Advances in secondary metabolites of coral epiphytic fungi

WANG Hongliang; ZHANG Wen

doi:10.3969/j.issn.1006-0111.2019.03.001

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Article Navigation > Journal of Pharmaceutical Practice and Service > 2019 > 37(3): 193-200,253

WANG Hongliang, ZHANG Wen. Advances in secondary metabolites of coral epiphytic fungi[J]. Journal of Pharmaceutical Practice and Service, 2019, 37(3): 193-200,253. doi: 10.3969/j.issn.1006-0111.2019.03.001

Citation:

WANG Hongliang, ZHANG Wen. Advances in secondary metabolites of coral epiphytic fungi[J]. Journal of Pharmaceutical Practice and Service, 2019, 37(3): 193-200,253. doi: 10.3969/j.issn.1006-0111.2019.03.001

Advances in secondary metabolites of coral epiphytic fungi

doi: 10.3969/j.issn.1006-0111.2019.03.001

WANG Hongliang¹,
ZHANG Wen^2
,

1.
School of Pharmacy, Naval Medical University, Shanghai 200433, China;Sergeant School of Army Medical College, Shijiazhuang 050000, China
2.
School of Pharmacy, Naval Medical University, Shanghai 200433, China

Received Date: 2018-10-02
Rev Recd Date: 2019-03-04

Abstract

More and more attentions had been paid to the chemical constituents of epiphytic fungi in coral.By the end of 2014,95 species of epiphytic fungi,involving 44 genera,were isolated from 38 coral species.More than 200 compounds were isolated from them.These compounds exhibited anti-tumor,anti-fungal,anti-inflammatory and anti-fouling biological activities.In recent years,the number of new compounds from coral epiphytic fungi had been increasing year by year,and nearly 100 compounds had been found in recent four years.These structures showed different biological activities.The progress on secondary metabolites of coral symbiotic epiphytic fungi in recent four years was reviewed from the aspects of chemical structure and biological activity,which could provide reference for further study.
- coral epiphytic fungi,
- secondary metabolites,
- chemical structure,
- bioactivity

References

[1]	KELECOM A.Secondary metabolites from marine microorganisms[J].An Acad Bras Cienc,2002,74(1):151-170.
[2]	RATEB M E,EBEL R.Secondary metabolites of fungi from marine habitats[J].Nat Prod Rep,2011,28(2):290-344.
[3]	SALEEM M,ALI M S,HUSSAIN S,et al.Marine natural products of fungal origin[J].Nat Prod Rep,2007,24(5):1142-1152.
[4]	HOU X M,XU R F,GU Y C,et al.Biological and chemical diversity of coral-derived microorganisms[J].Curr Med Chem,2015,22(32):3707-3762.
[5]	FRIEDRICH A B,MERKERT H,FENDERT T,et al.Microbial diversity in the marine sponge Aplysinacavernicola (formerly Verongia cavernicola) analyzed by fluorescence in situ hybridization (FISH)[J].Mar Biol,1999,134(3):461-470.
[6]	TAPIOLAS D M,ROMAN M,FENICAL W,et al.Octalactins A and B:cytotoxic eight-membered-ring lactones from a marine bacterium Streptomyces sp[J].J Ame Chem Soc,1991,113(113):4682-4683.
[7]	BLUNT J W,COPP B R,KEYZERS R A,et al.Marine natural products.[J].Nat Prod Rep,2018,35(1):8-53.
[8]	HILL A M.The biosynthesis,molecular genetics and enzymology of the polyketide-derived metabolites[J].Nat Prod Rep,2006,23(2):256-320.
[9]	SHI T,HOU X M,LI Z Y,et al.Harzianumnones A and B:two hydroxyanthraquinones from the coral-derived fungus Trichoderma harzianum[J].RSC Advances,2018,8(49):27596-27601.
[10]	WANG W Y,LIAO Y Y,TANG C,et al.Cytotoxic and antibacterial compounds from the coral-derived fungus Aspergillus tritici SP2-8-1[J].Mar Drugs,2017,15(11):348.
[11]	SUN Y Z,KURTÁN T,MÁNDI A,et al.Immunomodulatory polyketides from a phoma-like fungus isolated from a soft coral[J].J Nat Prod,2017,80(11):2930-2940.
[12]	LIU M T,ZHOU Q,et al.Anti-inflammatory butenolide derivatives from the coral-derived fungus Aspergillus terreus and structure revisions of aspernolides D and G,butyrolactone Ⅵ and 4',8″-diacetoxy butyrolactone Ⅵ[J].J Ame Chem Soc,2018,8:13040.
[13]	ZHU M,GAO H,WU C,et al.Lipid-lowering polyketides from a soft coral-derived fungus Cladosporium sp.TZP29[J].Bioorg Med Chem Lett,2015,25(17):3606-3609.
[14]	MA J,ZHANG X L,WANG Y,et al.Aspergivones A and B,two new flavones isolated from a gorgonian-derived Aspergillus candidus fungus[J].Nat Prod Res,2017,31(1):32-36.
[15]	ZHENG C J,SHAO C L,CHEN M,et al.Merosesquiterpenoids and ten-membered macrolides from a soft coral-derived Lophiostoma sp.fungus[J].Chem Biodivers,2015,12(9):1407-1414.
[16]	ELNAGGAR M S,EBADA S S,ASHOUR M L,et al.Two new triterpenoids and a new naphthoquinone derivative isolated from a hard coral-derived fungus Scopulariopsis sp.[J].Fitoterapia,2017,116:126-130.
[17]	ELNAGGAR M S,EBADA S S,ASHOUR M L,et al.Xanthones and sesquiterpene derivatives from a marine-derived fungus Scopulariopsis sp.[J].Tetrahedron,2016,72(19):2411-2419.
[18]	ZHENG C J,FU X M,ZHANG X L,et al.Bioactive perylene derivatives from asoft coral-derived fungus Alternaria sp.(ZJ-2008017)[J].Chem Nat Compd,2015,51(4):766-768.
[19]	KIM J W,KO S K,KIM H M,et al.Stachybotrysin,an osteoclast differentiation inhibitor from the marine-derived fungus Stachybotrys sp.KCB13F013[J].J Nat Prod,2016,79(10):2703-2708.
[20]	YANG B Y,SUN W G,WANG J P,et al.A new breviane spiroditerpenoid from the marine-derived fungus Penicillium sp.TJ403-1[J].Mar Drugs,2018,16(4):110-119
[21]	KOCHANOWSKA-KARAMYAN A J,HAMANN M T.Marine indole alkaloids:potential new drug leads for the control of depression and anxiety[J].Chem Rev,2010,110(8):4489-4497.
[22]	郭娜燕,吕国荣,邱丹缨.海洋来源放线菌中新生物碱成分研究进展[J].天然产物研究与开发,2017,29(1):159-171.
[23]	NETZ N,OPATZ T.Marine indole alkaloids[J].Mar Drugs,2015,13(8):4814-4914.
[24]	LIU W,LI H J,XU M Y,et al.ChemInform abstract:pseudellones A-C,three alkaloids from the marine-derived fungus Pseudallescheria ellipsoidea F42-3.[J].ChemInform,2016,47(12):5156-5159.
[25]	WANG K T,XU M Y,LIU W,et al.Two additional new compounds from the marine-derived fungus Pseudallescheria ellipsoidea F42-3[J].Molecules,2016,21(4):442.
[26]	SHAO C L,XU R F,WANG C Y,et al.Potent Antifouling marine dihydroquinolin-2(1H)-one-containing alkaloids from the gorgonian coral-derived fungus Scopulariopsis sp[J].Mar Biotechnol,2015,17(4):408-415.
[27]	管华诗,韩玉谦,冯晓梅.海洋活性多肽的研究进展[J].中国海洋大学学报(自然科学版),2004,34(5):761-766.
[28]	DAI Y,LIN Y,PANG X Y,et al.Peptides from the soft coral-associated fungus Simplicillium sp.SCSIO41209[J].Phytochemistry,2018,154:56-62.
[29]	MA X,NONG X H,REN Z,et al.Antiviral peptides from marine gorgonian-derived fungus Aspergillus sp.SCSIO 41501[J].Tetrahedron Lett,2017,58(12):1151-1155.
[30]	崔承彬.激活海洋真菌中沉默次级代谢产物的实验技术新方法探索[C]//2014年中国药学大会暨第十四届中国药师周论文集.石家庄,2014:82.
[31]	REEN F J,ROMANO S,DOBSON A D,et al.The sound of silence:activating silent biosynthetic gene clusters in marine microorganisms[J].Mar Drugs,2015,13(8):4754-4783.

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通讯作者: 陈斌, bchen63@163.com

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沈阳化工大学材料科学与工程学院沈阳 110142

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Advances in secondary metabolites of coral epiphytic fungi

1. School of Pharmacy, Naval Medical University, Shanghai 200433, China;Sergeant School of Army Medical College, Shijiazhuang 050000, China

2. School of Pharmacy, Naval Medical University, Shanghai 200433, China

Received Date: 2018-10-02

Rev Recd Date: 2019-03-04

Key words:

Abstract: More and more attentions had been paid to the chemical constituents of epiphytic fungi in coral.By the end of 2014,95 species of epiphytic fungi,involving 44 genera,were isolated from 38 coral species.More than 200 compounds were isolated from them.These compounds exhibited anti-tumor,anti-fungal,anti-inflammatory and anti-fouling biological activities.In recent years,the number of new compounds from coral epiphytic fungi had been increasing year by year,and nearly 100 compounds had been found in recent four years.These structures showed different biological activities.The progress on secondary metabolites of coral symbiotic epiphytic fungi in recent four years was reviewed from the aspects of chemical structure and biological activity,which could provide reference for further study.

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Reference (31)

[1]	KELECOM A.Secondary metabolites from marine microorganisms[J].An Acad Bras Cienc,2002,74(1):151-170.
[2]	RATEB M E,EBEL R.Secondary metabolites of fungi from marine habitats[J].Nat Prod Rep,2011,28(2):290-344.
[3]	SALEEM M,ALI M S,HUSSAIN S,et al.Marine natural products of fungal origin[J].Nat Prod Rep,2007,24(5):1142-1152.
[4]	HOU X M,XU R F,GU Y C,et al.Biological and chemical diversity of coral-derived microorganisms[J].Curr Med Chem,2015,22(32):3707-3762.
[5]	FRIEDRICH A B,MERKERT H,FENDERT T,et al.Microbial diversity in the marine sponge Aplysinacavernicola (formerly Verongia cavernicola) analyzed by fluorescence in situ hybridization (FISH)[J].Mar Biol,1999,134(3):461-470.
[6]	TAPIOLAS D M,ROMAN M,FENICAL W,et al.Octalactins A and B:cytotoxic eight-membered-ring lactones from a marine bacterium Streptomyces sp[J].J Ame Chem Soc,1991,113(113):4682-4683.
[7]	BLUNT J W,COPP B R,KEYZERS R A,et al.Marine natural products.[J].Nat Prod Rep,2018,35(1):8-53.
[8]	HILL A M.The biosynthesis,molecular genetics and enzymology of the polyketide-derived metabolites[J].Nat Prod Rep,2006,23(2):256-320.
[9]	SHI T,HOU X M,LI Z Y,et al.Harzianumnones A and B:two hydroxyanthraquinones from the coral-derived fungus Trichoderma harzianum[J].RSC Advances,2018,8(49):27596-27601.
[10]	WANG W Y,LIAO Y Y,TANG C,et al.Cytotoxic and antibacterial compounds from the coral-derived fungus Aspergillus tritici SP2-8-1[J].Mar Drugs,2017,15(11):348.
[11]	SUN Y Z,KURTÁN T,MÁNDI A,et al.Immunomodulatory polyketides from a phoma-like fungus isolated from a soft coral[J].J Nat Prod,2017,80(11):2930-2940.
[12]	LIU M T,ZHOU Q,et al.Anti-inflammatory butenolide derivatives from the coral-derived fungus Aspergillus terreus and structure revisions of aspernolides D and G,butyrolactone Ⅵ and 4',8″-diacetoxy butyrolactone Ⅵ[J].J Ame Chem Soc,2018,8:13040.
[13]	ZHU M,GAO H,WU C,et al.Lipid-lowering polyketides from a soft coral-derived fungus Cladosporium sp.TZP29[J].Bioorg Med Chem Lett,2015,25(17):3606-3609.
[14]	MA J,ZHANG X L,WANG Y,et al.Aspergivones A and B,two new flavones isolated from a gorgonian-derived Aspergillus candidus fungus[J].Nat Prod Res,2017,31(1):32-36.
[15]	ZHENG C J,SHAO C L,CHEN M,et al.Merosesquiterpenoids and ten-membered macrolides from a soft coral-derived Lophiostoma sp.fungus[J].Chem Biodivers,2015,12(9):1407-1414.
[16]	ELNAGGAR M S,EBADA S S,ASHOUR M L,et al.Two new triterpenoids and a new naphthoquinone derivative isolated from a hard coral-derived fungus Scopulariopsis sp.[J].Fitoterapia,2017,116:126-130.
[17]	ELNAGGAR M S,EBADA S S,ASHOUR M L,et al.Xanthones and sesquiterpene derivatives from a marine-derived fungus Scopulariopsis sp.[J].Tetrahedron,2016,72(19):2411-2419.
[18]	ZHENG C J,FU X M,ZHANG X L,et al.Bioactive perylene derivatives from asoft coral-derived fungus Alternaria sp.(ZJ-2008017)[J].Chem Nat Compd,2015,51(4):766-768.
[19]	KIM J W,KO S K,KIM H M,et al.Stachybotrysin,an osteoclast differentiation inhibitor from the marine-derived fungus Stachybotrys sp.KCB13F013[J].J Nat Prod,2016,79(10):2703-2708.
[20]	YANG B Y,SUN W G,WANG J P,et al.A new breviane spiroditerpenoid from the marine-derived fungus Penicillium sp.TJ403-1[J].Mar Drugs,2018,16(4):110-119
[21]	KOCHANOWSKA-KARAMYAN A J,HAMANN M T.Marine indole alkaloids:potential new drug leads for the control of depression and anxiety[J].Chem Rev,2010,110(8):4489-4497.
[22]	郭娜燕,吕国荣,邱丹缨.海洋来源放线菌中新生物碱成分研究进展[J].天然产物研究与开发,2017,29(1):159-171.
[23]	NETZ N,OPATZ T.Marine indole alkaloids[J].Mar Drugs,2015,13(8):4814-4914.
[24]	LIU W,LI H J,XU M Y,et al.ChemInform abstract:pseudellones A-C,three alkaloids from the marine-derived fungus Pseudallescheria ellipsoidea F42-3.[J].ChemInform,2016,47(12):5156-5159.
[25]	WANG K T,XU M Y,LIU W,et al.Two additional new compounds from the marine-derived fungus Pseudallescheria ellipsoidea F42-3[J].Molecules,2016,21(4):442.
[26]	SHAO C L,XU R F,WANG C Y,et al.Potent Antifouling marine dihydroquinolin-2(1H)-one-containing alkaloids from the gorgonian coral-derived fungus Scopulariopsis sp[J].Mar Biotechnol,2015,17(4):408-415.
[27]	管华诗,韩玉谦,冯晓梅.海洋活性多肽的研究进展[J].中国海洋大学学报(自然科学版),2004,34(5):761-766.
[28]	DAI Y,LIN Y,PANG X Y,et al.Peptides from the soft coral-associated fungus Simplicillium sp.SCSIO41209[J].Phytochemistry,2018,154:56-62.
[29]	MA X,NONG X H,REN Z,et al.Antiviral peptides from marine gorgonian-derived fungus Aspergillus sp.SCSIO 41501[J].Tetrahedron Lett,2017,58(12):1151-1155.
[30]	崔承彬.激活海洋真菌中沉默次级代谢产物的实验技术新方法探索[C]//2014年中国药学大会暨第十四届中国药师周论文集.石家庄,2014:82.
[31]	REEN F J,ROMANO S,DOBSON A D,et al.The sound of silence:activating silent biosynthetic gene clusters in marine microorganisms[J].Mar Drugs,2015,13(8):4754-4783.

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Advances in secondary metabolites of coral epiphytic fungi

doi: 10.3969/j.issn.1006-0111.2019.03.001

Abstract

References

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通讯作者: 陈斌, bchen63@163.com

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