PMID- 35970438 OWN - NLM STAT- MEDLINE DCOM- 20221010 LR - 20221011 IS - 1873-3700 (Electronic) IS - 0031-9422 (Linking) VI - 203 DP - 2022 Nov TI - 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. PG - 113366 LID - S0031-9422(22)00282-5 [pii] LID - 10.1016/j.phytochem.2022.113366 [doi] AB - 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-12alphaH-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-3alpha,21beta-diol, betulinic acid, 3beta-hydroxy-11-ursen-13(28)-olide, ursolic acid, and oleanolic acid were found to have considerable inhibitory effects against PTP1B, with IC(50) values ranging from 1.1 to 18.1 muM. 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 IC(50) values of 3.4 and 6.6 muM, respectively. CI - Copyright (c) 2022 Elsevier Ltd. All rights reserved. FAU - Jiang, Wei AU - Jiang W 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 Life Science and Technology, Wuhan Polytechnic University, Hubei, 430023, PR China; Department of Natural Medicine, School of Pharmacy, Fudan University, Shanghai, 201203, PR China. FAU - Zhao, Ze-Yu AU - Zhao ZY 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; Department of Natural Medicine, School of Pharmacy, Fudan University, Shanghai, 201203, PR China. FAU - Tong, Ying-Peng AU - Tong YP 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 - Ma, Guang-Lei AU - Ma GL AD - Department of Natural Medicine, 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 - Department of Natural Medicine, 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 - Xiong, Juan AU - Xiong J AD - Department of Natural Medicine, School of Pharmacy, Fudan University, Shanghai, 201203, PR China. Electronic address: jxiong@fudan.edu.cn. 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 - 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; Department of Natural Medicine, School of Pharmacy, Fudan University, Shanghai, 201203, PR China. Electronic address: jfhu@tzc.edu.cn. LA - eng PT - Journal Article DEP - 20220812 PL - England TA - Phytochemistry JT - Phytochemistry JID - 0151434 RN - 0 (Abietanes) RN - 0 (Diterpenes) RN - 0 (Phytochemicals) RN - 0 (Plant Extracts) RN - 0 (Terpenes) RN - 0 (Triterpenes) RN - 6SMK8R7TGJ (Oleanolic Acid) RN - EC 3.1.3.48 (Protein Tyrosine Phosphatase, Non-Receptor Type 1) RN - SAA04E81UX (Coenzyme A) SB - IM MH - Abietanes/pharmacology MH - Coenzyme A MH - *Diterpenes/chemistry MH - Humans MH - *Larix MH - Molecular Docking Simulation MH - Molecular Structure MH - *Oleanolic Acid MH - Phytochemicals/chemistry MH - *Picea MH - *Pinaceae MH - Plant Extracts MH - Plants MH - Protein Tyrosine Phosphatase, Non-Receptor Type 1 MH - Terpenes/pharmacology MH - *Triterpenes/chemistry OTO - NOTNLM OT - ACC1 OT - Endangered plants OT - Larix potaninii var. chinensis OT - Neoveitchins OT - PTP1B OT - Picea neoveitchii OT - Pinaceae OT - Potalarxins OT - Terpenoids COIS- Declaration of competing interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper. EDAT- 2022/08/16 06:00 MHDA- 2022/10/12 06:00 CRDT- 2022/08/15 19:34 PHST- 2022/05/17 00:00 [received] PHST- 2022/07/30 00:00 [revised] PHST- 2022/08/01 00:00 [accepted] PHST- 2022/08/16 06:00 [pubmed] PHST- 2022/10/12 06:00 [medline] PHST- 2022/08/15 19:34 [entrez] AID - S0031-9422(22)00282-5 [pii] AID - 10.1016/j.phytochem.2022.113366 [doi] PST - ppublish SO - Phytochemistry. 2022 Nov;203:113366. doi: 10.1016/j.phytochem.2022.113366. Epub 2022 Aug 12.