Structurally diverse diterpenoids from Isodon pharicus†,Organic Chemistry Frontiers

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Structurally diverse diterpenoids from Isodon pharicus†
Organic Chemistry Frontiers ( IF 4.6 ) Pub Date : 2018-07-02 00:00:00 , DOI: 10.1039/c8qo00477c
Zheng-Xi Hu _{1,

2,

3,

4,

5} , Hou-Chao Xu _{1,

2,

3,

4,

5} , Kun Hu _{1,

2,

3,

4,

5} , Miao Liu _{1,

2,

3,

4,

5} , Xiao-Nian Li _{1,

2,

3,

4,

5} , Xing-Ren Li _{1,

2,

3,

4,

5} , Xue Du _{1,

2,

3,

4,

5} , Yong-Hui Zhang _{6,

7,

8,

9,

10} , Pema-Tenzin Puno _{1,

2,

3,

4,

5} , Han-Dong Sun _{1,

2,

3,

4,

5}

Affiliation

Twenty-one diterpenoids with diverse structures, including twelve new compounds (1–12), were isolated from the aerial parts of Isodon pharicus. Structurally, pharicusin A (1), composed of a benzoyl group coupled to a 7α,20-epoxy-ent-kauranoid, represents an unprecedented C₂₇ meroditerpenoid; pharicusin B (2) is a novel trinorditerpenoid with an unreported 15,16,17-trinor-7α,20-epoxy-ent-kaurane skeleton; pharicusin C (4) represents the first example of 7α,20-epoxy-ent-atisane diterpenoids. Their structures were elucidated based on spectroscopic analysis, wherein the absolute configurations of 2 and 3 were further confirmed by single-crystal X-ray diffraction and computational analysis of the optical rotatory dispersion (ORD). Selected sixteen isolates were evaluated for their in vitro cytotoxicity against a small panel of human tumor cell lines (HL-60, SMMC-7721, A-549, MCF-7, and SW-480), and compounds 9, 10, 13, 16, and 18 exhibited significant inhibitory effects against all five cell lines, with IC₅₀ values in the range of 0.37–6.03 μM.

中文翻译：

从结构不同的二萜类化合物香茶pharicus †

从嘴I的地上部分中分离出二十一种具有不同结构的二萜类化合物，包括十二种新化合物（1–12）。在结构上，pharicusin A（1），耦合到7α苯甲酰基组成的，20-环氧ENT -kauranoid，代表着一种前所未有Ç ₂₇ meroditerpenoid; pharicusin B（2）是一种新型的用trinorditerpenoid未报告15,16,17-三去甲- 7α，20-环氧ENT -kaurane骨架; pharicusin C（4）表示7α，20-环氧基的第一示例ENT -atisane二萜类化合物。根据光谱分析阐明了它们的结构，其中的绝对构型通过单晶X射线衍射和旋光色散（ORD）的计算分析进一步确定了图2和图3。选择16株对他们进行了评价体外细胞毒性抗人肿瘤细胞系的小面板（HL-60，SMMC-7721，A-549，MCF-7，和SW-480），和化合物9，10，13，16和18对所有5种细胞系均表现出显着的抑制作用，IC ₅₀值在0.37–6.03μM的范围内。

更新日期：2018-07-02

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