Cytotoxic and antimicrobial constituents of the bark of Diospyros maritima collected in two geographical locations in Indonesia.
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.
Program for Collaborative Research in the Pharmaceutical Sciences and Department of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, University of Illinois at Chicago, 833 South Wood Street, Chicago, IL 60612, USA.
Jian-Qiao
JQ
Gu
Tyler N
TN
Graf
Dongho
D
Lee
Hee-Byung
HB
Chai
Qiuwen
Q
Mi
Leonardus B S
LB
Kardono
Fransisca M
FM
Setyowati
Rachman
R
Ismail
Soedarsono
S
Riswan
Norman R
NR
Farnsworth
Geoffrey A
GA
Cordell
John M
JM
Pezzuto
Steven M
SM
Swanson
David J
DJ
Kroll
Joseph O
JO
Falkinham
Monroe E
ME
Wall
Mansukh C
MC
Wani
A Douglas
AD
Kinghorn
Nicholas H
NH
Oberlies
D001234:Aspergillus niger / Q000187:drug effects; D001419:Bacteria / Q000187:drug effects; D002176:Candida albicans / Q000187:drug effects; D003374:Coumarins / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D029788:Diospyros / Q000737:chemistry*; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D007214:Indonesia; D007624:KB Cells / Q000187:drug effects; D008826:Microbial Sensitivity Tests; D009285:Naphthoquinones / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D024301:Plant Bark / Q000737:chemistry; D010946:Plants, Medicinal / Q000737:chemistry*; D012441:Saccharomyces cerevisiae / Q000187:drug effects
D003374:Coumarins; D009285:Naphthoquinones; C489089:chitranone; C489087:maritinone; C489088:zeylanone; C014758:plumbagin