Glaucarubin

Glaucarubin

Names
IUPAC name (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
Other names 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
Identifiers
CAS Number	1448-23-3^Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:5370
ChEMBL	ChEMBL1997250
ChemSpider	390386
KEGG	C08760
MeSH	D005900
PubChem CID	56840806
UNII	EH6H7VS52J^Y
InChI InChI=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 Key: LZKVXMYVBSNXER-YZPKDWIXSA-N
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
Properties
Chemical formula	C25H36O10
Molar mass	496.553 g·mol^−1
Melting point	185–186 °C (365–367 °F; 458–459 K)
Solubility in water	Insoluble in aq sodium bicarbonate solutions. Slightly soluble in water.
Chiral rotation ([α]D)	+45° (c = 1.7 in pyridine); +69° (c = 0.6 in methanol)
Hazards
Occupational safety and health (OHS/OSH):
Main hazards	Cytotoxic
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Glaucarubin is a quassinoid derived from the tropical shrub, Simarouba glauca. It is used as an antiamoebic agent.[1]

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.[2] 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.[3]

Toxicity

Being a cytotoxin, glaucarubin is capable of killing cells, which is why it has been tested as an anti-cancer drug.[4] 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.

References

1. Kartha, Gopinath; Haas, David J.; Schaffer, H. M.; Kaistha, K. K. (April 1964). "Crystal and Molecular Structure of Glaucarubin". Nature. 202 (4930): 389–390. Bibcode:1964Natur.202..389K. doi:10.1038/202389b0. ISSN 1476-4687. PMID 14152823. S2CID 4271990.
2. van Assendelft, F.; Miller, J. W.; Mintz, D. T.; Schack, J. A.; Ottolenghi, P.; Most, H. (1 May 1956). "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. 5 (3): 501–503. doi:10.4269/ajtmh.1956.5.501. PMID 13327185.
3. Woodruff, A.W.; Bell, S.; Schofield, F.D. (March 1956). "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. 50 (2): 114–138. doi:10.1016/0035-9203(56)90074-8. PMID 13324920.
4. Liu, Wei; Krump, Nathan A.; Herlyn, Meenhard; You, Jianxin (2020). "Combining DNA Damage Induction with BCL-2 Inhibition to Enhance Merkel Cell Carcinoma Cytotoxicity". Biology. 9 (2): 35. doi:10.3390/biology9020035. PMC 7168258. PMID 32093022.