glucopyranosyl-α,20,40,60- trihydroxy-4- methoxydihydrochalcone (56) and 30-C-β-glucopyranosyl-α,20,4-trihydroxy-40,60-dimethoxydihydrochalcone) (57) the rest (3-hydroxyphloretin-40-O-β-D-glucopyranoside (58), 3,40-dihydroxy-2,4,6-trimethoxydihydrochalcone (59), 20,40,4-trihydroxy-30-methoxy-dihydrochalcone (60), 20,40,60,4-tetrahydroxy-3, 5-diisoprenyl-dihydrochalcone (61), and 30-C-β-glucopyranosyl-α,20,40,3,4-penta-hydroxy- dihydroxychalcone (62)) had previously been elucidated [35]. In 2019, it was demonstrated that the bioactive 30-O-β-D-glucopyranosyl α,4,20,40,60- pentahydroxy–dihydrochalcone (63) isolated from Eysenhardtia polystachya is an excellent antiglycation compound capable of reducing glycation of proteins responsible for diabetic nephropathy in diabetic individuals. Tests were carried out using diabetic mice with kidney problems induced with stretozotocin; levels of glycated hemoglobin (HbA1c), the concentration of glycation end products advances in the kidney and circulatory system, as well as in pro-inflammatory markers ICAM-1 were then analyzed. The bioactive (63) was administered for five weeks at different concentrations (25, 50, and 100 mg/kg); at the end of the dosing period the diabetic animals showed a significant improvement, suggesting the ability of the bioactive to react and inhibit early and intermediate precursors in the formation of AGEs, responsible for damaging the structure of the kidneys [36]. Plants 2020, 9, 1124 29 of 33

4.4. Anti-Inflammatory Activity In 2015, the anti-inflammatory potential of the Eysenhardtia polystachya bark from hexane (PAH), chloroform (PAC), and methanol (PAM) extracts was researched. The extracts were evaluated using Wistar rats as an experimental model. To determine the anti-inflammatory activity of the extracts, different tests were used such as: carrageenan and croton oil induced edema. The tumor necrosis factor α (TNF-α), interleukin-1-β (1L-1β), prostaglandin E2 (PGE2) and leukotriene B4 (LTB4) were also quantified. The PAM extract showed anti-inflammatory activity in the different induced edema inhibited the expression of the cytokines (TNF-α, 1L-1β, PGE2 and LTB4), and the enzymes lipoxygenase and xanthine-oxidase linked to inflammatory problems [15]. Furthermore, in 2018 the properties of the ethanolic extract from the bark of E. polystachya to mitigate rheumatoid arthritis were analyzed. To do this, the antiarthritic activity induced by Complete Freund’s Adjuvant (CFA) in rats was determined. Trials showed that secondary metabolites of E. polystachya, mainly flavonoids, inhibited secondary inflammatory processes in arthritic rats, encouraged histopathological changes, and reduced serum levels of inflammatory cytokines [16]. Additionally, in that same year, the anti-inflammatory effect of ethanol extract from the leaves and branches of E. polystachya was examined using in vitro tests stimulating macrophages using LPS. The results demonstrated a decrease in the production of H O (IC = 43.9 3.8 µg/mL) and IL-6 2 2 50 ± (73.3 6.9 µg/mL) [12]. ± 4.5. Antinociceptive Activity The importance of reducing or mitigating the sensation of pain has been fundamental for the control and treatment of different conditions, this has prompted the search for natural alternatives. In 2018, the ethanolic extract of the bark of E. polystachya was evaluated, using the acetic acid-induced abdominal contraction test and the hot-plate test, which were performed on mice. A decrease in the spasms generated by acetic acid and a prolonged sensitivity time at the peripheral and central levels [16] were observed. Furthermore, in that same year, D-pinitol (80) isolated from ethanolic extract of Eysenhardia polystachya was examined to find out if it had the property to block or reduce pain. It was found that D-pinitol inhibited 67.58% with an effective dose of 10.7 mg/kg; its activity is associated with the serotoninergic system (5-HT3) and nitric oxide [42]. Additionally, the antinociceptive effect of the ethanolic extract from leaves and branches of E. polystachya (EPE) was also studied, following the acetic acid, formalin, and hot plate test. It was identified that the extract contained 26.93% D-pinitol, the bioactive responsible for an action. EPE presented an effective dose of 117 14.5 mg/kg and 33 3.2 mg/kg for D-pinitol in acetic acid test; ± ± in the case of formalin it was 48.9 3.9 mg/kg. The action of EPE is probably due to the involvement of ± ATP-sensitive K+ channels. As for D-pinitol, its route of action is considered to occur at nitric oxide receptors and 5-hydroxytryptamine 3 (5-HT3) [12].

4.6. Antidiarrheal The ability to stop diarrhea was analyzed from the ethanolic extract of the leaves and branches of E. polystachya (EPE) and the compound D-pinitol (80) isolated from E. polystachya. The results showed that the EPE extract had an eﬀective dose of 7.5 0.9 µg/mL and the D-pinitol 0.1 0.03 µg/mL. ± ± The results suggest that this was due to the elimination of intestinal ﬂuid [12].

4.7. Muscle Relaxant The pharmacological potential in Jejunum muscle contraction was explored using chloroform extract from the stems of E. polystachya in muscle tissue extracted from rabbits. The test showed that the extract presents an eﬀect on jejunum contractility [43]. Plants 2020, 9, 1124 30 of 33

4.8. Cytotoxic Activity

In 1998, the cytotoxic activity of the bioactives ((3S) -7-hydroxy-20,30,40,50,8-pentamethoxyisoflavan (10), (3S)-30,7-dihydroxy-20,40,50,8-tetramethoxyisoflavan (11), isoduartine (20,7-dihydroxy-30,40,8- trimethoxyisoflavan)(14)) was evaluated; these were isolated from the chloroform-methanol extract of the bark of E. polystachya. The identified metabolites showed slight cytotoxic activity against the cell lines (KB (nasopharyngeal carcinoma), P388 (murine leukemia) and SQC-1 UISO (squamous cell carcinoma of the cervix)) [8].

4.9. Nanoparticles and Eysenhardtia Furthermore, in 2018 silver nanoparticles were synthesized with the aqueous methanol extract of Eysendhartia polystachya and their performance in inhibiting AGEs in vitro tests cell viability with RAW-264.7 cells was analyzed and in vivo tests with diabetic zebrafish induced by glucose exposure were performed. It was found that the bioactives present in the nanostructures can counteract protein glycosylation through their intervention in the neutralization and elimination of fluorescent, non-fluorescent, free radical AGEs, and the catchment of methylglyoxal together with its derivatives. Regarding diabetic fish, these showed a decrease in the conditions caused by chronic hyperglycemia. Their results suggest the use of nanoparticles for diabetic pathology [44]. Also, in 2018, silver nanoparticles biosynthesized with the aqueous methanolic extract from the bark of E. polystachya were used as delivery and transport systems for polyphenolic constituents. The cell viability (murine RAW-264.7 macrophage cells) and biocompatibility of nanostructures was determined, as well as the E. polystachya extract. The antioxidant effect of the synthesized nanometric material on the biomarkers of zebrafish embryos exposed to a medium with high glucose concentrations was also studied. Treatments using nanoparticles and plant extracts increased the activity of the antioxidant enzymes (SOD, CAT, and GPx) and reduced the damage caused by the formation of reactive oxidative species, positively influencing the total protein concentration while decreasing the formation of malondialdehyde (MDA) and lipoperoxidation. Consequently, nanostructures with a high content of phenolic compounds could be a viable alternative in minimizing the diabetic complications associated with oxidative stress [45]. In that same year, the antidiabetic properties (qualities) of the bio-nanofabricated silver nanoparticles were evaluated using the hydroalcoholic extract of Eysenhardtia polystachya (EP/AgNPs). They demonstrated the protective action of EP/AgNPs against damage caused by hydrogen peroxide to INS-I cells, minimizing cell mortality, also having a cytoprotective action against oxidative laceration. Furthermore, it was observed that when administering the EP/AgNPs to glucose-induced diabetic zebrafish (111 mM), they showed an improvement in the levels of blood glucose, insulin, triglycerides, and cholesterol; helping to regulate hyperglycemic, hyperlipidemic, and insulin sensitivity. The authors suggest the possibility of using E. polystachya nanostructures as an alternative therapy for the control of diabetes due to their high concentration of chalcones, dihydrochalcones, and flavonoids [46]. Furthermore, nanoparticles have been synthesized and functionalized with the extract of E. polystachya using biological applications by taking advantage of the composition of the plant’s fluorescent biocomposites; these can then be used as a fluorescent cell nanomarker to detect cancer or pathogenic microorganisms [47].

4.10. Other Applications The bioactive molecules responsible for the fluorescence of E. polystachya were isolated and elucidated from the methanol extract of the heartwood. Among the bioactives isolated are; 7-hydroxy-20,40,50-trimethoxyisoflavone (16) and 9-methoxy-2,3-methylenedioxycoumestan (47) corresponding to Robert Boyle’s acid-base fluorescent indicator used in the 17th century [24]. Plants 2020, 9, 1124 31 of 33

Also, the activity of the extracts of ethyl acetate, dichloromethane, hexane, and methanol was determined from calluses and suspended cells of E. polystachya for the control of fungal phytopathogens. The information obtained provided an opportunity to propose plant extracts as a fungicide option [48]. Nine fractions of the E. polystachya ethanolic extract were also evaluated for use as ﬂuorescent biosensors. Six of the nine fractions tested positive for photoluminescence and only two were stable for use in the functionalization of silica nanoparticles. The G2 subfraction demonstrated appropriate ﬂuorescence qualities at a physiological pH and its detection also did not show toxicity, allowing cell viability [49].

5. Conclusions Currently, there are many diseases linked to factors related to metabolic syndrome. This condition has caused people to develop various health problems and increases their risk of mortality. This has caused a large part of society to live under a constant medication scheme that attempts to regulate the ailments that afflict them, which in turn stimulates the consumption of natural alternatives that have shown to help control symptoms. In this paper, we present the potential of the extracts and/or bioactives of the Eysenhardtia genus to limit the proliferation of microbial infections, urinary disorders, oxidative stress, protein glycation, lipoperoxidation, increase in blood sugar levels, inflammation, or the development of bodily discomfort. Furthermore, the introspection performed made it clear that the composition of phytochemical compounds and their diversity of secondary metabolites could be a complementary solution for individuals affected by comorbidity.

Author Contributions: Writing—original draft preparation, A.G.-C. and A.M.-R.; writing—review and editing, E.G. and A.M.-R. All authors have read and agreed to the published version of the manuscript. Funding: Consejo Nacional de Ciencia y Tecnología (CONACYT), project FORDECYT-CIIDZA: 296354. Acknowledgments: We acknowledge the funding from CONACYT (FORDECYT-CIIDZA: 296354). The authors thank Biologist Juan Pablo Brunei, for providing the images of the plant for publication. Conﬂicts of Interest: The authors declare no conﬂict of interest.

References

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