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New Cytotoxic Fatty Acid Esters from the Black Coral, Antipathes Dichotoma

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New Cytotoxic Fatty Acid Esters from the Black Coral, Antipathes Dichotoma Ghandourah & Alorfi Tropical Journal of Pharmaceutical Research January 2019; 18 (1): 69-74 ISSN: 1596-5996 (print); 1596-9827 (electronic) © Pharmacotherapy Group, Faculty of Pharmacy, University of Benin, Benin City, 300001 Nigeria. Available online at http://www.tjpr.org http://dx.doi.org/10.4314/tjpr.v18i1.11 Original Research Article New cytotoxic fatty acid esters from the black coral, Antipathes dichotoma Mohamed A Ghandourah1, Hajer S Alorfi2* 1Department of Marine Chemistry, Faculty of Marine Sciences, 2Department of Chemistry, Faculty of Science, King Abdulaziz University, PO Box 80203, Jeddah 21589, Saudi Arabia *For correspondence: Email: [email protected]; Tel: 0567663343 Sent for review: 23 July 2018 Revised accepted: 16 December 2018 Abstract Purpose: To isolate new fatty acid esters from Antipathes dichotoma and investigate their cytotoxic effects on HepG2, WI-38, VERO and MCF-7 cells. Methods: Antipathes dichotoma was collected using scuba at a depth of 10 to 20 m from the Red Sea, and the lyophilized sample (1500 g) was exhaustively extracted thrice using a mixture of chloroform and methanol (1:1, v/v). The extract was concentrated using a vacuum rotatory evaporator to obtain a brown gummy paste which was fractionated on a silica gel chromatography column and further purified using preparative thin layer chromatography (PTLC). The chemical structures of the newly isolated compounds were elucidated by spectroscopic methods such as infrared (IR), nuclear magnetic resonance (NMR) and mass spectrometry (MS). The cytotoxicity of the isolated compounds was examined in HepG2, WI 38, VERO and MCF-7 cell lines. Results: Three new aliphatic esters namely, (4Z, 7Z, 10Z, 13Z, 16Z)-1-hydroxynonadeca-4, 7, 10, 13, 16-pentaen-2-yl octanoate (1); (4Z, 7Z, 10Z, 13Z, 16Z)-1-hydroxynonadeca-4, 7, 10, 13, 16-pentaen-2- yl decanoate (2) and 1-hydroxynonadecan-2-yl-octanoate (3) were isolated from A. dichotoma. 1 and 2 displayed moderate cytotoxic activities against the examined cell lines with half-maximal inhibitory concentration (IC50) ranging from 30.1 to 43.0 µg/mL, while compound 3 exhibited poor anti-cancer activity. Conclusion: The results indicate that A. dichotoma is a reservoir of new compounds that have potential anticancer effects. Keywords: Red Sea, Black coral, Antipathes dichotoma, Esters, Cytotoxicity This is an Open Access article that uses a funding model which does not charge readers or their institutions for access and distributed under the terms of the Creative Commons Attribution License (http://creativecommons.org/licenses/by/4.0) and the Budapest Open Access Initiative (http://www.budapestopenaccessinitiative.org/read), which permit unrestricted use, distribution, and reproduction in any medium, provided the original work is properly credited. Tropical Journal of Pharmaceutical Research is indexed by Science Citation Index (SciSearch), Scopus, International Pharmaceutical Abstract, Chemical Abstracts, Embase, Index Copernicus, EBSCO, African Index Medicus, JournalSeek, Journal Citation Reports/Science Edition, Directory of Open Access Journals (DOAJ), African Journal Online, Bioline International, Open-J-Gate and Pharmacy Abstracts INTRODUCTION lack mechanical defense mechanisms [2,3]. These chemical factors have a broad spectrum Marine organisms live under tough of pharmaceutical applications [4-10]. Synthetic environmental conditions such as high salinity, antimicrobial and antitumor agents produce a high pressure, variable nutrient accessibility and range of adverse effects such as bleeding in the presence of predators [1]. Marine invertebrates gastrointestinal tract (GIT) and ulcer, renal produce chemical factors that enable them to tubular necrosis and cardiovascular diseases evade predation and sense danger because they ----------------------------------------------------------------------------------------------------------------------------------------------------- Trop J Pharm Res, January 2019; 18(1): 69 © 2019 The authors. This work is licensed under the Creative Commons Attribution 4.0 International License Ghandourah & Alorfi (CVDs), while natural products have gained wide transferred to the laboratory and immediately acceptance due to their safety profiles [11]. frozen and lyophilized. The lyophilized sample (1500 g) was exhaustively extracted thrice using The zoanthid black coral, Antipathes dichotoma a mixture of chloroform and methanol (1:1, v/v) at belongs to the Antipathidae family, and is known room temperature. The extract was concentrated among local people as a source of remedies and using a vacuum rotatory evaporator to obtain a charms [12]. Black coral of the genus Antipathes brown gummy paste. has been shown to contain carbazole, zoanthoxanthin alkaloids, polyhydroxy sterols A portion of the brown gummy residue (30 g) was and sphingolipids [13]. The carbazole and well mixed with silica gel (60G) until zoanthoxanthin alkaloids are cytotoxic to human homogenization. The obtained homogenous stomach carcinoma SGC-7901 and HepG2 cells; mixture was applied to Si-gel column for polyhydroxy sterols are cytotoxic to Artemia chromatographic separation of the extract salina [7, 14], and sphingolipids exhibit constituents. After adsorption of the analyte antimicrobial and antitumor activities [15,16]. material, elution process started with n-haxane and the polarity was gradually raised by adding Unsaturated fatty acids are widely distributed in volumes of ethylacetate followed by chloroform plants and marine organisms. Polyunsaturated and finally methanol. The TLC was carried out fatty acids reduce the risk of CVDs. Omega-3 using proper solvent system for elution and a and -6 unsaturated fatty acids slow down/prevent spray reagent and/or ultraviolet light for the development of cancers and inhibit arthritis- visualization of spots. Further purification of associated inflammation [17]. promising spots was carried out by means of PTLC. The aim of this work was to isolate new fatty acid esters from Antipathes dichotoma and The column eluted fractions with solvent system investigate their cytotoxic effects on HepG2, WI- n-hexane: ethylacetate (90:10, v/v), yielded 40.1 38, VERO and MCF-7 cells. mg (dry wt.), which was then further purified by PTLC and using the same column elution EXPERIMENTAL system. PTLC purification yielded two bands: a) a brownish color band with spray reagent at Rf= General 0.67, extraction and drying afforded oily material assigned for compound 1 (8.1 mg); b) the second Silica gel GF 254 was a product of Merck band displayed also a brownish color with spray (Germany), AVANCE I000 NMR was a product of reagent at Rf= 0.75, extraction and drying Bruker Co., Ltd. (Germany), while MTT assay kit afforded oily material assigned for compound 2 was purchased from Trevigen, (USA). Thin layer (10.0 mg). The column eluted fractions with chromatography (TLC) and PTLC were carried solvent system n-hexane: ethylacetate (80:20, out using silica gel GF 254. A solution of equal v/v), yielded 44.1 mg (dry wt.), which was then volumes of concentrated sulfuric acid (H2SO4) further purified by PTLC and using the same and methanol (CH3OH) was used as spray column elution system. PTLC purification yielded reagent. Freeze drying was carried out on an orange band after spraying with 50% H2SO4 VIRITIS Benchtop 4K Series, Model BT4KZL- Rf= 0.42, extraction and drying afforded oily 105. One-dimension and two-dimension (COSY, material assigned for compound 3 (7.7 mg). HSQC and HMBC), NMR (400 MHz) and 13C (100 MHz) spectra were carried out using Hydrolysis and methanolysis deuterated chloroform (CDCl3) and TMS (tetramethylsilane) as internal standards. The isolated compounds (5 mg) were refluxed HRESIMS spectra were recorded on liquid with 1.0 M HCl in 90% aq. MeOH (5 ml) for 24 h. chromatography-mass spectrometer-IT (LCMS- the resultant was fractionated between H2O and IT). Et2O. The upper layer (Et2O layer) was dried over anhydrous Na2SO4, and then directly Collection and processing of Antipathes injected in the GC-MS (QP 2014-mass dichotoma spectrometry). Antipathes dichotoma samples were collected Cytotoxicity bioassays using scuba at a depth of 10 to 20 meter from the Red Sea coast at Haqel, Saudi Arabia. A Four cancer cell lines were selected as targets to voucher specimen (No. B.C. 2009.77) was estimate the bioactivity of the isolated new prepared and kept at the Faculty of Marine compounds 1-3 which are HepG2 (human Sciences, KAU. The samples were then hepatocellular liver carcinoma), WI 38 (human Trop J Pharm Res, January 2019; 18(1): 70 Ghandourah & Alorfi lung fibroblast cell line), VERO (normal adult 3 showed weak activity. It is apparent the African green monkey kidney) (VERO) and MCF- presence of multiple isolated double bonds 7 (human caucasian breast adeno-carcinoma). enhanced the biological activity of the compound The cytotoxicity evaluation was carried out using under evaluation. MTT assay, and percentage viability was determined using trypan blue dye exclusion 19' technique [5]. 5-fluorouracil (positive control). 1' OH 10' 7' 4' 16' 13' 7 O Statistical analysis 1 8 3 5 1 Graph Pad InStat software, version 3.05 was O employed for statistical analysis. Data are OH expressed as mean SEM (n = 3), and were 10 O analyzed by ANOVA. P < 0.05 was considered 2 statistically significant. O OH RESULTS 8 1 O Spectra of isolated compounds 3 OH O Elucidation of chemical structures was achieved Figure 1: Compounds isolated from A. dichotoma after extensive analysis of their spectroscopic
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