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Versiquinazolines L-Q，源自海洋真菌的新型多环生物碱。

Versiquinazolines L-Q, new polycyclic alkaloids from the marine-derived fungus .

作者信息

Cheng Zhongbin, Liu Dong, Cheng Wei, Proksch Peter, Lin Wenhan

机构信息

State Key Laboratory of Natural and Biomimetic Drugs, Institute of Ocean Research, Peking University Beijing 100191 People's Republic of China

Pharmaceutical College, Henan University Kaifeng 475004 Henan People's Republic of China.

出版信息

RSC Adv. 2018 Sep 7;8(55):31427-31439. doi: 10.1039/c8ra06854b. eCollection 2018 Sep 5.

DOI:10.1039/c8ra06854b
PMID:35548256
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9085628/
Abstract

Further chemical examination of a coral-associated fungus LZD-14-1 by the PHLC-DAD detection resulted in the isolation of six new polycyclic alkaloids, namely versiquinazolines L-Q (1-6). Their structures were determined by extensive analyses of spectroscopic data, including quantum ECD calculation and X-ray single crystal diffraction for the assignment of absolute configurations. Versiquinazoline L bearing a d-Ala residue and versiquinazoline M containing an l-serine residue are rarely found in the fumiquinazoline-type alkaloids, while versiquinazoline P displayed an unusual scaffold with a spiro-γ-lactone. Versiquinazolines P and Q exhibited significant inhibition against thioredoxin reductase (TrxR) with IC values of 13.6 ± 0.6 and 12.2 ± 0.7 μM, which showed higher activity than the positive control curcumin (IC = 25 μM). The weak cytotoxicity and potent inhibition toward TrxR suggested that versiquinazolines P and Q are potential for microenvironmental regulation of tumor progression and metastasis.

摘要

通过PHLC-DAD检测对一种与珊瑚相关的真菌LZD-14-1进行进一步化学分析，分离出了六种新的多环生物碱，即versiquinazolines L-Q（1-6）。通过对光谱数据进行广泛分析来确定它们的结构，包括用于确定绝对构型的量子ECD计算和X射线单晶衍射。带有d-Ala残基的versiquinazoline L和含有l-丝氨酸残基的versiquinazoline M在烟曲喹唑啉型生物碱中很少见，而versiquinazoline P呈现出带有螺-γ-内酯的不寻常骨架。Versiquinazolines P和Q对硫氧还蛋白还原酶（TrxR）表现出显著抑制作用，IC值分别为13.6±0.6和12.2±0.7μM，其活性高于阳性对照姜黄素（IC = 25μM）。versiquinazolines P和Q较弱的细胞毒性以及对TrxR的有效抑制表明它们在肿瘤进展和转移的微环境调节方面具有潜力。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fee6/9085628/c6520ada966b/c8ra06854b-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fee6/9085628/30a7ce0d83fa/c8ra06854b-f1.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fee6/9085628/64ee45a7b41c/c8ra06854b-f6.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fee6/9085628/6112f2fc431a/c8ra06854b-f7.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fee6/9085628/98187d081e12/c8ra06854b-f8.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fee6/9085628/02b03a436722/c8ra06854b-f9.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fee6/9085628/46227e2fe12c/c8ra06854b-f10.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fee6/9085628/8c6d18ff76c0/c8ra06854b-f11.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fee6/9085628/6e89fcc60bf1/c8ra06854b-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fee6/9085628/c6520ada966b/c8ra06854b-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fee6/9085628/30a7ce0d83fa/c8ra06854b-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fee6/9085628/6229810f8e2c/c8ra06854b-f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fee6/9085628/5c48de4407f4/c8ra06854b-f3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fee6/9085628/8518bc37867f/c8ra06854b-f4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fee6/9085628/0276d4d64311/c8ra06854b-f5.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fee6/9085628/64ee45a7b41c/c8ra06854b-f6.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fee6/9085628/6112f2fc431a/c8ra06854b-f7.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fee6/9085628/98187d081e12/c8ra06854b-f8.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fee6/9085628/02b03a436722/c8ra06854b-f9.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fee6/9085628/46227e2fe12c/c8ra06854b-f10.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fee6/9085628/8c6d18ff76c0/c8ra06854b-f11.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fee6/9085628/6e89fcc60bf1/c8ra06854b-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fee6/9085628/c6520ada966b/c8ra06854b-s2.jpg

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