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波戈卡布连 A-O,十五种来自 Pogostemon cablin 的结构多样的未描述倍半萜。

Pogocablenes A-O, fifteen undescribed sesquiterpenoids with structural diversity from Pogostemon cablin.

机构信息

Faculty of Life Science and Technology, Kunming University of Science and Technology, Kunming, 650500, Yunnan, PR China.

Faculty of Life Science and Technology, Kunming University of Science and Technology, Kunming, 650500, Yunnan, PR China.

出版信息

Phytochemistry. 2023 Oct;214:113829. doi: 10.1016/j.phytochem.2023.113829. Epub 2023 Aug 18.

DOI:10.1016/j.phytochem.2023.113829
PMID:37597718
Abstract

Fifteen previously undescribed sesquiterpenoids (pogocablenes A-O), three first discovered natural patchoulol-type ones, coupled with fourteen known ones, were isolated from the aerial parts of Pogostemon cablin. Among them, pogocablenes A and B, a pair of C epimers, possessed an unusual carbon skeleton with bicyclo[4.3.1]decane core. Pogocablene C, originated from eudesmane-type sesquiterpenoid, had an unprecedented bicyclo[5.4.0]undecane scaffold with a peroxy hemiactetal moiety. Pogocablene D possessed a rare tricyclo[5.2.2.0]undecane carbon skeleton derived from guaiane-type sesquiterpenoid. Pogocablene E was a 4,5-seco-guaiane derivative owning a peroxy hemiactetal unit and a spirocyclic skeleton. Pogocablene M was a nor-patchoulol-type sesquiterpenoid with α,β-unsaturated ketone moiety. Their structures with absolute configuration were determined by extensive spectroscopic analysis, in combination with quantum chemical calculation. In addition, the plausible biogenetic pathways of pogocablenes A-E were proposed. Furthermore, all isolates were evaluated for anti-influenza virus and anti-inflammatory effects.

摘要

从中药广藿香( Pogostemon cablin )的地上部分分离得到了 15 个以前未描述的倍半萜( Pogocablenes A-O ),其中 3 个为首次发现的天然对叶姜烯型倍半萜,以及 14 个已知化合物。其中, Pogocablenes A 和 B 为一对 C 差向异构体,具有双环[4.3.1]癸烷核心的不寻常碳骨架。 Pogocablenes C 来源于艾里莫芬烷型倍半萜,具有前所未有的双环[5.4.0]十一烷骨架和过氧半缩醛部分。 Pogocablenes D 具有罕见的三环[5.2.2.0]十一烷碳骨架,来源于愈创木烷型倍半萜。 Pogocablenes E 是一个拥有过氧半缩醛单元和螺环骨架的 4,5-裂愈创木烷衍生物。 Pogocablenes M 是一个含有α,β-不饱和酮部分的对叶姜烯酮型倍半萜。通过广泛的光谱分析,结合量子化学计算,确定了它们的结构和绝对构型。此外,还提出了 Pogocablenes A-E 的可能生物合成途径。此外,对所有分离得到的化合物进行了抗流感病毒和抗炎活性评价。

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