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Volume 35 Issue 4
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Article Navigation >  Journal of Pharmaceutical Practice and Service  > 2017  >  35(4): 308-314

SUN Jiabao, WANG Shuping, WANG Jie, LIU Li, HAN Bingnan, LIN Houwen. Study on chemical constituents of sponge Mycale sp. from the South China Sea[J]. Journal of Pharmaceutical Practice and Service, 2017, 35(4): 308-314. doi: 10.3969/j.issn.1006-0111.2017.04.006
Citation: SUN Jiabao, WANG Shuping, WANG Jie, LIU Li, HAN Bingnan, LIN Houwen. Study on chemical constituents of sponge Mycale sp. from the South China Sea[J]. Journal of Pharmaceutical Practice and Service, 2017, 35(4): 308-314. doi: 10.3969/j.issn.1006-0111.2017.04.006
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Study on chemical constituents of sponge Mycale sp. from the South China Sea

doi: 10.3969/j.issn.1006-0111.2017.04.006
  • 1.

    Department of Pharmacy, Renji Hospital Affiliated to School of Medicine, Shanghai JiaoTong University, Shanghai 200127, China

  • 2.

    School of Traditional Chinese Materia Medica, Shenyang Pharmaceutical University, Shenyang 110016, China

  • Received Date: 2017-03-20
  • Rev Recd Date: 2017-05-19
  • Objective To investigate the chemical constituents of marine sponge Mycale sp. collected from the South China Sea. Methods The ethyl acetate extract of the marine sponge Mycale sp. was separated and purified by repeated column chromatography on silica gel, Sephadex LH-20 and reversed-phase high-performance liquid chromatography (RP-HPLC). The structures of these compounds were identified by means of various modern spectroscopic techniques and comparison with their physicochemical properties to reported data. The tumor cell growth inhibitory activities of these compounds against human breast cancer cell lines MCF-7 and human lung cancer cell lines PC9 were tested by Cell Counting Kit-8 (CCK-8) method. Results Ten compounds were isolated and identified as cyclo-(Pro-Ile)( 1 ),cyclo-(Pro-Leu)( 2 ),cyclo-(Ile-Leu)( 3 ),cyclo-(Phe-Pro)( 4 ),cyclo-(Phe-Val)( 5 ),cyclo-(Phe-Leu)( 6 ),cyclo-(Phe-Ile)( 7 ), 2'-deoxythymidine ( 8 ), thymine ( 9 ), 5-hydroxy-3,4-dimethyl-5-pentyl-2(5H)-furanone ( 10 ). These compounds showed weak tumor cell growth inhibitory activities toward cells MCF-7 and PC9 in vitro. Conclusion Compounds 1 , 2 , 4 , 5 , 6 , 7 and 10 were isolated from the sponge Mycale sp. for the first time. It is the first time to report the antitumor activity evaluation for compounds 1 ~ 10 .
  • [1] Ortega MJ, Zubia E, Carballo JL,et al. New cytotoxic metabolites from the sponge Mycale micracanthoxea[J]. Tetrahedron, 1997, 53(1):331-340.
    [2] Fusetani N, Yasumuro K, Matsunaga S,et al. Mycalolides A-C hybrid macrolides of ulapualides and halichondramide, from a sponge of the genus Mycale[J]. Tetrahedron Lett, 1989, 30(21):2809-2812.
    [3] Capon RJ. Two new norsesterterpene cyclic peroxides from a marine sponge,Mycale (Carmia)cf. spongiosa[J]. J NatProd, 1991, 54(1):190-195.
    [4] Capon RJ, Macleod JK. Structural and stereochemical studies on marine norterpene cyclic peroxides[J]. Tetrahedron, 1985, 41(16):3391-3404.
    [5] Zhou XF, Lin XP, Guo XY,et al. Chemical constituents of the sponge Mycale species from South China Sea[J]. Rec Nat Prod, 2013, 7(2):119-123.
    [6] Nakao Y, Yoshida S, Matsunaga S,et al. Azumamides A-E: histone deacetylase inhibitory cyclic tetrapeptides from the marine sponge Mycale izuensis[J].Angew Chem Int Ed,2006, 45(45):7553-7557.
    [7] Perry NB, Blunt JW, Munro MHG,et al. Mycalamide A, an antiviral compound from a New Zealand sponge of the genus Mycale[J]. J Am Chem Soc, 1988, 110(14):4850-4851.
    [8] Northcote PT, Blunt JW, Munro MHG. Pateamine: a potent cytotoxin from the New Zealand marine sponge, mycale sp.[J]. Tetrahedron Lett, 1991, 32(44):6411-6414.
    [9] West LM, Northcote PT, Battershill CN. Peloruside A: a potent cytotoxic macrolide isolated from the New Zealand marine sponge Mycale sp.[J]. J Org Chem,2000, 65(2):445-449.
    [10] Adamczeski M, Reed AR, Crews P. New and known diketopiperazines from the Caribbean sponge,Calyx cf. podatypa.[J].J NatProd, 1995, 58(2):201-208.
    [11] Zhao PJ, Wang HX, Li GH,et al. Secondary metabolites from endophytic Streptomyces sp. Lz531[J]. Chem Biodivers, 2007, 4(5):899-904.
    [12] Wang S, Tan N, Yang Y, et al. Cyclodipeptides from the roots of Panax notoginseng[J]. Nat Prod Res Dev, 2004, 16:383-386.
    [13] Shu ZP, Li XL, Xu BQ, et al.Piperazine constituents in fruits of Physalis alkekengi var. francheti[J]. Chin Tradit Herbal Drugs, 2014, 45(4):471-475.
    [14] Ouyang MA. A new adenosyl-alkaloid from Ostrea rivularis[J]. Nat Prod Res, 2006, 20(1): 79-83.
    [15] 苏丽丽,唐旭利,张 婧,等.中国南海海底柏柳珊瑚化学成分研究[J]. 中国海洋药物,2011, 30(5):18-22.
    [16] Degenkolb T, Gams W, Br ckner H. Natural cyclopeptaibiotics and related cyclic tetrapeptides: structural diversity and future prospects[J]. Chem Biodivers, 2008, 5(5):693-706.
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Study on chemical constituents of sponge Mycale sp. from the South China Sea

doi: 10.3969/j.issn.1006-0111.2017.04.006
  • 1. Department of Pharmacy, Renji Hospital Affiliated to School of Medicine, Shanghai JiaoTong University, Shanghai 200127, China
  • 2. School of Traditional Chinese Materia Medica, Shenyang Pharmaceutical University, Shenyang 110016, China
  • Received Date: 2017-03-20
  • Rev Recd Date: 2017-05-19

Abstract: Objective To investigate the chemical constituents of marine sponge Mycale sp. collected from the South China Sea. Methods The ethyl acetate extract of the marine sponge Mycale sp. was separated and purified by repeated column chromatography on silica gel, Sephadex LH-20 and reversed-phase high-performance liquid chromatography (RP-HPLC). The structures of these compounds were identified by means of various modern spectroscopic techniques and comparison with their physicochemical properties to reported data. The tumor cell growth inhibitory activities of these compounds against human breast cancer cell lines MCF-7 and human lung cancer cell lines PC9 were tested by Cell Counting Kit-8 (CCK-8) method. Results Ten compounds were isolated and identified as cyclo-(Pro-Ile)( 1 ),cyclo-(Pro-Leu)( 2 ),cyclo-(Ile-Leu)( 3 ),cyclo-(Phe-Pro)( 4 ),cyclo-(Phe-Val)( 5 ),cyclo-(Phe-Leu)( 6 ),cyclo-(Phe-Ile)( 7 ), 2'-deoxythymidine ( 8 ), thymine ( 9 ), 5-hydroxy-3,4-dimethyl-5-pentyl-2(5H)-furanone ( 10 ). These compounds showed weak tumor cell growth inhibitory activities toward cells MCF-7 and PC9 in vitro. Conclusion Compounds 1 , 2 , 4 , 5 , 6 , 7 and 10 were isolated from the sponge Mycale sp. for the first time. It is the first time to report the antitumor activity evaluation for compounds 1 ~ 10 .

SUN Jiabao, WANG Shuping, WANG Jie, LIU Li, HAN Bingnan, LIN Houwen. Study on chemical constituents of sponge Mycale sp. from the South China Sea[J]. Journal of Pharmaceutical Practice and Service, 2017, 35(4): 308-314. doi: 10.3969/j.issn.1006-0111.2017.04.006
Citation: SUN Jiabao, WANG Shuping, WANG Jie, LIU Li, HAN Bingnan, LIN Houwen. Study on chemical constituents of sponge Mycale sp. from the South China Sea[J]. Journal of Pharmaceutical Practice and Service, 2017, 35(4): 308-314. doi: 10.3969/j.issn.1006-0111.2017.04.006
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