Cytotoxic pheophorbide-related compounds from Clerodendrum calamitosum and C. cyrtophyllum

H. H. Cheng, H. K. Wang, J. Ito, K. F. Bastow, Y. Tachibana, Y. Nakanishi, Z. Xu, T. Y. Luo, K. H. Lee

Research output: Contribution to journalArticle

64 Citations (Scopus)

Abstract

Three pheophorbide-related compounds (1-3) were isolated from the leaves and stems of Clerodendrum calamitosum. The methyl ester of 3 (6) and the known (10S)-hydroxypheophytin a (7) also were isolated from leaves of the related plant Clerodendrum cyrtophyllum. Compounds 1 and 6 were isolated for the first time as naturally occurring products from a plant source. All structures were elucidated by detailed spectroscopic analysis. Biological evaluation showed that 1 and 2 exhibited strong cytotoxicity against human lung carcinoma (A549), ileocecal carcinoma (HCT-8), kidney carcinoma (CAKI-1), breast adenocarcinoma (MCF-7), malignant melanoma (SK-MEL-2), ovarian carcinoma (1A9), and epidermoid carcinoma of the nasopharynx (KB), and its etoposide- (KB-7d), vincristine- (KB-VCR), and camptothecin-resistant (KB-CPT) subclones. Compound 3 was less cytotoxic than 1 and 2. Compounds 4-6, the methyl esters of 1-3, showed strongly increased cytotoxicity compared with the parent acids. Interestingly, 6 was the most active derivative among these compounds. Compound 7 was inactive.

Original languageEnglish
Pages (from-to)915-919
Number of pages5
JournalJournal of Natural Products
Volume64
Issue number7
DOIs
Publication statusPublished - 2001
Externally publishedYes

Fingerprint

Clerodendrum
Cytotoxicity
carcinoma
Esters
Carcinoma
Camptothecin
Spectroscopic analysis
Vincristine
Etoposide
cytotoxicity
Derivatives
Acids
esters
Plant Leaves
Nasopharynx
nasopharynx
vincristine
Squamous Cell Carcinoma
Melanoma
melanoma

ASJC Scopus subject areas

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

Cite this

Cheng, H. H., Wang, H. K., Ito, J., Bastow, K. F., Tachibana, Y., Nakanishi, Y., ... Lee, K. H. (2001). Cytotoxic pheophorbide-related compounds from Clerodendrum calamitosum and C. cyrtophyllum. Journal of Natural Products, 64(7), 915-919. https://doi.org/10.1021/np000595b

Cytotoxic pheophorbide-related compounds from Clerodendrum calamitosum and C. cyrtophyllum. / Cheng, H. H.; Wang, H. K.; Ito, J.; Bastow, K. F.; Tachibana, Y.; Nakanishi, Y.; Xu, Z.; Luo, T. Y.; Lee, K. H.

In: Journal of Natural Products, Vol. 64, No. 7, 2001, p. 915-919.

Research output: Contribution to journalArticle

Cheng, HH, Wang, HK, Ito, J, Bastow, KF, Tachibana, Y, Nakanishi, Y, Xu, Z, Luo, TY & Lee, KH 2001, 'Cytotoxic pheophorbide-related compounds from Clerodendrum calamitosum and C. cyrtophyllum', Journal of Natural Products, vol. 64, no. 7, pp. 915-919. https://doi.org/10.1021/np000595b
Cheng, H. H. ; Wang, H. K. ; Ito, J. ; Bastow, K. F. ; Tachibana, Y. ; Nakanishi, Y. ; Xu, Z. ; Luo, T. Y. ; Lee, K. H. / Cytotoxic pheophorbide-related compounds from Clerodendrum calamitosum and C. cyrtophyllum. In: Journal of Natural Products. 2001 ; Vol. 64, No. 7. pp. 915-919.
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