College of Traditional Chinese Medicine, Jinan University, Guangzhou 510632, People's Republic of China.
Institute of Traditional Chinese Medicine and Natural Products, College of Pharmacy/Guangdong Province Key Laboratory of Pharmacodynamic Constituents of TCM and New Drugs Research, Jinan University, Guangzhou 510632, People's Republic of China.
J Org Chem. 2021 Aug 20;86(16):11177-11188. doi: 10.1021/acs.joc.1c00369. Epub 2021 May 27.
A secondary metabolites investigation on sp. 71-10-1-1 was carried out, which led to the obtention of nine new diisoprenyl-cyclohexene/ane-type meroterpenoids (-) and two new isoprenylbenzoic acid-type meroterpeniods (-). The structures of these isolates were established on the basis of multispectroscopic analyses, ECD, and C chemical shifts calculations, and single-crystal X-ray diffraction. Among them, biscognin A () is the first diisoprenyl-cyclohexene-type meroterpenoid with a unique 2-isopropyl-6'-methyloctahydro-1'-spiro[cyclopropane-1,2'-naphthalene] skeleton. Biscognienyne F () is the first diisoprenyl-cyclohexene-type meroterpenoid with a cyclic carbonate. The anti-inflammatory assays of the majority of compounds were evaluated, which exhibited that compounds and can obviously inhibit pro-inflammatory cytokines TNF-α and IL-6 productions. This is the first report for diisoprenyl-cyclohexene-type meroterpenoids with anti-inflammatory activity. Moreover, the possible biogenetic pathways of the majority of compounds (-) are proposed.
对 sp. 71-10-1-1 进行了次生代谢产物研究，从中获得了 9 个新的二异戊烯基环己烯/烷型倍半萜（(-)）和 2 个新的异戊烯基苯甲酸型倍半萜（(-)）。这些分离物的结构是基于多光谱分析、ECD 和 C 化学位移计算以及单晶 X 射线衍射确定的。其中，双柯宁 A () 是第一个具有独特 2-异丙基-6'-甲基八氢-1'-螺[环丙烷-1,2'-萘]骨架的二异戊烯基环己烯型倍半萜。双柯尼恩 F () 是第一个具有环状碳酸酯的二异戊烯基环己烯型倍半萜。对大多数化合物进行了抗炎活性评估，结果表明化合物 和 可以明显抑制促炎细胞因子 TNF-α 和 IL-6 的产生。这是第一个具有抗炎活性的二异戊烯基环己烯型倍半萜的报道。此外，还提出了大多数化合物（(-)）的可能生物合成途径。
