PMID- 35283166 OWN - NLM STAT- MEDLINE DCOM- 20220413 LR - 20220413 IS - 1873-3700 (Electronic) IS - 0031-9422 (Linking) VI - 198 DP - 2022 Jun TI - 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. PG - 113161 LID - S0031-9422(22)00077-2 [pii] LID - 10.1016/j.phytochem.2022.113161 [doi] AB - 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 IC(50) values of 3.1 and 6.8 muM, respectively. CI - Copyright (c) 2022 Elsevier Ltd. All rights reserved. FAU - Li, Hao AU - Li H AD - Institute of Natural Medicine and Health Products, School of Pharmaceutical Sciences, Zhejiang Provincial Key Laboratory of Plant Ecology and Conservation, Taizhou University, Zhejiang, 318000, PR China; School of Pharmacy, Fudan University, Shanghai, 201203, PR China. FAU - Tang, Yu AU - Tang Y AD - School of Pharmacy, Fudan University, Shanghai, 201203, PR China. FAU - Liang, Kai-Yuan AU - Liang KY AD - Institute of Natural Medicine and Health Products, School of Pharmaceutical Sciences, Zhejiang Provincial Key Laboratory of Plant Ecology and Conservation, Taizhou University, Zhejiang, 318000, PR China; School of Pharmacy, Fudan University, Shanghai, 201203, PR China. FAU - Zang, Yi AU - Zang Y AD - State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Science, Shanghai, 201203, PR China. FAU - Osman, Ezzat E A AU - Osman EEA AD - School of Pharmacy, Fudan University, Shanghai, 201203, PR China; Department of Biochemistry, Molecular Biology and Medicinal Chemistry, Theodor Bilharz Research Institute, P. O. Box 30 Imbaba, Giza, 12411, Egypt. FAU - Jin, Ze-Xin AU - Jin ZX AD - Institute of Natural Medicine and Health Products, School of Pharmaceutical Sciences, Zhejiang Provincial Key Laboratory of Plant Ecology and Conservation, Taizhou University, Zhejiang, 318000, PR China. FAU - Li, Jia AU - Li J AD - State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Science, Shanghai, 201203, PR China. FAU - Xiong, Juan AU - Xiong J AD - School of Pharmacy, Fudan University, Shanghai, 201203, PR China. Electronic address: jxiong@fudan.edu.cn. FAU - Li, Junmin AU - Li J AD - Institute of Natural Medicine and Health Products, School of Pharmaceutical Sciences, Zhejiang Provincial Key Laboratory of Plant Ecology and Conservation, Taizhou University, Zhejiang, 318000, PR China. Electronic address: lijm@tzc.edu.cn. FAU - Hu, Jin-Feng AU - Hu JF AD - Institute of Natural Medicine and Health Products, School of Pharmaceutical Sciences, Zhejiang Provincial Key Laboratory of Plant Ecology and Conservation, Taizhou University, Zhejiang, 318000, PR China; School of Pharmacy, Fudan University, Shanghai, 201203, PR China. Electronic address: jfhu@tzc.edu.cn. LA - eng PT - Journal Article DEP - 20220310 PL - England TA - Phytochemistry JT - Phytochemistry JID - 0151434 RN - 0 (Diterpenes) RN - 0 (Phytochemicals) SB - IM MH - *Diterpenes/chemistry MH - Molecular Structure MH - Phytochemicals/chemistry MH - Plant Leaves/chemistry MH - *Taxaceae MH - *Tracheophyta OTO - NOTNLM OT - 11,12-Seco-abietane OT - Acetyl-coenzyme A carboxylase 1 (ACC1) OT - Diterpenoids OT - Protein tyrosine phosphatase 1B (PTP1B) OT - Rare and endangered plants (REPs) OT - Taxaceae OT - Torreya jackii OT - Torreyins EDAT- 2022/03/15 06:00 MHDA- 2022/04/14 06:00 CRDT- 2022/03/14 05:42 PHST- 2021/12/05 00:00 [received] PHST- 2022/03/04 00:00 [revised] PHST- 2022/03/04 00:00 [accepted] PHST- 2022/03/15 06:00 [pubmed] PHST- 2022/04/14 06:00 [medline] PHST- 2022/03/14 05:42 [entrez] AID - S0031-9422(22)00077-2 [pii] AID - 10.1016/j.phytochem.2022.113161 [doi] PST - ppublish SO - Phytochemistry. 2022 Jun;198:113161. doi: 10.1016/j.phytochem.2022.113161. Epub 2022 Mar 10.