Cytotoxic and antimicrobial constituents of the bark of Diospyros maritima collected in two geographical locations in Indonesia

Jian Qiao Gu, Tyler N. Graf, Dongho Lee, Hee Byung Chai, Qiuwen Mi, Leonardus B S Kardono, Fransisca M. Setyowati, Rachman Ismail, Soedarsono Riswan, Norman R. Farnsworth, Geoffrey A. Cordell, John M. Pezzuto, Steven M. Swanson, David J. Kroll, Joseph O. Falkinham, Monroe E. Wall, Mansukh C. Wani, A. Douglas Kinghorn, Nicholas H. Oberlies

Research output: Contribution to journalArticle

74 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)1156-1161
Number of pages6
JournalJournal of Natural Products
Volume67
Issue number7
DOIs
Publication statusPublished - 2004 Jul 1
Externally publishedYes

Fingerprint

Diospyros
plumbagin
Indonesia
Geographical Locations
Naphthoquinones
naphthoquinones
bark
anti-infective agents
Oceans and Seas
Assays
coumarin
Sea level
extracts
assays
structure-activity relationships
Structure-Activity Relationship
Cytotoxicity
Fractionation
Beaches
Metabolites

ASJC Scopus subject areas

  • Plant Science
  • Chemistry (miscellaneous)
  • Drug Discovery
  • Organic Chemistry
  • Pharmacology

Cite this

Cytotoxic and antimicrobial constituents of the bark of Diospyros maritima collected in two geographical locations in Indonesia. / Gu, Jian Qiao; Graf, Tyler N.; Lee, Dongho; Chai, Hee Byung; Mi, Qiuwen; Kardono, Leonardus B S; Setyowati, Fransisca M.; Ismail, Rachman; Riswan, Soedarsono; Farnsworth, Norman R.; Cordell, Geoffrey A.; Pezzuto, John M.; Swanson, Steven M.; Kroll, David J.; Falkinham, Joseph O.; Wall, Monroe E.; Wani, Mansukh C.; Kinghorn, A. Douglas; Oberlies, Nicholas H.

In: Journal of Natural Products, Vol. 67, No. 7, 01.07.2004, p. 1156-1161.

Research output: Contribution to journalArticle

Gu, JQ, Graf, TN, Lee, D, Chai, HB, Mi, Q, Kardono, LBS, Setyowati, FM, Ismail, R, Riswan, S, Farnsworth, NR, Cordell, GA, Pezzuto, JM, Swanson, SM, Kroll, DJ, Falkinham, JO, Wall, ME, Wani, MC, Kinghorn, AD & Oberlies, NH 2004, 'Cytotoxic and antimicrobial constituents of the bark of Diospyros maritima collected in two geographical locations in Indonesia', Journal of Natural Products, vol. 67, no. 7, pp. 1156-1161. https://doi.org/10.1021/np040027m
Gu, Jian Qiao ; Graf, Tyler N. ; Lee, Dongho ; Chai, Hee Byung ; Mi, Qiuwen ; Kardono, Leonardus B S ; Setyowati, Fransisca M. ; Ismail, Rachman ; Riswan, Soedarsono ; Farnsworth, Norman R. ; Cordell, Geoffrey A. ; Pezzuto, John M. ; Swanson, Steven M. ; Kroll, David J. ; Falkinham, Joseph O. ; Wall, Monroe E. ; Wani, Mansukh C. ; Kinghorn, A. Douglas ; Oberlies, Nicholas H. / Cytotoxic and antimicrobial constituents of the bark of Diospyros maritima collected in two geographical locations in Indonesia. In: Journal of Natural Products. 2004 ; Vol. 67, No. 7. pp. 1156-1161.
@article{573daf628a934586a84256f9bbadf686,
title = "Cytotoxic and antimicrobial constituents of the bark of Diospyros maritima collected in two geographical locations in Indonesia",
abstract = "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.",
author = "Gu, {Jian Qiao} and Graf, {Tyler N.} and Dongho Lee and Chai, {Hee Byung} and Qiuwen Mi and Kardono, {Leonardus B S} and Setyowati, {Fransisca M.} and Rachman Ismail and Soedarsono Riswan and Farnsworth, {Norman R.} and Cordell, {Geoffrey A.} and Pezzuto, {John M.} and Swanson, {Steven M.} and Kroll, {David J.} and Falkinham, {Joseph O.} and Wall, {Monroe E.} and Wani, {Mansukh C.} and Kinghorn, {A. Douglas} and Oberlies, {Nicholas H.}",
year = "2004",
month = "7",
day = "1",
doi = "10.1021/np040027m",
language = "English",
volume = "67",
pages = "1156--1161",
journal = "Journal of Natural Products",
issn = "0163-3864",
publisher = "American Chemical Society",
number = "7",

}

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 - 2004/7/1

Y1 - 2004/7/1

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

UR - http://www.scopus.com/inward/citedby.url?scp=3242766672&partnerID=8YFLogxK

U2 - 10.1021/np040027m

DO - 10.1021/np040027m

M3 - Article

VL - 67

SP - 1156

EP - 1161

JO - Journal of Natural Products

JF - Journal of Natural Products

SN - 0163-3864

IS - 7

ER -