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Estrogenic and anti-estrogenic compounds from the Thai medicinal plant, Smilax corbularia (Smilacaceae)
- Source :
- Phytochemistry. 72:495-502
- Publication Year :
- 2011
- Publisher :
- Elsevier BV, 2011.
-
Abstract
- From the rhizomes of Smilax corbularia Kunth. (Smilacaceae), 11 compounds, (2R,3R)-2″-acetyl astilbin, (2R,3R)-3″-acetyl astilbin, (2R,3R)-4″-acetyl astilbin, (2R,3R)-3″-acetyl engeletin, (2R,3S)-4″-acetyl isoastilbin, 2-(4-hydroxyphenyl)-3,4,9,10-tetrahydro-3,5-dihydroxy-10-(3,4-dihydroxyphenyl)-(2R,3R,10R)-2H,8H-benzo [1,2-b:3,4-b'] dipyran-8-one, 2-(4-hydroxyphenyl)-3,4,9,10-tetrahydro-3,5-dihydroxy-10-(3,4-dihydroxyphenyl)-(2R,3R,10S)-2H, 8H-benzo [1,2-b:3,4-b'] dipyran-8-one, 3,4-dihydro-7-hydroxy-4-(3,4-dihydroxyphenyl)-5-[(1E)-2-(4-hydroxyphenyl) ethenyl]-2H-1-benzopyran-2-one, 3,4-dihydro-7-hydroxy-4-(3,4-dihydroxy-phenyl)-5-[(1E)-2-(3,4-dihydroxyphenyl) ethenyl]-2H-1-benzopyran-2-one, 3,4-dihydro-7-hydroxy-4-(4-hydroxy-3-methoxyphenyl)-5-[(1E)-2-(4-hydroxyphenyl) ethenyl]-2H-1-benzopyran-2-one, and 5,7,3',4'-tetrahydroxy-3-phenylcoumarin along with 34 known compounds were isolated and characterized as 19 flavonoids, 14 catechin derivatives, 6 stilbene derivatives, and 6 miscellaneous substances. All isolates had their estrogenic and anti-estrogenic activities determined using the estrogen-responsive human breast cancer cell lines MCF-7 and T47D. The major constituents were recognized as flavanonol rhamnosides by the suppressive effect on estradiol induced cell proliferation at a concentration of 1μM. Meanwhile, flavanonol rhamnoside acetates demonstrated estrogenic activity in both MCF-7 and T47D cells at a concentration of 100μM, and they enhanced the effects of co-treated E2 on T47D cell proliferation at concentrations of more than 0.1μM.
- Subjects :
- Stereochemistry
Flavonoid
Engeletin
Antineoplastic Agents
Plant Science
Horticulture
Pharmacognosy
Biochemistry
chemistry.chemical_compound
Cell Line, Tumor
Humans
Smilacaceae
Molecular Biology
Cell Proliferation
chemistry.chemical_classification
Plants, Medicinal
Dose-Response Relationship, Drug
Molecular Structure
biology
Estrogen Antagonists
Smilax
Estrogens
Stereoisomerism
Catechin
Flavanonol
General Medicine
Thailand
biology.organism_classification
chemistry
Astilbin
Drug Screening Assays, Antitumor
Subjects
Details
- ISSN :
- 00319422
- Volume :
- 72
- Database :
- OpenAIRE
- Journal :
- Phytochemistry
- Accession number :
- edsair.doi.dedup.....986bdee88bc55890739bbeea055c2c8f