Chemical constituents from <i>Spongia</i> sp., a marine sponge in Xisha Islands

TIAN Yuan; XU Bin; WANG Jingfeng; LIN Houwen; YANG Lianjuan; YANG Fan

doi:10.3969/j.issn.1006-0111.2017.04.007

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Article Navigation > Journal of Pharmaceutical Practice and Service > 2017 > 35(4): 315-320,382

TIAN Yuan, XU Bin, WANG Jingfeng, LIN Houwen, YANG Lianjuan, YANG Fan. Chemical constituents from Spongia sp., a marine sponge in Xisha Islands[J]. Journal of Pharmaceutical Practice and Service, 2017, 35(4): 315-320,382. doi: 10.3969/j.issn.1006-0111.2017.04.007

Citation:

TIAN Yuan, XU Bin, WANG Jingfeng, LIN Houwen, YANG Lianjuan, YANG Fan. Chemical constituents from Spongia sp., a marine sponge in Xisha Islands[J]. Journal of Pharmaceutical Practice and Service, 2017, 35(4): 315-320,382. doi: 10.3969/j.issn.1006-0111.2017.04.007

Chemical constituents from Spongia sp., a marine sponge in Xisha Islands

doi: 10.3969/j.issn.1006-0111.2017.04.007

1.
College of Food and Biological Engineering, Jimei University, Xiamen 361021, China;Department of Pharmacy, Renji Hospital Affiliated to School of Medicine, Shanghai JiaoTong University, Shanghai, 200127, China
2.
Department of Pharmacy, Renji Hospital Affiliated to School of Medicine, Shanghai JiaoTong University, Shanghai, 200127, China
3.
Technology Research Institute, Western Mining Group Co., Ltd., Qinghai 810000, China
4.
Department of Fungal Diseases, Shanghai Dematology Hospital, Shanghai 200050, China

Received Date: 2017-01-17
Rev Recd Date: 2017-04-14

Abstract

Objective To investigate the chemical constituents in the marine sponge, Spongia sp., collected from the Xisha Islands. Methods The pure chemical components from the petroleum ether extract of Spongia sp.were obtained by repeated column chromatography on silica gel,ODS,Sephadex LH-20 and semi-preparative HPLC.Their structures were determined by spectroscopic analysis and comparison with the reported data.The antifungal activity of those compounds was evaluated by dilution method. Results 9 compounds were isolated and identified,including smenodiol( 1 ),smenospongorine( 2 ),5-epi-smenospongorine( 3 ),dictyoceratin C( 4 ),epi-smenospongidine( 5 ),dictyoceratin A( 6 ),stigmasta-4,6,8(14),22-tetraen-3-one( 7 ),3-oxo-4,6,8(14)-triunsaturated steroids( 8 ),ergosta-4,6,8(14),22-tetraen-3-one( 9 ). Conclusion Compounds 1 ~ 9 were isolated from the sponge of genus spongia for the first time.Compound 2 、 3 、 5 and 9 exhibited antifungal activities against Candida albicans,Trichophyton mentaqrophytes and Trichophyton rubrum with the MIC values of 12.5~25 μg/ml.
- Spongia sp.,
- chemical constituents,
- sequiterpene quinone,
- antifungal activity

References

[1]	Rueda A,Zubía E,Ortega MJ,et al.New metabolites from the sponge Spongia agaricina[J].J Nat Prod,1998,61(2):258-261.
[2]	Li CJ,Schmitz FJ,Kelly-Borges M.Six new spongian diterpenes from the sponge spongia matamat [J].J Nat Prod,1999,62(2):287-290.
[3]	Garrido L,Zubía E,Ortega MJ,et al.New furanoterpenoids from the sponge spongia officinalis[J].J Nat Prod,1997,60(8):794-797.
[4]	Guella G,Mancini I,Chiasera G,et al.Rogiolol acetate: A novel β-chamigrene-type sesquiterpeneisolated from a marine sponge[J].Helv Chim Acta,1990,73(6):1612-1620.
[5]	Utkina NK,Denisenko VA,Scholokova OV,et al.Cyclosmenospongine,a new sesquiterpenoid aminoquinone from an Australian marine sponge spongia sp.[J].Tetrahedron Lett,2003,44(1):101-102.
[6]	Sunassee SN,Davies-Coleman MT.Cytotoxic and antioxidant marine prenylated quinones and hydroquinones[J].Nat Prod Rep,2012,29(5):513-535.
[7]	Sladic D,Gasic MJ.Reactivity and biological activity of the marine sesquiterpene hydroquinone avarol and related compounds from sponges of the order dictyoceratida[J].Molecules,2006,11(1):1-33.
[8]	Yamakawa Y,Kato T,Ito J,et al.Identification of growth-promoting factors from various glioma cell lines and partial purification of the factor from C6 solid tumor[J].Neurochem Int,2014,4(5):367-373.
[9]	Qiu Y,Wang XM.A new sesquiterpenoid hydroquinone from the marine sponge Dysidea arenaria[J].Molecules,2008,13(6):1275-1281.
[10]	Nguyen HM,Ito T,Win NN,et al.New antibacterial sesquiterpene aminoquinones from a Vietnamese marine sponge of Spongia sp.[J].Phytochem Lett,2016,17(3):288-292.
[11]	Kondracki ML,Guyot M.Biologically active quinone and hydroquinone sesquiterpenoids from the sponge Smenospongia sp.[J].Tetrahedron,1989,45(7):1995-2004.
[12]	Zhang Y,Li Y,Guo YW,et al.A sesquiterpene quinone,dysidine,from the sponge Dysidea villosa,activates the insulin pathway through inhibition of PTPases[J].Acta Pharmacol Sin,2009,30(3):333-345.
[13]	Liu H,Wang G,Namikoshi M,et al.Sesquiterpene quinones from a marine sponge Hippospongia sp.that inhibit maturation of starfish oocytes and induce cell cycle arrest with HepG2 cells[J].Pharm Biol,2006,44(7):522-527.
[14]	Laube T,Bernet A,Dahse HM,et al.Synthesis and pharmacological activities of some sesquiterpene quinones and hydroquinones[J].Bioorg Med Chem,2009,17(4):1422-1427.
[15]	Bernet A,Schr der J,Seifert K.Total synthesis of the marine sesquiterpene quinones hyatellaquinone and spongiaquinone[J].Helv Chim Acta,2003,86(6):2009-2020.
[16]	Marcos IS,Conde A,Moro RF,et al.Synthesis of quinone/hydroquinone sesquiterpenes[J].Tetrahedron,2010,66(42):8280-8290.
[17]	Venkateswarlu Y,Faulkner DJ,Steiner JLR,et al.Smenochromenes,unusual macrocyclic sesquiterpene hydroquinone derivatives from a Seychelles sponge of the genus Smenospongia[J].J Org Chem,1991,56(22):6271-6274.
[18]	Kondracki ML,Guyot M.Smenospongine: acytotoxic and antimicrobial aminoquinone isolated from smenospongia sp.[J].Tetrahedron Lett,28(47):5815-5818.
[19]	Aoki S,Kong D,Matsui K,et al.Sesquiterpene aminoquinones,from a marine sponge,induce erythroid differentiation in human chronic myelogenous leukemia,K562 cells[J].Chem Pharm Bull,2004,52(8):935-937.
[20]	Mitome H,Nagasawa T,Miyaoka H,et al.Dactyloquinones C,D and E novel sesquiterpenoid quinones,from the Okinawan marine sponge,Dactylospongia elegans[J].J Nat Prod,2002,58(9):1693-1696.
[21]	Rodriguez J,Quinoa E,Riguera R,et al. The structures and stereochemistry of cytotoxic sesquiterpene quinones from dactylospongia elegans[J].Tetrahedron,1992,48(32):6667-6680.
[22]	Ibrahim SRM, Elkhayat ES, Mohamed GA,et al.Aspernolides F and G,new butyrolactones from the endophytic fungus Aspergillus terreus[J].Phytochem Lett,2015,14(4):84-90.
[23]	Kobayashi M,Krishna MM,Ishida K,et al.Marine sterols.XXⅡ.occurrence of 3-oxo-4,6,8(14)-triunsaturated steroids in the sponge dysidea herbacea[J].Chem Pharm Bull,1992,40(1):72-74.
[24]	Fujimoto H, Nakamura E, Okuyama E,et al.Six immunosuppressive features from an ascomycete,Zopfiella longicaudata,found in a screening study monitored by immunomodulatory activity[J].Chem Pharm Bull,2004,52(8):1005-1008.
[25]	Pierce CG,Uppuluri P,Tristan AR,et al.A simple and reproducible 96-well plate-based method for the formation of fungal biofilms and its application to antifungal susceptibility testing[J].Nat Protoc,2008,3(9):1494-1500.
[26]	Espinel-Ingroff A,Fothergill A,Fuller J,et al.Wild-type MIC distributions and epidemiological cutoff values for caspofungin and Aspergillus spp.for the CLSI broth microdilution method(M38-A2 document)[J].Antimicrob Agents Chemother,2011,55(6):2855-2859.

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通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142

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Chemical constituents from Spongia sp., a marine sponge in Xisha Islands

1. College of Food and Biological Engineering, Jimei University, Xiamen 361021, China;Department of Pharmacy, Renji Hospital Affiliated to School of Medicine, Shanghai JiaoTong University, Shanghai, 200127, China

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

3. Technology Research Institute, Western Mining Group Co., Ltd., Qinghai 810000, China

4. Department of Fungal Diseases, Shanghai Dematology Hospital, Shanghai 200050, China

Received Date: 2017-01-17

Rev Recd Date: 2017-04-14

Key words:

Abstract: Objective To investigate the chemical constituents in the marine sponge, Spongia sp., collected from the Xisha Islands. Methods The pure chemical components from the petroleum ether extract of Spongia sp.were obtained by repeated column chromatography on silica gel,ODS,Sephadex LH-20 and semi-preparative HPLC.Their structures were determined by spectroscopic analysis and comparison with the reported data.The antifungal activity of those compounds was evaluated by dilution method. Results 9 compounds were isolated and identified,including smenodiol( 1 ),smenospongorine( 2 ),5-epi-smenospongorine( 3 ),dictyoceratin C( 4 ),epi-smenospongidine( 5 ),dictyoceratin A( 6 ),stigmasta-4,6,8(14),22-tetraen-3-one( 7 ),3-oxo-4,6,8(14)-triunsaturated steroids( 8 ),ergosta-4,6,8(14),22-tetraen-3-one( 9 ). Conclusion Compounds 1 ~ 9 were isolated from the sponge of genus spongia for the first time.Compound 2 、 3 、 5 and 9 exhibited antifungal activities against Candida albicans,Trichophyton mentaqrophytes and Trichophyton rubrum with the MIC values of 12.5~25 μg/ml.

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Reference (26)

[1]	Rueda A,Zubía E,Ortega MJ,et al.New metabolites from the sponge Spongia agaricina[J].J Nat Prod,1998,61(2):258-261.
[2]	Li CJ,Schmitz FJ,Kelly-Borges M.Six new spongian diterpenes from the sponge spongia matamat [J].J Nat Prod,1999,62(2):287-290.
[3]	Garrido L,Zubía E,Ortega MJ,et al.New furanoterpenoids from the sponge spongia officinalis[J].J Nat Prod,1997,60(8):794-797.
[4]	Guella G,Mancini I,Chiasera G,et al.Rogiolol acetate: A novel β-chamigrene-type sesquiterpeneisolated from a marine sponge[J].Helv Chim Acta,1990,73(6):1612-1620.
[5]	Utkina NK,Denisenko VA,Scholokova OV,et al.Cyclosmenospongine,a new sesquiterpenoid aminoquinone from an Australian marine sponge spongia sp.[J].Tetrahedron Lett,2003,44(1):101-102.
[6]	Sunassee SN,Davies-Coleman MT.Cytotoxic and antioxidant marine prenylated quinones and hydroquinones[J].Nat Prod Rep,2012,29(5):513-535.
[7]	Sladic D,Gasic MJ.Reactivity and biological activity of the marine sesquiterpene hydroquinone avarol and related compounds from sponges of the order dictyoceratida[J].Molecules,2006,11(1):1-33.
[8]	Yamakawa Y,Kato T,Ito J,et al.Identification of growth-promoting factors from various glioma cell lines and partial purification of the factor from C6 solid tumor[J].Neurochem Int,2014,4(5):367-373.
[9]	Qiu Y,Wang XM.A new sesquiterpenoid hydroquinone from the marine sponge Dysidea arenaria[J].Molecules,2008,13(6):1275-1281.
[10]	Nguyen HM,Ito T,Win NN,et al.New antibacterial sesquiterpene aminoquinones from a Vietnamese marine sponge of Spongia sp.[J].Phytochem Lett,2016,17(3):288-292.
[11]	Kondracki ML,Guyot M.Biologically active quinone and hydroquinone sesquiterpenoids from the sponge Smenospongia sp.[J].Tetrahedron,1989,45(7):1995-2004.
[12]	Zhang Y,Li Y,Guo YW,et al.A sesquiterpene quinone,dysidine,from the sponge Dysidea villosa,activates the insulin pathway through inhibition of PTPases[J].Acta Pharmacol Sin,2009,30(3):333-345.
[13]	Liu H,Wang G,Namikoshi M,et al.Sesquiterpene quinones from a marine sponge Hippospongia sp.that inhibit maturation of starfish oocytes and induce cell cycle arrest with HepG2 cells[J].Pharm Biol,2006,44(7):522-527.
[14]	Laube T,Bernet A,Dahse HM,et al.Synthesis and pharmacological activities of some sesquiterpene quinones and hydroquinones[J].Bioorg Med Chem,2009,17(4):1422-1427.
[15]	Bernet A,Schr der J,Seifert K.Total synthesis of the marine sesquiterpene quinones hyatellaquinone and spongiaquinone[J].Helv Chim Acta,2003,86(6):2009-2020.
[16]	Marcos IS,Conde A,Moro RF,et al.Synthesis of quinone/hydroquinone sesquiterpenes[J].Tetrahedron,2010,66(42):8280-8290.
[17]	Venkateswarlu Y,Faulkner DJ,Steiner JLR,et al.Smenochromenes,unusual macrocyclic sesquiterpene hydroquinone derivatives from a Seychelles sponge of the genus Smenospongia[J].J Org Chem,1991,56(22):6271-6274.
[18]	Kondracki ML,Guyot M.Smenospongine: acytotoxic and antimicrobial aminoquinone isolated from smenospongia sp.[J].Tetrahedron Lett,28(47):5815-5818.
[19]	Aoki S,Kong D,Matsui K,et al.Sesquiterpene aminoquinones,from a marine sponge,induce erythroid differentiation in human chronic myelogenous leukemia,K562 cells[J].Chem Pharm Bull,2004,52(8):935-937.
[20]	Mitome H,Nagasawa T,Miyaoka H,et al.Dactyloquinones C,D and E novel sesquiterpenoid quinones,from the Okinawan marine sponge,Dactylospongia elegans[J].J Nat Prod,2002,58(9):1693-1696.
[21]	Rodriguez J,Quinoa E,Riguera R,et al. The structures and stereochemistry of cytotoxic sesquiterpene quinones from dactylospongia elegans[J].Tetrahedron,1992,48(32):6667-6680.
[22]	Ibrahim SRM, Elkhayat ES, Mohamed GA,et al.Aspernolides F and G,new butyrolactones from the endophytic fungus Aspergillus terreus[J].Phytochem Lett,2015,14(4):84-90.
[23]	Kobayashi M,Krishna MM,Ishida K,et al.Marine sterols.XXⅡ.occurrence of 3-oxo-4,6,8(14)-triunsaturated steroids in the sponge dysidea herbacea[J].Chem Pharm Bull,1992,40(1):72-74.
[24]	Fujimoto H, Nakamura E, Okuyama E,et al.Six immunosuppressive features from an ascomycete,Zopfiella longicaudata,found in a screening study monitored by immunomodulatory activity[J].Chem Pharm Bull,2004,52(8):1005-1008.
[25]	Pierce CG,Uppuluri P,Tristan AR,et al.A simple and reproducible 96-well plate-based method for the formation of fungal biofilms and its application to antifungal susceptibility testing[J].Nat Protoc,2008,3(9):1494-1500.
[26]	Espinel-Ingroff A,Fothergill A,Fuller J,et al.Wild-type MIC distributions and epidemiological cutoff values for caspofungin and Aspergillus spp.for the CLSI broth microdilution method(M38-A2 document)[J].Antimicrob Agents Chemother,2011,55(6):2855-2859.

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Chemical constituents from Spongia sp., a marine sponge in Xisha Islands

doi: 10.3969/j.issn.1006-0111.2017.04.007

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Chemical constituents from Spongia sp., a marine sponge in Xisha Islands

doi: 10.3969/j.issn.1006-0111.2017.04.007

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