Neolignans and Norlignans from Insect Medicine Polyphaga plancyi and Their Biological Activities
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ORIGINAL ARTICLE
Neolignans and Norlignans from Insect Medicine Polyphaga plancyi and Their Biological Activities Hong‑Jie Zhu2 · Te Xu1 · Yong‑Ming Yan1 · Zheng‑Chao Tu3,4 · Yong‑Xian Cheng1 Received: 3 July 2020 / Accepted: 23 August 2020 © The Author(s) 2020
Abstract Ten neolignans or norlignans (1–10) including eight new compounds were isolated from the whole bodies of Polyphaga plancyi Bolivar. Their structures were identified by spectroscopic data. Compounds 3, 4, 8, and 9 are racemates indicated by chiral HPLC analysis. Chiral separation followed by ECD calculations allowed to clarify the absolute configurations of all the antipodes. All the new compounds were evaluated for their biological properties toward extracellular matrix in rat renal proximal tubular cells, human cancer cells (K562, A549, and Huh7), EV71, ROCK2, JAK3, DDR1, and coagulation. Graphic Abstract
HO
HO
OH
OH O HO
O
O
(+)-3 R1=OH (+)-4 R1=OCH3
HO
5
O
OH
OH
O HO OH
R1
HO O
1 R=OH 2 R=OCH3
HO
R
O O
HO
HO
6
O OH
O O
7
Keywords Polyphaga plancyi · Insect medicine · Lignans · Renal protection · Anticoagulant activity In honor of Professor Jun Zhou. Hong-Jie Zhu and Te Xu have contributed equally to this work. Electronic supplementary material The online version of this article (https://doi.org/10.1007/s13659-020-00262-0) contains supplementary material, which is available to authorized users. * Yong‑Xian Cheng [email protected] 1
School of Pharmaceutical Sciences, Shenzhen University Health Science Center, Shenzhen 518060, People’s Republic of China
State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, People’s Republic of China
2
3
International Cooperative Laboratory of Traditional Chinese Medicine Modernization and Innovative Drug Development of Chinese Ministry of Education (MOE), College of Pharmacy, Jinan University, Guangzhou 510632, People’s Republic of China
4
Drug Discovery Pipeline & Guangdong Provincial Key Laboratory of Biocomputing, Guangzhou Institutes of Biomedicine and Health, Guangzhou 510530, People’s Republic of China
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1 Introduction
was aided by electronic circular dichroism (ECD) calculations. In addition, the biological activities of all the new compounds were assessed using multiple assays.
Insects are a special group of existence on the earth. Facing the changing environment, they have strong adaptability, productivity and continuity. They seem small and insignificant, but the largest number of living beings on the planet, and their presence has created a huge molecular libraries [1, 2]. The tenacious vitality of insects is highly likely to be related to their unique molecular mechanisms [2], which provides us a confidence to track their bioactive molecules. In China, the insect Polyphaga plancyi Bolivar has been used for promoting blood circulation [3]. Whereas, so far there have few reports about its chemical composition [4]. Pr
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