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瑞香烷 A,一种来源于瑞香狼毒根的罕见的 6/6/5/5/5/6/6 个七元碳环骨架的倍半萜。

Fischeriana A, a meroterpenoid with an unusual 6/6/5/5/5/6/6 heptacyclic carbon skeleton from the roots of Euphorbia fischeriana.

机构信息

Institute of Clinical Medical Sciences & Department of Pharmacy, China-Japan Friendship Hospital, Beijing 100029, People's Republic of China.

出版信息

Org Biomol Chem. 2019 Mar 6;17(10):2721-2724. doi: 10.1039/c9ob00013e.

DOI:10.1039/c9ob00013e
PMID:30775763
Abstract

Fischeriana A (1), a new meroterpenoid with a rare carbon skeleton, along with one of its known biosynthesis-related compounds 2,4-dihydroxy-6-methoxyacetophenone (2) and two known ent-abietane-type diterpenoids (3-4), were isolated from the roots of Euphorbia fischeriana. Their structures, including the stereochemistry, were elucidated using comprehensive spectroscopic methods, single-crystal X-ray diffraction, and electronic circular dichroism analysis. Compound 1 was found to be made up of an unusual heptacyclic ring system (6/6/5/5/5/6/6) featuring a modified ent-abietane diterpene with a phloroglucinol moiety. A possible biogenetic pathway for 1 was proposed. Compound 1 exhibited marked anti-tumor activities against the HepG2 cell line.

摘要

从大飞扬Euphorbia fischeriana 的根部分离得到 Fischeriana A (1),这是一种具有罕见碳骨架的新型倍半萜类化合物,以及其已知的生物合成相关化合物 2,4-二羟基-6-甲氧基苯乙酮 (2) 和两种已知的-ent-贝壳杉烷型二萜 (3-4)。采用综合光谱方法、单晶 X 射线衍射和电子圆二色性分析阐明了它们的结构,包括立体化学。发现化合物 1 由一个不寻常的七元环体系(6/6/5/5/5/6/6)组成,具有修饰的-ent-贝壳杉二萜和间苯三酚部分。提出了 1 的可能生物合成途径。化合物 1 对 HepG2 细胞系表现出显著的抗肿瘤活性。

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