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Derivatives of pheophorbide-a and pheophorbide-b from photocytotoxic Piper penangense extract.
- Source :
-
Chemistry & biodiversity [Chem Biodivers] 2011 Mar; Vol. 8 (3), pp. 494-502. - Publication Year :
- 2011
-
Abstract
- In our screening program for new photosensitizers from Malaysian biodiversity for photodynamic therapy (PDT) of cancer, MeOH extracts of ten terrestrial plants from Cameron Highlands in Pahang, Peninsular Malaysia, were tested. In a short-term 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl-2H-tetrazolium bromide (MTT) assay, 20 μg/ml each of these extracts were incubated in a pro-myelocytic leukemia cell-line, HL60, with or without irradiation with 9.6 J/cm(2) of a broad spectrum light. Three samples, Labisia longistyla, Dichroa febrifuga, and Piper penangense, were photocytotoxic by having at least twofold lower cell viability when irradiated compared to the unirradiated assay. The extract of the leaves of Piper penangense, a shrub belonging to the family Piperaceae and widely distributed in the tropical and subtropical regions in the world, was subsequently subjected to bioassay-guided fractionation using standard chromatography methods. Eight derivatives of pheophorbide-a and -b were identified from the fractions that exhibited strong photocytotoxicity. By spectroscopic analysis, these compounds were identified as pheophorbide-a methyl ester (1), (R,S)-13(2) -hydroxypheophorbide-a methyl ester (2 and 3), pheophorbide-b methyl ester (4), 13(2) -hydroxypheophorbide-b methyl ester (5), 15(2) -hydroxylactone pheophorbide-a methyl ester (6), 15(2) -methoxylactone pheophorbide-a methyl ester (7), 15(2) -methoxylactone pheophorbide-b methyl ester (8).<br /> (Copyright © 2011 Verlag Helvetica Chimica Acta AG, Zürich.)
- Subjects :
- Antineoplastic Agents, Phytogenic chemistry
Antineoplastic Agents, Phytogenic pharmacology
Cell Survival drug effects
Chlorophyll chemistry
Chlorophyll isolation & purification
Chlorophyll pharmacology
Drug Screening Assays, Antitumor
HL-60 Cells
Humans
Molecular Structure
Photosensitizing Agents chemistry
Photosensitizing Agents pharmacology
Plant Leaves chemistry
Stereoisomerism
Structure-Activity Relationship
Antineoplastic Agents, Phytogenic isolation & purification
Chlorophyll analogs & derivatives
Photosensitizing Agents isolation & purification
Piperaceae chemistry
Plant Extracts chemistry
Plant Extracts pharmacology
Subjects
Details
- Language :
- English
- ISSN :
- 1612-1880
- Volume :
- 8
- Issue :
- 3
- Database :
- MEDLINE
- Journal :
- Chemistry & biodiversity
- Publication Type :
- Academic Journal
- Accession number :
- 21404433
- Full Text :
- https://doi.org/10.1002/cbdv.201000341