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Pogocablanols A–G, a new class of sesquiterpenoids with an unprecedented bicyclic sesquiterpenoid skeleton from Pogostemon cablin (patchouli) and their activities
Arabian Journal of Chemistry ( IF 5.3 ) Pub Date : 2023-09-06 , DOI: 10.1016/j.arabjc.2023.105245
Qin-Mei Zhou , Huan Zhu , Chuan Ma , Li Guo , Cheng Peng , Liang Xiong
Arabian Journal of Chemistry ( IF 5.3 ) Pub Date : 2023-09-06 , DOI: 10.1016/j.arabjc.2023.105245
Qin-Mei Zhou , Huan Zhu , Chuan Ma , Li Guo , Cheng Peng , Liang Xiong
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Pogocablanols A–G (–), seven new compounds with an unprecedented sesquiterpenoid skeleton, were isolated from the aerial parts of . This novel type of sesquiterpenoids, named pogocablane-type sesquiterpenoids, possesses a bicyclic nonisoprenoid system, including a five-membered carbocycle with a methyl group, a six-membered carbocycle with two methyl groups, and a methylene connecting the two carbocycles. Particularly, three isomers have an interesting 1-oxaspiro[4,4]nonane moiety. Their structures and absolute configurations were determined using extensive spectroscopic evidence, single-crystal X-ray diffraction, and electronic circular dichroism calculations. Pogocablanols A–D (–) exhibited a concentration-dependent inhibitory effect on rat jejunum smooth muscle contraction induced by acetylcholine, with values varying from 48.87 ± 4.01% to 69.02 ± 7.54%. Preliminary structure–activity relationship analysis suggested that the oxaspirocycle and the pyran ring in pogocablanols are important structural features for the relaxing effects on jejunum smooth muscle. This study offered crucial support for more investigation and development of by showing that these pogocablane-type sesquiterpenoids had the potential to be applied in pharmaceutical and functional food formulations.
中文翻译:
Pogocablaanols A–G,一类新的倍半萜类化合物,具有来自广藿香的前所未有的双环倍半萜类骨架及其活性
Pogocablaanols A–G (–) 是从 的地上部分分离出来的七种具有前所未有的倍半萜类骨架的新化合物。这种新型倍半萜类化合物被称为pogocablane型倍半萜类化合物,具有双环非异戊二烯系统,包括带有甲基的五元碳环、带有两个甲基的六元碳环以及连接两个碳环的亚甲基。特别是,三种异构体具有有趣的 1-氧杂螺[4,4]壬烷部分。它们的结构和绝对构型是通过广泛的光谱证据、单晶 X 射线衍射和电子圆二色性计算来确定的。 Pogocablaanols A–D (–) 对乙酰胆碱诱导的大鼠空肠平滑肌收缩表现出浓度依赖性抑制作用,其值在 48.87 ± 4.01% 至 69.02 ± 7.54% 之间变化。初步构效关系分析表明,pogocablaanols 中的氧杂螺环和吡喃环是对空肠平滑肌具有松弛作用的重要结构特征。该研究表明这些pogocablane型倍半萜类化合物具有在药物和功能性食品配方中应用的潜力,为更多的研究和开发提供了重要支持。
更新日期:2023-09-06
中文翻译:

Pogocablaanols A–G,一类新的倍半萜类化合物,具有来自广藿香的前所未有的双环倍半萜类骨架及其活性
Pogocablaanols A–G (–) 是从 的地上部分分离出来的七种具有前所未有的倍半萜类骨架的新化合物。这种新型倍半萜类化合物被称为pogocablane型倍半萜类化合物,具有双环非异戊二烯系统,包括带有甲基的五元碳环、带有两个甲基的六元碳环以及连接两个碳环的亚甲基。特别是,三种异构体具有有趣的 1-氧杂螺[4,4]壬烷部分。它们的结构和绝对构型是通过广泛的光谱证据、单晶 X 射线衍射和电子圆二色性计算来确定的。 Pogocablaanols A–D (–) 对乙酰胆碱诱导的大鼠空肠平滑肌收缩表现出浓度依赖性抑制作用,其值在 48.87 ± 4.01% 至 69.02 ± 7.54% 之间变化。初步构效关系分析表明,pogocablaanols 中的氧杂螺环和吡喃环是对空肠平滑肌具有松弛作用的重要结构特征。该研究表明这些pogocablane型倍半萜类化合物具有在药物和功能性食品配方中应用的潜力,为更多的研究和开发提供了重要支持。