Caffeic acid oligomers in Lithospermum erythrorhizon cell suspension cultures

• Published in: Phytochemistry (Oxford) Vol. 53; no. 6; pp. 651 - 657
• Main Authors: Yamamoto, Hirobumi, Inoue, Kenichiro, Yazaki, Kazufumi
• Format: Journal Article
• Language: English
• Published: Amsterdam Elsevier Ltd 01.03.2000; Elsevier
• Subjects: (+)-Rabdosiin; Benzofurans - chemistry; Benzofurans - metabolism; Biological and medical sciences; Biotechnology; Boraginaceae; Caffeic acid oligomers; Caffeic Acids - chemistry; Caffeic Acids - metabolism; Cell suspension cultures; Cells, Cultured; Depsides; Dimerization; Fundamental and applied biological sciences. Psychology; Lignans; Lithospermic acid B; Lithospermum erythrorhizon; Magnetic Resonance Spectroscopy; Naphthoquinones - chemistry; Naphthoquinones - metabolism; Plant physiology and development; Plants - chemistry; Plants - metabolism; Secondary metabolite production; Shikonin; Tissue cultures, protoplasts; Secondary metabolite production; Cell suspension cultures; (+)-Rabdosiin; Shikonin; Lithospermic acid B; Lithospermum erythrorhizon; Caffeic acid oligomers; Boraginaceae; Cell culture; Hairy root; Oligomer; Caffeic acid; Ester; Dicotyledones; Angiospermae; Pigments; Spermatophyta; Dimer; Secondary metabolism; Quantitative analysis
• ISSN: 0031-9422; 1873-3700
• DOI: 10.1016/S0031-9422(99)00623-8

Lithospermum erythrorhizon cells cultured in pigment production (M-9) medium produced lithospermic acid B, a dimerized caffeic acid ester derivative, in quantities similar to the production of shikonin. The cells also produced a related dimer, (+)-rabdosiin. In Linsmaier–Skoog liquid medium, which suppresses shikonin production, both lithospermic acid B and (+)-rabdosiin were still formed. Lithospermic acid, a caffeic acid–rosmarinic acid conjugate, was isolated as a main constituent in Lithospermum hairy root cultures. In the aerial parts of L. erythrorhizon, the content of these phenylpropanoid oligomers was relatively low compared to that of rosmarinic acid.