게라니인

게라니인
IUPAC명 (1R,7R,8S,26R,28S,29R,38R)-1,13,14,15,18,19,20,34,35,39,39-Undecahydroxy-2,5,10,23,31-pentaoxo-6,9,24,27,30,40-hexaoxaoctacyclo[34.3.1.04,38.07,26.08,29.011,16.017,22.032,37]tetraconta-3,1 1,13,15,17,19,21,32,34,36-decaen-28-yl 3,4,5-trihydroxybenzoate
식별 정보
CAS 등록 번호	60976-49-0
PubChem	3001497
ChemSpider	10270376
KEGG	C10230
SMILES Oc1cc(cc(O)c1O)C(=O)O[C@@H]9O[C@@H]7COC(=O)c2cc(O)c(O)c(O)c2c3c(O)c(O)c(O)cc3C(=O)O[C@@H]8[C@H]9OC(=O)c4cc(O)c(O)c5O[C@@]6(O)C(=O)/C=C(\[C@@H](c45)C6(O)O)C(=O)O[C@H]78
특성
화학식	C41H28O27
몰 질량	952.64 g/mol
정밀 질량	952.081787 u
밀도	2.26 g/mL
특기없는 경우, 데이터는 상온(25оC)・상압(100 kPa)에 있어서의 것이다.

게라니인(Geraniin)은, 후우로소우속에서 볼 수 있는 데히드로에라지탄닌인[¹].예를 들면 민간 요법약이나 일본의 설사의 약에 이용되는 겐노쇼우코[²]나 람부탄의 외피[³]에도 포함된다.

사람의 악성 흑색종에 대해 Fas 리간드의 발현을 정말로 제어해, PTK2를 절단 해, 아포토시스를 일으키는[¹].

헤키사히드로키시지펜산 1 분자, 데히드로헤키사히드로키시지펜산 1 분자, 글루코오스와 결합한 몰식자산 1 분자로부터 된다.6원환과 5원환의 헤미케타르를 등량 함축 평형이 되고 있는[⁴].

케브라진산은, 글루타치온의 중개에 의해 게라니인으로부터 변환되는[⁵].

출전

1. ^ ^{a b} Lee, Jang-Chang; Tsai, Chih-Yen; Kao, Jung-Yie; Kao, Ming-Ching; Tsai, Shih-Chang; Chang, Chih-Shiang; Huang, Li-Jiau; Kuo, Sheng-Chu et al. (2008). "Geraniin-mediated apoptosis by cleavage of focal adhesion kinase through up-regulation of Fas ligand expression in human melanoma cells". Molecular Nutrition & Food Research 52 (6): 655-63. doi:10.1002/mnfr. 200700381. PMID 18435487. 
2. ^ Luger, P.; Weber, M.; Kashino, S.; Amakura, Y.; Yoshida, T.; Okuda, T.; Beurskens, G.; Dauter, Z. (1998). "Structure of the Tannin Geraniin Based on Conventional X-ray Data at 295 K and on Synchrotron Data at 293 and 120 K". Acta Crystallographica Section B Structural Science 54 (5): 687. doi:10.1107/S0108768198000081. 
3. ^ Rapid isolation of geraniin from Nephelium lappaceum rind waste and its anti-hyperglycemic activity. Uma D. Palanisamy, Lai Teng Ling, Thamilvaani Manaharan, and David Appleton, Food Chemistry, 1 July 2011, Volume 127, Issue 1, Pages 21-27, doi:10.1016/j.foodchem.2010.12.070
4. ^ Herbal Drugs in Traditional Japanese Medicine, Tsutomu Hatano, doi:10.5772/53126
5. ^ Glutathione-mediated conversion of the ellagitannin geraniin into chebulagic acid. Tanaka T, Kouno I and Nonaka G.I, Chemical and pharmaceutical bulletin, 1996, volume 44, no 1, pages 34-40, INIST:3003361

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