TY - JOUR
T1 - Isolation and characterization of cancer chemopreventive compounds from Barringtonia maunwongyathiae
AU - Jutiviboonsuk, Aranya
AU - ZHANG, Hongjie
AU - Kondratyuk, Tamara P.
AU - Herunsalee, Angkana
AU - Chaukul, Wongsatit
AU - Pezzuto, John M.
AU - Fong, Harry H.S.
AU - Bunyapraphatsara, Nuntavan
N1 - Funding Information:
This study was supported by the Thailand Research Fund through the Royal Golden Jubilee Ph.D. program (grant no. PHD/5.A.MU/44/D.1) to A.J. and N.B. and by program project P01 CA48112 funded by the National Cancer Institute, NIH, Bethesda, Maryland. The authors are grateful to the NMR Lab of the Department of Medicinal Chemistry and Pharmacognosy, and the Research Resources Center, University of Illinois at Chicago, for access to the Bruker DPX 300 and 400 MHz instruments, as well as the acquisition of MS data.
PY - 2007/3
Y1 - 2007/3
N2 - A new plant species, Barringtonia maunwongyathiae W. Chuakul (Lecythidaceae), was recently discovered in Khuan Thon Forest, Ao Luek District, Krabi Province, Thailand. Chemical investigation of the leaves of this plant led to the isolation of 10 triterpenes, 3 steroids, and a vitamin E derivative. The structures of these compounds were identified as taraxerol (1), 3-(E)-coumaroyltaraxerol (2), 3-(Z)-coumaroyltaraxerol (3), 3-(E)-coumaroyl β-amyrin (4), 3-(Z)-coumaroyl β-amyrin (5), 3-(E)-coumaroyl α-amyrin (6), 3-(Z)-coumaroyl α-amyrin (7), 3-(E)-coumaroyllupeol (8), 3-(Z)-coumaroyllupeol (9), 3,19,24-trihydroxyurs-12-ene-28-oic acid (10), stigma-4,22-dien-3-one (11), β-stigmasterol (12), 3-O-β-D- glucopyranosyl-stigmasta-5,22-diene (13), and α-tocopherylquinone (14). All compounds were evaluated for their cancer chemopreventive potential based on inhibition of TPA-induced ornithine decarboxylase expression, COX-1 and COX-2 activities, and phorbol ester-induced NF-κB luciferase expression, as well as activation of antioxidant response element-mediated luciferase expression. Compounds 1, 2, and 14 demonstrated greatest promise, while 12 and 13 showed moderate activity.
AB - A new plant species, Barringtonia maunwongyathiae W. Chuakul (Lecythidaceae), was recently discovered in Khuan Thon Forest, Ao Luek District, Krabi Province, Thailand. Chemical investigation of the leaves of this plant led to the isolation of 10 triterpenes, 3 steroids, and a vitamin E derivative. The structures of these compounds were identified as taraxerol (1), 3-(E)-coumaroyltaraxerol (2), 3-(Z)-coumaroyltaraxerol (3), 3-(E)-coumaroyl β-amyrin (4), 3-(Z)-coumaroyl β-amyrin (5), 3-(E)-coumaroyl α-amyrin (6), 3-(Z)-coumaroyl α-amyrin (7), 3-(E)-coumaroyllupeol (8), 3-(Z)-coumaroyllupeol (9), 3,19,24-trihydroxyurs-12-ene-28-oic acid (10), stigma-4,22-dien-3-one (11), β-stigmasterol (12), 3-O-β-D- glucopyranosyl-stigmasta-5,22-diene (13), and α-tocopherylquinone (14). All compounds were evaluated for their cancer chemopreventive potential based on inhibition of TPA-induced ornithine decarboxylase expression, COX-1 and COX-2 activities, and phorbol ester-induced NF-κB luciferase expression, as well as activation of antioxidant response element-mediated luciferase expression. Compounds 1, 2, and 14 demonstrated greatest promise, while 12 and 13 showed moderate activity.
KW - Antioxidant responsive element (ARE)
KW - ARE luciferase reporter system
KW - Barringtonia maunwongyathiae
KW - Cancer chemoprevention
KW - Coumaroyl triterpenes
KW - COX-1
KW - COX-2
KW - Lecythidaceae
KW - NF-κB luciferase reporter system
KW - Ornithine decarboxylase (ODC)g48
UR - http://www.scopus.com/inward/record.url?scp=34247584005&partnerID=8YFLogxK
U2 - 10.1080/13880200701213062
DO - 10.1080/13880200701213062
M3 - Journal article
AN - SCOPUS:34247584005
SN - 1388-0209
VL - 45
SP - 185
EP - 194
JO - Pharmaceutical Biology
JF - Pharmaceutical Biology
IS - 3
ER -
