Diastereomers of lithospermic acid and lithospermic acid B from Monarda fistulosa and Lithospermum erythrorhizon

作者：Murata Toshihiro^*; Oyama Kanae; Fujiyama Minami; Oobayashi Bunmei; Umehara Kaoru; Miyase Toshio; Yoshizaki Fumihiko

来源：Fitoterapia, 2013, 91: 51-59.

DOI：10.1016/j.fitote.2013.08.009

• Monarda fistulosa
• Lithospermum erythrorhizon
• Phenylpropanoid oligomers
• Hyaluronidase inhibitors
• Histamine release inhibitors

Monardic acids A (1) and B (2), which are (7R,8R) diastereomers of lithospermic acid (LA) and lithospermic acid B, respectively, were isolated from Monarda fistulosa. A (75,8R) isomer (3) of LA was also isolated from this plant, and a (7R,8S) isomer (7) of LA was obtained from Lithospermum erythrorhizon. The absolute configuration of 1 was confirmed by analysis of its hydrolysates, 7-epiblechnic acid and 2R-3-(3,4-dihydroxyphenyl)-2-hydroxypropanoic acid. The configuration in the dihydrobenzofuran moieties of 2, 3, and 7 was extrapolated by using the phenylglycine methyl ester method and a Cotton effect at approximately 250-260 nm in their electronic circular dichroism spectra. Diastereomers (1-3 and 7) displayed moderate hyaluronidase inhibitory and histamine release inhibitory activities.

• 出版日期2013-12