Cytotoxic flavone analogues of vitexicarpin, a constituent of the leaves of Vitex negundo

Fredyc Díaz; Daniel Chávez; Dongho Lee; Qiuwen Mi; Hee Byung Chai; Ghee T. Tan; Leonardus B.S. Kardono; Soedarsono Riswan; Craig R. Fairchild; Robert Wild; Norman R. Farnsworth; Geoffrey A. Cordell; John M. Pezzuto; A. Douglas Kinghorn

doi:10.1021/np0300784

Cytotoxic flavone analogues of vitexicarpin, a constituent of the leaves of Vitex negundo

Fredyc Díaz, Daniel Chávez, Dongho Lee, Qiuwen Mi, Hee Byung Chai, Ghee T. Tan, Leonardus B.S. Kardono, Soedarsono Riswan, Craig R. Fairchild, Robert Wild, Norman R. Farnsworth, Geoffrey A. Cordell, John M. Pezzuto, A. Douglas Kinghorn

Research output: Contribution to journal › Article › peer-review

81 Citations (Scopus)

Abstract

Bioassay-guided fractionation of the chloroform-soluble extract of the leaves of Vitex negundo led to the isolation of the known flavone vitexicarpin (1), which exhibited broad cytotoxicity in a human cancer cell line panel. In an attempt to increase the cytotoxic potency of 1, a series of acylation reactions was performed on this compound to obtain its methylated (2), acetylated (3), and six new acylated (4-9) derivatives. Compound 9, the previously unreported 5,3′-dihexanoyloxy-3,6,7,4′-tetramethoxyflavone, showed comparative cytotoxic potency to compound 1 and was selected for further evaluation, However, this compound was found to be inactive when evaluated in the in vivo hollow fiber assay with Lul, KB, and LNCaP cells at the highest dose (40 mg/kg/body weight) tested, and in the in vivo P-388 leukemia model (135 mg/kg), using the ip administration route.

Original language	English
Pages (from-to)	865-867
Number of pages	3
Journal	Journal of Natural Products
Volume	66
Issue number	6
DOIs	https://doi.org/10.1021/np0300784
Publication status	Published - 2003 Jun 1
Externally published	Yes

ASJC Scopus subject areas

Analytical Chemistry
Molecular Medicine
Pharmacology
Pharmaceutical Science
Drug Discovery
Complementary and alternative medicine
Organic Chemistry

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This output contributes to the following UN Sustainable Development Goals (SDGs)

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10.1021/np0300784

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Díaz, F., Chávez, D., Lee, D., Mi, Q., Chai, H. B., Tan, G. T., Kardono, L. B. S., Riswan, S., Fairchild, C. R., Wild, R., Farnsworth, N. R., Cordell, G. A., Pezzuto, J. M., & Kinghorn, A. D. (2003). Cytotoxic flavone analogues of vitexicarpin, a constituent of the leaves of Vitex negundo. Journal of Natural Products, 66(6), 865-867. https://doi.org/10.1021/np0300784

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title = "Cytotoxic flavone analogues of vitexicarpin, a constituent of the leaves of Vitex negundo",

abstract = "Bioassay-guided fractionation of the chloroform-soluble extract of the leaves of Vitex negundo led to the isolation of the known flavone vitexicarpin (1), which exhibited broad cytotoxicity in a human cancer cell line panel. In an attempt to increase the cytotoxic potency of 1, a series of acylation reactions was performed on this compound to obtain its methylated (2), acetylated (3), and six new acylated (4-9) derivatives. Compound 9, the previously unreported 5,3′-dihexanoyloxy-3,6,7,4′-tetramethoxyflavone, showed comparative cytotoxic potency to compound 1 and was selected for further evaluation, However, this compound was found to be inactive when evaluated in the in vivo hollow fiber assay with Lul, KB, and LNCaP cells at the highest dose (40 mg/kg/body weight) tested, and in the in vivo P-388 leukemia model (135 mg/kg), using the ip administration route.",

author = "Fredyc D{\'i}az and Daniel Ch{\'a}vez and Dongho Lee and Qiuwen Mi and Chai, {Hee Byung} and Tan, {Ghee T.} and Kardono, {Leonardus B.S.} and Soedarsono Riswan and Fairchild, {Craig R.} and Robert Wild and Farnsworth, {Norman R.} and Cordell, {Geoffrey A.} and Pezzuto, {John M.} and Kinghorn, {A. Douglas}",

year = "2003",

month = jun,

day = "1",

doi = "10.1021/np0300784",

language = "English",

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T1 - Cytotoxic flavone analogues of vitexicarpin, a constituent of the leaves of Vitex negundo

AU - Díaz, Fredyc

AU - Chávez, Daniel

AU - Lee, Dongho

AU - Mi, Qiuwen

AU - Chai, Hee Byung

AU - Tan, Ghee T.

AU - Kardono, Leonardus B.S.

AU - Riswan, Soedarsono

AU - Fairchild, Craig R.

AU - Wild, Robert

AU - Farnsworth, Norman R.

AU - Cordell, Geoffrey A.

AU - Pezzuto, John M.

AU - Kinghorn, A. Douglas

PY - 2003/6/1

Y1 - 2003/6/1

N2 - Bioassay-guided fractionation of the chloroform-soluble extract of the leaves of Vitex negundo led to the isolation of the known flavone vitexicarpin (1), which exhibited broad cytotoxicity in a human cancer cell line panel. In an attempt to increase the cytotoxic potency of 1, a series of acylation reactions was performed on this compound to obtain its methylated (2), acetylated (3), and six new acylated (4-9) derivatives. Compound 9, the previously unreported 5,3′-dihexanoyloxy-3,6,7,4′-tetramethoxyflavone, showed comparative cytotoxic potency to compound 1 and was selected for further evaluation, However, this compound was found to be inactive when evaluated in the in vivo hollow fiber assay with Lul, KB, and LNCaP cells at the highest dose (40 mg/kg/body weight) tested, and in the in vivo P-388 leukemia model (135 mg/kg), using the ip administration route.

AB - Bioassay-guided fractionation of the chloroform-soluble extract of the leaves of Vitex negundo led to the isolation of the known flavone vitexicarpin (1), which exhibited broad cytotoxicity in a human cancer cell line panel. In an attempt to increase the cytotoxic potency of 1, a series of acylation reactions was performed on this compound to obtain its methylated (2), acetylated (3), and six new acylated (4-9) derivatives. Compound 9, the previously unreported 5,3′-dihexanoyloxy-3,6,7,4′-tetramethoxyflavone, showed comparative cytotoxic potency to compound 1 and was selected for further evaluation, However, this compound was found to be inactive when evaluated in the in vivo hollow fiber assay with Lul, KB, and LNCaP cells at the highest dose (40 mg/kg/body weight) tested, and in the in vivo P-388 leukemia model (135 mg/kg), using the ip administration route.

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Cytotoxic flavone analogues of vitexicarpin, a constituent of the leaves of Vitex negundo

Abstract

ASJC Scopus subject areas

UN SDGs

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