New diarylheptanoids and diarylheptanoid glucosides from the rhizomes of Tacca chantrieri and their cytotoxic activity.
Two new diarylheptanoids (1, 2) and seven new diarylheptanoid glucosides (3-9) were isolated from the rhizomes of Tacca chantrieri. Their structures were determined by spectroscopic analysis, including 2D NMR data, and the results of hydrolytic cleavage. The absolute configurations of the 3,5-dihydroxyheptane moieties of the new diarylheptanoids were determined to be 3R and 5R by the application of the CD exciton chirality method to the corresponding 3,5-bis-p-bromobenzoyl derivatives. The cytotoxic activities of the isolated compounds and some derivatives against HL-60 human promyelocytic leukemia cells, HSC-2 human oral squamous carcinoma cells, and normal human gingival fibroblasts (HGF) are reported.
Yokosuka
Akihito
A
Laboratory of Medicinal Plant Science, School of Pharmacy, Tokyo University of Pharmacy and Life Science, 1432-1, Horinouchi, Hachiouji, Tokyo 192-0392, Japan.
Mimaki
Yoshihiro
Y
Sakagami
Hiroshi
H
Sashida
Yutaka
Y
D000972:Antineoplastic Agents, Phytogenic / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D002294:Carcinoma, Squamous Cell; D002851:Chromatography, High Pressure Liquid; D002942:Circular Dichroism; D036381:Diarylheptanoids; D004354:Drug Screening Assays, Antitumor; D004365:Drugs, Chinese Herbal; D005347:Fibroblasts / Q000187:drug effects; D005881:Gingiva; D005960:Glucosides / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D006026:Glycoside Hydrolases / Q000378:metabolism; D006536:Heptanes / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D006801:Humans; D006868:Hydrolysis; D007951:Leukemia, Myeloid; D008968:Molecular Conformation; D015394:Molecular Structure; D009097:Multienzyme Complexes / Q000378:metabolism; D019906:Nuclear Magnetic Resonance, Biomolecular; D010636:Phenols / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D010946:Plants, Medicinal / Q000737:chemistry*; D027343:Rhizome / Q000737:chemistry; D014407:Tumor Cells, Cultured / Q000187:drug effects; D001617:beta-Glucosidase / Q000378:metabolism
C452838:3,5-dihydroxy-1,7-bis(3,4-dihydroxyphenyl)heptane; C452837:3,5-dihydroxy-1-(3,4-dihydroxyphenyl)-7-(4-hydroxyphenyl)heptane; D000972:Antineoplastic Agents, Phytogenic; D036381:Diarylheptanoids; D004365:Drugs, Chinese Herbal; D005960:Glucosides; D006536:Heptanes; D009097:Multienzyme Complexes; D010636:Phenols; D006026:Glycoside Hydrolases; C039827:naringinase; D001617:beta-Glucosidase