Glaucarubin

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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
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
KEGG
MeSH D005900
UNII
  • 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
  • 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
C25H36O10
Molar mass 496.553 g·mol−1
Melting point 185–186 °C (365–367 °F; 458–459 K)
Insoluble in aq sodium bicarbonate solutions. Slightly soluble in water.
+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).

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.
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