大黃酸

大黃酸
	IUPAC名; 4,5-Dihydroxy-9,10-dioxo-9,10-dihydroanthracene-2-carboxylic acid
別名	山扁豆酸; 決明酸; 柯嗪-3-甲酸; 4,5′-二羥蒽醌-2- 甲酸
識別
CAS號	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
性質
化學式	C15H8O6
摩爾質量	284.22 g/mol g·mol⁻¹
外觀	Orange crystals
密度	1.687 g/cm3
熔點	350 - 352 °C（271 K）
沸點	597.8 °C（871 K）
溶解性（水）	不溶於水
危險性
	GHS危險性符號;
GHS提示詞	Warning
H-術語	H315, H319, H335
P-術語	?
主要危害	刺激性物質
	若非註明，所有數據均出自標準狀態（25 ℃，100 kPa）下。

大黃酸（英語：Rhein）, 又稱山扁豆酸、決明酸（英語：cassic acid）^[2]，是從大黃中提取得到的蒽醌衍生物^[3]。作為蒽醛衍生物，大黃酸具有瀉藥作用，在植物體內常以糖苷的形式存在，如大黃酸-8-糖苷或葡萄糖大黃苷等^[3]。大黃酸於1895年首次分離得到^[4]。其可以在波葉大黃^[5]、掌葉大黃^[6]等大黃屬植物中發現，也可以在豆科決明屬翅莢決明中發現^[7]。

最初，含有大黃酸的大黃屬植物被用作瀉藥。人們認為大黃酸連同其他蒽醌苷一起具有這種性質^[3]。2008年，大黃酸發現其具有抗金黃色葡萄球菌的作用。大黃酸與抗生素苯唑西林和氨苄西林之間已證實具有協同作用或部分協同作用^[8]。

大黃酸具有抑制脂肪和肥胖相關蛋白生成的作用，這種蛋白可將mRNA上的N⁶-甲基腺苷去甲基化成腺苷^[9]^[10]。

大黃酸的藥代動力學目前尚未開展廣泛研究，但至少一項研究表明口服大黃酸的吸收效果比保留灌腸好^[11] 。研究顯示，對於患有慢性充血性心力衰竭的老年患者，連續五天口服劑量為50 mg，每天兩次的大黃酸是安全的^[12]。

參考文獻

^ Cassic acid on www.naturestandard.com 網際網路檔案館的存檔，存檔日期2011-07-14.
^ 蘇子仁、賴小平 (編). 汉英、英汉中草药化学成分词汇. 北京: 中國中醫藥出版社. 2006: 444+690.
^ ^3.0 ^3.1 ^3.2 Pharmacognosy of Rhubarb | Chemical Constituents. [2024-07-04]. （原始內容存檔於2015-06-26）.
^ 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 （德語）.
^ 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 （英語）.
^ 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 （英語）.
^ 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 網際網路檔案館的存檔，存檔日期2011-07-14.

[2] 蘇子仁、賴小平 (編). 汉英、英汉中草药化学成分词汇. 北京: 中國中醫藥出版社. 2006: 444+690.

[mehta-3] 3.0 ^3.1 ^3.2 Pharmacognosy of Rhubarb | Chemical Constituents. [2024-07-04]. （原始內容存檔於2015-06-26）.

[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 （德語）.

[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 （英語）.

[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 （英語）.

[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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