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从养殖海绵 Spongia officinalis L. 中提取的 Jellynolide A、pokepola 酯和 sponalisolides

Jellynolide A, pokepola esters, and sponalisolides from the aquaculture sponge Spongia officinalis L.

机构信息

Key Laboratory of Marine Drugs, Chinese Ministry of Education, School of Medicine and Pharmacy Department, Ocean University of China, Qingdao, 266003, People's Republic of China; Laboratory of Marine Drugs and Biological Products, National Laboratory for Marine Science and Technology, Qingdao, 266235, People's Republic of China.

Key Laboratory of Marine Drugs, Chinese Ministry of Education, School of Medicine and Pharmacy Department, Ocean University of China, Qingdao, 266003, People's Republic of China; Laboratory of Marine Drugs and Biological Products, National Laboratory for Marine Science and Technology, Qingdao, 266235, People's Republic of China.

出版信息

Phytochemistry. 2022 Feb;194:113006. doi: 10.1016/j.phytochem.2021.113006. Epub 2021 Nov 25.

DOI:10.1016/j.phytochem.2021.113006
PMID:34837765
Abstract

Jellynolide A, an unreported bicyclic diterpenoid with an unprecedented penta-substituted carbon skeleton which implied an irregular biogenic pathway, together with four pairs of rare phosphate triesters, (±)-pokepola ester B-E, one undescribed related racemic furanoterpenoid, (±)-sponalisolide C, one undescribed furanoterpenoid, (-)-sponalisolide D, and two known (±)-sponalisolide B and dendrolasin carboxylic acid were isolated from the aquaculture Spongia officinalis L. Their structures were elucidated by comprehensive spectroscopic analysis, quantum chemical calculation of NMR parameters, and electronic circular dichroism (ECD). The plausible biosynthetic pathway of jellynolide A was proposed. (±)-Pokepola ester C exhibited significant inhibition against Wnt, HIF1 signaling pathways. (+)-Pokepola ester B and (-)-pokepola ester D showed moderate cytotoxicity activities.

摘要

从养殖的海绵中分离得到一个新型五环二萜化合物 jellynolide A,它具有一个前所未有的五取代的碳骨架,暗示了一种不规则的生物合成途径,此外还分离得到四个对映磷三酯对 (±)-pokepola 酯 B-E、一个未被描述的相关外消旋呋喃萜类化合物 (±)-sponalisolide C、一个未被描述的呋喃萜类化合物 (-)-sponalisolide D、两个已知的 (±)-sponalisolide B 和 dendrolasin 羧酸。通过全面的光谱分析、NMR 参数的量子化学计算和电子圆二色性 (ECD) 确定了它们的结构。提出了 jellynolide A 的可能生物合成途径。(±)-Pokepola 酯 C 对 Wnt、HIF1 信号通路具有显著的抑制作用。(+)-Pokepola 酯 B 和 (-)-pokepola 酯 D 表现出中等的细胞毒性活性。

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