2007 Fiscal Year Final Research Report Summary
Studies on the Bioactive Pigments isolated from mammalian secretions
| Project/Area Number |
17310133
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| Research Category |
Grant-in-Aid for Scientific Research (B)
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| Allocation Type | Single-year Grants |
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| Section | 一般 |
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| Research Field |
Living organism molecular science
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| Research Institution | Kyoto Pharmaceutical University |
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Principal Investigator |
HASHIMOTO Kimiko Kyoto Pharmaceutical University, Pharmaceutical Department, Associate Professor (90286641)
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| Project Period (FY) |
2005 – 2007
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| Keywords | hippopotamus / hippsudoric acid / Pigment / secretion / oxidation / enzyme / homogentisic acid / sweat gland |
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| Research Abstract |
The hippopotamus' skin produces a colorless viscous sweat over its entire hairless body from unknown big subdermal glands. The colorless secretion changes its color to red within a few minutes, and then brown as the pigment polymerizes about within a few hours. Tow unstable pigments, red and orange, responsible to the red coloration were isolated and called hipposudoric acid and norhipposudoric acid, respectively.
In order to study these structures more precisely, chemical synthesis was performed. Starting from 2,5-dimethoxytoluene and 2,5-dimethoxybenzaldehyde through coupling reaction and then Pscorr reaction, the fluorenone core, the common intermediate for the both pigments, was synthesized. Several steps led this intermediate to the corresponding unstable dihydroquinones which were oxidized to the unstable diquinones using air with copper(II) as the catalyst. Using a model compound, the tautomeric structures of these pigments both in an aqueous (polar) and an organic (lesspolar) solvents were revealed. The red sweat has been said to be a medicine for the hippopotamus, that is, the sweat protect hippo from strong sunlight and also from infection of microbes. These stories based on the following observations; (1) some adult albino hippos are survived, although these mutants are usually short-lived (2) hippos are always injured by quarrel, however, the wounds are smoothly cured, in spite of their living in the mud. These pigments were proved to absorb the UV light (280-400nm) and also exhibited antimicrobial activities against some gram-negative bacteria, Pseudomonas aeruginosa and Krebsiella pneumoniae.
From the colorless sweat, homogentisic acid was isolated and when it was mixed with polymer portion of the sweat, the pigments were produced. Accordingly, the acid was proved to be the precursor of the pigments and the reaction was proved to be catalyzed by an enzyme.
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Research Products
(60 results)
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[Presentation] The red sweat of the hippopotamus2006
Author(s)
Kimiko Hashimoto, Yoko Saikwa, Masaya Nakata
Organizer
ICOB-5 & ISCNP-25 IUPAC International Conference on Biodiversity and Natural Products
Place of Presentation
Kyoto
Year and Date
20060700
Description
「研究成果報告書概要(欧文)」より
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[Presentation] Chemical studies on the red sweat of the hippopotamus2006
Author(s)
Kimiko Hashimoto, Yoko Saikwa, Masaya Nakata
Organizer
Pre-Symposium Nagoya-Bioorganic Chemistry and Chemical Biology-ICOB-5 & ISCNP-25 IUPAC International Conference on Biodiversity and Natural Products
Place of Presentation
Shizuoka
Year and Date
20060700
Description
「研究成果報告書概要(欧文)」より
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[Presentation] カバの汗はなぜ赤いのか2006
Author(s)
橋本 貴美子
Organizer
市民公開講座 文化としての天然物化学
Place of Presentation
京都
Year and Date
2006-07-26
Description
「研究成果報告書概要(和文)」より
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[Presentation] カバの汗の化学2006
Author(s)
橋本 貴美子
Organizer
日本化学会中国四国支部 天然物化学の新展開
Place of Presentation
高知
Year and Date
2006-05-26
Description
「研究成果報告書概要(和文)」より
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[Presentation] カバの汗の話2006
Author(s)
橋本 貴美子
Organizer
杏林大学医学部皮膚科学教室勉強会
Place of Presentation
東京
Year and Date
2006-03-10
Description
「研究成果報告書概要(和文)」より
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[Presentation] カバの赤い汗の話2006
Author(s)
橋本 貴美子
Organizer
第163回動物園研究会
Place of Presentation
京都
Year and Date
2006-01-30
Description
「研究成果報告書概要(和文)」より
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[Presentation] 自然科学と薬学2005
Author(s)
橋本 貴美子
Organizer
東大津高等学校模擬授業
Place of Presentation
滋賀
Year and Date
2005-09-29
Description
「研究成果報告書概要(和文)」より
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[Presentation] カバの赤い汗の化学2005
Author(s)
橋本 貴美子
Organizer
第36回中部化学関係学協会支部連合秋季大会
Place of Presentation
静岡
Year and Date
2005-09-23
Description
「研究成果報告書概要(和文)」より
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