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3-Methyl-4,5-dihydro-oxepine, polyoxygenated seco-cyclohexenes and cyclohexenes from Uvaria flexuosa and their anti-inflammatory activity.
Phytochemistry. 2016 Feb; 122:184-192.P

Abstract

The phytochemical investigation of the methanolic extract of Uvaria flexuosa (Annonaceae) leaves led to the isolation of seven compounds including, 3-methyl-4,5-dihydro-oxepine (flexuvaroxepine A), four polyoxygenated seco-cyclohexene (flexuvarin A-D) and two polyoxygenated cyclohexene (flexuvarol A-B) derivatives, together with four known flavones. The structures of the isolated compounds were elucidated using different spectroscopic techniques. A plausible biogenetic route of the new compounds was discussed. The anti-inflammatory activity of the isolated compounds was evaluated by superoxide anion generation and elastase release assays. Among the tested compounds, flexuvarol B and chrysin showed the most potent anti-inflammatory effect by inhibiting superoxide anion generation and elastase release from human neutrophils in response to fMLP with IC50 2.25-5.55μM. Moreover, 5-hydroxy-6,7-dimethoxy-flavone showed selective inhibitory activity on superoxide anion generation (IC50=1.19±0.34μM).

Authors+Show Affiliations

Graduate Institute of Natural Products, College of Pharmacy, Kaohsiung Medical University, Kaohsiung, Taiwan.Chinese Medicine Research and Development Center, China Medical University Hospital, Taichung 404, Taiwan.Graduate Institute of Natural Products, College of Pharmacy, Kaohsiung Medical University, Kaohsiung, Taiwan.Graduate Institute of Natural Products, College of Pharmacy, Kaohsiung Medical University, Kaohsiung, Taiwan; Department of Pharmacognosy and Natural Products Chemistry, Faculty of Pharmacy, Ain-Shams University, Cairo 11566, Egypt.Institute of Pharmaceutical Biology, Technische Universität Braunschweig, 38106 Braunschweig, Germany.Faculty of Chemistry, Vinh University, 182-Le Duan, Vinh City, Nghean Province, Viet Nam.Faculty of Chemistry, Vinh University, 182-Le Duan, Vinh City, Nghean Province, Viet Nam.Graduate Institute of Natural Products, College of Medicine, Chang Gung University, Taoyuan 333, Taiwan; Research Center for Industry of Human Ecology and Graduate Institute of Health Industry Technology, Chang Gung University of Science and Technology, Taoyuan 333, Taiwan; Immunology Consortium, Chang Gung Memorial Hospital, Taoyuan 333, Taiwan.Graduate Institute of Natural Products, College of Pharmacy, Kaohsiung Medical University, Kaohsiung, Taiwan; R & D Center of Chinese Herbal Medicines & New Drugs, College of Pharmacy, Kaohsiung Medical University, Kaohsiung 807, Taiwan; Department of Marine Biotechnology and Resources, National Sun Yat-sen University, Kaohsiung, Taiwan. Electronic address: aaronfrc@kmu.edu.tw.Graduate Institute of Natural Products, College of Pharmacy, Kaohsiung Medical University, Kaohsiung, Taiwan; Chinese Medicine Research and Development Center, China Medical University Hospital, Taichung 404, Taiwan; School of Pharmacy, College of Pharmacy, China Medical University, Taichung 404, Taiwan; Center for Molecular Medicine, China Medical University Hospital, Taichung 404, Taiwan. Electronic address: yachwu@mail.cmu.edu.tw.

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

26732672

Citation

Hsu, Yu-Ming, et al. "3-Methyl-4,5-dihydro-oxepine, Polyoxygenated Seco-cyclohexenes and Cyclohexenes From Uvaria Flexuosa and Their Anti-inflammatory Activity." Phytochemistry, vol. 122, 2016, pp. 184-192.
Hsu YM, Wu TY, Du YC, et al. 3-Methyl-4,5-dihydro-oxepine, polyoxygenated seco-cyclohexenes and cyclohexenes from Uvaria flexuosa and their anti-inflammatory activity. Phytochemistry. 2016;122:184-192.
Hsu, Y. M., Wu, T. Y., Du, Y. C., El-Shazly, M., Beerhues, L., Thang, T. D., Van Luu, H., Hwang, T. L., Chang, F. R., & Wu, Y. C. (2016). 3-Methyl-4,5-dihydro-oxepine, polyoxygenated seco-cyclohexenes and cyclohexenes from Uvaria flexuosa and their anti-inflammatory activity. Phytochemistry, 122, 184-192. https://doi.org/10.1016/j.phytochem.2015.12.013
Hsu YM, et al. 3-Methyl-4,5-dihydro-oxepine, Polyoxygenated Seco-cyclohexenes and Cyclohexenes From Uvaria Flexuosa and Their Anti-inflammatory Activity. Phytochemistry. 2016;122:184-192. PubMed PMID: 26732672.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - 3-Methyl-4,5-dihydro-oxepine, polyoxygenated seco-cyclohexenes and cyclohexenes from Uvaria flexuosa and their anti-inflammatory activity. AU - Hsu,Yu-Ming, AU - Wu,Tung-Ying, AU - Du,Ying-Chi, AU - El-Shazly,Mohamed, AU - Beerhues,Ludger, AU - Thang,Tran Dinh, AU - Van Luu,Hoang, AU - Hwang,Tsong-Long, AU - Chang,Fang-Rong, AU - Wu,Yang-Chang, Y1 - 2015/12/28/ PY - 2015/07/11/received PY - 2015/12/01/revised PY - 2015/12/15/accepted PY - 2016/1/7/entrez PY - 2016/1/7/pubmed PY - 2016/9/28/medline KW - 3-Methyl-4,5-dihydro-oxepine KW - Annonaceae KW - Anti-inflammatory KW - Polyoxygenated cyclohexenes KW - Polyoxygenated seco-cyclohexenes KW - Uvaria flexuosa SP - 184 EP - 192 JF - Phytochemistry JO - Phytochemistry VL - 122 N2 - The phytochemical investigation of the methanolic extract of Uvaria flexuosa (Annonaceae) leaves led to the isolation of seven compounds including, 3-methyl-4,5-dihydro-oxepine (flexuvaroxepine A), four polyoxygenated seco-cyclohexene (flexuvarin A-D) and two polyoxygenated cyclohexene (flexuvarol A-B) derivatives, together with four known flavones. The structures of the isolated compounds were elucidated using different spectroscopic techniques. A plausible biogenetic route of the new compounds was discussed. The anti-inflammatory activity of the isolated compounds was evaluated by superoxide anion generation and elastase release assays. Among the tested compounds, flexuvarol B and chrysin showed the most potent anti-inflammatory effect by inhibiting superoxide anion generation and elastase release from human neutrophils in response to fMLP with IC50 2.25-5.55μM. Moreover, 5-hydroxy-6,7-dimethoxy-flavone showed selective inhibitory activity on superoxide anion generation (IC50=1.19±0.34μM). SN - 1873-3700 UR - https://www.unboundmedicine.com/medline/citation/26732672/3_Methyl_45_dihydro_oxepine_polyoxygenated_seco_cyclohexenes_and_cyclohexenes_from_Uvaria_flexuosa_and_their_anti_inflammatory_activity_ L2 - https://linkinghub.elsevier.com/retrieve/pii/S0031-9422(15)30129-1 DB - PRIME DP - Unbound Medicine ER -