Phytochemical and biological studies on rare and endangered plants endemic to China. Part XXII. Structurally diverse diterpenoids from the leaves and twigs of the endangered conifer Torreya jackii and their bioactivities

Theodor Bilharz Research Institute

Bibliographic Information

Authors: Li H.; Tang Y.; Liang K.-Y.; Zang Y.; Osman E.E.A.; Jin Z.-X.; Li J.; Xiong J.; Li J.; Hu J.-F.

Journal: Phytochemistry

Publisher: Elsevier Ltd

Publication Date: June 2022

Volume / Issue: Volume 198

Article No.: 113161

ISSN: 319422

DOI: 10.1016/j.phytochem.2022.113161

Scopus: View on Scopus

PubMed: 35283166

Document Type: Article

Access: All Open Access; Hybrid Gold Open Access

Authors and Affiliations

Li H., 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 Pharmacy, Fudan University, Shanghai, 201203, China; Tang Y., School of Pharmacy, Fudan University, Shanghai, 201203, China; Liang K.-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, 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., 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; Li J., State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Science, Shanghai, 201203, China; Xiong J., School of Pharmacy, Fudan University, Shanghai, 201203, China; Li J., 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; 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, School of Pharmacy, Fudan University, Shanghai, 201203, China

Abstract

A phytochemical investigation on the MeOH extract of the leaves and twigs of the endangered conifer Torreya jackii Chun led to the isolation and characterization of 21 structurally diverse diterpenoids. Among them, six are previously undescribed, including four abietane-type (torreyins A−D, resp.) and two labdane-type diterpenoids (torreyins E and F). Their structures and absolute configurations were determined by a combination of spectroscopic methods, calculated/experimental electronic circular dichroism (ECD) data, and single-crystal X-ray diffraction analyses. In particular, torreyins A−C are rare 11,12-seco-abietane type diterpenoids possessing a dilactone moiety, and their biosynthetic pathway starting from a co-occurring abietane derivative (i.e., cyrtophyllone B) was briefly proposed. Among the isolates, 7-oxo-dehydroabietic acid and 15-methoxy-7,13-abietadien-18-oic acid showed considerable inhibitory effects against acetyl-coenzyme A carboxylase 1 (ACC1) and protein tyrosine phosphatase 1 B (PTP1B), with IC50 values of 3.1 and 6.8 μM, respectively. © 2022 Elsevier Ltd

Keywords

11,12-Seco-abietane; Acetyl-coenzyme A carboxylase 1 (ACC1); Diterpenoids; Protein tyrosine phosphatase 1B (PTP1B); Rare and endangered plants (REPs); Taxaceae; Torreya jackii; Torreyins; Diterpenes; Molecular Structure; Phytochemicals; Plant Leaves; Tracheophyta; diterpenoid; phytochemical; chemical structure; chemistry; plant leaf; vascular plant

Citation Information

Scopus Citations: 12

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