- Monoterpene glycosides, phenylpropanoids, and acacetin glycosides from Dracocephalum foetidum
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Chemical investigation of the acetone extract from the aerial parts of the Mongolian medicinal plant Dracocephalum foetidum resulted in the isolation of three limonene glycosides, a caffeic acid trimer, four rosmarinic acid glucosides, and five acacetin acyl glycosides, together with 13 known natural products. The chemical structures of all of the compounds were determined by spectroscopic analyses. Among these compounds three showed hyaluronidase inhibitory activity. In addition, one other compound showed stronger 1,1-diphenyl-2-picrylhydrazyl radical scavenging activity than the positive control Trolox, whereas three other compounds demonstrated a similar activity to that of Trolox.
- Selenge, Erdenechimeg,Murata, Toshihiro,Tanaka, Shiho,Sasaki, Kenroh,Batkhuu, Javzan,Yoshizaki, Fumihiko
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- Diastereomers of lithospermic acid and lithospermic acid B from Monarda fistulosa and Lithospermum erythrorhizon
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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.
- Murata, Toshihiro,Oyama, Kanae,Fujiyama, Minami,Oobayashi, Bunmei,Umehara, Kaoru,Miyase, Toshio,Yoshizaki, Fumihiko
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- Caffeic acid oligomers with hyaluronidase inhibitory activity from Clinopodium gracile
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Eight new caffeic acid oligomers, clinopodic acids J-Q (1-8), were isolated from whole plants of Clinopodium gracile, together with nine known caffeic acid oligomers. The caffeic acid oligomers with two to four dihydrobenzofuran rings were isolated as natural products for the first time. Clinopodic acid M (4) showed the strongest hyaluronidase inhibitory activity, IC50 (19 μM) among the 22 compounds isolated from this plant.
- Aoshima, Hiroaki,Miyase, Toshio,Warashina, Tsutomu
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p. 499 - 507
(2012/06/01)
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- Hyaluronidase inhibitory rosmarinic acid derivatives from Meehania urticifolia
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Nine new phenylpropanoids, rashomonic acids A-D (1-4) and meehaniosides A-E (5-9), along with four known compounds were isolated from Meehania urticifolia. The structure of each new compound was elucidated based on the results of spectroscopic analyses. Compounds 3-8 showed moderate hyaluronidase inhibitory activity with IC50 values of 183-1049 μM.
- Murata, Toshihiro,Miyase, Toshio,Yoshizaki, Fumihiko
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- Hyaluronidase inhibitors from Takuran, Lycopus lucidus
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Takuran is a traditional herbal medicine that is produced from the herbal plant Lycopus lucidas TURCZ. (Lamiaceae). Takuran is used as a treatment for diseases in women. From Takuran, four new phenylpropanoids along with 18 known compounds were isolated, and their structures were elucidated by spectroscopic analyses. Five phenylpropanoids isolated from the plant showed hyaluronidase inhibitory activity comparable to that of rosmarinic acid.
- Murata, Toshihiro,Watahiki, Mai,Tanaka, Yu,Miyase, Toshio,Yoshizaki, Fumihiko
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experimental part
p. 394 - 397
(2011/02/26)
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