去甲二氫愈創木酸

去甲二氫愈創木酸
	IUPAC名; 4,4'-(2,3-Dimethylbutane-1,4-diyl)dibenzene-1,2-diol
識別
CAS編號	500-38-9
PubChem	4534
SMILES	Oc2ccc(CC(C)C(C)Cc1ccc(O)c(O)c1)cc2O;
ChEBI	7625
MeSH	Nordihydroguaiaretic+acid
IUPHAR配體	4265
性質
化學式	C18H22O4
摩爾質量	302.36 g·mol−1
	若非註明，所有數據均出自標準狀態（25 ℃，100 kPa）下。

去甲二氫愈創木酸（英語：Nordihydroguaiaretic acid，NDGA）是一種木脂素，是發現於三齒拉雷亞灌木（英語：creosote bush）（學名：Larrea tridentata）的天然化合物，化學式為 C₁₈H₂₂O₄。

醫學性質

NDGA作為一種木脂素，是植物雌激素的一種。雖然人們普遍認為木脂素本身對人體無生物活性，只有經腸道菌群從木脂素中產生的腸木脂素（英語：Enterolignan）、腸二醇和腸內酯才具備生物活性^[1]。NDGA在體外研究和動物研究中體現出抗氧化性質^[2]。其對花生四烯酸5-脂氧合酶（ALOX5）是一種氧化還原型抑制劑^[3]。

在1986年，有一項實驗給母蚊子餵食NDGA，來探究NDGA對蚊子平均壽命的影響。結果顯示餵食NDGA的蚊子平均壽命為45天，相比於一般蚊子29天的平均壽命，延長了近一半^[4]。2008年一項報告顯示NDGA能延長雄性小鼠的壽命，但對雌性小鼠無效^[5]。

三齒拉雷亞灌木作為一種草藥一直存在爭議，NDGA具有抗氧化性，在20世紀50年代曾被作為食品和天然纖維的防腐劑，在20世紀60年代因為有報道稱其長期使用會有肝腎毒性而導致被禁止用於食物防腐劑^[6]^[7]^[8]。

參考文獻

^ Clavel, Thomas; Henderson, Gemma; Alpert, Carl-Alfred; Philippe, Catherine; Rigottier-Gois, Lionel; Doré, Joël; Blaut, Michael. Intestinal Bacterial Communities That Produce Active Estrogen-Like Compounds Enterodiol and Enterolactone in Humans. Applied and Environmental Microbiology. October 2005, 71 (10): 6077–6085. Bibcode:2005ApEnM..71.6077C. PMC 1265965 . PMID 16204524. doi:10.1128/aem.71.10.6077-6085.2005.
^ Wang, Liang; Li, Lin; Quan, Mo-Yuan; Wang, Dong; Jia, Zhen; Li, Zhen-Fei; Li, Bin; Guo, Li; Tan, Guo-Jun. Nordihydroguaiaretic acid can suppress progression of experimental autoimmune encephalomyelitis. IUBMB Life. May 2018, 70 (5): 432–436. PMID 29637686. S2CID 5010565. doi:10.1002/iub.1739 .
^ Gilbert, Nathaniel C.; Gerstmeier, Jana; Schexnaydre, Erin E.; Börner, Friedemann; Garscha, Ulrike; Neau, David B.; Werz, Oliver; Newcomer, Marcia E. Structural and mechanistic insights into 5-lipoxygenase inhibition by natural products. Nature Chemical Biology. July 2020, 16 (7): 783–790. PMC 7747934 . PMID 32393899. doi:10.1038/s41589-020-0544-7.
^ Richie Jr, J. P.; Mills, B. J.; Lang, C. A. Dietary nordihydroguaiaretic acid increases the life span of the mosquito. Proceedings of the Society for Experimental Biology and Medicine. 1986, 183 (1): 81–85. PMID 3749035. S2CID 45324341. doi:10.3181/00379727-183-42389.
^ Strong, R.; Miller, R. A.; Astle, C. M.; Floyd, R. A.; Flurkey, K.; Hensley, K. L.; Javors, M. A.; Leeuwenburgh, C.; Nelson, J. F.; Ongini, E.; Nadon, N. L.; Warner, H. R.; Harrison, D. E. Nordihydroguaiaretic acid and aspirin increase lifespan of genetically heterogeneous male mice. Aging Cell. 2008, 7 (5): 641–650. PMC 2695675 . PMID 18631321. doi:10.1111/j.1474-9726.2008.00414.x.
^ Arteaga, S.; Andrade-Cetto, A.; Cárdenas, R. Larrea tridentata (Creosote bush), an abundant plant of Mexican and US-American deserts and its metabolite nordihydroguaiaretic acid. Journal of Ethnopharmacology. 2005, 98 (3): 231–239. PMID 15814253. doi:10.1016/j.jep.2005.02.002.
^ Sahu, Saura C.; Ruggles, Dennis I.; O』Donnell, Michael W. Prooxidant activity and toxicity of nordihydroguaiaretic acid in clone-9 rat hepatocyte cultures. Food and Chemical Toxicology. October 2006, 44 (10): 1751–1757 [2024-07-09]. PMID 16839654. doi:10.1016/j.fct.2006.05.016. （原始內容存檔於2020-08-03）.
^ Lambert, J. D.; Zhao, D; Meyers, R. O.; Kuester, R. K.; Timmermann, B. N.; Dorr, R. T. Nordihydroguaiaretic acid: Hepatotoxicity and detoxification in the mouse. Toxicon. 2002, 40 (12): 1701–8. PMID 12457882. doi:10.1016/s0041-0101(02)00203-9.

[1] Clavel, Thomas; Henderson, Gemma; Alpert, Carl-Alfred; Philippe, Catherine; Rigottier-Gois, Lionel; Doré, Joël; Blaut, Michael. Intestinal Bacterial Communities That Produce Active Estrogen-Like Compounds Enterodiol and Enterolactone in Humans. Applied and Environmental Microbiology. October 2005, 71 (10): 6077–6085. Bibcode:2005ApEnM..71.6077C. PMC 1265965 . PMID 16204524. doi:10.1128/aem.71.10.6077-6085.2005.

[2] Wang, Liang; Li, Lin; Quan, Mo-Yuan; Wang, Dong; Jia, Zhen; Li, Zhen-Fei; Li, Bin; Guo, Li; Tan, Guo-Jun. Nordihydroguaiaretic acid can suppress progression of experimental autoimmune encephalomyelitis. IUBMB Life. May 2018, 70 (5): 432–436. PMID 29637686. S2CID 5010565. doi:10.1002/iub.1739 .

[3] Gilbert, Nathaniel C.; Gerstmeier, Jana; Schexnaydre, Erin E.; Börner, Friedemann; Garscha, Ulrike; Neau, David B.; Werz, Oliver; Newcomer, Marcia E. Structural and mechanistic insights into 5-lipoxygenase inhibition by natural products. Nature Chemical Biology. July 2020, 16 (7): 783–790. PMC 7747934 . PMID 32393899. doi:10.1038/s41589-020-0544-7.

[4] Richie Jr, J. P.; Mills, B. J.; Lang, C. A. Dietary nordihydroguaiaretic acid increases the life span of the mosquito. Proceedings of the Society for Experimental Biology and Medicine. 1986, 183 (1): 81–85. PMID 3749035. S2CID 45324341. doi:10.3181/00379727-183-42389.

[5] Strong, R.; Miller, R. A.; Astle, C. M.; Floyd, R. A.; Flurkey, K.; Hensley, K. L.; Javors, M. A.; Leeuwenburgh, C.; Nelson, J. F.; Ongini, E.; Nadon, N. L.; Warner, H. R.; Harrison, D. E. Nordihydroguaiaretic acid and aspirin increase lifespan of genetically heterogeneous male mice. Aging Cell. 2008, 7 (5): 641–650. PMC 2695675 . PMID 18631321. doi:10.1111/j.1474-9726.2008.00414.x.

[6] Arteaga, S.; Andrade-Cetto, A.; Cárdenas, R. Larrea tridentata (Creosote bush), an abundant plant of Mexican and US-American deserts and its metabolite nordihydroguaiaretic acid. Journal of Ethnopharmacology. 2005, 98 (3): 231–239. PMID 15814253. doi:10.1016/j.jep.2005.02.002.

[7] Sahu, Saura C.; Ruggles, Dennis I.; O』Donnell, Michael W. Prooxidant activity and toxicity of nordihydroguaiaretic acid in clone-9 rat hepatocyte cultures. Food and Chemical Toxicology. October 2006, 44 (10): 1751–1757 [2024-07-09]. PMID 16839654. doi:10.1016/j.fct.2006.05.016. （原始內容存檔於2020-08-03）.

[8] Lambert, J. D.; Zhao, D; Meyers, R. O.; Kuester, R. K.; Timmermann, B. N.; Dorr, R. T. Nordihydroguaiaretic acid: Hepatotoxicity and detoxification in the mouse. Toxicon. 2002, 40 (12): 1701–8. PMID 12457882. doi:10.1016/s0041-0101(02)00203-9.

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