Rhuschalcones II-VI, five new bichalcones from the root bark of Rhus pyroides

• Published in: Journal of natural products (Washington, D.C.) Vol. 66; no. 5; pp. 599 - 604
• Main Authors: Mdee, L.K, Yeboah, S.O, Abegaz, B.M
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 01.05.2003; Amer Chemical Soc; American Society of Pharmacognosy
• Subjects: acetone; Anacardiaceae; Antineoplastic Agents, Phytogenic - chemistry; Antineoplastic Agents, Phytogenic - isolation & purification; Antineoplastic Agents, Phytogenic - pharmacology; bark; bichalcones; biflavonoids; Biological and medical sciences; Botswana; cell lines; Chalcone - analogs & derivatives; Chalcone - chemistry; Chalcone - isolation & purification; Chalcone - pharmacology; chalcones; chemical structure; Chemistry, Medicinal; Colonic Neoplasms; cytotoxicity; Drug Screening Assays, Antitumor; Flavonoids; General pharmacology; humans; Life Sciences & Biomedicine; Medical sciences; Melanoma; methine; methylene; Molecular Structure; Pharmacognosy. Homeopathy. Health food; Pharmacology & Pharmacy; Pharmacology. Drug treatments; phytochemicals; Plant Bark - chemistry; plant extracts; Plant Roots - chemistry; Plant Sciences; Plants, Medicinal - chemistry; protons; Rhus; Rhus - chemistry; Rhus pyroides; rhuschalcones; roots; Science & Technology; spectral analysis; stereochemistry; Tumor Cells, Cultured - drug effects; Botswana; Africa; FLAVONOIDS; Antineoplastic agent; Human; Ether; Root; Pharmacognosy; Bark; Cytotoxicity; In vitro; Biological activity; Medicinal plant; Polyphenol; Cell line; Dicotyledones; Angiospermae; Plant origin; Phenols; Benzenic compound; Isolation; Spermatophyta; Enone; Tumor cell; Anacardiaceae; Structural analysis
• ISSN: 0163-3864; 1520-6025
• DOI: 10.1021/np020138q

Biflavonoids detected in trace amounts in an earlier investigation of the twigs of Rhus pyroides have now been found in the root bark of this species. These new flavonoids belong to a rare bichalcone class and have been identified as 2',4',4",2'",4"'-pentahydroxy-4-O-5"'-bichalcone (rhuschalcone II, 2), 2',4',4",2'"-tetrahydroxy-4"'-methoxy-4-O-5"'-bichalcone (rhuschalcone III, 3), 4,2',4",2"'-tetrahydroxy-4"'-methoxy4'-O-5"'-bichalcone (rhuschalcone IV, 4), 4,2',4',4",2"',4"'-hexahydroxy-3,5"'-dihydrochalcone-chalcone (rhuschalcone V, 5), and 4,2',4',4",2"',4"'-hexahydroxy-3,5"'-bichalcone (rhuschalcone VI, 6), repectively. Also obtained was the known compound rhuschalcone 1 (1). Their structures were determined by spectroscopic and chemical methods, and for 1-3 by total synthesis. All the bichalcones (1-6) tested exhibited selective cytotoxic activity against the HT29 and HCT-116 colon tumor cell lines.