倒千里光碱

倒千里光碱
	首选IUPAC名; (1R,4Z,6R,7S,17R)-4-ethylidene-7-hydroxy-7-(hydroxymethyl)-6-methyl-2,9-dioxa-14-azatricyclo[9.5.1.014,17]heptadec-11-ene-3,8-dione
别名	Retrorsin; β-Longilobine
识别
CAS号	480-54-6 ; 36168-23-7（盐酸盐）
PubChem	5281743
ChemSpider	13076866
SMILES	C/C=C\1/C[C@H]([C@@](C(=O)OCC2=CCN3[C@H]2[C@@H](CC3)OC1=O)(CO)O)C;
InChI	1S/C18H25NO6/c1-3-12-8-11(2)18(23,10-20)17(22)24-9-13-4-6-19-7-5-14(15(13)19)25-16(12)21/h3-4,11,14-15,20,23H,5-10H2,1-2H3/b12-3-/t11-,14-,15-,18-/m1/s1;
InChIKey	BCJMNZRQJAVDLD-CQRYIUNCSA-N
ChEBI	8822
KEGG	C10364
性质
化学式	C18H25NO6
摩尔质量	351.39 g·mol−1
外观	无色柱状晶体
密度	1.38 g/cm3
熔点	212 °C（485 K）
溶解性	可溶于氯仿; 微溶于水、丙酮、乙醇
危险性
	GHS危险性符号;
GHS提示词	Danger
H-术语	H300
P-术语	P264, P270, P301+316, P321, P330, P405, P501
	若非注明，所有数据均出自标准状态（25 ℃，100 kPa）下。

倒千里光碱（英語：Retrorsine，简称RTS或RS）是一种主要天然存在于千里光属植物中的吡咯里西啶类生物碱。^[1]^[2]其最早由加拿大化学家理查德·曼斯克（Richard H.F. Manske）于 1931 年从倒千里光（Senecio retrorsus）中首次分离并命名。^[3]倒千里光碱具有致癌性及显著的肝毒性（为吡咯里西啶生物碱中肝毒性最强的之一），常通过污染饲料或草药制品对牲畜及人类健康造成严重威胁。^[1]^[2]^[4]^[5]

在生物医学研究中，倒千里光碱凭借其能阻断宿主肝细胞的细胞周期而又不立即导致细胞死亡的特征，被用于构建选择性肝损伤的动物模型，以研究肝脏再生与肝脏移植机制，如倒千里光碱/肝脏部分切除组术（RS/PH）的模型即为该领域的典型研究方法。^[2]^[6]^[7]^[8]^[9]

参考资料

^ ^1.0 ^1.1 Guo, Li; Zhang, Li; Xu, Haiman; Yu, Pei; Wang, Zhigang; Lu, Danyi; Chen, Min; Wu, Baojian. Diurnal hepatic CYP3A11 contributes to chronotoxicity of the pyrrolizidine alkaloid retrorsine in mice. Xenobiotica. 2021-09-02, 51 (9): 1019–1028. ISSN 0049-8254. PMID 34311664. doi:10.1080/00498254.2021.1950867.
^ ^2.0 ^2.1 ^2.2 Zhu, Yanli; Zhang, Shuhang; Shao, Yin; Tang, Lihui; Zhang, Congcheng; Tang, Shiyu; Lu, Hao. Regulatory role of oxidative stress in retrorsine – Induced apoptosis and autophagy in primary rat hepatocytes. Ecotoxicology and Environmental Safety. 2024, 279. Bibcode:2024EcoES.27916515Z. PMID 38810283. doi:10.1016/j.ecoenv.2024.116515.
^ Manske, Richard H. F. THE ALKALOIDS OF SENECIO SPECIES: I. THE NECINES AND NECIC ACIDS FROM S . RETRORSUS AND S . JACOBAEA. Canadian Journal of Research. 1931-12-01, 5 (6): 651–659. Bibcode:1931CJRes...5..651M. ISSN 1923-4287. doi:10.1139/cjr31-103.
^ Schoental, Regina. Liver lesions in young rats suckled by mothers treated with the pyrrolizidine (Senecio) alkaloids, lasiocarpine and retrorsine. The Journal of Pathology and Bacteriology. 1959, 77 (2): 485–495. ISSN 0368-3494. PMID 13642195. doi:10.1002/path.1700770220.
^ Mulder, Patrick P.J.; López, Patricia; Castelari, Massimo; Bodi, Dorina; Ronczka, Stefan; Preiss-Weigert, Angelika; These, Anja. Occurrence of pyrrolizidine alkaloids in animal- and plant-derived food: results of a survey across Europe. Food Additives & Contaminants: Part A. 2018-01-02, 35 (1): 118–133. ISSN 1944-0049. PMID 28942718. doi:10.1080/19440049.2017.1382726.
^ Laconi, Ezio; Oren, Ran; Mukhopadhyay, Deb K.; Hurston, Ethel; Laconi, Sergio; Pani, Paolo; Dabeva, Mariana D.; Shafritz, David A. Long-Term, Near-Total Liver Replacement by Transplantation of Isolated Hepatocytes in Rats Treated with Retrorsine. The American Journal of Pathology. 1998, 153 (1): 319–329. PMC 1852941 . PMID 9665494. doi:10.1016/S0002-9440(10)65574-5.
^ Shafritz, David A.; Oertel, Michael. Model systems and experimental conditions that lead to effective repopulation of the liver by transplanted cells. The International Journal of Biochemistry & Cell Biology. 2011, 43 (2): 198–213. PMC 2907475 . PMID 20080205. doi:10.1016/j.biocel.2010.01.013.
^ Laconi, Sergio; Doratiotto, Silvia; Montisci, Stefania; Pani, Paolo; Laconi, Ezio. Repopulation by Endogenous Hepatocytes Does Not Reconstitute Liver Mass in Rats Treated with Retrorsine. Cell Transplantation. 2008, 17 (12): 1415–1421. ISSN 0963-6897. PMID 19364078. doi:10.3727/096368908787648128.
^ Tsuchida, Tomonori; Murata, Soichiro; Matsuki, Koichiro; Mori, Akihiro; Matsuo, Megumi; Mikami, Satoshi; Okamoto, Satoshi; Ueno, Yasuharu; Tadokoro, Tomomi; Zheng, Yun-Wen; Taniguchi, Hideki. The Regenerative Effect of Portal Vein Injection of Liver Organoids by Retrorsine/Partial Hepatectomy in Rats. International Journal of Molecular Sciences. 2019-12-26, 21 (1): 178. ISSN 1422-0067. PMC 6981799 . PMID 31887985. doi:10.3390/ijms21010178 .

[guo-1] 1.0 ^1.1 Guo, Li; Zhang, Li; Xu, Haiman; Yu, Pei; Wang, Zhigang; Lu, Danyi; Chen, Min; Wu, Baojian. Diurnal hepatic CYP3A11 contributes to chronotoxicity of the pyrrolizidine alkaloid retrorsine in mice. Xenobiotica. 2021-09-02, 51 (9): 1019–1028. ISSN 0049-8254. PMID 34311664. doi:10.1080/00498254.2021.1950867.

[zhu-2] 2.0 ^2.1 ^2.2 Zhu, Yanli; Zhang, Shuhang; Shao, Yin; Tang, Lihui; Zhang, Congcheng; Tang, Shiyu; Lu, Hao. Regulatory role of oxidative stress in retrorsine – Induced apoptosis and autophagy in primary rat hepatocytes. Ecotoxicology and Environmental Safety. 2024, 279. Bibcode:2024EcoES.27916515Z. PMID 38810283. doi:10.1016/j.ecoenv.2024.116515.

[Manske-3] Manske, Richard H. F. THE ALKALOIDS OF SENECIO SPECIES: I. THE NECINES AND NECIC ACIDS FROM S . RETRORSUS AND S . JACOBAEA. Canadian Journal of Research. 1931-12-01, 5 (6): 651–659. Bibcode:1931CJRes...5..651M. ISSN 1923-4287. doi:10.1139/cjr31-103.

[sch-4] Schoental, Regina. Liver lesions in young rats suckled by mothers treated with the pyrrolizidine (Senecio) alkaloids, lasiocarpine and retrorsine. The Journal of Pathology and Bacteriology. 1959, 77 (2): 485–495. ISSN 0368-3494. PMID 13642195. doi:10.1002/path.1700770220.

[mul-5] Mulder, Patrick P.J.; López, Patricia; Castelari, Massimo; Bodi, Dorina; Ronczka, Stefan; Preiss-Weigert, Angelika; These, Anja. Occurrence of pyrrolizidine alkaloids in animal- and plant-derived food: results of a survey across Europe. Food Additives & Contaminants: Part A. 2018-01-02, 35 (1): 118–133. ISSN 1944-0049. PMID 28942718. doi:10.1080/19440049.2017.1382726.

[laco-6] Laconi, Ezio; Oren, Ran; Mukhopadhyay, Deb K.; Hurston, Ethel; Laconi, Sergio; Pani, Paolo; Dabeva, Mariana D.; Shafritz, David A. Long-Term, Near-Total Liver Replacement by Transplantation of Isolated Hepatocytes in Rats Treated with Retrorsine. The American Journal of Pathology. 1998, 153 (1): 319–329. PMC 1852941 . PMID 9665494. doi:10.1016/S0002-9440(10)65574-5.

[sha-7] Shafritz, David A.; Oertel, Michael. Model systems and experimental conditions that lead to effective repopulation of the liver by transplanted cells. The International Journal of Biochemistry & Cell Biology. 2011, 43 (2): 198–213. PMC 2907475 . PMID 20080205. doi:10.1016/j.biocel.2010.01.013.

[lac-8] Laconi, Sergio; Doratiotto, Silvia; Montisci, Stefania; Pani, Paolo; Laconi, Ezio. Repopulation by Endogenous Hepatocytes Does Not Reconstitute Liver Mass in Rats Treated with Retrorsine. Cell Transplantation. 2008, 17 (12): 1415–1421. ISSN 0963-6897. PMID 19364078. doi:10.3727/096368908787648128.

[tsu-9] Tsuchida, Tomonori; Murata, Soichiro; Matsuki, Koichiro; Mori, Akihiro; Matsuo, Megumi; Mikami, Satoshi; Okamoto, Satoshi; Ueno, Yasuharu; Tadokoro, Tomomi; Zheng, Yun-Wen; Taniguchi, Hideki. The Regenerative Effect of Portal Vein Injection of Liver Organoids by Retrorsine/Partial Hepatectomy in Rats. International Journal of Molecular Sciences. 2019-12-26, 21 (1): 178. ISSN 1422-0067. PMC 6981799 . PMID 31887985. doi:10.3390/ijms21010178 .

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