著者

毛利 公則 竹本 常松 近藤 嘉和

出版者

公益社団法人日本薬学会

雑誌

薬学雑誌 (ISSN:00316903)

巻号頁・発行日

vol.102, no.3, pp.p310-312, 1982-03

被引用文献数

2

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Two new C-methyl flavanones, named matteucin (III) and methoxymatteucin (IV) were isolated from the root of Matteuccia orientalis TREV. (Aspidiaceae), together with the known desmethoxymatteucinol (I) and matteucinol (II). The structures of these flavanones were determined to be (2S)-5,7,2'-trihydroxy-6,8-dimethylflavanone and (2S)-5,7,2'-trihydroxy-5'-methoxy-6,8-dimethylflavanone, respectively, by spectroscopic evidence.

著者

竹本 常松 醍醐 皓二 近藤 嘉和 近藤 一恵

出版者

公益社団法人日本薬学会

雑誌

藥學雜誌 (ISSN:00316903)

巻号頁・発行日

vol.86, no.10, pp.874-877, 1966-10-25

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The NMR spectrum of domoic acid (in CF_3COOH) indicates signals for a methyl at 1.43 p.p.m. (d;J=6.6 c.p.s.) and at 1.94 p.p.m. (a broad singlet), and no signal for an ethyl group. The methyl signal at 1.94 p.p.m. shows a long-range I-I coupling due to spin decoupling. The NMR spectrum of trimethyl domoate (in CDCl_3) shows a doublet methyl (J=7.0 c.p.s.) at 1.29 p.p.m., a methyl signal which indicates an allylic coupling at 1.79 p.p.m., and an olefinic proton signal corresponding to 3H at 5.5〜6.6 p.p.m. From its first-order analysis, the configuration of the 1,3-hexadienyl side chain was determined as trans : trans : S-trans. The infrared spectra of both domoic acid and trimethyl domoate show absorption due to the trans-double bond. The NMR spectrum of tetrahydrodomoic acid (in CF_3COOH) shows signals for a methyl bonded to a secondary carbon at 1.12 p.p.m. (d;J=6.0 c.p.s.) and at 1.22 p.p.m. (d;J=6.6 c.p.s.). It was concluded from these observations that the structure of domoic acid would be more appropriately represented as L_s-arabo-2-carboxy-4-(1-methyl-5-carboxy-trans : trans : S-trans-1,3-hexadienyl)-3-pyrrolidineacetic acid (VIII) rather than the previously proposed L_s-arabo-2-carboxy-4-(1-methyl-2-carboxy-1,3-hexadieny1)-3-pyrrolidineacetic acid (I).