Glaucarubin
{{Chembox
|Name = Glaucarubin
|ImageFile = Glaucarubin.png
|IUPACName = (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
|SystematicName =
|OtherNames = 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
|Section1 = {{Chembox Identifiers
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| CASNo = 1448-23-3
| CASNo_Ref = {{cascite|correct|CAS}}
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = EH6H7VS52J
| ChEBI = 5370
| ChEMBL = 1997250
| ChemSpiderID = 390386
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| StdInChI=1S/C25H36O10/c1-6-22(4,31)21(30)35-16-15-11(3)17(27)25(32)20-23(5)12(10(2)7-13(26)18(23)28)8-14(34-19(16)29)24(15,20)9-33-25/h7,11-18,20,26-28,31-32H,6,8-9H2,1-5H3/t11-,12+,13+,14-,15-,16-,17-,18-,20-,22?,23-,24+,25?/m1/s1
| StdInChIKey = LZKVXMYVBSNXER-YZPKDWIXSA-N
| KEGG = C08760
| MeSHName =D005900
| PubChem = 56840806
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| 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
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}}|Section2 = {{Chembox Properties
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| C=25 | H=36 | O=10
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| MeltingPtC = 185–186
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| Solubility = Insoluble in aq sodium bicarbonate solutions. Slightly soluble in water.
| SpecRotation = +45° (c = 1.7 in pyridine); +69° (c = 0.6 in methanol)
| Solvent = Acidification of an alkaline soln regenerates glaucararubin, standing in alkaline solution leads to decomposition
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|Section3 = {{Chembox Structure
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|Section7 = {{Chembox Hazards
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| MainHazards = Cytotoxic
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|Section8 = {{Chembox Related
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Glaucarubin is a quassinoid derived from the tropical shrub, Simarouba glauca. It is used as an antiamoebic agent.{{cite journal |last1=Kartha |first1=Gopinath |last2=Haas |first2=David J. |last3=Schaffer |first3=H. M. |last4=Kaistha |first4=K. K. |title=Crystal and Molecular Structure of Glaucarubin |journal=Nature |date=April 1964 |volume=202 |issue=4930 |pages=389–390 |doi=10.1038/202389b0 |pmid=14152823 |bibcode=1964Natur.202..389K |s2cid=4271990 |language=en |issn=1476-4687}}
Structure and properties
Glaucarubin is a bitter lactone found in Simaruba glauca. The compound is an acidic amino acid transporter, which is potassium-dependent and is often found in neuronal tissue.
Uses in medicine
Glaucarubin has been tested for the treatment of amebiasis, an infection of the intestines caused by Entamoeba histolytica. In one clinical trial, cure-rates of around 70% were observed, with few side-effects.{{cite journal |title= The Use of Glaucarubin (a Crystalline Glycoside Isolated from Simarouba glauca) in the Treatment of Human Colonic Amebiasis |first1= F. |last1= van Assendelft |first2= J. W. |last2= Miller |first3= D. T. |last3= Mintz |first4= J. A. |last4= Schack |first5= P. |last5= Ottolenghi |first6= H. |last6= Most |journal= The American Journal of Tropical Medicine and Hygiene |volume= 5 |issue= 3 |date= 1 May 1956 |pages= 501–503 |doi= 10.4269/ajtmh.1956.5.501 |pmid= 13327185 }} In a clinical trial comparing various treatment options for intestinal amoebiasis, patients treated with glaucarubin had a relapse rate of 12%, four times the rate of those treated with emetine–bismuth iodide.{{cite journal |title= II. The treatment of intestinal amoebiasis with emetine bismuth iodide, glaucarubin, dichloroacet-hydroxy-methylanilide, camoform and various antibiotics |first1= A.W. |last1= Woodruff |first2= S. |last2= Bell |first3= F.D. |last3= Schofield |journal= Transactions of the Royal Society of Tropical Medicine and Hygiene |volume= 50| issue= 2 |date= March 1956 |pages= 114–138 |doi= 10.1016/0035-9203(56)90074-8 |pmid= 13324920 }}
Toxicity
Being a cytotoxin, glaucarubin is capable of killing cells, which is why it has been tested as an anti-cancer drug.{{cite journal |first1= Wei |last1= Liu |first2= Nathan A. |last2= Krump |first3= Meenhard |last3= Herlyn |first4= Jianxin |last4= You |title= Combining DNA Damage Induction with BCL-2 Inhibition to Enhance Merkel Cell Carcinoma Cytotoxicity |journal= Biology |volume= 9 |issue= 2 |year= 2020 |page= 35 |doi= 10.3390/biology9020035 |pmid= 32093022 |pmc= 7168258 |doi-access= free }} Although it helps in the process of killing the uncontrollable cancer cells, it has the tendency to spread and cause harm to unwanted parts of the body, such as the lymphatic system or the blood stream.