去甲二氢愈创木酸

去甲二氢愈创木酸
	IUPAC名; 4,4'-(2,3-Dimethylbutane-1,4-diyl)dibenzene-1,2-diol
识别
CAS号	500-38-9
PubChem	4534
SMILES	Oc2ccc(CC(C)C(C)Cc1ccc(O)c(O)c1)cc2O;
ChEBI	7625
MeSH	Nordihydroguaiaretic+acid
IUPHAR配体	4265
性质
化学式	C18H22O4
摩尔质量	302.36 g·mol−1
	若非注明，所有数据均出自标准状态（25 ℃，100 kPa）下。

去甲二氢愈创木酸（英语：Nordihydroguaiaretic acid，NDGA）是一种木脂素，是发现于三齿拉雷亚灌木（英语：creosote bush）（学名：Larrea tridentata）的天然化合物，化学式为 C₁₈H₂₂O₄。

医学性质

NDGA作为一种木脂素，是植物雌激素的一种。虽然人们普遍认为木脂素本身对人体无生物活性，只有经肠道菌群从木脂素中产生的肠木脂素（英语：Enterolignan）、肠二醇和肠内酯才具备生物活性^[1]。NDGA在体外研究和动物研究中体现出抗氧化性质^[2]。其对花生四烯酸5-脂氧合酶（ALOX5）是一种氧化还原型抑制剂^[3]。

在1986年，有一项实验给母蚊子喂食NDGA，来探究NDGA对蚊子平均寿命的影响。结果显示喂食NDGA的蚊子平均寿命为45天，相比于一般蚊子29天的平均寿命，延长了近一半^[4]。2008年一项报告显示NDGA能延长雄性小鼠的寿命，但对雌性小鼠无效^[5]。

三齿拉雷亚灌木作为一种草药一直存在争议，NDGA具有抗氧化性，在20世纪50年代曾被作为食品和天然纤维的防腐剂，在20世纪60年代因为有报道称其长期使用会有肝肾毒性而导致被禁止用于食物防腐剂^[6]^[7]^[8]。

参考文献

^ 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. （原始内容存档于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. （原始内容存档于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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