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Isolation and characterization of three pairs of indolediketopiperazine enantiomers containing infrequent N-methoxy substitution from the marine algal-derived endophytic fungus Acrostalagmus luteoalbus TK-43
Cao, Jin1,2,3; Li, Xiao-Ming1,2; Meng, Ling-Hong1,2; Konuklugil, Belma4; Li, Xin1,2,5; Li, Hong-Lei1,2,5; Wang, Bin-Gui1,2,5
2019-09-01
Source PublicationBIOORGANIC CHEMISTRY
ISSN0045-2068
Volume90Pages:7
Corresponding AuthorWang, Bin-Gui(wangbg@ms.qdio.ac.cn)
AbstractThree pairs of new N-methoxy-containing indolediketopiperazine enantiomers, acrozines A-C (1-3), were isolated from the culture extract of Acrostalagmus luteoalbus TK-43, an endophytic fungus obtained from the marine green alga Codium fragile. The optical resolution of compounds 1-3 by chiral HPLC successfully afforded individual enantiomers (+)-1/(-)-1, (+)-2/(-)-2, and (+)-3/(-)-3, respectively. The structures of all these compounds were established on the basis of detailed interpretation of their NMR and mass spectroscopic data. X-ray crystallographic analysis confirmed the structures of compounds 1-3, while the absolute configurations were determined by TDDFT-ECD calculations. All these compounds containing a N-methoxy group which is uncommon in indolediketopiperazines. The enantiomers, (+)-2/(-)- 2, showed different antimicrobial activities against several plant-pathogenic fungi, while (+)-1 displayed better inhibitory activity against acetylcholinesterase than that of (-)-1.
KeywordAcrostalagmus luteoalbus N-methoxy Indolediketopiperazine enantiomers Anti-acetylcholinesterase activity Anti-microbial activity
DOI10.1016/j.bioorg.2019.103030
Indexed BySCI
Language英语
Funding ProjectNational Natural Science Foundation of China (NSFC)[81673351] ; National Natural Science Foundation of China (NSFC)[31330009] ; European Commission under the program Marie Curie Actions-International Research Staff Exchange Scheme (IRSES)[PIRSES-GA-2011-295226] ; Taishan Scholar Project from Shandong Province of China
WOS Research AreaBiochemistry & Molecular Biology ; Chemistry
WOS SubjectBiochemistry & Molecular Biology ; Chemistry, Organic
WOS IDWOS:000479184600030
PublisherACADEMIC PRESS INC ELSEVIER SCIENCE
Citation statistics
Document Type期刊论文
Identifierhttp://ir.qdio.ac.cn/handle/337002/162403
Collection实验海洋生物学重点实验室
Corresponding AuthorWang, Bin-Gui
Affiliation1.Chinese Acad Sci, Inst Oceanol, Key Lab Expt Marine Biol, Nanhai Rd 7, Qingdao 266071, Shandong, Peoples R China
2.Qingdao Natl Lab Marine Sci & Technol, Lab Marine Biol & Biotechnol, Nanhai Rd 7, Qingdao 266071, Shandong, Peoples R China
3.Univ Chinese Acad Sci, Yuquan Rd 19A, Beijing 100049, Peoples R China
4.Ankara Univ, Fac Pharm, Dept Pharmacognosy, TR-06110 Ankara, Turkey
5.Chinese Acad Sci, Ctr Ocean Mega Sci, Nanhai Rd 7, Qingdao 266071, Shandong, Peoples R China
First Author AffilicationInstitute of Oceanology, Chinese Academy of Sciences
Corresponding Author AffilicationInstitute of Oceanology, Chinese Academy of Sciences
Recommended Citation
GB/T 7714
Cao, Jin,Li, Xiao-Ming,Meng, Ling-Hong,et al. Isolation and characterization of three pairs of indolediketopiperazine enantiomers containing infrequent N-methoxy substitution from the marine algal-derived endophytic fungus Acrostalagmus luteoalbus TK-43[J]. BIOORGANIC CHEMISTRY,2019,90:7.
APA Cao, Jin.,Li, Xiao-Ming.,Meng, Ling-Hong.,Konuklugil, Belma.,Li, Xin.,...&Wang, Bin-Gui.(2019).Isolation and characterization of three pairs of indolediketopiperazine enantiomers containing infrequent N-methoxy substitution from the marine algal-derived endophytic fungus Acrostalagmus luteoalbus TK-43.BIOORGANIC CHEMISTRY,90,7.
MLA Cao, Jin,et al."Isolation and characterization of three pairs of indolediketopiperazine enantiomers containing infrequent N-methoxy substitution from the marine algal-derived endophytic fungus Acrostalagmus luteoalbus TK-43".BIOORGANIC CHEMISTRY 90(2019):7.
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