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Two New Glycerides from Red Sea Ascidian Didemnum Species Sabrin R.M This article was downloaded by: [Gamal Mohamed] On: 20 June 2014, At: 08:21 Publisher: Taylor & Francis Informa Ltd Registered in England and Wales Registered Number: 1072954 Registered office: Mortimer House, 37-41 Mortimer Street, London W1T 3JH, UK Natural Product Research: Formerly Natural Product Letters Publication details, including instructions for authors and subscription information: http://www.tandfonline.com/loi/gnpl20 Didemnacerides A and B: two new glycerides from Red Sea ascidian Didemnum species Sabrin R.M. Ibrahimab, Gamal A. Mohamedcd, Lamiaa A. Shaalaef, Diaa T.A. Youssefcg & Ali A. Gab-Allah a Department of Pharmacognosy and Medicinal Chemistry, Faculty of Pharmacy, Taibah University, Al Madinah Al Munawwarah 41477, Saudi Arabia b Department of Pharmacognosy, Faculty of Pharmacy, Assiut University, Assiut 71526, Egypt c Department of Natural Products, Faculty of Pharmacy, King Abdulaziz University, Jeddah 21589, Saudi Arabia d Department of Pharmacognosy, Faculty of Pharmacy, Al-Azhar University, Assiut Branch, Assiut 71524, Egypt e Natural Products Unit, King Fahd Medical Research Center, King Abdulaziz University, Jeddah 21589, Saudi Arabia f Suez Canal University Hospital, Suez Canal University, Ismailia 41522, Egypt g Department of Pharmacognosy, Faculty of Pharmacy, Suez Canal University, Ismailia 41522, Egypt h Biological Sciences Department, Faculty of Science, Um Al-Qura University, Makkah, Saudi Arabia Published online: 18 Jun 2014. To cite this article: Sabrin R.M. Ibrahim, Gamal A. Mohamed, Lamiaa A. Shaala, Diaa T.A. Youssef & Ali A. Gab-Alla (2014): Didemnacerides A and B: two new glycerides from Red Sea ascidian Didemnum species, Natural Product Research: Formerly Natural Product Letters, DOI: 10.1080/14786419.2014.927874 To link to this article: http://dx.doi.org/10.1080/14786419.2014.927874 PLEASE SCROLL DOWN FOR ARTICLE Taylor & Francis makes every effort to ensure the accuracy of all the information (the “Content”) contained in the publications on our platform. However, Taylor & Francis, our agents, and our licensors make no representations or warranties whatsoever as to the accuracy, completeness, or suitability for any purpose of the Content. Any opinions and views expressed in this publication are the opinions and views of the authors, and are not the views of or endorsed by Taylor & Francis. The accuracy of the Content should not be relied upon and should be independently verified with primary sources of information. Taylor and Francis shall not be liable for any losses, actions, claims, proceedings, demands, costs, expenses, damages, and other liabilities whatsoever or howsoever caused arising directly or indirectly in connection with, in relation to or arising out of the use of the Content. This article may be used for research, teaching, and private study purposes. Any substantial or systematic reproduction, redistribution, reselling, loan, sub-licensing, systematic supply, or distribution in any form to anyone is expressly forbidden. Terms & Conditions of access and use can be found at http://www.tandfonline.com/page/terms- and-conditions Downloaded by [Gamal Mohamed] at 08:21 20 June 2014 Natural Product Research, 2014 http://dx.doi.org/10.1080/14786419.2014.927874 Didemnacerides A and B: two new glycerides from Red Sea ascidian Didemnum species Sabrin R.M. Ibrahimab, Gamal A. Mohamedcd, Lamiaa A. Shaalaef, Diaa T.A. Youssefcg* and Ali A. Gab-Allah aDepartment of Pharmacognosy and Medicinal Chemistry, Faculty of Pharmacy, Taibah University, Al Madinah Al Munawwarah 41477, Saudi Arabia; bDepartment of Pharmacognosy, Faculty of Pharmacy, Assiut University, Assiut 71526, Egypt; cDepartment of Natural Products, Faculty of Pharmacy, King Abdulaziz University, Jeddah 21589, Saudi Arabia; dDepartment of Pharmacognosy, Faculty of Pharmacy, Al-Azhar University, Assiut Branch, Assiut 71524, Egypt; eNatural Products Unit, King Fahd Medical Research Center, King Abdulaziz University, Jeddah 21589, Saudi Arabia; fSuez Canal University Hospital, Suez Canal University, Ismailia 41522, Egypt; gDepartment of Pharmacognosy, Faculty of Pharmacy, Suez Canal University, Ismailia 41522, Egypt; hBiological Sciences Department, Faculty of Science, Um Al-Qura University, Makkah, Saudi Arabia (Received 13 April 2014; final version received 20 May 2014) Two new glycerides, didemnacerides A (1) and B (2), together with three known sterols, 24-ethyl-25-hydroxycholesterol (3), cholest-6-en-3,5,8-triol (4) and choles- tane-3b,5a,6b-26-tetrol (5), were isolated from the Red Sea ascidian Didemnum sp. Their structures were elucidated by using extensive 1D (1H, 13C) and 2D (1H–1H COSY, HSQC and HMBC) NMR studies and mass spectroscopic data (GC-MS and HR-MS) as well as alkaline hydrolysis followed by GC–MS and NMR spectral analyses of the fatty acid methyl esters. This is the first report of compounds 3–5 from the Red Sea ascidian Didemnum species. Keywords: marine ascidian; Didemnum species; glycerides; sterols 1. Introduction Recently, marine ascidians have been widely recognised as a rich source of bioactive natural products. Members of the genus Didemnum have yielded a variety of interesting secondary Downloaded by [Gamal Mohamed] at 08:21 20 June 2014 metabolites. Examples of these secondary metabolites include alkaloids (Davis et al. 1999; Oku et al. 2000), lipids (Mitchell et al. 2000), peptides (Rudi et al. 2003; Toshiaki et al. 2008) and macrolides (Potts & Faulkner 1991; Pika & Faulkner 1995). Many of the isolated compounds were found to possess significant biological activities including antiplasmodial (Wright et al. 2002), antibacterial (Kumaran et al. 2011), antiviral (Davis et al. 1999), cytotoxic (Segraves et al. 2003) and antileukaemic (Takeara et al. 2008). Previous investigation of the Red Sea Didemnum species led to the isolation of two new spiroketals, didemnaketals D and E (Mohamed et al. 2014). In continuation of our investigation of the same species, we describe here the isolation and structural elucidation of two new glycerides named didemnacerides A (1) and B (2), along with three known sterols, 24-ethyl-25-hydroxycholesterol (3) (Siddiqui et al. 1989), cholest-6-en-3,5,8-triol (4) (Youssef et al. 2010) and cholestane-3b,5a,6b-26-tetrol (5) (Liyanage & Schmitz 1996). Compounds 3–5 are reported here for the first time from the Red Sea ascidian Didemnum species (Figure 1). *Corresponding author. Email: [email protected] q 2014 Taylor & Francis 2 S.R.M. Ibrahim et al. Figure 1. Structures of the isolated compounds 1–5. 2. Results and discussion Compound 1 was isolated as colourless oil. Its HR-ESI-MS revealed a pseudo-molecular ion þ peak at m/z 1011.9239 [M þ H] , which is consistent with a molecular formula C66H122O6, requiring six degrees of unsaturation. Its IR spectrum revealed absorption bands at 2925 and 2850 (alkyl chain), 1655 (double bond) and 1732 (ester carbonyl) cm21 (Silverstein & Webster 1998; Ibrahim et al. 2009). The presence of a strong absorption band at 1732 cm21 in the IR 0 000 00 13 spectrum along with signals at dC 172.8 (C-1 ,1 ) and 173.3 (C-1 )in C NMR spectrum suggested the presence of three ester carbonyls in 1 (Shiao & Shiao 1989; Vlahov 1999; Swaroop et al. 2005; Vlahov 2009; Wang et al. 2010) (Supplementary Figure S2). The appearance of only two signals for three ester carbonyls suggested the symmetric nature of 1 (Swaroop et al. 2005; Ibrahim 2014). The signals at dH 4.29 and 4.15/dC 62.0 (H-1/C-1), 5.27/68.4 (H-2/C-2), and 4.31 and 4.14/62.1 (H-3/C-3) along with the fragment ion peaks at m/z þ þ 704.6235 [M þ H–C21H39O] and 397.3242 [M þ H–C42H78O2] confirmed that 1 is a triglyceride with C21 fatty acids, which was further confirmed by the observed COSY correlations (Supplementary Figures S1, S3, and S11). The 1H NMR spectrum exhibited signals 0 00 000 for olefinic protons at dH 5.36 (3H, each t, J ¼ 6.0 Hz, H-6 ,6,6 ) and 5.34 (3H, each t, Downloaded by [Gamal Mohamed] at 08:21 20 June 2014 0 00 000 0 000 00 J ¼ 6.0 Hz, H-7 ,7 ,7 ) correlated with carbons at dH 129.9 (C-6 ,6 ), 130.0 (C-6 ), 129.8 (C- 700) and 129.7 (C-70,7000) in the HSQC spectrum, also indicating the presence of three olefinic double bonds in 1. The geometry of the double bonds was deduced to be Z based on the coupling constant values (J60,70 ¼ J600,700 ¼ J6000,7000 ¼ 6.0 Hz) (de Carvalho et al. 2000; Ibrahim 2014). The 1H NMR spectrum revealed characteristic signals for the terminal methyl protons of the fatty 00 0 000 acids at dH 0.87 (t, J ¼ 6.5 Hz, H-21 ) and 0.85 (t, J ¼ 6.5 Hz, H-21 ,21 ), broad signals at dH 00 0 1.23–1.38 for the methylene protons, two methylene triplets at dH 2.32 (H-2 ) and 2.31 (H-2 , 000 00 0 000 00 2 ), and two multiplets at dH 1.63 (H-3 ) and 1.61 (H-3 ,3 ). In the COSY spectrum, H-2 and H-20,2000 correlated with H-300 and H-30,3000, which further correlated to H-400 and H-40,4000, respectively. The coupling observed in the COSY spectrum between the proton signals at dH 2.01 (H-50,5000,80,8000) and 2.02 (H-500,800) and the olefinic protons indicated its connection to the double bond carbon. In HMBC spectrum (Supplementary Figures S5 and S11), the carbonyl 00 0 000 carbon signals at dC 173.3 (C-1 ) and 172.8 (C-1 ,1 ) showed correlations with proton signals at 00 0 000 00 dH 2.32 (2H, t, J ¼ 7.5 Hz, H-2 ), 2.31 (4H, t, J ¼ 7.5 Hz, H-2 , H-2 ), 1.63 (2H, m, H-3 ) and 1.61 (4H, t, H-30,3000), also confirming that 1 is a triglyceride with long chain fatty acid esters.
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