熊果酸

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Ursolic acid
IUPAC名
(1S,2R,4aS,6aR,6aS,6bR,8aR,10S,12aR,14bS)-10-Hydroxy-1,2,6a,6b,9,9,12a-heptamethyl-2,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydro-1H-picene-4a-carboxylic acid[1]
系统名
(1R,2S,5S,8R,9S,10S,14R,15R,18S,20R)-18-hydroxy-1,2,8,9,15,19,19-heptamethylpe ntacyclo[12.8.0.02,11.05,10.015,20]docos-11-ene-5-carboxylic acid
(1R,2S,5S,8R,9S,10S,14R,15R,18S,20R)-1,2,8,9,15,19,19-七甲基-18-羟基五环[12.8.0.02,11.05,10.015,20]-11-二十二烯-5-甲酸
别名 Prunol, Malol, beta-Ursolic acid, NSC4060, CCRIS 7123, TOS-BB-0966, 3-beta-hydroxyurs-12-en-28-oic acid[1]
识别
CAS号 77-52-1  ✓
PubChem 64945
ChemSpider 58472
SMILES
 
  • O=C(O)[C@@]54[C@H](/C3=C/C[C@H]1[C@](CC[C@@H]2[C@]1(C)CC[C@H](O)C2(C)C)(C)[C@]3(C)CC4)[C@@H](C)[C@H](C)CC5
InChI
 
  • 1/C30H48O3/c1-18-10-15-30(25(32)33)17-16-28(6)20(24(30)19(18)2)8-9-22-27(5)13-12-23(31)26(3,4)21(27)11-14-29(22,28)7/h8,18-19,21-24,31H,9-17H2,1-7H3,(H,32,33)/t18-,19+,21+,22-,23+,24+,27+,28-,29-,30+/m1/s1
InChIKey WCGUUGGRBIKTOS-GPOJBZKABB
ChEBI 9908
性质
化学式 C30H48O3
摩尔质量 456.7 g·mol−1
熔点 285 - 288 °C(270 K)
若非注明,所有数据均出自标准状态(25 ℃,100 kPa)下。

熊果酸(英语:Ursolic acid,也译为乌索酸3-β-羟基-熊果-12-烯-28-羧酸,3-beta-3-hydroxy-urs-12-ene-28-oic-acid)是一种五环三萜物质,最早在1920年发现于苹果表皮蜡质中。熊果酸也存在于许多植物的果皮中以及迷迭香麝香草等草药中。

自然发生[编辑]

熊果酸存在于许多植物,如紫茉莉[2]以及日常生活中使用的许多水果和草药(例如苹果罗勒越桔蔓越莓接骨木花薄荷迷迭香薰衣草牛至百里香山楂李子)中。苹果皮含有大量的熊果酸以及相关化合物。 [3]

潜在的生物化学作用[编辑]

已经研究了熊果酸的许多潜在生化作用,但是没有临床研究表明它对人类健康有益。在体外,熊果酸通过抑制STAT3激活途径抑制各种类型癌细胞的增殖,[4] [5]并且还可以减少癌细胞的增殖并诱导细胞凋亡[6]熊果酸也已显示能抑制JURK白血病T细胞的JNK表达和IL-2活化,导致增殖和T细胞活化的减少。[7]熊果酸是一种弱芳香酶抑制剂(IC50 = 32μM),[8]并且已经显示当添加到喂养给小鼠的饮食中时增加肌肉和棕色脂肪的量并减少白色脂肪肥胖和相关病症。 在生理浓度下,熊果酸还诱导了eryptosis(有缺陷的红细胞中的类似凋亡的细胞自杀死亡)。 [9]已经发现它可以减少肌肉萎缩并刺激小鼠的肌肉生长,也显示出潜在的心脏保护作用。 [10]

在小鼠中,熊果酸在坐骨神经损伤后诱导神经再生。[11] 熊果酸可改善多摩酸诱导的小鼠认知功能障碍。[12] 熊果酸可通过阻断内质网应激和IκB激酶β/核因子-κB介导的炎症通路来改善高脂饮食引起的认知障碍。 [13] 熊果酸通过抑制p38 /NF-κB介导的炎症途径减轻脂多糖诱导的小鼠大脑认知功能障碍。[14] 熊果酸可改善认知障碍并减轻D-半乳糖诱导的衰老小鼠大脑中的氧化损伤。[15]熊果酸可促进部分肝切除术后小鼠肝脏的再生。 [16]在以高脂饮食喂养的链脲佐菌素诱导的糖尿病小鼠中,熊果酸可增强细胞免疫系统和胰腺β细胞功能。[17]UA增加骨骼肌质量,以及握力和运动能力。 增强耐力,减少与肌肉萎缩发展有关的基因的表达,并减少累积疲劳和运动引起的压力的指标。 [18]

在大鼠中,熊果酸改善了高脂饮食诱导的肝脂肪变性,并改善了高脂饮食诱导的非酒精性脂肪肝疾病的代谢紊乱。 [19]

用途[编辑]

熊果酸可以在用于化妆品添加剂的植物中发现。 熊果酸可以作为合成更有效的生物活性衍生物的起始材料,例如实验性抗肿瘤剂。 [20]

请参见[编辑]

参考文献[编辑]

  1. ^ 1.0 1.1 CID 64945 from PubChem
  2. ^ Constituents of Mirabilis jalapa. Siddiqui S., Siddiqui B.S., Adil Q. and Begum S., Fitoterapia, 1990, Volume 61, No. 5, page 471 (abstract页面存档备份,存于互联网档案馆))
  3. ^ Ursolic acid from apple pomace and traditional plants: A valuable triterpenoid with functional properties. Food Chem. April 2017, 220: 477–489. PMID 27855928. doi:10.1016/j.foodchem.2016.10.029. 
  4. ^ Ursolic acid inhibits nuclear factor-kappaB activation induced by carcinogenic agents through suppression of IkappaBalpha kinase and p65 phosphorylation: correlation with down-regulation of cyclooxygenase 2, matrix metalloproteinase 9, and cyclin D1 (PDF). Cancer Res. 2003, 63 (15): 4375–83 [2020-03-02]. PMID 12907607. (原始内容存档 (PDF)于2013-02-21). 
  5. ^ Pathak AK; Bhutani M; Nair AS; et al. Ursolic acid inhibits STAT3 activation pathway leading to suppression of proliferation and chemosensitization of human multiple myeloma cells. Mol. Cancer Res. 2007, 5 (9): 943–55. PMID 17855663. doi:10.1158/1541-7786.MCR-06-0348. 
  6. ^ Wang X, Zhang F, Yang L, Mei Y, Long H, Zhang X, Zhang J, Qimuge-Suyila, Su X.,"Ursolic acid inhibits proliferation and induces apoptosis of cancer cells in vitro and in vivo", J Biomed Biotechnol. 2011;2011:419343 Full-text pdf页面存档备份,存于互联网档案馆
  7. ^ Kaewthawee, Narawan; Brimson, Sirikalaya. The Effects of Ursolic Acid on Cytokine Production via the MAPK Pathways in Leukemic T-Cells (PDF). EXCLI. February 2013, 12 (February): 102–114 [2020-03-02]. (原始内容存档 (PDF)于2013-05-25). 
  8. ^ Gnoatto, SC; Dassonville-Klimpt, A; Da Nascimento, S; Galéra, P; Boumediene, K; Gosmann, G; Sonnet, P; Moslemi, S. Evaluation of ursolic acid isolated from Ilex paraguariensis and derivatives on aromatase inhibition. European Journal of Medicinal Chemistry. 2008, 43 (9): 1865–77. PMID 18192087. doi:10.1016/j.ejmech.2007.11.021. 
  9. ^ Triggering of erythrocyte cell membrane scrambling by ursolic acid. J Nat Prod. 2011, 74 (10): 2181–2186. PMID 21923134. doi:10.1021/np2005133. 
  10. ^ Uncoupling and antioxidant effects of ursolic acid in isolated rat heart mitochondria. J. Nat. Prod. July 2011, 74 (7): 1640–4. PMID 21648406. doi:10.1021/np200060p. 
  11. ^ Liu, Biao; Liu, Yan; Yang, Guang; Xu, Zemin; Chen, Jiajun. Ursolic acid induces neural regeneration after sciatic nerve injury. Neural Regeneration Research. 2013-09-25, 8 (27): 2510–2519. ISSN 1673-5374. PMC 4145935可免费查阅. PMID 25206561. doi:10.3969/j.issn.1673-5374.2013.27.002. 
  12. ^ Wu, Dong-mei; Lu, Jun; Zhang, Yan-qiu; Zheng, Yuan-lin; Hu, Bin; Cheng, Wei; Zhang, Zi-feng; Li, Meng-qiu. Ursolic acid improves domoic acid-induced cognitive deficits in mice. Toxicology and Applied Pharmacology. 2013-09-01, 271 (2): 127–136. ISSN 1096-0333. PMID 23707761. doi:10.1016/j.taap.2013.04.038. 
  13. ^ Lu, Jun; Wu, Dong-mei; Zheng, Yuan-lin; Hu, Bin; Cheng, Wei; Zhang, Zi-feng; Shan, Qun. Ursolic acid improves high fat diet-induced cognitive impairments by blocking endoplasmic reticulum stress and IκB kinase β/nuclear factor-κB-mediated inflammatory pathways in mice. Brain, Behavior, and Immunity. 2011-11-01, 25 (8): 1658–1667. ISSN 1090-2139. PMID 21708244. doi:10.1016/j.bbi.2011.06.009. 
  14. ^ Wang, Yong-Jian; Lu, Jun; Wu, Dong-mei; Zheng, Zi-hui; Zheng, Yuan-Lin; Wang, Xiao-hui; Ruan, Jie; Sun, Xiao; Shan, Qun. Ursolic acid attenuates lipopolysaccharide-induced cognitive deficits in mouse brain through suppressing p38/NF-κB mediated inflammatory pathways. Neurobiology of Learning and Memory. 2011-09-01, 96 (2): 156–165. ISSN 1095-9564. PMID 21496491. doi:10.1016/j.nlm.2011.03.010. 
  15. ^ Lu, Jun; Zheng, Yuan-Lin; Wu, Dong-Mei; Luo, Lan; Sun, Dong-Xu; Shan, Qun. Ursolic acid ameliorates cognition deficits and attenuates oxidative damage in the brain of senescent mice induced by D-galactose. Biochemical Pharmacology. 2007-10-01, 74 (7): 1078–1090. ISSN 0006-2952. PMID 17692828. doi:10.1016/j.bcp.2007.07.007. 
  16. ^ Jin, Yong-Ri; Jin, Jing-Ling; Li, Cheng-Hao; Piao, Xi-Xu; Jin, Nan-Ge. Ursolic acid enhances mouse liver regeneration after partial hepatectomy. Pharmaceutical Biology. 2012-04-01, 50 (4): 523–528. ISSN 1744-5116. PMID 22136205. doi:10.3109/13880209.2011.611143. 
  17. ^ Jang, Sun-Mi; Yee, Sung-Tae; Choi, Jina; Choi, Myung-Sook; Do, Gyeong-Min; Jeon, Seon-Min; Yeo, Jiyoung; Kim, Myung-Joo; Seo, Kwon-Il. Ursolic acid enhances the cellular immune system and pancreatic beta-cell function in streptozotocin-induced diabetic mice fed a high-fat diet. International Immunopharmacology. 2009-01-01, 9 (1): 113–119. ISSN 1567-5769. PMID 19013541. doi:10.1016/j.intimp.2008.10.013. 
  18. ^ Jeong, Ji-Woong; Shim, Jae-Jung; Choi, Il-Dong; Kim, Sung-Hwan; Ra, Jehyeon; Ku, Hyung Keun; Lee, Dong Eun; Kim, Tae-Youl; Jeung, Woonhee. Apple Pomace Extract Improves Endurance in Exercise Performance by Increasing Strength and Weight of Skeletal Muscle. Journal of Medicinal Food. 2015-12-01, 18 (12): 1380–1386. ISSN 1557-7600. PMID 26331671. doi:10.1089/jmf.2014.3401. 
  19. ^ Li, Songtao; Liao, Xilu; Meng, Fanyu; Wang, Yemei; Sun, Zongxiang; Guo, Fuchuan; Li, Xiaoxia; Meng, Man; Li, Ying. Therapeutic role of ursolic acid on ameliorating hepatic steatosis and improving metabolic disorders in high-fat diet-induced non-alcoholic fatty liver disease rats. PLoS One. 2014-01-01, 9 (1): e86724. ISSN 1932-6203. PMC 3906058可免费查阅. PMID 24489777. doi:10.1371/journal.pone.0086724. 
  20. ^ The cytotoxic activity of ursolic acid derivatives. Eur J Med Chem. June 2005, 40 (6): 582–9. PMID 15922841. doi:10.1016/j.ejmech.2005.01.001.