Pulicaria Jaubertii
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molecules Article Phytochemical Characterization, In Vitro Anti-Inflammatory, Anti-Diabetic, and Cytotoxic Activities of the Edible Aromatic Plant; Pulicaria jaubertii Hamdoon A. Mohammed 1,2,* , Mohammed F. Abdelwahab 2, El-Sayed M. El-Ghaly 2 and Ehab A. Ragab 2 1 Department of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, Qassim University, Buraydah 51452, Saudi Arabia 2 Department of Pharmacognosy, Faculty of Pharmacy, Al-Azhar University, Cairo 11371, Egypt; [email protected] (M.F.A.); [email protected] (E.-S.M.E.-G.); [email protected] (E.A.R.) * Correspondence: [email protected]; Tel.: +966-56-61-76-074 Abstract: Pulicaria jaubertii is a medicinal herb that alleviates inflammations and fever. Chromato- graphic separation, phytochemical characterization, and in vitro biological activities of the plant n-hexane extract were conducted for the first time in this study. Six compounds were isolated for the first time from the n-hexane fraction of Pulicaria jaubertii aerial parts and were identified on the bases of NMR and MS analyses as pseudo-taraxaterol (1), pseudo-taraxasterol acetate (2), 3β-acetoxytaraxaster-20-en-30-aldehyde (3), calenduladiol-3-O-palmitate (4), stigmasterol (5), and α-tocospiro B (6). Compound (6) was a rare tocopherol-related compound and was isolated for the first time from family Asteraceae, while compound (3) was isolated for the first time from genus Pulicaria. The total alcoholic extract and n-hexane fraction were tested for their anti-inflammatory, antidiabetic, and cytotoxic activities. The n-hexane fraction has dose dependent red blood cells (RBCs) Citation: Mohammed, H.A.; membrane stabilization and inhibition of histamine release activities with IC50: 60.8 and 72.9 µg/mL, Abdelwahab, M.F.; El-Ghaly, E.M.; respectively. As antidiabetic activity, the alcoholic extract exerted the most inhibition on the activity Ragab, E.A. Phytochemical α µ Characterization, In Vitro of yeast -glucosidase, with an IC50: 76.8 g/mL. The n-hexane fraction showed cytotoxic activity Anti-Inflammatory, Anti-Diabetic, against hepatocarcinoma (HepG-2), breast carcinoma (MCF-7), and prostate carcinoma (PC-3) cell and Cytotoxic Activities of the Edible lines with IC50: 51.8, 90.8 and 62.2 µg/mL, respectively. In conclusion, the anti-inflammatory effect Aromatic Plant; Pulicaria jaubertii. of Pulicaria jaubertii might be attributed to the triterpenoid constituents of the n-hexane extract of Molecules 2021, 26, 203. https:// the plant. doi.org/10.3390/molecules26010203 Keywords: Pulicaria jaubertii; triterpenes; anti-inflammatory; anti-diabetic; cytotoxicity Academic Editor: Gianni Sacchetti Received: 3 December 2020 Accepted: 28 December 2020 Published: 3 January 2021 1. Introduction Medicinal plants and their products have been used in human life quality improve- Publisher’s Note: MDPI stays neu- tral with regard to jurisdictional clai- ment [1]. They have been used in disease remediation processes around the world and ms in published maps and institutio- their natural derived product is still the focus of researchers in the drug discovery and in nal affiliations. the areas of biology [1–3]. Genus Pulicaria, belonging to the Asteraceae family, tribe Inuleae, consists of 100 species distributed in Europe, North Africa, and Asia, especially in Yemen and Saudi Arabia and is known for its medicinal properties [4]. In Yemen and Saudi Arabia, plants of genus Pulicaria are known for their common uses as herbal teas, insect repellant, Copyright: © 2021 by the authors. Li- and alleviate inflammations [4]. In addition, antiproliferative and anti-inflammatory ac- censee MDPI, Basel, Switzerland. tivities were also reported for these plants [5]. Earlier phytochemical investigations on This article is an open access article different Pulicaria species afforded several sesquiterpenoids [6,7], diterpenoids [8], triter- distributed under the terms and con- penes [9], flavonoids [10], and phenolics [11,12]. Pulicaria jaubertii [syn. Pulicaria orientalis ditions of the Creative Commons At- Jaub. and Spach] is one of the Pulicaria species indigenous in Yemen. It is a perennial tribution (CC BY) license (https:// aromatic plant used by local people as a flavoring agent for food preparation [5]. The plant creativecommons.org/licenses/by/ is used also in the preparation of soaps and as a spicing agent due to their essential oil 4.0/). Molecules 2021, 26, 203. https://doi.org/10.3390/molecules26010203 https://www.mdpi.com/journal/molecules Molecules 2021, 26, x FOR PEER REVIEW 2 of 11 Molecules 2021, 26, 203 2 of 11 [5]. The plant is used also in the preparation of soaps and as a spicing agent due to their essential oil constituents [5,6]. In addition, Pulicaria jaubertii has an important application constituentsin the folk medicine [5,6]. In, addition,as it is usedPulicaria for treatment jaubertii ofhas inflammation, an important urogenital application pyritic in the condi- folk medicine,tions, andas for it isrelieving used for fever treatment [5]. In of addition, inflammation, it has urogenital been used pyritic as a diuretic conditions, and and insect for relievingrepellent fever[5,7,8] [.5 The]. In volatile addition, oil itcomposition has been used of Pulicaria as a diuretic jaubertii and species insect repellentoriginated [5 from,7,8]. Thedifferent volatile sources oil composition was reported of Pulicaria. In addition, jaubertii thespecies antimicrobial, originated antifungal, from different antimalarial, sources wasand insecticidal reported. In activities addition, of thethe antimicrobial,plant were previously antifungal, investigated antimalarial, [5,7,8] and. Flavonols, insecticidal di- activities of the plant were previously investigated [5,7,8]. Flavonols, dihydroflavonols, hydroflavonols, monoterpene glucosides, stigmasterol glucoside, and hydroquinones monoterpene glucosides, stigmasterol glucoside, and hydroquinones were isolated from were isolated from the ethyl acetate fraction and CH2Cl2-MeOH extract of Pulicaria the ethyl acetate fraction and CH Cl -MeOH extract of Pulicaria jaubertii [9–11]. Despite the jaubertii [9–11]. Despite the large2 numbers2 of the articles dealing with the chemical inves- large numbers of the articles dealing with the chemical investigation and constituents’ iden- tigation and constituents’ identification of the Pulicaria jaubertii, the nonpolar n-hexane tification of the Pulicaria jaubertii, the nonpolar n-hexane fraction has not been chemically fraction has not been chemically inspected. Phytochemical investigation of the plant n- inspected. Phytochemical investigation of the plant n-hexane extract was conducted in hexane extract was conducted in the current study as a part of Pulicaria jaubertii phyto- the current study as a part of Pulicaria jaubertii phytochemical characterization. Biological chemical characterization. Biological investigations in this study were conducted for the investigations in this study were conducted for the total alcoholic and n-hexane extracts of total alcoholic and n-hexane extracts of the plant and were rationally selected according the plant and were rationally selected according to the reported traditional use of the plant. to the reported traditional use of the plant. 2. Results and Discussion 2.1.2. Results Isolation and and Discussion Structural Identification of n-hexane Constituents 2.1. IsolationThe present and Structural work describes Identification the identification of n-hexane Constituents of four triterpenes (1–4), one sterol (5) and oneThe tocopherol-relatedpresent work describes compound the identification (6) from the ofn -hexanefour triterpenes extract of(1–Pulicaria4), one sterol jaubertii (5) aerialand one parts. tocopherol The total-related alcoholic compound extract ( of6) Pulicariafrom the jaubertiin-hexanewas extract fractionated of Pulicaria between jaubertiin- hexane,aerial parts. ethyl The acetate, total andalcoholicn-butanol extract in sequence.of Pulicaria Successive jaubertii was chromatographic fractionated between work-up n- onhexane, the n ethyl-hexane acetate, soluble and part n-butanol using differentin sequence. techniques, Successive i.e., chromatographic VLC, solid-phase work extrac--up tionon the (RP-C n-hexane18) and soluble open columnpart using chromatography different techniques, gives sixi.e., compounds VLC, solid-phase (1–6) (Figureextraction1). 1 13 These(RP-C18 compounds) and open column were identified chromatography by analysis gives of six their compoundsH and (C-NMR1–6) (Figure (Supplemen- 1). These tarycompounds Materials) were and identified MS spectroscopic by analysis data of and their comparison 1H and 13C with-NMR those and inMS the spectroscopic literature as pseudo-taraxateroldata and comparison (1)[ with12,13 those], pseudo-taraxasterol in the literature as acetatepseudo (-2taraxaterol)[14], β-acetoxytaraxaster-20- (1) [12,13], pseudo- en-30-aldehydetaraxasterol acetate (3)[ (152) ],[14] calenduladiol-3-, -acetoxytaraxasterO- palmitate-20-en-30 (4-)[aldehyde16,17], stigmasterol (3) [15], calenduladiol (5)[18,19],- and3-O-α palmitate-tocospiro (4 B) ([16,17]6)[20]., stigmasterol (5) [18,19], and -tocospiro B (6) [20]. 30 30 R` 20 29 20 29 21 19 19 13 11 17 17 1 14 9 O OH 10 16` 14` 3 3` 7 1` O RO 5 15` 2` 4`-13` 24 23 1 R = H, R` = CH3 2 R = COCH3, R` = CH3 4 3 R = COCH3, R` = CHO 21 28 22 O 18 3a 20 OH 11 24 5a 3 8 7 10 22 19 13 17 25 5 4 13 17 21 1 2 9 6 9 14 1 O 10 3 6a 9a 13a 17a 21a 7 O HO 5 5 6 Figure 1. Chemical structures of the isolated compoundscompounds ((11--66).). ◦ Compound (1))