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.
Gu
Jian-Qiao
JQ
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.
Graf
Tyler N
TN
Lee
Dongho
D
Chai
Hee-Byung
HB
Mi
Qiuwen
Q
Kardono
Leonardus B S
LB
Setyowati
Fransisca M
FM
Ismail
Rachman
R
Riswan
Soedarsono
S
Farnsworth
Norman R
NR
Cordell
Geoffrey A
GA
Pezzuto
John M
JM
Swanson
Steven M
SM
Kroll
David J
DJ
Falkinham
Joseph O
JO
Wall
Monroe E
ME
Wani
Mansukh C
MC
Kinghorn
A Douglas
AD
Oberlies
Nicholas H
NH
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