Morindolestatin, Naturally Occurring Dehydromorpholinocarbazole Alkaloid from Soil-Derived Bacterium of the Genus Streptomyces

Novel antilipid peroxidative carbazole alkaloids, antiostatin A5 (1), antiostatin A6 (2), and (±)-morindolestatin (3), were isolated from a new soil-derived Streptomyces sp. Compound 2 possesses an unusual cyclohexene side chain. Compound 3 was a pair of enantiomers featuring an unprecedented [1,4]­...

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Published inOrganic letters Vol. 22; no. 3; pp. 1113 - 1116
Main Authors Zhang, Shao-Yong, Zhan, Zha-Jun, Zhang, Hui, Qi, Huan, Zhang, Li-Qin, Chen, Shi-Xin, Gan, Li-She, Wang, Ji-Dong, Ma, Lie-Feng
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 07.02.2020
Amer Chemical Soc
Subjects
Alkaloids - chemistry
Alkaloids - isolation & purification
Alkaloids - metabolism
Biological Products - chemistry
Biological Products - isolation & purification
Biological Products - metabolism
Carbazoles - chemistry
Carbazoles - isolation & purification
Chemistry
Chemistry, Organic
Molecular Structure
Physical Sciences
Science & Technology
Stereoisomerism
Streptomyces - chemistry
Streptomyces - metabolism
IN-VITRO
AGENTS
CARBAZOLE
PEROXIDATION
BIOSYNTHESIS
NEOCARAZOSTATIN
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Summary:Novel antilipid peroxidative carbazole alkaloids, antiostatin A5 (1), antiostatin A6 (2), and (±)-morindolestatin (3), were isolated from a new soil-derived Streptomyces sp. Compound 2 possesses an unusual cyclohexene side chain. Compound 3 was a pair of enantiomers featuring an unprecedented [1,4]­oxazino­[2,3-c]­carbazole ring system. The absolute configuration of 3 was determined by online HPLC-ECD and ECD calculation. A racemization mechanism and putative biosynthetic pathway are discussed.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
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content type line 23
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.9b04609