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超基烷醇 F-Q,来自贯叶连翘花的多样单萜聚异戊烯基酰基间苯三酚。

Hyperbeanols F-Q, diverse monoterpenoid polyprenylated acylphloroglucinols from the flowers of Hypericum beanii.

机构信息

State Key Laboratory of Natural Medicines and Jiangsu Key Laboratory of Bioactive Natural Product Research, School of Traditional Chinese Pharmacy, China Pharmaceutical University, Nanjing, 210009, PR China.

State Key Laboratory of Natural Medicines and Jiangsu Key Laboratory of Bioactive Natural Product Research, School of Traditional Chinese Pharmacy, China Pharmaceutical University, Nanjing, 210009, PR China.

出版信息

Phytochemistry. 2019 Mar;159:56-64. doi: 10.1016/j.phytochem.2018.12.005. Epub 2018 Dec 20.

DOI:10.1016/j.phytochem.2018.12.005
PMID:30578929
Abstract

Hyperbeanols F-Q, which are twelve undescribed monoterpenoid polyprenylated acylphloroglucinols, and four known analogues were isolated from the dried flowers of Hypericum beanii. Their structures were elucidated by detailed HRESIMS and 1D and 2D NMR data analyses. The absolute configurations of hyperbeanols FH were established by the circular dichroism (CD) exciton chirality method. The plausible biosynthetic pathway speculation of hyperbeanols F-Q indicated that diverse reactions, including prenylation, 1,6-ene reaction, rearrangement, epoxidation and dehydration, contributed to their diverse skeletons. Hyperbeanols FI, O and hypercalin B exhibited moderate nitric oxide (NO) inhibitory activities in LPS-induced RAW 264.7 macrophages, with IC values in the range of 17.11-28.74 μM.

摘要

从 Hypericum beanii 的干燥花中分离得到了 12 个未描述的单萜聚异戊二烯基酰基间苯三酚和 4 个已知类似物,分别命名为 hyperbeanols F-Q。通过详细的高分辨质谱和 1D 和 2D NMR 数据分析阐明了它们的结构。通过圆二色(CD)外消旋手性方法确定了 hyperbeanols FH 的绝对构型。hyperbeanols F-Q 的可能生物合成途径推测表明,各种反应,包括prenylation、1,6-ene 反应、重排、环氧化和脱水,有助于它们的多样性骨架。Hyperbeanols FI、O 和 hypercalin B 在 LPS 诱导的 RAW 264.7 巨噬细胞中表现出适度的一氧化氮(NO)抑制活性,IC 值范围为 17.11-28.74 μM。

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