Three new clerodane diterpenes from Polyalthia longifolia var. pendula

Tung-Ho Wu; Yung-Yi Cheng; Chao-Jung Chen; Lean-Teik Ng; Li-Chen Chou; Li-Jiau Huang; Yung-Husan Chen; Sheng-Chu Kuo; Mohamed El-Shazly; Yang-Chang Wu; Fang-Rong Chang; Chih-Chuang Liaw

doi:10.3390/molecules19022049

Three new clerodane diterpenes from Polyalthia longifolia var. pendula

Molecules. 2014 Feb 13;19(2):2049-60. doi: 10.3390/molecules19022049.

Authors

Affiliations

¹ Graduate Institute of Natural Products, Kaohsiung Medical University, Kaohsiung 807, Taiwan. thwu@isca.vghks.gov.tw.
² Graduate Institute of Pharmaceutical Chemistry, China Medical University, Taichung 404, Taiwan. vivinecheng001@yahoo.com.tw.
³ Proteomics Core Laboratory, Department of Medical Research, China Medical University Hospital, Taichung 404, Taiwan. cjchen@mail.cmu.edu.tw.
⁴ Department of Agricultural Chemistry, National Taiwan University, Taipei 106, Taiwan. nglt97@ntu.edu.tw.
⁵ Graduate Institute of Pharmaceutical Chemistry, China Medical University, Taichung 404, Taiwan. lichen1973@gmail.com.
⁶ Graduate Institute of Pharmaceutical Chemistry, China Medical University, Taichung 404, Taiwan. ljhuang@mail.cmu.edu.tw.
⁷ National Museum of Marine Biology and Aquarium, Pingtung 944, Taiwan. tony_chen72001@yahoo.com.tw.
⁸ Graduate Institute of Pharmaceutical Chemistry, China Medical University, Taichung 404, Taiwan. sckuo@mail.cmu.edu.tw.
⁹ Department of Pharmacognosy and Natural Products Chemistry, Faculty of Pharmacy, Ain-Shams University, Organization of African Unity Street, Abassia, Cairo 11566, Egypt. mohamed.elshazly@pharm.asu.edu.eg.
¹⁰ Graduate Institute of Natural Products, Kaohsiung Medical University, Kaohsiung 807, Taiwan. yachwu@mail.cmu.edu.tw.
¹¹ Graduate Institute of Natural Products, Kaohsiung Medical University, Kaohsiung 807, Taiwan. aaronfrc@kmu.edu.tw.
¹² Graduate Institute of Natural Products, Kaohsiung Medical University, Kaohsiung 807, Taiwan. ccliaw@mail.nsysu.edu.tw.

Abstract

Three new clerodane diterpenes, (4→2)-abeo-cleroda-2,13E-dien-2,14-dioic acid (1), (4→2)-abeo-2,13-diformyl-cleroda-2,13E-dien-14-oic acid (2), and 16(R&S)- methoxycleroda-4(18),13-dien-15,16-olide (3), were isolated from the unripe fruit of Polyalthia longifolia var. pendula (Annonaceae) together with five known compounds (4-8). The structures of all isolates were determined by spectroscopic analysis. The anti-inflammatory activity of the isolates was evaluated by testing their inhibitory effect on NO production in LPS-stimulated RAW 264.7 macrophages. Among the isolated compounds, 16-hydroxycleroda-3,13-dien-15,16-olide (6) and 16-oxocleroda-3,13-dien-15-oic acid (7) showed promising NO inhibitory activity at 10 µg/mL, with 81.1% and 86.3%, inhibition, respectively.

Publication types

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

MeSH terms

Animals
Anti-Inflammatory Agents / chemistry
Anti-Inflammatory Agents / isolation & purification
Anti-Inflammatory Agents / pharmacology*
Antineoplastic Agents, Phytogenic
Diterpenes, Clerodane / chemistry
Diterpenes, Clerodane / isolation & purification
Diterpenes, Clerodane / pharmacology*
Humans
Inflammation / chemically induced
Inflammation / drug therapy*
Macrophages / drug effects
Mice
Polyalthia / chemistry*

Substances

Anti-Inflammatory Agents
Antineoplastic Agents, Phytogenic
Diterpenes, Clerodane