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Diastereomers of Lithospermic Acid and Lithospermic Acid B From Monarda Fistulosa and Lithospermum Erythrorhizon

Diastereomers of Lithospermic Acid and Lithospermic Acid B From Monarda Fistulosa and Lithospermum Erythrorhizon

Toshihiro Murata, Kanae Oyama, Minami Fujiyama, Bunmei Oobayashi, Kaoru Umehara, Toshio Miyase, Fumihiko Yoshizaki

Fitoterapia. 2013 Dec;91:51-59.

PMID: 23978578

Abstract:

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 (7S,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.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP28831654	Lithospermic acid		28831-65-4	Price

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