著者

岡 希太郎

出版者

日本薬史学会

雑誌

薬史学雑誌 (ISSN:02852314)

巻号頁・発行日

vol.51, no.1, pp.5-10, 2016 (Released:2020-08-16)

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Scurvy, a vitamin C deficiency, was rampant during the age of discovery in Europe. In the mid-17th century, Pasqua Rosee, the first coffee house in London, put an ad in the newspaper Publick Adviser clearly stating, It (coffee) is excellent to prevent and cure dropsy, gout, and scurvy. A Netherlands trade merchant carried the information to Nagasaki, Japan, along with coffee beans harvested in the Netherlands’new territory, Java Island. A Japanese physician in Nagasaki, Dr. Kai Hirokawa, translated the information into Japanese in his new book, Dutch Medicines, published in 1803. According to the ancient documents stored in Wakkanai City, Japan, the coffee beans were distributed to Tsugaru Clan soldiers who were guarding the northern coastline from 1855 to 1856. The purpose of the distribution was the prevention of scurvy and dropsy. As the result, none of the soldiers died from scurvy during the winter of 1855-1856. This paper discusses the pharmacological relationship between coffee micronutrients and vitamin deficiency syndrome.

著者

岡 希太郎 池 祥雅 木下 仁 原 昭二

出版者

天然有機化合物討論会

雑誌

天然有機化合物討論会講演要旨集

巻号頁・発行日

no.15, pp.169-176, 1971-10-01

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The results of the synthetic studies on several steroidal alkaloids of salamander and frog venoms were presented. (1) Cycloneosamandione (VIII) and Cycloneosamandaridine (IX) Recently, the early proposed structure of cycloneosamandione (VI), which had been determined by G. Habermehl with the X-ray diffraction method, has been revised to be VIII on the basis of his own synthetic work. In order to reconfirm this structure, the compound VIII was synthesized by the sequre synthetic sequence. As a result, the physical data of the synthetic specimen were consistent with those of the natural product. Cycloneosamandaridine has been known as one of the minor constituents of the salamander alkaloids. Since this alkaloid has been recognized to have the identical skeleton with cycloneosamandione, the structure, we suppose, should be also revised to be IX from VII. Consequently, we have synthesized the compound IX via the same intermediate 16 as the synthesis of cycloneosamandione (VIII). The identification of our synthetic product with the natural one is now in progress. (2) Batrachotoxin (XI) The synthesis of batrachotoxin has been attempted. The treatment of the hemiacetal 27 with aminoethanol followed by reduction afforded a mixture of 18-hydroxyethylamino steroids (28a and 28b). Then the mixture was converted into the enone 36, which might serve as an useful intermediate for our purpose.

著者

岡 希太郎 原 昭二

出版者

The Society of Synthetic Organic Chemistry, Japan

雑誌

有機合成化学協会誌 (ISSN:00379980)

巻号頁・発行日

vol.37, no.1, pp.25-39, 1979-01-01 (Released:2010-01-22)

参考文献数

105

被引用文献数

1

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This review involves the synthetic studies on the salamander alkaloids isolated from an animal venom in the skin gland of Salamandra maculosa Laurenti. Syntheses of three groups of the alkaloids, one with a bicyclo-oxazolidine system, one with a carbinolamine system, and another with a pure 3-aza-A-homo steroid system, are discussed separately. It will be emphasized that the synthetic works described herein made a considerable contribution to the structure analyses of this field of alkaloids and earlier proposed structures based on X-ray and spectroscopic analyses have been changed step by step. Regio and stereospecific syntheses of the alkaloids are mainly discussed in connection with the construction of the bicyclo-oxazolidine system of the major alkaloids and with Beckmann rearrangement of steroid 3-ketoximes for the syntheses of the other alkaloids.

著者

岡 希太郎 原 昭二

出版者

社団法人 有機合成化学協会

雑誌

有機合成化学協会誌 (ISSN:00379980)

巻号頁・発行日

vol.37, no.1, pp.25-39, 1979

被引用文献数

1

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This review involves the synthetic studies on the salamander alkaloids isolated from an animal venom in the skin gland of Salamandra maculosa <I>Laurenti</I>. Syntheses of three groups of the alkaloids, one with a bicyclo-oxazolidine system, one with a carbinolamine system, and another with a pure 3-aza-A-homo steroid system, are discussed separately. It will be emphasized that the synthetic works described herein made a considerable contribution to the structure analyses of this field of alkaloids and earlier proposed structures based on X-ray and spectroscopic analyses have been changed step by step. Regio and stereospecific syntheses of the alkaloids are mainly discussed in connection with the construction of the bicyclo-oxazolidine system of the major alkaloids and with Beckmann rearrangement of steroid 3-ketoximes for the syntheses of the other alkaloids.

著者

岡 希太郎

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.100, no.3, pp.227-240, 1980

被引用文献数

1

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Synthetic studies on salamander alkaloids isolated from animal venom in the skin gland of Salamandra maculosa LAURENTI were performed. Syntheses of three groups of alkaloids, one with a bicyclo-oxazolidine, one with a carbinolamine, and another with a pure 3-aza-A-homo steroid, are discussed. Regio- and stereospecific syntheses of the alkaloids are discussed in connection with the construction of the bicyclo-oxazolidine system of the major alkaloids and in connection with Beckmann rearrangement of steroid 3-ketoximes for the syntheses of the other alkaloids. A theoretical approach to the resolution of the geometrical isomers of oximes by adsorption chromatography is also discussed.

著者

岡 希太郎

出版者

日本コーヒー文化学会

雑誌

コーヒー文化研究 (ISSN:18824617)

巻号頁・発行日

no.23, pp.11-19, 2016-12