大黄酸

大黄酸
	IUPAC名; 4,5-Dihydroxy-9,10-dioxo-9,10-dihydroanthracene-2-carboxylic acid
别名	山扁豆酸; 决明酸; 柯嗪-3-甲酸; 4,5′-二羟蒽醌-2- 甲酸
识别
CAS号	478-43-3
PubChem	10168
ChemSpider	9762
SMILES	C1=CC2=C(C(=C1)O)C(=O)C3=C(C=C(C=C3C2=O)C(=O)O)O;
InChI	1/C15H8O6/c16-9-3-1-2-7-11(9)14(19)12-8(13(7)18)4-6(15(20)21)5-10(12)17/h1-5,16-17H,(H,20,21);
InChIKey	FCDLCPWAQCPTKC-UHFFFAOYAT
EINECS	207-521-4
ChEBI	8825
DrugBank	DB13174
KEGG	C10401
MeSH	Rhein
性质
化学式	C15H8O6
摩尔质量	284.22 g/mol g·mol⁻¹
外观	Orange crystals
密度	1.687 g/cm3
熔点	350 - 352 °C（271 K）
沸点	597.8 °C（871 K）
溶解性（水）	不溶于水
危险性
	GHS危险性符号;
GHS提示词	Warning
H-术语	H315, H319, H335
P-术语	?
主要危害	刺激性物质
	若非注明，所有数据均出自标准状态（25 ℃，100 kPa）下。

大黄酸（英語：Rhein）, 又称山扁豆酸、决明酸（英語：cassic acid）^[2]，是从大黄中提取得到的蒽醌衍生物^[3]。作为蒽醛衍生物，大黄酸具有泻药作用，在植物体内常以糖苷的形式存在，如大黄酸-8-糖苷或葡萄糖大黄苷等^[3]。大黄酸于1895年首次分离得到^[4]。其可以在波叶大黄^[5]、掌叶大黄^[6]等大黄属植物中发现，也可以在豆科决明属翅荚决明中发现^[7]。

最初，含有大黄酸的大黄属植物被用作泻药。人们认为大黄酸连同其他蒽醌苷一起具有这种性质^[3]。2008年，大黄酸发现其具有抗金黃色葡萄球菌的作用。大黄酸与抗生素苯唑西林和氨苄西林之间已证实具有协同作用或部分协同作用^[8]。

大黄酸具有抑制脂肪和肥胖相关蛋白生成的作用，这种蛋白可将mRNA上的N⁶-甲基腺苷去甲基化成腺苷^[9]^[10]。

大黄酸的药代动力学目前尚未开展广泛研究，但至少一项研究表明口服大黄酸的吸收效果比保留灌肠好^[11] 。研究显示，对于患有慢性充血性心力衰竭的老年患者，连续五天口服剂量为50 mg，每天两次的大黄酸是安全的^[12]。

参考文献[编辑]

^ Cassic acid on www.naturestandard.com 互联网档案馆的存檔，存档日期2011-07-14.
^ 苏子仁、赖小平 (编). 汉英、英汉中草药化学成分词汇. 北京: 中国中医药出版社. 2006: 444+690.
^ ^3.0 ^3.1 ^3.2 Pharmacognosy of Rhubarb | Chemical Constituents
^ Hesse O. The Chemistry of rhubarb (EN).. Pharmaceutical Journal and Transactions. 1895, 1: 325.
^ Lee JH, Kim JM, Kim CS. Pharmacokinetic analysis of rhein in Rheum undulatum L.. J Ethnopharmacol. 2003, 84 (1): 5–9. PMID 12499069. doi:10.1016/S0378-8741(02)00222-2.
^ Hoerhammer L, Wagner H, Koehler I. Neue Untersuchungen über die Inhaltsstoffe von Rheum palmatum L. 1. Mitteilung: Zur Analytik des Rheins [New investigations on the components of Rheum palmatum L. Part 1: On the analysis of rhein]. Archiv der Pharmazie. 1959, 292 (64): 591–601. PMID 14402302. S2CID 94169376. doi:10.1002/ardp.19592921105 （德语）.
^ Anchel M. Identification of the antibiotic substance from Cassia reticulata as 4,5-Dihydroxyanthraquinone-2-carboxylic acid (PDF). J Biol Chem. 1949, 177 (1): 169–177. PMID 18123056. doi:10.1016/S0021-9258(18)57072-1 .
^ Joung DK, Joung H, Yang DW, et al. Synergistic effect of rhein in combination with ampicillin or oxacillin against methicillin-resistant Staphylococcus aureus. Exp Ther Med. 2012, 3 (4): 608–612. PMC 3438619 . PMID 22969937. doi:10.3892/etm.2012.459.
^ Yu, Jun; Chen, Mengxian; Huang, Haijiao; Zhu, Junda; Song, Huixue; Zhu, Jian; Park, Jaewon; Ji, Sheng-Jian. Dynamic m⁶A modification regulates local translation of mRNA in axons. Nucleic Acids Research. 2017-11-23, 46 (3): 1412–1423. ISSN 0305-1048. PMC 5815124 . PMID 29186567. doi:10.1093/nar/gkx1182 （英语）.
^ Jia, Guifang; Fu, Ye; Zhao, Xu; Dai, Qing; Zheng, Guanqun; Yang, Ying; Yi, Chengqi; Lindahl, Tomas; Pan, Tao. N⁶-Methyladenosine in nuclear RNA is a major substrate of the obesity-associated FTO. Nature Chemical Biology. 2011-10-16, 7 (12): 885–887. ISSN 1552-4450. PMC 3218240 . PMID 22002720. doi:10.1038/nchembio.687 （英语）.
^ Zhu W, Wang XM, Zhang L, Li XY, Wang BX. Pharmacokinetic of rhein in healthy male volunteers following oral and retention enema administration of rhubarb extract: a single dose study. Am J Chin Med. 2005, 33 (6): 839–850. PMID 16355440. doi:10.1142/S0192415X05003508.
^ La Villa G, Marra F, Laffi G, et al. Effects of rhein on renal arachidonic acid metabolism and renal function in patients with congestive heart failure. Eur J Clin Pharmacol. 1989, 37 (1): 1–5. PMID 2512175. S2CID 6338421. doi:10.1007/bf00609415.

[naturestandard-1] Cassic acid on www.naturestandard.com 互联网档案馆的存檔，存档日期2011-07-14.

[2] 苏子仁、赖小平 (编). 汉英、英汉中草药化学成分词汇. 北京: 中国中医药出版社. 2006: 444+690.

[mehta-3] 3.0 ^3.1 ^3.2 Pharmacognosy of Rhubarb | Chemical Constituents

[4] Hesse O. The Chemistry of rhubarb (EN).. Pharmaceutical Journal and Transactions. 1895, 1: 325.

[5] Lee JH, Kim JM, Kim CS. Pharmacokinetic analysis of rhein in Rheum undulatum L.. J Ethnopharmacol. 2003, 84 (1): 5–9. PMID 12499069. doi:10.1016/S0378-8741(02)00222-2.

[6] Hoerhammer L, Wagner H, Koehler I. Neue Untersuchungen über die Inhaltsstoffe von Rheum palmatum L. 1. Mitteilung: Zur Analytik des Rheins [New investigations on the components of Rheum palmatum L. Part 1: On the analysis of rhein]. Archiv der Pharmazie. 1959, 292 (64): 591–601. PMID 14402302. S2CID 94169376. doi:10.1002/ardp.19592921105 （德语）.

[7] Anchel M. Identification of the antibiotic substance from Cassia reticulata as 4,5-Dihydroxyanthraquinone-2-carboxylic acid (PDF). J Biol Chem. 1949, 177 (1): 169–177. PMID 18123056. doi:10.1016/S0021-9258(18)57072-1 .

[8] Joung DK, Joung H, Yang DW, et al. Synergistic effect of rhein in combination with ampicillin or oxacillin against methicillin-resistant Staphylococcus aureus. Exp Ther Med. 2012, 3 (4): 608–612. PMC 3438619 . PMID 22969937. doi:10.3892/etm.2012.459.

[9] Yu, Jun; Chen, Mengxian; Huang, Haijiao; Zhu, Junda; Song, Huixue; Zhu, Jian; Park, Jaewon; Ji, Sheng-Jian. Dynamic m⁶A modification regulates local translation of mRNA in axons. Nucleic Acids Research. 2017-11-23, 46 (3): 1412–1423. ISSN 0305-1048. PMC 5815124 . PMID 29186567. doi:10.1093/nar/gkx1182 （英语）.

[10] Jia, Guifang; Fu, Ye; Zhao, Xu; Dai, Qing; Zheng, Guanqun; Yang, Ying; Yi, Chengqi; Lindahl, Tomas; Pan, Tao. N⁶-Methyladenosine in nuclear RNA is a major substrate of the obesity-associated FTO. Nature Chemical Biology. 2011-10-16, 7 (12): 885–887. ISSN 1552-4450. PMC 3218240 . PMID 22002720. doi:10.1038/nchembio.687 （英语）.

[11] Zhu W, Wang XM, Zhang L, Li XY, Wang BX. Pharmacokinetic of rhein in healthy male volunteers following oral and retention enema administration of rhubarb extract: a single dose study. Am J Chin Med. 2005, 33 (6): 839–850. PMID 16355440. doi:10.1142/S0192415X05003508.

[12] La Villa G, Marra F, Laffi G, et al. Effects of rhein on renal arachidonic acid metabolism and renal function in patients with congestive heart failure. Eur J Clin Pharmacol. 1989, 37 (1): 1–5. PMID 2512175. S2CID 6338421. doi:10.1007/bf00609415.

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