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

doi:10.1016/j.fitote.2013.08.009

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

Fitoterapia. 2013 Dec:91:51-59. doi: 10.1016/j.fitote.2013.08.009. Epub 2013 Aug 23.

Authors

Toshihiro Murata¹, Kanae Oyama², Minami Fujiyama³, Bunmei Oobayashi³, Kaoru Umehara³, Toshio Miyase³, Fumihiko Yoshizaki²

Affiliations

¹ Tohoku Pharmaceutical University, 4-4-1 Komatsushima, Aoba-ku, Sendai 981-8558, Japan. Electronic address: murata-t@tohoku-pharm.ac.jp.
² Tohoku Pharmaceutical University, 4-4-1 Komatsushima, Aoba-ku, Sendai 981-8558, Japan.
³ School of Pharmaceutical Sciences, University of Shizuoka, 52-1, Yada, Suruga-ku, Shizuoka 422-8526, Japan.

PMID: 23978578
DOI: 10.1016/j.fitote.2013.08.009

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.

Keywords: Histamine release inhibitors; Hyaluronidase inhibitors; Lithospermic acid (PubChem CID: 6441498); Lithospermic acid B (PubChem CID: 6451084); Lithospermum erythrorhizon; Monarda fistulosa; Phenylpropanoid oligomers; Rosmarinic acid (PubChem CID: 5281792).

MeSH terms

Animals
Benzofurans / chemistry
Benzofurans / isolation & purification*
Benzofurans / pharmacology
Depsides / chemistry
Depsides / isolation & purification*
Depsides / pharmacology
Enzyme Inhibitors / chemistry
Enzyme Inhibitors / isolation & purification
Enzyme Inhibitors / pharmacology
Histamine Antagonists / chemistry
Histamine Antagonists / isolation & purification*
Histamine Antagonists / pharmacology
Humans
Hyaluronoglucosaminidase / antagonists & inhibitors*
Isomerism
Lithospermum / chemistry*
Molecular Structure
Monarda / chemistry*
Plant Extracts / chemistry
Plant Extracts / pharmacology

Substances

Benzofurans
Depsides
Enzyme Inhibitors
Histamine Antagonists
Plant Extracts
lithospermic acid
salvianolic acid B
Hyaluronoglucosaminidase