Sesquiterpenoids and triterpenoids from Abies holophylla and their bioactivities |
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| Affiliation: | 1. Department of Natural Product Chemistry, School of Pharmacy, Second Military Medical University, 325 Guohe Road, Shanghai 200433, China;2. Laboratory of Plant Molecular Biology, Luxembourg Public Research Center for Health (CRP-SANTE), 84 Val Fleuri, L-1526 Luxembourg, Luxembourg;3. Key Laboratory of Marine Bio-resources Sustainable Utilization, Guangdong Key Laboratory of Marine Materia Medica, and RNAM Center for Marine Microbes, South China Sea Institute of Oceanology, Chinese Academy of Sciences, Guangzhou 510301, China;4. School of Pharmacy, Shanghai Jiao Tong University, Shanghai 200240, China;5. Shanghai Key Laboratory of Chemical Biology, School of Pharmacy, East China University of Science and Technology, Shanghai 200237, China;1. Department of Chemistry and Center of Excellence for Innovation in Chemistry (PERCH-CIC), Faculty of Science, Mahidol University, Rama 6 Road, Bangkok 10400, Thailand;2. Department of Chemistry and Center of Excellence for Innovation in Chemistry (PERCH-CIC), Faculty of Science and Technology, Suratthani Rajabhat University, Suratthani 84100, Thailand;3. Department of Physiology, Faculty of Science, Mahidol University, Rama 6 Road, Bangkok 10400, Thailand;4. Department of Microbiology, Faculty of Science, Mahidol University, Rama 6 Road, Bangkok 10400, Thailand;5. Department of Pharmacology, Faculty of Medicine, Chiang Mai University, Chiang Mai 50200, Thailand;1. Department of Internal Medicine III, University Hospital RWTH Aachen, Pauwelsstrasse 30, D-52074, Aachen, Germany;2. Department of Internal Medicine I, Evangelical Hospital Bethesda, Ludwig-Weber-Strasse 15, 41061, Mönchengladbach, Germany;1. School of Pharmacy, Zunyi Medical University, Zunyi 563000, China;2. Chengdu Institute of Biology, Chinese Academy of Sciences, Chengdu 610041, China;3. College of Life Science, Sichuan University, Chengdu 610064, China;1. Université des frères Mentouri Constantine, Department of Chemistry, Laboratory of Therapeutic Substances (L.O.S.T), 25000, Constantine, Algeria;2. Groupe Isolement et Structure, Institut de Chimie Moléculaire de Reims (ICMR), CNRS UMR 7312, Moulin de la Housse, BP 1039, 51687 Reims, France;3. Laboratoire de Microbiologie, EA 4691, UFR de Pharmacie, 51096, Reims Cedex, France;1. School of Pharmacy, Shanghai Jiao Tong University, Shanghai 200240, PR China;2. Department of Phytochemistry, Second Military Medical University, Shanghai 200433, PR China;3. College of Pharmaceutical Sciences and Chinese Medicine, Southwest University, Chongqing 400715, PR China;4. School of Pharmacy, Fujian University of Traditional Chinese Medicine, Fujian 350108, PR China |
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| Abstract: | Six previously unreported and 11 known terpenoids were isolated from Abies holophylla. The structures of the six compounds were established as two unusual bisabolane sesquiterpenoids, three nortriterpenoids, and one 3,4-seco-triterpenoid based on the detailed analysis of their 1D and 2D NMR spectroscopic data. In addition, electronic circular dichroism (ECD) calculations and molecular orbital (MO) analysis were used to assign the absolute configuration of one bisabolane sesquiterpenoid, abiesesquine A. Abiesesquine A showed the strongest inhibitory effects against LPS-induced nitric oxide (NO) production in RAW264.7 macrophages with an IC50 value of 113.1 μM. Lanosta-7,9(11),24-trien-26-oic acid showed potent cytotoxic activity against COLO-205, LOVO, and QGY-7703 tumor cells with IC50 values of 0.9, 4.2, and 2.0 μM, respectively. (23R,25R)-3,4-seco-9βH-Lanosta-4(28),7-dien-26,23-olid-3-oic acid, exhibited a significant antiproliferation effect against A549 cells (IC50 = 14.7 μM). |
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