Phytochemical and biological studies on rare and endangered plants endemic to China. Part XXV. Structurally diverse triterpenoids and diterpenoids from two endangered Pinaceae plants endemic to the Chinese Qinling Mountains and their bioactivities

Theodor Bilharz Research Institute

Bibliographic Information

Authors: Jiang W.; Zhao Z.-Y.; Tong Y.-P.; Ma G.-L.; Zang Y.; Osman E.E.A.; Jin Z.-X.; Xiong J.; Li J.; Hu J.-F.

Journal: Phytochemistry

Publisher: Elsevier Ltd

Publication Date: November 2022

Volume / Issue: Volume 203

Article No.: 113366

ISSN: 319422

DOI: 10.1016/j.phytochem.2022.113366

Scopus: View on Scopus

PubMed: 35970438

Document Type: Article

Authors and Affiliations

Jiang W., Institute of Natural Medicine and Health Products, School of Pharmaceutical Sciences, Zhejiang Provincial Key Laboratory of Plant Ecology and Conservation, Taizhou University, Zhejiang, 318000, China, School of Life Science and Technology, Wuhan Polytechnic University, Hubei, 430023, China, Department of Natural Medicine, School of Pharmacy, Fudan University, Shanghai, 201203, China; Zhao Z.-Y., Institute of Natural Medicine and Health Products, School of Pharmaceutical Sciences, Zhejiang Provincial Key Laboratory of Plant Ecology and Conservation, Taizhou University, Zhejiang, 318000, China, Department of Natural Medicine, School of Pharmacy, Fudan University, Shanghai, 201203, China; Tong Y.-P., Institute of Natural Medicine and Health Products, School of Pharmaceutical Sciences, Zhejiang Provincial Key Laboratory of Plant Ecology and Conservation, Taizhou University, Zhejiang, 318000, China; Ma G.-L., Department of Natural Medicine, School of Pharmacy, Fudan University, Shanghai, 201203, China; Zang Y., State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Science, Shanghai, 201203, China; Osman E.E.A., Department of Natural Medicine, School of Pharmacy, Fudan University, Shanghai, 201203, China, Department of Biochemistry, Molecular Biology and Medicinal Chemistry, Theodor Bilharz Research Institute, P. O. Box 30 Imbaba, Giza, 12411, Egypt; Jin Z.-X., Institute of Natural Medicine and Health Products, School of Pharmaceutical Sciences, Zhejiang Provincial Key Laboratory of Plant Ecology and Conservation, Taizhou University, Zhejiang, 318000, China; Xiong J., Department of Natural Medicine, School of Pharmacy, Fudan University, Shanghai, 201203, China; Li J., State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Science, Shanghai, 201203, China; Hu J.-F., Institute of Natural Medicine and Health Products, School of Pharmaceutical Sciences, Zhejiang Provincial Key Laboratory of Plant Ecology and Conservation, Taizhou University, Zhejiang, 318000, China, Department of Natural Medicine, School of Pharmacy, Fudan University, Shanghai, 201203, China

Abstract

A joint phytochemical investigation on the MeOH extracts of the twigs and needles of two endangered Pinaceae plants endemic to the Chinese Qinling Mountains, Picea neoveitchii (an evergreen spruce) and Larix potaninii var. chinensis (a deciduous larch), led to the isolation and characterization of 34 and 24 structurally diverse terpenoids, respectively. Among them, seven are previously undescribed, including a picane-type [i.e., 14(13 → 12)abeo-12αH-serratane] (neoveitchin A) and a serratane-type (neoveitchin B) triterpenoids, and an abietane-type (neoveitchin C) as well as four labdane-type (potalarxins A–D) diterpenoids. Their structures and absolute configurations were established by extensive spectroscopic methods and/or X-ray diffraction analyses. All isolates were evaluated for their inhibitory activities against the human protein tyrosine phosphatase 1B (PTP1B). Serrat-14-en-3α,21β-diol, betulinic acid, 3β-hydroxy-11-ursen-13(28)-olide, ursolic acid, and oleanolic acid were found to have considerable inhibitory effects against PTP1B, with IC50 values ranging from 1.1 to 18.1 μM. The interactions of the bioactive triterpenoids with PTP1B were thereafter performed by employing molecular docking studies. In addition, 7-oxo-dehydroabietic acid (an abietane-type diterpenoid) and mangiferonic acid (a cycloartane-type triterpenoid) inhibited acetyl-coenzyme A carboxylase 1 (ACC1), with IC50 values of 3.4 and 6.6 μM, respectively. © 2022 Elsevier Ltd

Keywords

ACC1; Endangered plants; Larix potaninii var. chinensis; Neoveitchins; Picea neoveitchii; Pinaceae; Potalarxins; PTP1B; Terpenoids; Abietanes; Coenzyme A; Diterpenes; Humans; Larix; Molecular Docking Simulation; Molecular Structure; Oleanolic Acid; Phytochemicals; Picea; Plant Extracts; Plants; Protein Tyrosine Phosphatase, Non-Receptor Type 1; Terpenes; Triterpenes; diterpenoid; phytochemical; plant extract; protein tyrosine phosphatase 1B; terpene; triterpene; chemical structure; chemistry; human; molecular docking; pharmacology; plant; spruce

Citation Information

Scopus Citations: 9

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