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
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.
Journal of Natural Products
https://doi.org/10.1021/np040027m
Published - 2004 Jul
10.1021/np040027m
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plumbagin Medicine & Life Sciences 99%
7-methyljuglone Medicine & Life Sciences 98%
Plumbagin Chemical Compounds 97%
maritinone Medicine & Life Sciences 71%
Indonesia Medicine & Life Sciences 70%
Naphthoquinones Medicine & Life Sciences 70%
Naphthoquinone Chemical Compounds 56%
Gu, J. Q., Graf, T. N., Lee, D., Chai, H. B., Mi, Q., Kardono, L. B. S., Setyowati, F. M., Ismail, R., Riswan, S., Farnsworth, N. R., Cordell, G. A., Pezzuto, J. M., Swanson, S. M., Kroll, D. J., Falkinham, J. O., Wall, M. E., Wani, M. C., Kinghorn, A. D., & Oberlies, N. H. (2004). Cytotoxic and antimicrobial constituents of the bark of Diospyros maritima collected in two geographical locations in Indonesia. Journal of Natural Products, 67(7), 1156-1161. https://doi.org/10.1021/np040027m
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, 07.2004, p. 1156-1161.
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 JQ, Graf TN, Lee D, Chai HB, Mi Q, Kardono LBS et al. Cytotoxic and antimicrobial constituents of the bark of Diospyros maritima collected in two geographical locations in Indonesia. Journal of Natural Products. 2004 Jul;67(7):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.}",
doi = "10.1021/np040027m",
journal = "Journal of Natural Products",
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.
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.
U2 - 10.1021/np040027m
DO - 10.1021/np040027m
JO - Journal of Natural Products
JF - Journal of Natural Products