Cycloheximide congeners produced by Streptomyces sp. SC0581 and photoinduced interconversion between (E)- and (Z)-2,3-dehydroanhydrocycloheximides

Three new cycloheximide congeners, 2,3-dehydro-α-epi-isocycloheximide (1), (E)- and (Z)-2,3-dehydroanhydrocycloheximides (2 and 3), together with three known compounds, anhydroisoheximide (4), cycloheximide (5), and isocycloheximide (6), were obtained from the cultures of Streptomyces sp. SC0581. Th...

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Main Authors: Li Yang, Ping Wu, Jinghua Xue, Huitong Tan, Zheng Zhang, Xiaoyi Wei
Format: Article
Language:English
Published: Beilstein-Institut 2017-05-01
Series:Beilstein Journal of Organic Chemistry
Subjects:
Online Access:https://doi.org/10.3762/bjoc.13.103
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spelling doaj-1984e15320ca46d8be8669da962d853e2021-04-02T10:09:35ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972017-05-011311039104910.3762/bjoc.13.1031860-5397-13-103Cycloheximide congeners produced by Streptomyces sp. SC0581 and photoinduced interconversion between (E)- and (Z)-2,3-dehydroanhydrocycloheximidesLi Yang0Ping Wu1Jinghua Xue2Huitong Tan3Zheng Zhang4Xiaoyi Wei5Key Laboratory of Plant Resources Conservation and Sustainable Utilization, Guangdong Provincial Key Laboratory of Digital Botanical Garden, South China Botanical Garden, Chinese Academy of Sciences, Xingke Road 723, Tianhe District, Guangzhou 510650, ChinaKey Laboratory of Plant Resources Conservation and Sustainable Utilization, Guangdong Provincial Key Laboratory of Digital Botanical Garden, South China Botanical Garden, Chinese Academy of Sciences, Xingke Road 723, Tianhe District, Guangzhou 510650, ChinaKey Laboratory of Plant Resources Conservation and Sustainable Utilization, Guangdong Provincial Key Laboratory of Digital Botanical Garden, South China Botanical Garden, Chinese Academy of Sciences, Xingke Road 723, Tianhe District, Guangzhou 510650, ChinaKey Laboratory of Plant Resources Conservation and Sustainable Utilization, Guangdong Provincial Key Laboratory of Digital Botanical Garden, South China Botanical Garden, Chinese Academy of Sciences, Xingke Road 723, Tianhe District, Guangzhou 510650, ChinaKey Laboratory of Plant Resources Conservation and Sustainable Utilization, Guangdong Provincial Key Laboratory of Digital Botanical Garden, South China Botanical Garden, Chinese Academy of Sciences, Xingke Road 723, Tianhe District, Guangzhou 510650, ChinaKey Laboratory of Plant Resources Conservation and Sustainable Utilization, Guangdong Provincial Key Laboratory of Digital Botanical Garden, South China Botanical Garden, Chinese Academy of Sciences, Xingke Road 723, Tianhe District, Guangzhou 510650, ChinaThree new cycloheximide congeners, 2,3-dehydro-α-epi-isocycloheximide (1), (E)- and (Z)-2,3-dehydroanhydrocycloheximides (2 and 3), together with three known compounds, anhydroisoheximide (4), cycloheximide (5), and isocycloheximide (6), were obtained from the cultures of Streptomyces sp. SC0581. Their structures were elucidated by extensive spectroscopic analysis in combination with theoretical conformational analysis and ECD computations. The photoinduced interconversion between 2 and 3 was observed and verified and the possible reaction path and mechanism were proposed by theoretical computations. The antifungal and cytotoxic activities of 1–6 were evaluated and suggested that 2,3-dehydrogenation results in the loss of the activities and supported that the OH-α is important to the activities of cycloheximide congeners.https://doi.org/10.3762/bjoc.13.103antifungal activitycycloheximide derivativesE/Z photoisomerizationStreptomyces sptheoretical conformational analysis
collection DOAJ
language English
format Article
sources DOAJ
author Li Yang
Ping Wu
Jinghua Xue
Huitong Tan
Zheng Zhang
Xiaoyi Wei
spellingShingle Li Yang
Ping Wu
Jinghua Xue
Huitong Tan
Zheng Zhang
Xiaoyi Wei
Cycloheximide congeners produced by Streptomyces sp. SC0581 and photoinduced interconversion between (E)- and (Z)-2,3-dehydroanhydrocycloheximides
Beilstein Journal of Organic Chemistry
antifungal activity
cycloheximide derivatives
E/Z photoisomerization
Streptomyces sp
theoretical conformational analysis
author_facet Li Yang
Ping Wu
Jinghua Xue
Huitong Tan
Zheng Zhang
Xiaoyi Wei
author_sort Li Yang
title Cycloheximide congeners produced by Streptomyces sp. SC0581 and photoinduced interconversion between (E)- and (Z)-2,3-dehydroanhydrocycloheximides
title_short Cycloheximide congeners produced by Streptomyces sp. SC0581 and photoinduced interconversion between (E)- and (Z)-2,3-dehydroanhydrocycloheximides
title_full Cycloheximide congeners produced by Streptomyces sp. SC0581 and photoinduced interconversion between (E)- and (Z)-2,3-dehydroanhydrocycloheximides
title_fullStr Cycloheximide congeners produced by Streptomyces sp. SC0581 and photoinduced interconversion between (E)- and (Z)-2,3-dehydroanhydrocycloheximides
title_full_unstemmed Cycloheximide congeners produced by Streptomyces sp. SC0581 and photoinduced interconversion between (E)- and (Z)-2,3-dehydroanhydrocycloheximides
title_sort cycloheximide congeners produced by streptomyces sp. sc0581 and photoinduced interconversion between (e)- and (z)-2,3-dehydroanhydrocycloheximides
publisher Beilstein-Institut
series Beilstein Journal of Organic Chemistry
issn 1860-5397
publishDate 2017-05-01
description Three new cycloheximide congeners, 2,3-dehydro-α-epi-isocycloheximide (1), (E)- and (Z)-2,3-dehydroanhydrocycloheximides (2 and 3), together with three known compounds, anhydroisoheximide (4), cycloheximide (5), and isocycloheximide (6), were obtained from the cultures of Streptomyces sp. SC0581. Their structures were elucidated by extensive spectroscopic analysis in combination with theoretical conformational analysis and ECD computations. The photoinduced interconversion between 2 and 3 was observed and verified and the possible reaction path and mechanism were proposed by theoretical computations. The antifungal and cytotoxic activities of 1–6 were evaluated and suggested that 2,3-dehydrogenation results in the loss of the activities and supported that the OH-α is important to the activities of cycloheximide congeners.
topic antifungal activity
cycloheximide derivatives
E/Z photoisomerization
Streptomyces sp
theoretical conformational analysis
url https://doi.org/10.3762/bjoc.13.103
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