Diterpenes from Grangea maderaspatana

Fang-Rong Chang; Shih-Ting Huang; Chih-Chuang Liaw; Ming-Hong Yen; Tsong-Long Hwang; Ching-Yeu Chen; Ming-Feng Hou; Shyng-Shiou Yuan; Yuan-Bin Cheng; Yang-Chang Wu

doi:10.1016/j.phytochem.2016.08.009

Diterpenes from Grangea maderaspatana

Phytochemistry. 2016 Nov:131:124-129. doi: 10.1016/j.phytochem.2016.08.009. Epub 2016 Aug 23.

Authors

Affiliations

¹ Graduate Institute of Natural Products, College of Pharmacy, Kaohsiung Medical University, Kaohsiung 807, Taiwan; Translational Research Center and Cancer Center, Kaohsiung Medical University Hospital, Kaohsiung 807, Taiwan.
² Graduate Institute of Natural Products, College of Pharmacy, Kaohsiung Medical University, Kaohsiung 807, Taiwan.
³ Department of Marine Biotechnology and Resources, National Sun Yat-sen University, Kaohsiung 804, Taiwan.
⁴ Graduate Institute of Natural Products, College of Pharmacy, Kaohsiung Medical University, Kaohsiung 807, Taiwan; School of Pharmacy, College of Pharmacy, Kaohsiung Medical University, Kaohsiung 807, Taiwan.
⁵ Graduate Institute of Natural Products, School of Traditional Chinese Medicine, College of Medicine, and Chinese Herbal Medicine Research Team, Healthy Aging Research Center, 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.
⁶ Department of Physical Therapy, Tzu-Hui Institute of Technology, Pingtung 926, Taiwan.
⁷ Translational Research Center and Cancer Center, Kaohsiung Medical University Hospital, Kaohsiung 807, Taiwan.
⁸ Graduate Institute of Natural Products, College of Pharmacy, Kaohsiung Medical University, Kaohsiung 807, Taiwan; Research Center for Natural Products & Drug Development, Kaohsiung Medical University, Kaohsiung 807, Taiwan. Electronic address: jmb@kmu.edu.tw.
⁹ Graduate Institute of Natural Products, College of Pharmacy, Kaohsiung Medical University, Kaohsiung 807, Taiwan; School of Pharmacy, College of Pharmacy, China Medical University, Taichung 404, Taiwan; Chinese Medicine Research and Development Center, China Medical University Hospital, Taichung 404, Taiwan; Center for Molecular Medicine, China Medical University Hospital, Taichung 404, Taiwan; Research Center for Chinese Herbal Medicine, China Medical University, Taichung 404, Taiwan. Electronic address: yachwu@mail.cmu.edu.tw.

PMID: 27567453
DOI: 10.1016/j.phytochem.2016.08.009

Abstract

Phytochemical investigation of the ethanolic extract of Grangea maderaspatana led to isolation of gramaderins A-D, together with thirteen known compounds. All isolates were assayed for their anti-inflammatory activities. Consequently, 5,7-dihydroxy-3,6,3',4',5'-pentamethoxyflavone and 5,3'-dihydroxy-3,6,7,4',5'-pentamethoxyflavone showed significant bioactivities by inhibiting superoxide anion generation. 8-Acetoxy-pentadeca-1,9Z,14-trien-4,6-diyne-3-ol also demonstrated potent inhibition on elastase release. The gramaderins A/C (β-alkyl linked γ-lactone) and gramaderins B/D (α-alkyl linked γ-lactone) co-exist in this plant material, of which the latter derivatives are few in nature. Gramaderins C/D possess a special linear dilactone diterpene skeleton, which never been reported.

Keywords: Anti-inflammatory; Asteraceae; Diterpenes; Grangea maderaspatana.

MeSH terms

Anti-Inflammatory Agents / chemistry
Anti-Inflammatory Agents / isolation & purification*
Anti-Inflammatory Agents / pharmacology
Anti-Inflammatory Agents, Non-Steroidal / chemistry
Anti-Inflammatory Agents, Non-Steroidal / isolation & purification*
Anti-Inflammatory Agents, Non-Steroidal / pharmacology*
Asteraceae / chemistry*
Diterpenes / chemistry
Diterpenes / isolation & purification*
Diterpenes / pharmacology
Flavones / chemistry
Lactones / chemistry
Molecular Structure

Substances

5,3'-dihydroxy-3,6,7,4',5'-pentamethoxyflavone
Anti-Inflammatory Agents
Anti-Inflammatory Agents, Non-Steroidal
Diterpenes
Flavones
Lactones
gramaderin A
gramaderin B