Plagiochianins A and B, Two ent-2,3-seco-Aromadendrane Derivatives from the Liverwort Plagiochila duthiana

• Published in: Organic letters Vol. 20; no. 20; pp. 6550 - 6553
• Main Authors: Han, Jing-Jing, Zhang, Jiao-Zhen, Zhu, Rong-Xiu, Li, Yi, Qiao, Ya-Nan, Gao, Yun, Jin, Xue-Yang, Chen, Wang, Zhou, Jin-Chuan, Lou, Hong-Xiang
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 19.10.2018; Amer Chemical Soc
• Subjects: acetylcholinesterase; alkaloids; carbon; chemical reactions; chemical structure; Chemistry; Chemistry, Organic; circular dichroism spectroscopy; enzyme inhibition; mosses and liverworts; Physical Sciences; pyridines; Science & Technology; spectral analysis; X-ray diffraction; LABDANE-TYPE DITERPENOIDS; ACANTHOPHYLLA SUBSP JAPONICA; CHEMICAL-CONSTITUENTS; BRYOPHYTES; SEMIDECURRENS; SECOAROMADENDRANE-TYPE SESQUITERPENES; BIOSYNTHESIS; MYLIA-TAYLORII; BIOLOGICAL-ACTIVITY; CHINESE LIVERWORT
• ISSN: 1523-7060; 1523-7052; 1523-7052
• DOI: 10.1021/acs.orglett.8b02888

Two novel ent-aromadendrane derivatives, plagiochianin A (1), possessing an unprecedented 2,3:6,7-di-seco-6,8-cyclo-aromadendrane carbon scaffold conjugated with three cyclic acetals, and plagiochianin B (2), an exceptional pyridine type aromadendrane alkaloid, were isolated from the Chinese liverwort Plagiochila duthiana. Their structures were established by comprehensive spectroscopic analysis coupled with single-crystal X-ray diffraction and electronic circular dichroism calculations. A plausible biogenetic pathway of these two compounds is presented, and their acetylcholinesterase inhibitory activities are preliminarily tested using TLC-bioautographic assays.