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Hepatoprotective and Cytotoxic Activities of Anvillea Garcinii and Isolation of Four New Secondary Metabolites

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Hepatoprotective and Cytotoxic Activities of Anvillea Garcinii and Isolation of Four New Secondary Metabolites Hepatoprotective and cytotoxic activities of Anvillea garcinii and isolation of four new secondary metabolites Shagufta Perveen, Areej Mohammad Al-Taweel, Hasan Soliman Yusufoglu, Ghada Ahmed Fawzy, Ahmed Foudah & Maged Saad Abdel-Kader Journal of Natural Medicines ISSN 1340-3443 Volume 72 Number 1 J Nat Med (2018) 72:106-117 DOI 10.1007/s11418-017-1118-1 1 23 Your article is protected by copyright and all rights are held exclusively by The Japanese Society of Pharmacognosy and Springer Japan KK. This e-offprint is for personal use only and shall not be self-archived in electronic repositories. If you wish to self-archive your article, please use the accepted manuscript version for posting on your own website. You may further deposit the accepted manuscript version in any repository, provided it is only made publicly available 12 months after official publication or later and provided acknowledgement is given to the original source of publication and a link is inserted to the published article on Springer's website. The link must be accompanied by the following text: "The final publication is available at link.springer.com”. 1 23 Author's personal copy J Nat Med (2018) 72:106–117 https://doi.org/10.1007/s11418-017-1118-1 ORIGINAL PAPER Hepatoprotective and cytotoxic activities of Anvillea garcinii and isolation of four new secondary metabolites 1 1 2 Shagufta Perveen • Areej Mohammad Al-Taweel • Hasan Soliman Yusufoglu • 1,3 2 2,4 Ghada Ahmed Fawzy • Ahmed Foudah • Maged Saad Abdel-Kader Received: 14 June 2017 / Accepted: 26 July 2017 / Published online: 9 August 2017 Ó The Japanese Society of Pharmacognosy and Springer Japan KK 2017 Abstract Anvillea garcinii is a medicinal plant tradition- fractions and compounds 3, 4, 7 and 8 displayed significant ally used for the treatment of dysentery, gastrointestinal cytotoxic activity against these cell lines. troubles, hepatitis, lung disease, colds, digestive problems and pulmonary affections and in liver diseases. Four new Keywords Anvillea garcinii Á Sesquiterpene lactones Á sesquiterpene lactones, garcinamines A–D, along with Hepatoprotective activity Á Cytotoxicity seven known compounds, were isolated from the leaves of A. garcinii. This is the first report of the isolation of amino acid analogues of parthenolide-type sesquiterpene lactones Introduction from the family Asteraceae. Total ethanol extract of leaves as well as the chloroform and n-butanol fractions were For centuries, medicinal plants have traditionally been used tested for their hepatoprotective effect using the carbon for treating liver diseases. Several natural leads with tetrachloride liver toxicity model. The chloroform fraction, diverse chemical structures were discovered as potential at a dose of 400 mg/kg, demonstrated a significant hep- hepatoprotective agents. Moreover, the development of atoprotective effect comparable to silymarin in all serum new natural anti-cancer drugs with specificity and higher and tissue parameters. The cytotoxicity of all extracts and potency against different cancer cells has become an compounds were evaluated against five human cancer cell important target in biomedical research. In continuation of lines: MCF-7, HCT-116, HepG2, Hela and A-549. The our work on medicinal Saudi plants, we selected Anvillea results indicated that the chloroform and n-butanol garcinii (Burm.f.) DC. (Anvillea garcinii subsp. radiata), which is a shrub with florescent yellow flowers. The genus Anvillea belongs to the family Asteraceae, and comprises Electronic supplementary material The online version of this four species distributed in the region from North Africa to article (doi:10.1007/s11418-017-1118-1) contains supplementary Iran, including a number of Middle Eastern countries, such material, which is available to authorized users. as Egypt, Palestine and Saudi Arabia [1]. Anvillea garcinii & Shagufta Perveen is widely used by local people for its medicinal properties [email protected]; [email protected] and is traditionally used for the treatment of dysentery, 1 gastrointestinal troubles, hepatitis, lung disease, colds, Department of Pharmacognosy, College of Pharmacy, King digestive problems and pulmonary affections, and in liver Saud University, P. O. Box 22452, Riyadh 11495, Kingdom of Saudi Arabia diseases [2]. Anvillea garcinii was proven to have signifi- cant antidiabetic potential by decreasing blood glucose 2 Department of Pharmacognosy, College of Pharmacy, Prince Sattam Bin Abdulaziz University, P.O. Box 173, levels and maintaining serum lipid concentrations at nor- Al-Kharj 11942, Saudi Arabia mal [3]. Previous phytochemical studies on the various 3 Department of Pharmacognosy, Faculty of Pharmacy, Cairo parts of A. garcinii have led to the isolation of different University, Cairo 11562, Egypt biologically active compounds, including germacranolides 4 Department of Pharmacognosy, Faculty of Pharmacy, [4–8], flavanoids and their glycosides [9, 10]. Germacra- Alexandria University, Alexandria 21215, Egypt nolides and their isomers isolated from A. garcinii were 123 Author's personal copy J Nat Med (2018) 72:106–117 107 shown to possess anti-tumor, anti-HIV and cytotoxic sesquiterpene lactone attached with an aromatic moiety and activities in both in vitro and vivo assays [5, 6]. It has been closely resembled the 9a-hydroxyparthenolide, isolated reported recently that different extracts of A. garcinii previously from the chloroform-soluble fraction of the inhibit the oxidative burst of primary neutrophils in same plant A. garcinii [8]. 1 humans which, together with its high anti-inflammatory The H-NMR spectrum showed specific signals of an L- 0 potential, make it a promising candidate for further phenylalanine amino acid group at dH3.46 (1H, m, H-2 ), medicinal uses and applications [11]. Previous phyto- 2.92 (2H, d, J = 5.0 Hz, H-30), 7.27 (2H, m, H-50,90), 7.26 chemical work on the Saudi A. garcinii has revealed that (2H, m, H-60,80) and 7.21 (1H, m, H-70). The 13C-NMR this plant is a rich source of sesquiterpenes. In the present signals of an L-phenylalanine group appeared at dC174.0 study, we have isolated four new sesquiterpene lactones (C-10), 63.4 (C-20), 38.2 (C-30), 138.1 (C-40), 130.0 (C-50, along with seven known compounds from different frac- 90), 128.7 (C-60,80), 126.8 (C-70) and confirmed the pres- tions of the plant extract. In addition, the total ethanol ence of an L-phenylalanine amino acid group (Tables 1, 2) extract of the leaves as well as the chloroform and n-bu- [12]. The missing C-13 methyl signal in NMR and the tanol fractions were tested for their hepatoprotective effect appearance of an additional downfield methylene group at against liver toxicity induced by carbon tetrachloride. dH 2.91 (1H, J = 10.0 Hz, H-13a) and 2.74 (1H, m, H-13b) Additionally, the cytotoxic activities of A. garcinii extracts strongly suggested that C-13 is attached to the nitrogen of and its isolates were evaluated against five human cancer L-phenylalanine amino acid. The point of attachment of the cell lines (MCF-7 breast adenocarcinoma, HCT-116 colon L-phenylalanine group was further confirmed by the carcinoma, HePG-2 liver hepatocellular carcinoma, Hela HMBC spectrum, in which H-13a (dH 2.91) showed 2 cervical cells and A-549 lung carcinoma). J correlations with the methine carbon (dC 46.8, C-11) and 3J correlations with C-12 (177.6) and C-20 (63.4). Further confirmation of the position and presence of the L-pheny- Results and discussion lalanine moiety was made by the acid hydrolysis of com- pound 1. The a-orientation of the hydroxyl group at C-9 Structure elucidation of new compounds (1–4) was confirmed by the upfield chemical shift of the C-9 at dC 70.4 ppm; in the case of 9b-hydroxyparthenolide, the Chromatographic separation of the chloroform and n-bu- C-9 b-orieanted hydroxymethine carbon usually appeared 13 tanol fractions of the ethanol extract of A. garcinii, using in the range of dC 78–79 ppm in the C-NMR spectrum silica, Sephadex LH-20, and RP-18 column chromatogra- [4]. In the nuclear Overhauser enhancement (NOE) phy, yielded four new (1–4) and seven known compounds experiment on 1, correlations were observed between the (5–11) (Fig. 1). Their structures were elucidated by spec- 6b-proton, 11b-proton and 9b-proton, which further con- tral data analysis, including IR, 1D, 2D NMR, and ESI– firmed the a-position of the hydroxyl group at C-9 carbon. MS. The relative configuration of C-4 and C-5 was determined Garcinamine A (1) obtained as yellow gummy solid by NOE experiments. NOE correlations were observed 25 [a] D = –27.0 (c = 0.10, CH3OH) and the molecular between the 5a-H and 7a-H, 7a-H and13a-H2,6b-H and formula was established as C24H30NO6 at m/z 428.2068 9b-H, and 6b-H and 15b-H3. Acid hydrolysis of 1 provided - (calcd 428.2073) [M–H] by negative ESI–MS. The IR the L-phenylalanine and 9a-hydroxyparthenolide [8] and spectrum showed characteristic signals for a hydroxyl this was confirmed through co-TLC, the 1H-NMR spectrum group (3442 cm-1), a c-lactone group (1762 cm-1) and a and the sign of their optical rotation with standards. double bond (1650 cm-1). The 1H-NMR spectrum showed Therefore, compound 1 was unambiguously elucidated as a downfield signal at dH 5.48 (d, J = 10.0 Hz) for an 13-L-phenylalanine-9a-hydroxyparthenolide, and named olefinic proton, three hydroxymethine protons at dH 2.51 garcinamine A. (m, H-5), 4.02 (m, H-6) and 3.98 (m, H-9) and character- Garcinamine B (2) was obtained as a yellow gummy 25 istic signals at dH 1.59 (s, H-14), 1.19 (s, H-15) were solid, [a] D =-29 (c = 0.15, CH3OH).
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