title: Diastereomers of lithospermic acid and lithospermic acid B from Monarda fistulosa and Lithospermum erythrorhizon.
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.
authors: Tohoku Pharmaceutical University, 4-4-1 Komatsushima, Aoba-ku, Sendai 981-8558, Japan. Electronic address: murata-t@tohoku-pharm.ac.jp.
authors: Toshihiro
authors: T
authors: Murata
authors: Tohoku Pharmaceutical University, 4-4-1 Komatsushima, Aoba-ku, Sendai 981-8558, Japan.
authors: Kanae
authors: K
authors: Oyama
authors: School of Pharmaceutical Sciences, University of Shizuoka, 52-1, Yada, Suruga-ku, Shizuoka 422-8526, Japan.
authors: Minami
authors: M
authors: Fujiyama
authors: School of Pharmaceutical Sciences, University of Shizuoka, 52-1, Yada, Suruga-ku, Shizuoka 422-8526, Japan.
authors: Bunmei
authors: B
authors: Oobayashi
authors: School of Pharmaceutical Sciences, University of Shizuoka, 52-1, Yada, Suruga-ku, Shizuoka 422-8526, Japan.
authors: Kaoru
authors: K
authors: Umehara
authors: School of Pharmaceutical Sciences, University of Shizuoka, 52-1, Yada, Suruga-ku, Shizuoka 422-8526, Japan.
authors: Toshio
authors: T
authors: Miyase
authors: Tohoku Pharmaceutical University, 4-4-1 Komatsushima, Aoba-ku, Sendai 981-8558, Japan.
authors: Fumihiko
authors: F
authors: Yoshizaki
mesh_terms: D000818:Animals; D001572:Benzofurans / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D053630:Depsides / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D004791:Enzyme Inhibitors / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D006633:Histamine Antagonists / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D006801:Humans; D006821:Hyaluronoglucosaminidase / Q000037:antagonists & inhibitors*; D007536:Isomerism; D029684:Lithospermum / Q000737:chemistry*; D015394:Molecular Structure; D031338:Monarda / Q000737:chemistry*; D010936:Plant Extracts / Q000737:chemistry / Q000494:pharmacology
chemical_list: D001572:Benzofurans; D053630:Depsides; D004791:Enzyme Inhibitors; D006633:Histamine Antagonists; D010936:Plant Extracts; C046833:lithospermic acid; C076944:salvianolic acid B; D006821:Hyaluronoglucosaminidase
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)