大戟科植物中具有抗脂肪生成活性的骨架重排和氧合的ent-Rosane二萜类化合物

IF 5.5 1区 化学 Q2 CHEMISTRY, MULTIDISCIPLINARY
Qin-Qin Song, Yue Guo, Peng Sun, Yao-Yue Fan, Kai-Long Ji
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引用次数: 0

摘要

综合摘要从大戟科植物 Euphorbia milii 中分离出了五种未报道的含氧内rosane 二萜(ent-RDs),即 Euphomillanols A-E(1-5)。其中,化合物 1 和 2 是前所未有的 7/7/6 融合三环 5,10-seco-ent-RD,具有独特的 11-氧杂双环[4.4.1]十一碳-1(10),5-二烯分子,而化合物 3 的特征是环 A 具有 1-甲基-6-氧杂双环[3.2.1]辛-2-烯结构。提出了 1-3 号化合物的推测生物合成途径。所有化合物在 3T3-L1 脂肪细胞中都表现出抗脂肪生成作用,其中最有效的化合物 4 的 EC50 值为 3.92 μmol/L,细胞毒性较低(IC50 > 89.54 μmol/L)。
本文章由计算机程序翻译,如有差异,请以英文原文为准。

Skeleton Rearranged and Oxygenated ent-Rosane Diterpenoids with Antiadipogenic Activity from Euphorbia milii

Skeleton Rearranged and Oxygenated ent-Rosane Diterpenoids with Antiadipogenic Activity from Euphorbia milii

Five unreported and oxygenated ent-rosane diterpenoids (ent-RDs), Euphomillanols A—E (15), were isolated from Euphorbia milii. Among them, compounds 1 and 2 are unprecedented 7/7/6-fused tricyclic 5,10-seco-ent-RDs and possess a unique 11-oxabicyclo[4.4.1]undeca-1(10),5-diene moiety, while 3 is characterized by a 1-methyl-6-oxabicyclo[3.2.1]oct-2-ene motif of ring A. Their structures with absolute configurations were unambiguously determined by the extensive spectroscopic methods, X-ray crystallography, and ECD calculation. Putative biosynthetic pathways for compounds 13 are proposed. All compounds exhibited antiadipogenic effects in 3T3-L1 adipocytes, and the most potent compound 4 showed an EC50 value of 3.92 μmol/L with low cytotoxicity (IC50 > 89.54 μmol/L).

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来源期刊
Chinese Journal of Chemistry
Chinese Journal of Chemistry 化学-化学综合
CiteScore
8.80
自引率
14.80%
发文量
422
审稿时长
1.7 months
期刊介绍: The Chinese Journal of Chemistry is an international forum for peer-reviewed original research results in all fields of chemistry. Founded in 1983 under the name Acta Chimica Sinica English Edition and renamed in 1990 as Chinese Journal of Chemistry, the journal publishes a stimulating mixture of Accounts, Full Papers, Notes and Communications in English.
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