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Volume 36 Issue 1
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Article Navigation >  Journal of Pharmaceutical Practice and Service  > 2018  >  36(1): 55-60

LI Yanyun, XU Bin, CHENG Chunwei, LIN Houwen, YANG Fan. Chemical constituents from the marine sponge Theonella swinhoei[J]. Journal of Pharmaceutical Practice and Service, 2018, 36(1): 55-60. doi: 10.3969/j.issn.1006-0111.2018.01.011
Citation: LI Yanyun, XU Bin, CHENG Chunwei, LIN Houwen, YANG Fan. Chemical constituents from the marine sponge Theonella swinhoei[J]. Journal of Pharmaceutical Practice and Service, 2018, 36(1): 55-60. doi: 10.3969/j.issn.1006-0111.2018.01.011
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Chemical constituents from the marine sponge Theonella swinhoei

doi: 10.3969/j.issn.1006-0111.2018.01.011

  • Department of Pharmacy, Renji Hospital Affiliated to School of Medicine, Shanghai Jiao Tong University, Shanghai 200127, China

  • Received Date: 2017-04-06
  • Rev Recd Date: 2017-09-12
  • Objective To investigate the chemical constituents of the marine sponge Theonella swinhoei collected from the Xisha Islands in the South China Sea. Methods The petroleum ether and dichloromethane extract of the marine sponge T. swinhoei were purified by solvent extraction and chromatographic methods including vacuum liquid chromatography(VLC), medium pressure liquid chromatography(MPLC), thin layer chromatography(TLC) on silica gel, high performance liquid chromatography(HPLC), and Sephadex LH-20. The chemical structures were determined by spectroscopic analysis and comparison with the reported data. Results Eight compounds were isolated and their structures were determined as cholest-7-ene-3β,5α,6β-triol ( 1 ), ergosta-7,22-diene-3β,5α,6β-triol ( 2 ), 25-norcycloartane-3β,6α,16β,24-tetraol ( 3 ), sinuflexibilin D ( 4 ), 14-deoxycrassin ( 5 ), N-(2-phenylethyl)-(9Z)-tetradecanamide( 6 ), N-(2-phenylethyl)-tetradecanamide ( 7 ), 7,8-dimethyl-isoalloxazine ( 8 ). Conclusion Compounds 1 ~ 7 were isolated from the sponge of genus Theonella for the first time.
  • [1] 釜野德明,张惠平. 海洋抗肿瘤活性大环内酯类化合物化学成分研究近况[J].天然产物研究与开发,1992,4(3):48-72.
    [2] Sinisi A, Calcinai B, Cerrano C, et al. New tridecapeptides of the theonellapeptolide family from the Indonesian sponge Theonella swinhoei[J]. Beilstein J Org Chem, 2013, 9:1643-1651.
    [3] Gong J, Sun P, Jiang N, et al. New steroids with a rearranged skeleton as (h)P300 inhibitors from the sponge Theonella swinhoei[J]. Org Lett, 2014, 16(8):2224-2227.
    [4] Gerwick WH, Moore BS. Lessons from the past and charting the future of marine natural products drug discovery and chemical biology[J]. Chem Biol, 2012, 19(1):85-98.
    [5] Keren R, Lavy A, Mayzel B, et al. Culturable associated-bacteria of the sponge Theonella swinhoei show tolerance to high arsenic concentrations[J]. Front Microbiol, 2015, 6:154-163.
    [6] Keren R, Mayzel B, Lavy A. Sponge-associated bacteria mineralize arsenic and barium on intracellular vesicles[J]. Nat Commun, 2017, 8:14393-14405.
    [7] Wilson MC, Mori T, Ruckert C, et al. An environmental bacterial taxon with a large and distinct metabolic repertoire[J]. Nature, 2014, 506(7486):58-62.
    [8] Jin L, Liu F, Sun W, et al. Pezizomycotina dominates the fungal communities of South China sea sponges Theonella swinhoei and Xestospongia testudinaria[J]. FEMS Microbiol Ecol, 2014, 90(3):935-945.
    [9] 张红军. 三种西沙海绵化学成分和生物活性研究[D]. 上海:第二军医大学, 2009.
    [10] Zhang HJ, Yi YH, Lin HW. Oxygenated 4-methylidene sterols from the south China sea sponge Theonella swinhoei[J]. Helv Chim Acta, 2010, 93(6):1120-1126.
    [11] Zipser B, Bradford JJ, Hollingsworth RI. Cholesterol and its derivatives, are the principal steroids isolated from the leech species Hirudo medicinalis[J]. Comp Biochem Physiol C Pharmacol Toxicol Endocrinol, 1998, 120(2):269-282.
    [12] Musumeci D, Sica D. CH(3)ReO(3)-catalyzed oxidation of cholesta-5,7-dien-3beta-yl acetate with the urea-hydrogen peroxide adduct under various conditions. Synthesis of the natural epoxy sterol 9alpha,11alpha-epoxy-5alpha-cholest-7-en-3beta,5,6beta-triol[J]. Steroids, 2002, 67(7):661-668.
    [13] 高慧敏, 吴喜燕, 李宗云,等. 蟾衣化学成分及体外抗肿瘤活性研究[J]. 中国中药杂志, 2011, 36(16):2207-2210.
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    [21] 甘建红,席达,于豪冰,等. 中国南海隋氏蒂壳海绵Theonella swinhoei的化学成分研究[J]. 天然产物研究与开发,2014, (2):209-211.
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Chemical constituents from the marine sponge Theonella swinhoei

doi: 10.3969/j.issn.1006-0111.2018.01.011
  • Department of Pharmacy, Renji Hospital Affiliated to School of Medicine, Shanghai Jiao Tong University, Shanghai 200127, China
  • Received Date: 2017-04-06
  • Rev Recd Date: 2017-09-12

Abstract: Objective To investigate the chemical constituents of the marine sponge Theonella swinhoei collected from the Xisha Islands in the South China Sea. Methods The petroleum ether and dichloromethane extract of the marine sponge T. swinhoei were purified by solvent extraction and chromatographic methods including vacuum liquid chromatography(VLC), medium pressure liquid chromatography(MPLC), thin layer chromatography(TLC) on silica gel, high performance liquid chromatography(HPLC), and Sephadex LH-20. The chemical structures were determined by spectroscopic analysis and comparison with the reported data. Results Eight compounds were isolated and their structures were determined as cholest-7-ene-3β,5α,6β-triol ( 1 ), ergosta-7,22-diene-3β,5α,6β-triol ( 2 ), 25-norcycloartane-3β,6α,16β,24-tetraol ( 3 ), sinuflexibilin D ( 4 ), 14-deoxycrassin ( 5 ), N-(2-phenylethyl)-(9Z)-tetradecanamide( 6 ), N-(2-phenylethyl)-tetradecanamide ( 7 ), 7,8-dimethyl-isoalloxazine ( 8 ). Conclusion Compounds 1 ~ 7 were isolated from the sponge of genus Theonella for the first time.

LI Yanyun, XU Bin, CHENG Chunwei, LIN Houwen, YANG Fan. Chemical constituents from the marine sponge Theonella swinhoei[J]. Journal of Pharmaceutical Practice and Service, 2018, 36(1): 55-60. doi: 10.3969/j.issn.1006-0111.2018.01.011
Citation: LI Yanyun, XU Bin, CHENG Chunwei, LIN Houwen, YANG Fan. Chemical constituents from the marine sponge Theonella swinhoei[J]. Journal of Pharmaceutical Practice and Service, 2018, 36(1): 55-60. doi: 10.3969/j.issn.1006-0111.2018.01.011
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