Asperfloketals A and B, the first two ergostanes with rearranged A and D rings: From the Sponge-Associated Aspergillus flocculosus 16D-1

Fu Rong Jiao; Bin Bin Gu; Hong Rui Zhu; Yun Zhang; Ke Chun Liu; Wei Zhang; Hua Han; Shi Hai Xu; Hou Wen Lin

doi:10.1021/acs.joc.0c02049

Asperfloketals A and B, the first two ergostanes with rearranged A and D rings: From the Sponge-Associated Aspergillus flocculosus 16D-1

Fu Rong Jiao, Bin Bin Gu, Hong Rui Zhu, Yun Zhang, Ke Chun Liu, Wei Zhang, Hua Han, Shi Hai Xu, Hou Wen Lin

Research output: Contribution to journal › Article › peer-review

19 Citations (Scopus)

Abstract

Asperfloketals A (1) and B (2), two 1(10 → 6)-abeo-14,15-secosteroids featuring a novel trioxahexaheterocyclic ring system, were isolated from the sponge-associated fungus Aspergillus flocculosus 16D-1. Their structures were elucidated by extensive spectroscopic analysis and NMR chemical shifts calculations, supported by DP4+ probability analysis, and their absolute configurations were determined by ECD calculations and the modified Mosher's method. Asperfloketals A and B showed strong anti-inflammatory activity in the CuSO4-induced transgenic fluorescent zebrafish but displayed no cytotoxicity against HeLa, HepG2, and SW480 cell lines.

Original language	English
Pages (from-to)	10954-10961
Number of pages	8
Journal	Journal of Organic Chemistry
Volume	86
Issue number	16
DOIs	https://doi.org/10.1021/acs.joc.0c02049
Publication status	Published - 20 Aug 2021
Externally published	Yes

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title = "Asperfloketals A and B, the first two ergostanes with rearranged A and D rings: From the Sponge-Associated Aspergillus flocculosus 16D-1",

abstract = "Asperfloketals A (1) and B (2), two 1(10 → 6)-abeo-14,15-secosteroids featuring a novel trioxahexaheterocyclic ring system, were isolated from the sponge-associated fungus Aspergillus flocculosus 16D-1. Their structures were elucidated by extensive spectroscopic analysis and NMR chemical shifts calculations, supported by DP4+ probability analysis, and their absolute configurations were determined by ECD calculations and the modified Mosher's method. Asperfloketals A and B showed strong anti-inflammatory activity in the CuSO4-induced transgenic fluorescent zebrafish but displayed no cytotoxicity against HeLa, HepG2, and SW480 cell lines.",

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doi = "10.1021/acs.joc.0c02049",

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T2 - From the Sponge-Associated Aspergillus flocculosus 16D-1

AU - Jiao, Fu Rong

AU - Gu, Bin Bin

AU - Zhu, Hong Rui

AU - Zhang, Yun

AU - Liu, Ke Chun

AU - Zhang, Wei

AU - Han, Hua

AU - Xu, Shi Hai

AU - Lin, Hou Wen

PY - 2021/8/20

Y1 - 2021/8/20

N2 - Asperfloketals A (1) and B (2), two 1(10 → 6)-abeo-14,15-secosteroids featuring a novel trioxahexaheterocyclic ring system, were isolated from the sponge-associated fungus Aspergillus flocculosus 16D-1. Their structures were elucidated by extensive spectroscopic analysis and NMR chemical shifts calculations, supported by DP4+ probability analysis, and their absolute configurations were determined by ECD calculations and the modified Mosher's method. Asperfloketals A and B showed strong anti-inflammatory activity in the CuSO4-induced transgenic fluorescent zebrafish but displayed no cytotoxicity against HeLa, HepG2, and SW480 cell lines.

AB - Asperfloketals A (1) and B (2), two 1(10 → 6)-abeo-14,15-secosteroids featuring a novel trioxahexaheterocyclic ring system, were isolated from the sponge-associated fungus Aspergillus flocculosus 16D-1. Their structures were elucidated by extensive spectroscopic analysis and NMR chemical shifts calculations, supported by DP4+ probability analysis, and their absolute configurations were determined by ECD calculations and the modified Mosher's method. Asperfloketals A and B showed strong anti-inflammatory activity in the CuSO4-induced transgenic fluorescent zebrafish but displayed no cytotoxicity against HeLa, HepG2, and SW480 cell lines.

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DO - 10.1021/acs.joc.0c02049

M3 - Article

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SN - 0022-3263

VL - 86

SP - 10954

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JO - Journal of Organic Chemistry

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Asperfloketals A and B, the first two ergostanes with rearranged A and D rings: From the Sponge-Associated Aspergillus flocculosus 16D-1

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