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Planta Med 2015; 81(12/13): 1133-1140
DOI: 10.1055/s-0035-1546118
Natural Product Chemistry
Original Papers
Georg Thieme Verlag KG Stuttgart · New York

New Bioactive Lupane Triterpene Coumaroyl Esters Isolated from Buxus cochinchinensis [*]

Li Pan
1   Division of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, The Ohio State University, Columbus, OH, USA
,
Ulyana Muñoz Acuña
2   Division of Pharmacy Practice and Administration, College of Pharmacy, The Ohio State University, Columbus, OH, USA
,
Heebyung Chai
1   Division of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, The Ohio State University, Columbus, OH, USA
,
Hyun-Young Park
1   Division of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, The Ohio State University, Columbus, OH, USA
,
Tran Ngoc Ninh
3   Institute of Ecology and Biological Resources, Vietnam Academy of Science and Technology, Hoang Quoc Viet, Cau Giay, Hanoi, Vietnam
,
Bui Van Thanh
3   Institute of Ecology and Biological Resources, Vietnam Academy of Science and Technology, Hoang Quoc Viet, Cau Giay, Hanoi, Vietnam
,
Emilio F. Merino
4   Department of Biochemistry and the Virginia Tech Center for Drug Discovery, M/C 0308, Virginia Tech, Blacksburg, VA, USA
,
Maria B. Cassera
4   Department of Biochemistry and the Virginia Tech Center for Drug Discovery, M/C 0308, Virginia Tech, Blacksburg, VA, USA
,
L. Harinantenaina Rakotondraibe
1   Division of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, The Ohio State University, Columbus, OH, USA
,
Esperanza J. Carcache de Blanco
1   Division of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, The Ohio State University, Columbus, OH, USA
2   Division of Pharmacy Practice and Administration, College of Pharmacy, The Ohio State University, Columbus, OH, USA
,
Djaja D. Soejarto
5   Department of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, University of Illinois at Chicago, Chicago, IL, USA
6   Science and Education, Field Museum of Natural History, Chicago, IL, USA
,
A. Douglas Kinghorn
1   Division of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, The Ohio State University, Columbus, OH, USA
› Author Affiliations
Further Information

Publication History

received 24 February 2015
revised 17 April 2015

accepted 20 April 2015

Publication Date:
01 July 2015 (online)

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Abstract

Five new lupane triterpene coumaroyl esters (1–5), together with betulin (6) and a known Buxus alkaloid, N-3-benzoyldihydrocyclomicrophylline F (7), were isolated from a CHCl3-soluble partition of a methanol extract of Buxus cochinchinensis Pierre ex Gagnep. (Buxaceae) collected in Vietnam. Isolation work was monitored using human colon cancer cells (HT-29). The structures of the new compounds (1–5) were determined on the basis of spectroscopic data interpretation. In addition to their cytotoxicity against HT-29 cells and nuclear factor-kappa B (p65) inhibitory activity in an enzyme-linked immunosorbent assay, all isolates as well as two semisynthetic compounds derived from betulin and 5, respectively, were also evaluated for their in vitro antiplasmodial activities against the drug-resistant Dd2 strain of Plasmodium falciparum and antifungal effects on the growth of the pathogenic yeast Candida albicans. The new lupane triterpene coumaroyl esters (1–5), along with a betulin derivative and the known Buxus alkaloid, were found to show significant in vitro antimalarial activities, with IC50 values ranging from 0.26 to 2.07 µM.

Key words

lupane triterpenes - coumaroyl esters - Buxus cochinchinensis - Buxaceae - cytotoxicity - antimalarial activity

* Dedicated to Professor Dr. Adolf Nahrstedt on the occasion of his 75th birthday.


Supporting Information

 

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