鞣花酸

鞣花酸
	IUPAC名; 2,3,7,8-Tetrahydroxy-chromeno[5,4,3-cde]chromene-5,10-dione
識別
CAS號	476-66-4
PubChem	5281855
ChemSpider	4445149
SMILES	O=C1Oc3c2c4c1cc(O)c(O)c4OC(=O)c2cc(O)c3O;
InChI	1/C14H6O8/c15-5-1-3-7-8-4(14(20)22-11(7)9(5)17)2-6(16)10(18)12(8)21-13(3)19/h1-2,15-18H;
InChIKey	AFSDNFLWKVMVRB-UHFFFAOYAQ
KEGG	C10788
性質
化學式	C14H6O8
摩爾質量	302.197 g·mol⁻¹
密度	1.67 g/cm³
	若非註明，所有數據均出自標準狀態（25 ℃，100 kPa）下。

鞣花酸（Ellagic acid）是存在於眾多水果和蔬菜中的天然酚類抗氧化劑，包括黑莓、草莓、石榴、枸杞、覆盆子、白橡實、蔓越莓、山核桃等植物。鞣花酸的抗增生和抗氧化特性，刺激了對鞣花酸潛在價值的研究。

發現歷史

植物可自體生成鞣花酸，並將其轉化為鞣花丹寧。這些苷類易水解，當植物體被食用後易再生為鞣花酸。草莓、覆盆子、蔓越莓和葡萄內鞣花酸的含量較高。^[1]

化學家米歇爾·歐仁·切維爾（Michel Eugène Cheverul）在橡木蟲癭中首次發現了鞣花酸。1831年，亨利·布拉科諾（英語：Henri Braconnot）（Henri Braconnot）進行了更深入的研究。

生理作用

飲料廣告上的營養成分表，標示其多酚類化合物及鞣花酸的含量

鞣花酸在大量體外組織及小動物模型中都具有抗增生和抗氧化的性質。^[2]^[3] 鞣花酸的抗增生性是由於它能直接抑制某些致癌物與DNA結合，包括亞硝胺^[4]^[5] 和多環芳香烴^[6]。與其他多酚類抗氧化劑一樣，鞣花酸通過降低氧化應激，對細胞起到化學保護的作用。^[1] 但其可被茶葉中的兒茶素拮抗。^[7]

鞣花酸的這些特性有應用於人類健康的可能。2010年報道了一個關於其潛在藥用價值的小實驗。其對19名頸內動脈狹窄患者進行了一個小型的隨機對照實驗，發現鞣花酸含量較高的石榴汁似乎具有降低血壓及降低頸動脈壁厚度的作用。^[8] 2005年對48名接受化療的前列腺癌患者進行了對照研究，發現補充鞣花酸可緩解化療造成的中性粒細胞減少（雖然在實驗組和對照組中都沒有重症中性粒細胞減少的病例）。但在該試驗中，鞣花酸並不能提高前列腺癌患者的生存率。^[9]

雖然僅有非常初步的證據支持鞣花酸對人體的益處，但鞣花酸已被作為一種防癌，防心臟病及其他疾病的保健品進行銷售。所以美國食品藥品監督管理局已將其確定為「消費者應該規避的假癌症藥物」。^[10] 許多美國保健品銷售商已收到美國食品藥品監督管理局的警告信，稱推廣鞣花酸違反《聯邦食品、藥品及化妝品法》（Federal Food, Drug, and Cosmetic Act）。^[11]^[12]

參考文獻

^ ^1.0 ^1.1 D. A. Vattem and K. Shetty. Biological Function of Ellagic Acid: A Review. Journal of Food Biochemistry. 2005, 29 (3): 234–266. doi:10.1111/j.1745-4514.2005.00031.x.
^ Seeram NP, Adams LS, Henning SM; et al. In vitro antiproliferative, apoptotic and antioxidant activities of punicalagin, ellagic acid and a total pomegranate tannin extract are enhanced in combination with other polyphenols as found in pomegranate juice. J. Nutr. Biochem. June 2005, 16 (6): 360–7. PMID 15936648. doi:10.1016/j.jnutbio.2005.01.006.
^ Narayanan BA, Geoffroy O, Willingham MC, Re GG, Nixon DW. p53/p21(WAF1/CIP1) expression and its possible role in G1 arrest and apoptosis in ellagic acid treated cancer cells. Cancer Lett. March 1999, 136 (2): 215–21 [2011-06-30]. PMID 10355751. doi:10.1016/S0304-3835(98)00323-1. （原始內容存檔於2020-07-25）.
^ Madal, Shivappurkar, Galati, and Stoner. Inhibition of N-nitrosobenzymethylamine metabolism and DNA binding in cultured rat esophagus by ellagic acid. Carcinogenesis. 1988, 9 (7): 1313–1316. PMID 3383347. doi:10.1093/carcin/9.7.1313.
^ Mandal and Stoner; Stoner, GD. Inhibition of N-nitrosobenzymethylamine-induced esophageal tumorigenesis in rats by ellagic acid. Carcinogenesis. 1990, 11 (1): 55–61. PMID 2295128. doi:10.1093/carcin/11.1.55.
^ Teel, Babcock, Dixit, and Stoner. Ellagic acid toxicity and interaction with benzo[a]pyrene and benzo[a]pyrene 7,8-dihydrodiol in human bronchial epithelial cells. Cell Biol. Toxicol. 1986, 2 (1): 53–62. PMID 3267445. doi:10.1007/BF00117707.
^ Anne S. Meyer, Marina Heinonen, Edwin N. Frankel. Antioxidant interactions of catechin, cyanidin, caffeic acid, quercetin, and ellagic acid on human LDL oxidation. Food Chemistry. January 1998, 61 (1-2): 71–75. doi:10.1016/S0308-8146(97)00100-3.
^ Aviram M, Rosenblat M, Gaitini D; et al. Pomegranate juice consumption for 3 years by patients with carotid artery stenosis reduces common carotid intima-media thickness, blood pressure and LDL oxidation. Clin Nutr. June 2004, 23 (3): 423–33. PMID 15158307. doi:10.1016/j.clnu.2003.10.002.
^ Falsaperla M, Morgia G, Tartarone A, Ardito R, Romano G. Support ellagic acid therapy in patients with hormone refractory prostate cancer (HRPC) on standard chemotherapy using vinorelbine and estramustine phosphate. Eur. Urol. April 2005, 47 (4): 449–54; discussion 454–5. PMID 15774240. doi:10.1016/j.eururo.2004.12.001.
^ 187 Fake Cancer 'Cures' Consumers Should Avoid （頁面存檔備份，存於互聯網檔案館）, from the U.S. Food and Drug Administration. Accessed June 17 2008.
^ Warning Letter （頁面存檔備份，存於互聯網檔案館） sent to Millennium Health by the United States Food and Drug Administration, dated May 21, 2008.
^ Warning Letter （頁面存檔備份，存於互聯網檔案館） sent to Kenton Campbell at Prime Health Direct, Ltd. by the United States Food and Drug Administration dated July 2, 2007.

擴展閱讀

多酚類作為癌症的化學防治劑, J. Cell Biochem Suppl. 1995'22:169-80

[vattem-1] 1.0 ^1.1 D. A. Vattem and K. Shetty. Biological Function of Ellagic Acid: A Review. Journal of Food Biochemistry. 2005, 29 (3): 234–266. doi:10.1111/j.1745-4514.2005.00031.x.

[2] Seeram NP, Adams LS, Henning SM; et al. In vitro antiproliferative, apoptotic and antioxidant activities of punicalagin, ellagic acid and a total pomegranate tannin extract are enhanced in combination with other polyphenols as found in pomegranate juice. J. Nutr. Biochem. June 2005, 16 (6): 360–7. PMID 15936648. doi:10.1016/j.jnutbio.2005.01.006.

[3] Narayanan BA, Geoffroy O, Willingham MC, Re GG, Nixon DW. p53/p21(WAF1/CIP1) expression and its possible role in G1 arrest and apoptosis in ellagic acid treated cancer cells. Cancer Lett. March 1999, 136 (2): 215–21 [2011-06-30]. PMID 10355751. doi:10.1016/S0304-3835(98)00323-1. （原始內容存檔於2020-07-25）.

[4] Madal, Shivappurkar, Galati, and Stoner. Inhibition of N-nitrosobenzymethylamine metabolism and DNA binding in cultured rat esophagus by ellagic acid. Carcinogenesis. 1988, 9 (7): 1313–1316. PMID 3383347. doi:10.1093/carcin/9.7.1313.

[5] Mandal and Stoner; Stoner, GD. Inhibition of N-nitrosobenzymethylamine-induced esophageal tumorigenesis in rats by ellagic acid. Carcinogenesis. 1990, 11 (1): 55–61. PMID 2295128. doi:10.1093/carcin/11.1.55.

[6] Teel, Babcock, Dixit, and Stoner. Ellagic acid toxicity and interaction with benzo[a]pyrene and benzo[a]pyrene 7,8-dihydrodiol in human bronchial epithelial cells. Cell Biol. Toxicol. 1986, 2 (1): 53–62. PMID 3267445. doi:10.1007/BF00117707.

[7] Anne S. Meyer, Marina Heinonen, Edwin N. Frankel. Antioxidant interactions of catechin, cyanidin, caffeic acid, quercetin, and ellagic acid on human LDL oxidation. Food Chemistry. January 1998, 61 (1-2): 71–75. doi:10.1016/S0308-8146(97)00100-3.

[8] Aviram M, Rosenblat M, Gaitini D; et al. Pomegranate juice consumption for 3 years by patients with carotid artery stenosis reduces common carotid intima-media thickness, blood pressure and LDL oxidation. Clin Nutr. June 2004, 23 (3): 423–33. PMID 15158307. doi:10.1016/j.clnu.2003.10.002.

[9] Falsaperla M, Morgia G, Tartarone A, Ardito R, Romano G. Support ellagic acid therapy in patients with hormone refractory prostate cancer (HRPC) on standard chemotherapy using vinorelbine and estramustine phosphate. Eur. Urol. April 2005, 47 (4): 449–54; discussion 454–5. PMID 15774240. doi:10.1016/j.eururo.2004.12.001.

[10] 187 Fake Cancer 'Cures' Consumers Should Avoid （頁面存檔備份，存於互聯網檔案館）, from the U.S. Food and Drug Administration. Accessed June 17 2008.

[11] Warning Letter （頁面存檔備份，存於互聯網檔案館） sent to Millennium Health by the United States Food and Drug Administration, dated May 21, 2008.

[12] Warning Letter （頁面存檔備份，存於互聯網檔案館） sent to Kenton Campbell at Prime Health Direct, Ltd. by the United States Food and Drug Administration dated July 2, 2007.

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鞣花酸

IUPAC名 2,3,7,8-Tetrahydroxy-chromeno[5,4,3-cde]chromene-5,10-dione
識別
CAS號	476-66-4 ^Y
PubChem	5281855
ChemSpider	4445149
SMILES	O=C1Oc3c2c4c1cc(O)c(O)c4OC(=O)c2cc(O)c3O
InChI	1/C14H6O8/c15-5-1-3-7-8-4(14(20)22-11(7)9(5)17)2-6(16)10(18)12(8)21-13(3)19/h1-2,15-18H
InChIKey	AFSDNFLWKVMVRB-UHFFFAOYAQ
KEGG	C10788
性質
化學式	C₁₄H₆O₈
摩爾質量	302.197 g·mol⁻¹
密度	1.67 g/cm³
若非註明，所有數據均出自標準狀態（25 ℃，100 kPa）下。