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Pogocablanols A--G, a new class of sesquiterpenoids from Pogostemon cablin and their activities
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  • Qin-Mei Zhou,
  • Huan Zhu,
  • Chuan Ma,
  • Li Guo,
  • Cheng Peng,
  • Liang Xiong
Qin-Mei Zhou
Chengdu University of Traditional Chinese Medicine
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Huan Zhu
Chengdu University of Traditional Chinese Medicine
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Chuan Ma
Chengdu University of Traditional Chinese Medicine
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Li Guo
Chengdu University of Traditional Chinese Medicine
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Cheng Peng
Chengdu University of Traditional Chinese Medicine
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Liang Xiong
Chengdu University of Traditional Chinese Medicine

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Abstract

Pogocablanols A–G (1–7), seven new compounds with an unprecedented sesquiterpenoid skeleton, were isolated from the aerial parts of Pogostemon cablin. 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 (1–4) exhibited a concentration-dependent inhibitory effect on rat jejunum smooth muscle contraction induced by acetylcholine, with Emax 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.