綠原酸

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綠原酸
Chlorogenic acid
IUPAC名
(1S,3R,4R,5R)-3[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy1,4,5-trihydroxycyclohexanecarboxylic acid
別名 3-(3,4-Dihydroxycinnamoyl)quinate
3-(3,4-Dihydroxycinnamoyl)quinic acid
3-Caffeoylquinate
3-Caffeoylquinic acid
3-CQA
3-O-Caffeoylquinic acid
Chlorogenate
Chlorogenic acid
Heriguard
3-trans-Caffeoylquinic acid
識別
CAS號 327-97-9  ✓
PubChem 1794427
ChemSpider 1405788
SMILES
InChI
InChIKey CWVRJTMFETXNAD-JUHZACGLBD
ChEBI 16112
RTECS GU8480000
性質
化學式 C16H18O9
摩爾質量 354.31 g·mol−1
密度 1.28 g/cm3
熔點 207-209 °C(271 K)
危險性
警示術語 R:-
安全術語 S:S24 S25 S28 S37 S45
NFPA 704
NFPA 704.svg
0
1
0
 
若非註明,所有數據均出自一般條件(25 ℃,100 kPa)下。

綠原酸Chlorogenic acidCGA),又名氯吉酸氯原酸咖啡單寧酸杜仲綠原酸全蠍提取物咖啡醯奎尼酸[1],是一天然的化合物,由咖啡酸及(−)-奎尼酸酯化而成。 綠原酸是一種重要的生物合成中間體[2]。綠原酸是木質素lignin)的生物合成的重要中間生成物。綠原素作為一種抗氧化劑,可令餐後葡萄醣釋出進入血液的過程減慢[3]

綠原酸這個名詞也泛指羥基肉桂酸(即:咖啡酸、阿魏酸對香豆酸)與奎尼酸的酯化物[4]

結構與性質[編輯]

綠原酸是咖啡酸L-奎尼酸和3號位羥基縮合形成的[5]綠原酸的異構體包括奎尼酸其它位置羥基酯化的產物,如4-O-咖啡醯奎尼酸(cryptochlorogenic acid或簡稱4-CQA)和5-O-咖啡醯奎尼酸(neochlorogenic acid或稱5-CQA,新綠原酸)。一位羥基的異構體尚未在自然界中發現。[4]

兩個羥基被酯化則稱異綠原酸(isochlorogenic acid),存在於咖啡中。[6]例如3,4-二咖啡醯奎尼酸和3,5-二咖啡醯奎尼酸。[7] 和1,5-二咖啡醯奎尼酸。

綠原酸的紫外-可見光譜,最大吸收峰位於325nm

綠原酸可溶於乙醇丙酮

自然來源[編輯]

綠原酸存在於毛竹Phyllostachys edulis[8]以及其它植物中[9],也是中常見的酚類化合物[10]

綠原酸也在健康的帚石楠Calluna vulgaris)嫩芽中發現[11]

綠原酸是金銀花的主要抗、抗病毒有效藥理成分之一。[12]

參考文獻[編輯]

  1. ^ 绿原酸 CAS: 327-97-9. 2016-08-05 [2016-08-07]. (原始內容存檔於2016-08-14) (中文(簡體)‎). 
  2. ^ Boerjan, Wout; Ralph, John; Baucher, Marie. Lignin biosynthesis. Annu. Rev. Plant Biol. 2003, 54: 519–46. PMID 14503002. doi:10.1146/annurev.arplant.54.031902.134938. 
  3. ^ Johnston, K. L.; Clifford, M. N.; Morgan, L. M. Coffee acutely modifies gastrointestinal hormone secretion and glucose tolerance in humans: glycemic effects of chlorogenic acid and caffeine. Am. J. Clin. Nutrit.英語The American Journal of Clinical Nutrition. 2003-10, 78 (4): 728–733 [2016-08-07]. PMID 14522730. (原始內容存檔於2010-04-21) (英語). 
  4. ^ 4.0 4.1 Clifford, M. N.; Johnston, K. L.; Knigh, S.; Kuhnert, N. Hierarchical Scheme for LC-MSn Identification of Chlorogenic Acids. Journal of Agricultural and Food Chemistry. 2003, 51 (10): 2900–2911. PMID 12720369. doi:10.1021/jf026187q. 
  5. ^ Clifford, M. N. Chlorogenic acids and other cinnamates – nature, occurrence and dietary burden. J. Sci. Food Agr. 1999, 79 (3): 362–372. doi:10.1002/(SICI)1097-0010(19990301)79:3<362::AID-JSFA256>3.0.CO;2-D. 
  6. ^ Isochlorogenic Acid. Isolation from Coffee and Structure Studies. H. M. Barnes, J. R. Feldman and W. V. White, J. Am. Chem. Soc., 1950, volume 72, issue 9, pages 4178–4182, doi:10.1021/ja01165a095
  7. ^ Corse, J.; Lundin, R. E.; Waiss, A. C. Identification of several components of isochlorogenic acid. Phytochem. May 1965, 4 (3): 527–529. doi:10.1016/S0031-9422(00)86209-3. 
  8. ^ Kweon, Mee-Hyang; Hwang, Han-Joon; Sung, Ha-Chin. Identification and Antioxidant Activity of Novel Chlorogenic Acid Derivatives from Bamboo (Phyllostachys edulis). Journal of Agricultural and Food Chemistry. 2001, 49 (20): 4646–46552. doi:10.1021/jf010514x. 
  9. ^ Clifford, M. N. 14. The analysis and characterization of chlorogenic acids and other cinnamates. C. Santos-Buelga & G. Williamson (Eds.) (編). Methods in Polyphenol Analysis. Cambridge: Royal Society of Chemistry. 2003: 314–337. ISBN 0-85404-580-5. 
  10. ^ Cheng, G. W.; Crisosto, C. H. Browning Potential, Phenolic Composition, and Polyphenoloxidase Activity of Buffer Extracts of Peach and Nectarine Skin Tissue (PDF). J. Amer. Soc. Hort. Sci. September 1995, 120 (5): 835–838 [2016-08-07]. (原始內容 (PDF)存檔於2014-05-14). 
  11. ^ Jalal, Mahbubul A.F.; Read, David J.; Haslam, E. Phenolic composition and its seasonal variation in Calluna vulgaris. Phytochem. 1982, 21 (6): 1397–1401. doi:10.1016/0031-9422(82)80150-7. 
  12. ^ Ding, Yue; Cai, Zeyu. Antiviral activity of chlorogenic acid against influenza A (H1N1/H3N2) virus and its inhibition of neuraminidase. Scientific Reports. 2017, 7: 45723. PMC 5385491. PMID 28393840. doi:10.1038/srep45723.