TY - JOUR
T1 - Cytotoxic and antimicrobial constituents of the bark of Diospyros maritima collected in two geographical locations in Indonesia
AU - Gu, Jian Qiao
AU - Graf, Tyler N.
AU - Lee, Dongho
AU - Chai, Hee Byung
AU - Mi, Qiuwen
AU - Kardono, Leonardus B.S.
AU - Setyowati, Fransisca M.
AU - Ismail, Rachman
AU - Riswan, Soedarsono
AU - Farnsworth, Norman R.
AU - Cordell, Geoffrey A.
AU - Pezzuto, John M.
AU - Swanson, Steven M.
AU - Kroll, David J.
AU - Falkinham, Joseph O.
AU - Wall, Monroe E.
AU - Wani, Mansukh C.
AU - Kinghorn, A. Douglas
AU - Oberlies, Nicholas H.
PY - 2004/7
Y1 - 2004/7
N2 - Bioactivity-directed fractionation of extracts of two Diospyros maritima bark samples from Indonesia, one collected at sea level in a beach forest in Java and the other collected at a slight elevation away from the sea shore on the island of Lombok, yielded a diverse set of secondary metabolites. The naphthoquinone plumbagin (1), although found in extracts of both specimens, constituted a much larger percentage of the former sample, which also yielded a series of plumbagin dimers, maritinone (2), chitranone (3), and zeylanone (4). The latter sample yielded a new naphthoquinone derivative, (4S)-shinanolone (5), and a new natural product coumarin, 7,8-dimethoxy-6-hydroxycoumarin (6), along with three other analogues of plumbagin, 2-methoxy-7-methyljuglone (7), 3-methoxy-7-methyljuglone (8), and 7-methyljuglone (9). The structures of compounds 5 and 6 were elaborated by physical, spectral, and chemical methods. All of the isolates were evaluated in both cytotoxicity and antimicrobial assays, and structure-activity relationships of these naphthoquinones are proposed. Plumbagin (1) and maritinone (2) were evaluated also for in vivo antitumor activity in the hollow fiber assay, but both were found to be inactive.
AB - Bioactivity-directed fractionation of extracts of two Diospyros maritima bark samples from Indonesia, one collected at sea level in a beach forest in Java and the other collected at a slight elevation away from the sea shore on the island of Lombok, yielded a diverse set of secondary metabolites. The naphthoquinone plumbagin (1), although found in extracts of both specimens, constituted a much larger percentage of the former sample, which also yielded a series of plumbagin dimers, maritinone (2), chitranone (3), and zeylanone (4). The latter sample yielded a new naphthoquinone derivative, (4S)-shinanolone (5), and a new natural product coumarin, 7,8-dimethoxy-6-hydroxycoumarin (6), along with three other analogues of plumbagin, 2-methoxy-7-methyljuglone (7), 3-methoxy-7-methyljuglone (8), and 7-methyljuglone (9). The structures of compounds 5 and 6 were elaborated by physical, spectral, and chemical methods. All of the isolates were evaluated in both cytotoxicity and antimicrobial assays, and structure-activity relationships of these naphthoquinones are proposed. Plumbagin (1) and maritinone (2) were evaluated also for in vivo antitumor activity in the hollow fiber assay, but both were found to be inactive.
UR - http://www.scopus.com/inward/record.url?scp=3242766672&partnerID=8YFLogxK
U2 - 10.1021/np040027m
DO - 10.1021/np040027m
M3 - Article
C2 - 15270571
AN - SCOPUS:3242766672
SN - 0163-3864
VL - 67
SP - 1156
EP - 1161
JO - Journal of Natural Products
JF - Journal of Natural Products
IS - 7
ER -