Bangladesh Pharmaceutical Journal 23(1): 65-77, 2020 (January) - Review paper A Further Comprehensive Review on the Phytoconstituents from the Genus Erythrina Mohammad Musarraf Hussain Department of Pharmacy, Faculty of Life and Earth Sciences, Jagannath University Dhaka-1100, Bangladesh (Received: August 22, 2019; Accepted: January 28, 2020; Published: January 30, 2020) Abstract: Erythrina is a significant source of phytoconstituents. The aim of this review is to solicitude of classification, synthesis, and phytochemicals with biological activities of Erythrina. In our previous review on this genus (Hussain et. al., 2016a) fifteen species (Erythrina addisoniae, E. caribeae, E. indica, E. lattisima, E. melanacantha, E. mildbraedii, E. poeppigiama, E. stricta, E. subumbrans, E. veriagata, E. vespertilio, E. velutina, E. zeberi, E. zeyheri and E. americana) have been studied and 155 molecules with chemical structures were reported. A further comprehensive review was done upon continuation on the same genus and thirteen species (E. abyssinica, E. arborescens, E. berteroana, E. burttii, E. caffra, E. coralloids, E. crista-galli, E. fusca, E. herbaceae, E. lysistemon, E. mulungu, E. speciosa and E. tahitensis) of Erythrina have been studied and 127 compounds are reported as phytoconstituents with their chemical structure in this review. Erythrina crista-galli and E. lysistemon consist of highest number of chemical constituents. Key words: Phytoconstituents, classification, Erythrina, leguminoseae, biological properties. Introduction orange flowers. E. herbaceae (Coral bean) is a shrub One hundred and ten species of shrubs and trees (20 ft in height) but sometimes it may be smaller and are present under the genus Erythrina (Family: leaves are semi deciduous 6-8 inch long. E. Leguminosae). A total thirteen medicinal plants have lysistemon is a small to medium sized deciduous and been reviewed comprehensively in this study lovely tree (10 m in height) with brilliant and (Hussain et. al., 2016a). E. abyssinica is a medium spreading crown red flowers. E. mulungu sized tree, 5-15 m in height, well branched and leaves (Ornamental tree) is a medicinal plant native to are compounded. E. arborescens (Himalayan coral Brazil and South America. E. speciosa is a tree native tree) is a deciduous tree growing up to 5 m tall; to Brazil, cultivated, and introduced populations in branches and trunk have been covered with prickles. Africa and India. E. tahitensis is a species of legume E. berteroana (Coral bean) is a shrub like tree (10 m (Family: Fabaceae) endemic to French Polynesia. tall) and trunk (48 cm) having red flower. E. burttii Species of Erythrina have been used as a traditional is a flowering plant found in Kenya and Ethiopia. E. medicine in sedative, febrifuge, anti-asthmatic, anti- caffra is a medium to large sized deciduous tree, 9-12 epileptic, convulsion, fever, inflammation, bacterial × 7-11 m in height. E. coralloides (Nacked coral tree) infection, insomnia, helminthiasis, cough, cuts, and is a fast growing deciduous tree 30 ft in height with wounds (Kumar et. al., 2010). bright red flowers in early spring. E. crista-galli is a Classification of Erythrina alkaloids: Depending deciduous tree growing to 15-20 ft tall having dark on skeleton, two types of Erythrina alkaloids are furrowed bark and green leaflets. E. fusca (Coral present i) Erythrinane (1) consisting of a 6,5,6,6 bean) is deciduous tree having spiny bark and light Indoloisoquinoline and ii) Homoerythrinane (2) Correspondence to: Mohammad Musarraf Hussain. Email: [email protected] and [email protected], ORCID: 0000-0001-9270-0474. DOI: https://doi.org/10.3329/bpj.v23i1.45321 66 Hussain / Bangladesh Pharmaceutical Journal 23(1): 65-77, 2020 (January) containing 6, 5, 7,6 Indolobenzazepine skeleton Carmack et al., 1951; Folkers et. al., 1939, 1940a, (Figure 1). On the basis of D ring present in the 1940b, 1940c, 1937; Garin-Aguilar et. al., 2000; skeleton, Erythrina alkaloids are classified as Maier et. al., 1097, 1999; Soto-Hernandez et. al., aromatics (3, 4, 5, 6, 7, 8, 9, 10), hetero-aromatics 2012) (Figure 2). (11, 12, 13) and non-aromatics (14, 15) (Amer et. al., 1991; Barton et. al., 1970; Barton et. al., 1974; N N H H RO 1 RO 2 Figure 1. Erythrina alkaloids depending on skeleton Figure 2. Classification of Erythrina alkaloids on the basis of D ring present. Biosynthesis of Erythrina alkaloids: medicines and in the recovery of poison. Angiosperms is the key source of alkaloids, but it can Metabolically, alkaloids are playing a significant be exists in animals as well as in microorganisms, function in the physiology at organism and plants. insects, plants, and marine organism. Alkaloids are Three types of alkaloids are presents such as true, secondary metabolites that consist of secondary, proto, and pseudo-alkaloids. Different bio-synthetic tertiary, and quaternary nitrogen atoms in their pathway of alkaloids had been offered, but the molecular formula. Alkaloids have been used as objective of this review is the demonstration of a bio- Hussain / Bangladesh Pharmaceutical Journal 23(1): 65-77, 2020 (January) 67 synthetic pathway of Erythrina alkaloid. According through synthesis of few intermediate products such to the Maier and Soto-Hernandez (Maier et. al., 1997, as Norisosalutaridine (17), Noramurine (18), 1999; Soto-Hernandez et. al., 2012) Erythrina Neospirinic cation (20), and Diallylic cation (23) alkaloid, Δ3-Erythratinone (24) can be synthesized (Scheme 1). from the starting material (S)-Norreticuline (16) Scheme 1. Synthetic pathway of Erythrina alkaloids 68 Hussain / Bangladesh Pharmaceutical Journal 23(1): 65-77, 2020 (January) Chemical synthesis of the Erythrinane alkaloid: (26), (Z)-2,12-Dimethoxy-6,9-dihydro-5H-dibenzo- Erythrinane alkaloid Erysodienone (30) can be [d,f]-azonine-3,11-diol (27), Dibenzazonine (28), and synthesized form the precursor of S- Dibenzazonine dione (29) (Soto-Hernansez et. al., Norprotosinomenine (25) with the synthesis of some 2012; Cui et. al., 2009) (Scheme 2). intermediate compounds such as Neoproaporphine OH HO O O NH O O NH H O H N n n n O O O OH OH OH 25 26 27 H2 O OH HO O O n N O n :NH NH n O O O O O OH 30 29 28 Scheme 2. Synthesis of Erythrinane alkaloid. Phytoconstituents: A total thirteen species of Erythribyssins B (37), Erythribyssins C (38), Erythrina have been studied and ninety six molecules Eryvarin K (39), Neurautenol (40), Erybraedin B (31-127) with chemical structures are reported in this (41), 3,9-Dihydroxy-4-prenyl-[6aR:11aR]- review as bioactive compounds (Figure 3-15). pterocarpan (42), Folitenol (43), Erybraedin D (44), Erythrina abyssinica: A bunch of chemical Erysubin E (45), Erybraedin C (46), Phaseollidin compounds such as Abyssinone A (31), Abyssinone (47), Sophora pterocarpan A (48), Erythrabyssin-II B (32), Abyssinone C (33), Abyssinone D (34), (49), and Erystagallin (50) were reported from E. Abyssinone V (35), Erythribyssins A (36), abyssinica (Figure 3) (Cui et. al., 2008; Kabenei et. al., 2011; Nguyen et. al., 2009). Hussain / Bangladesh Pharmaceutical Journal 23(1): 65-77, 2020 (January) 69 Erythrina arborescens: Eight phytochemicals Erysophorine chloride (55), (+)-Erysodinophorine were reported from E. arborescens for example (+)- hydroxide (56), (+)-Erysopinophorine hydroxide Erysotramidine (51), (+)-11-β-Hydroxyerysotrine (57), and (+)-Isoerysopinophorine hydroxide (58) (52), (+)-Erythrascine (53), (+)-Erytharbine (54), (+)- (Figure 4) (Amer et. al., 1991). Figure 3. Molecules from Erythrina abyssinica H OH MeO OAc MeO MeO MeO N MeO O N N O MeO N MeO MeO MeO MeO MeO 51 MeO 52 54 53 HN HN HN MeO O O Me3N N - Me3N OH O - O Me3N OH O Cl- O MeO N N HO 55 56 MeO MeO MeO HN 57 HO N O Me3N OH- O MeO 58 Figure 4. Chemical constituents from Erythrina arborescens. 70 Hussain / Bangladesh Pharmaceutical Journal 23(1): 65-77, 2020 (January) Erythrina berteroana: The reported chemical Erythroidine (62), (+)-β-Erythroidine (63), (+)-8- compounds from this plants are (+)-11- Oxo-α-erythroidine (64), and (+)-8-Oxo-β- Hydroxyerythratidine (59), (+)-Hydroxyerysosalvine erythroidine (65) (Figure 5) (Amer et. al., 1991). (60), (+)-11-Hydroxyerysotine (61), (+)-α- Figure 5. Phytoconstituents from Erythrina berteroana Figure 6. Secondary metabolites from Erythrina burttii Hussain / Bangladesh Pharmaceutical Journal 23(1): 65-77, 2020 (January) 71 Erythrina burttii: The isolated bioactive moieties Bidwillon A (83), Erythrinasinate (84), 7ʹ-O- from this medicinal plants are Abyssinone V (35), Methyllutenone (85), Burttinonedehydrate (86), 8- Bruttinol-A (66), Burtinol-A diacetate (67), Prenyllutenone (87), 3-O-methylcalopocarpin (88), Bruttinol-B (68), Bruttinol-B acetate (69) Bruttinol-C and Genistein (89) (Figure 6) (Yenesew et. al., 2002, (70), Bruttinol-C diacetate (71), Eryvarin-H (72), 1998, 2003, 2012; Hussain, 2018). Eryvarin-H diacetate (73), Bruttinol-D (74), Erythrina caffra: Four secondary metabolites Bruttinol-D diacetate (75), Abyssinone-V-4´-methyl such as (+)-Erysotrine (90), (+)-Erysodine (91), (+)- ether (76), Calopocarpin (77), Alpinumisoflavone 8-Oxo-erysodine (92), and (+)-11-Methoxyerysopine (78), Erythrabissin-II (49), Isobavachalcone (79), (93) were reported from this plants (Figure 7) (Amer Phaseollidin (47), Phaseollin (80), Burttinone (81), et. al., 1991; Taria et. al., 1994). Neurautenol (40), 4ʹ-O-Methylsigmoidin (82), Figure 7. Molecules from Erythrina caffra. Figure 8. Compounds from Erythrina coralloides. Figure 9. Constituents from Erythrina crista-galli 72 Hussain / Bangladesh Pharmaceutical Journal 23(1): 65-77, 2020 (January) HO O HO O O O R1 OH H OH O O O R2 OCH3 OCH3 R O 3 113 115 107: R = H, R = OH, R = 1 2 3 HO 108: R1 = OH, R2 = OCH3, R3 = HO 109: R1 = OH, R2 = OCH3, R3 = HO O 110: R1 = H, R2 = OCH3, R3 = O O 111: R = OH, R = OCH , R = 1 2 3 3 OH O OH 112: R = R = H, R = OH O OH O 1 3 2 OH 117 89 114: R1 = OH, R2 = OCH3, R3 = HO OH 116: R1 = OH, R2 = OCH3, R3 = OH OH OH HO O HO O HO HO O OH O O OH O O HO OCH3 121 118 119 120 Figure 10.