乐园树素

乐园树素
	IUPAC名; (1β,2α,11β,12α,15β(S))-11,20-Epoxy-1,2,11,12-tetrahydroxy-15-(2-hydroxy-2-methyl-1-oxobutoxy)picras-3-en-16-one
别名	Simarubaceae, Glarubin, Glaumeba, Glaucarubine, 2-hydroxy-2-methylbutyric acid 4-ester with 1,2,3,3ab,4,6ab,7,7aa,10,11,11a,11ba-dodecahydro-1a,2a,4b,10a,11b-pentahydroxy-3a,8,11ab-trimethyl-5H-1,11cb-(epoxymethano)phenanthro[10,1-bc]pyran-5-one; α-kirondrin
识别
CAS号	1448-23-3
PubChem	56840806
ChemSpider	390386
SMILES	CCC(C)(C(=O)O[C@@H]1[C@H]2[C@H]([C@H](C3([C@H]4[C@@]2(CO3)[C@@H](C[C@@H]5[C@@]4([C@@H]([C@H](C=C5C)O)O)C)OC1=O)O)O)C)O;
ChEBI	5370
KEGG	C08760
MeSH	D005900
性质
化学式	C25H36O10
摩尔质量	496.55 g·mol−1
熔点	185-186 °C（272 K）
溶解性（水）	不溶于碳酸氢钠水溶液. 微溶于水.
[α]20; D	+45° (c = 1.7 吡啶溶液); +69° (c = 0.6 甲醇溶液)
危险性
主要危害	细胞毒性
	若非注明，所有数据均出自标准状态（25 ℃，100 kPa）下。

乐园树素（英語：Glaucarubin）是一种从苦木科苦椿属热带灌木乐园树（英语：Simarouba glauca）（非正式名，学名：Simarouba glauca）中产生苦木苦味素，常作为抗阿米巴原虫药剂使用。在化学上，其为一种具有苦味的内酯化合物，在植物体内为一种钾依赖型酸性氨基酸转运体，常见于植物神经系统中^[1]。

医学用途

乐园树素曾被用于测试溶组织内阿米巴感染引起的阿米巴痢疾治疗效果。在一次临床测试中，乐园树素展现出了70%治愈率的效果，而且不良反应发生率很低^[2]。在另一项比对研究中，接受乐园树素的患者复发率为12%，是接受碘化铋吐根碱患者的四倍^[3]。

毒性

乐园树素具有细胞毒性，因此曾被用于测试消灭癌细胞^[4]。虽然其能很好地消灭癌细胞，但正常细胞也会受其影响，包括淋巴系统以及血液循环系统等。

参考文献

^ Kartha, Gopinath; Haas, David J.; Schaffer, H. M.; Kaistha, K. K. Crystal and Molecular Structure of Glaucarubin. Nature. April 1964, 202 (4930): 389–390. Bibcode:1964Natur.202..389K. ISSN 1476-4687. PMID 14152823. S2CID 4271990. doi:10.1038/202389b0 （英语）.
^ van Assendelft, F.; Miller, J. W.; Mintz, D. T.; Schack, J. A.; Ottolenghi, P.; Most, H. The Use of Glaucarubin (a Crystalline Glycoside Isolated from Simarouba glauca) in the Treatment of Human Colonic Amebiasis. The American Journal of Tropical Medicine and Hygiene. 1 May 1956, 5 (3): 501–503. PMID 13327185. doi:10.4269/ajtmh.1956.5.501.
^ Woodruff, A.W.; Bell, S.; Schofield, F.D. II. The treatment of intestinal amoebiasis with emetine bismuth iodide, glaucarubin, dichloroacet-hydroxy-methylanilide, camoform and various antibiotics. Transactions of the Royal Society of Tropical Medicine and Hygiene. March 1956, 50 (2): 114–138. PMID 13324920. doi:10.1016/0035-9203(56)90074-8.
^ Liu, Wei; Krump, Nathan A.; Herlyn, Meenhard; You, Jianxin. Combining DNA Damage Induction with BCL-2 Inhibition to Enhance Merkel Cell Carcinoma Cytotoxicity. Biology. 2020, 9 (2): 35. PMC 7168258 . PMID 32093022. doi:10.3390/biology9020035 .

[1] Kartha, Gopinath; Haas, David J.; Schaffer, H. M.; Kaistha, K. K. Crystal and Molecular Structure of Glaucarubin. Nature. April 1964, 202 (4930): 389–390. Bibcode:1964Natur.202..389K. ISSN 1476-4687. PMID 14152823. S2CID 4271990. doi:10.1038/202389b0 （英语）.

[2] van Assendelft, F.; Miller, J. W.; Mintz, D. T.; Schack, J. A.; Ottolenghi, P.; Most, H. The Use of Glaucarubin (a Crystalline Glycoside Isolated from Simarouba glauca) in the Treatment of Human Colonic Amebiasis. The American Journal of Tropical Medicine and Hygiene. 1 May 1956, 5 (3): 501–503. PMID 13327185. doi:10.4269/ajtmh.1956.5.501.

[3] Woodruff, A.W.; Bell, S.; Schofield, F.D. II. The treatment of intestinal amoebiasis with emetine bismuth iodide, glaucarubin, dichloroacet-hydroxy-methylanilide, camoform and various antibiotics. Transactions of the Royal Society of Tropical Medicine and Hygiene. March 1956, 50 (2): 114–138. PMID 13324920. doi:10.1016/0035-9203(56)90074-8.

[4] Liu, Wei; Krump, Nathan A.; Herlyn, Meenhard; You, Jianxin. Combining DNA Damage Induction with BCL-2 Inhibition to Enhance Merkel Cell Carcinoma Cytotoxicity. Biology. 2020, 9 (2): 35. PMC 7168258 . PMID 32093022. doi:10.3390/biology9020035 .

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