关键词: Caged polycyclic polyprenylated acylphloroglucinols Garcinia yunnanensis hu Guttiferae Lavandulyl X-ray diffraction

Mesh : Garcinia / chemistry Humans Phloroglucinol / chemistry pharmacology isolation & purification Antineoplastic Agents, Phytogenic / pharmacology chemistry isolation & purification Molecular Structure Drug Screening Assays, Antitumor Cell Line, Tumor Models, Molecular Structure-Activity Relationship Cell Proliferation / drug effects Plant Bark / chemistry

来  源:   DOI:10.1016/j.phytochem.2024.114167

Abstract:
Garciyunnanones A-R (1-18), eighteen undescribed caged polycyclic polyprenylated acylphloroglucinols, two undescribed biogenetic congeners (19-20), and nineteen known analogues (21-39), were isolated from the stem barks of Garcinia yunnanensis Hu. All of these isolates are decorated with a C-5 lavandulyl substituent. Their structures and absolute configurations were confirmed by HRESIMS, 1D & 2D NMR spectroscopic analysis, quantum chemical calculations of electronic circular dichroism data, and single-crystal X-ray diffraction analysis. The X-ray crystallographic data of ten isolated caged compounds ascertained the absolute configuration of C-23 in the lavandulyl as S. The cytotoxicity on three cancer cell lines and the anti-nonalcoholic steatohepatitis activity of the isolates were tested. In a free fatty acid-induced L02 cell model, compounds 33 and 39 decreased intracellular lipid accumulation significantly.
摘要:
GarciyunnanonesA-R(1-18),18个未描述的笼式多环聚戊烯化酰基间苯三酚,两个未描述的生物同源物(19-20),和19个已知的类似物(21-39),从云南藤黄的茎皮中分离得到。所有这些分离物均装饰有C-5lavandulyl取代基。它们的结构和绝对构型被HRESIMS证实,1D&2DNMR光谱分析,电子圆二色性数据的量子化学计算,和单晶X射线衍射分析。十个分离的笼状化合物的X射线晶体学数据确定了C-23在lavandulyl中的绝对构型为S。测试了三种癌细胞系的细胞毒性和分离株的抗非酒精性脂肪性肝炎活性。在游离脂肪酸诱导的L02细胞模型中,化合物33和39显著降低细胞内脂质积累。
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