Polycyclic polyprenylated acylphloroglucinols from Hypericum beanii and their hepatoprotective activity.

Yonghui Ma, Xinyue Suo, Xiaoxiu Li, Tingting Zhu, Jin Li, Tengfei Ji, Bo Liu

Journal: Phytochemistry 2022;203():113413

PMID: 36044959

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Abstract

Twenty-seven polycyclic polyprenylated acylphloroglucinols (PPAPs) with diverse skeletons, including seven previously undescribed ones (hyperbeanins A-G), were isolated from the aerial parts of Hypericum beanii. Their structures were established by comprehensive analysis of NMR, HRESIMS, and experimental electronic circular dichroism (ECD) spectra. Hyperbeanin A was a monocyclic polyprenylated acylphloroglucinols (MPAPs) with an unusual spiro-fused cyclopropane ring. Four of the isolated compounds showed obvious hepatoprotective activity against paracetamol-induced HepG2 cell damage at 10 μM. The present results suggested that these compounds would be potential hepatoprotective agents. In addition, the plausible biogenetic pathways of hyperbeanins A-G were proposed, which gave an insight for future biomimetic synthesis of them.

Address: State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing, 100050, People's Republic of China; The Key Laboratory of Plant Stress Biology in Arid Land, College of Life Sciences, Xinjiang Normal University, Ürümqi, Xinjiang, 830054, People's Republic of China.; State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing, 100050, People's Republic of China.; School of Pharmacy, Shenyang Medical College, Shenyang, Liaoning, 110034, People's Republic of China.; The Key Laboratory of Plant Stress Biology in Arid Land, College of Life Sciences, Xinjiang Normal University, Ürümqi, Xinjiang, 830054, People's Republic of China. Electronic address: [email protected].; State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing, 100050, People's Republic of China; Key Laboratory of Tibetan Medicine Research, Northwest Institute of Plateau Biology, Chinese Academy of Sciences, Xining, Qinghai, 810008, People's Republic of China. Electronic address: [email protected].; School of Pharmacy, Shenyang Medical College, Shenyang, Liaoning, 110034, People's Republic of China. Electronic address: [email protected].

DOI: 10.1016/j.phytochem.2022.113413

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MeSH Terms: Acetaminophen, Cyclopropanes, Hypericum, Molecular Structure, Phloroglucinol