WARNING: This product is for research use only, not for human or veterinary use.
MedKoo CAT#: 412433
CAS#: 79786-01-9
Description: Casuarinin is an ellagitannin. It is found in the pericarp of pomegranates. It is also found in Casuarina and Stachyurus species and in Alnus sieboldiana. It is an isomer of casuarictin. It is a highly active carbonic anhydrase inhibitor. It is a compound that causes the contraction of body tissues, typically used to reduce bleeding from minor abrasions.
MedKoo Cat#: 412433
Name: Casuarinin
CAS#: 79786-01-9
Chemical Formula: C41H28O26
Exact Mass: 936.0869
Molecular Weight: 936.65
Elemental Analysis: C, 52.58; H, 3.01; O, 44.41
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Synonym: Casuarinin
IUPAC/Chemical Name: 7-(1,2,3,12,13,14,15-heptahydroxy-5,10-dioxo-5,7,8,10-tetrahydro-4,7-methanodibenzo[f,h][1,4]dioxecin-8-yl)-1,2,3,13,14,15-hexahydroxy-5,11-dioxo-5,8,9,11-tetrahydro-7H-dibenzo[g,i][1,5]dioxacycloundecin-8-yl 3,4,5-trihydroxybenzoate
InChi Key: MMQXBTULXAEKQE-UHFFFAOYSA-N
InChi Code: InChI=1S/C41H28O26/c42-11-1-7(2-12(43)23(11)47)37(58)64-16-6-63-38(59)8-3-13(44)24(48)27(51)17(8)18-9(4-14(45)25(49)28(18)52)39(60)65-34(16)36-35-32(56)22-21(41(62)66-35)20(30(54)33(57)31(22)55)19-10(40(61)67-36)5-15(46)26(50)29(19)53/h1-5,16,32,34-36,42-57H,6H2
SMILES Code: OC1C2OC(c3c(c4c(C(OC2C5OC(c6c(c7c(C(OCC5OC(c8cc(O)c(O)c(O)c8)=O)=O)cc(O)c(O)c7O)c(O)c(O)c(O)c6)=O)=O)cc(O)c(O)c4O)c(O)c(O)c(O)c31)=O
Appearance: Solid powder
Purity: >98% (or refer to the Certificate of Analysis)
Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility: Soluble in DMSO
Shelf Life: >3 years if stored properly
Drug Formulation: This drug may be formulated in DMSO
Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code: 2934.99.9001
The following data is based on the product molecular weight 936.65 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass | 1 mg | 5 mg | 10 mg |
|---|---|---|---|
| 1 mM | 1.15 mL | 5.76 mL | 11.51 mL |
| 5 mM | 0.23 mL | 1.15 mL | 2.3 mL |
| 10 mM | 0.12 mL | 0.58 mL | 1.15 mL |
| 50 mM | 0.02 mL | 0.12 mL | 0.23 mL |
1: Al-Sayed E, Michel HE, Khattab MA, El-Shazly M, Singab AN. Protective Role of Casuarinin from Melaleuca leucadendra against Ethanol-Induced Gastric Ulcer in Rats. Planta Med. 2020 Jan;86(1):32-44. doi: 10.1055/a-1031-7328. Epub 2019 Nov 5. PMID: 31689719.
2: Song JH, Kang KS, Choi YK. Protective effect of casuarinin against glutamate- induced apoptosis in HT22 cells through inhibition of oxidative stress-mediated MAPK phosphorylation. Bioorg Med Chem Lett. 2017 Dec 1;27(23):5109-5113. doi: 10.1016/j.bmcl.2017.10.075. Epub 2017 Nov 1. PMID: 29122481.
3: Kwon DJ, Bae YS, Ju SM, Goh AR, Choi SY, Park J. Casuarinin suppresses TNF-α- induced ICAM-1 expression via blockade of NF-κB activation in HaCaT cells. Biochem Biophys Res Commun. 2011 Jun 17;409(4):780-5. doi: 10.1016/j.bbrc.2011.05.088. Epub 2011 May 20. PMID: 21621513.
4: Kwon DJ, Bae YS, Ju SM, Goh AR, Youn GS, Choi SY, Park J. Casuarinin suppresses TARC/CCL17 and MDC/CCL22 production via blockade of NF-κB and STAT1 activation in HaCaT cells. Biochem Biophys Res Commun. 2012 Jan 27;417(4):1254-9. doi: 10.1016/j.bbrc.2011.12.119. Epub 2011 Dec 29. PMID: 22227193.
5: Chen CH, Liu TZ, Kuo TC, Lu FJ, Chen YC, Chang-Chien YW, Lin CC. Casuarinin protects cultured MDCK cells from hydrogen peroxide-induced oxidative stress and DNA oxidative damage. Planta Med. 2004 Nov;70(11):1022-6. doi: 10.1055/s-2004-832641. PMID: 15549656.
6: Kuo PL, Hsu YL, Lin TC, Lin LT, Chang JK, Lin CC. Casuarinin from the bark of Terminalia arjuna induces apoptosis and cell cycle arrest in human breast adenocarcinoma MCF-7 cells. Planta Med. 2005 Mar;71(3):237-43. doi: 10.1055/s-2005-837823. PMID: 15770544.
7: Wakamori S, Matsumoto S, Kusuki R, Ikeuchi K, Yamada H. Total Synthesis of Casuarinin. Org Lett. 2020 May 1;22(9):3392-3396. doi: 10.1021/acs.orglett.0c00876. Epub 2020 Apr 10. PMID: 32275157.
8: Cheng HY, Lin CC, Lin TC. Antiherpes simplex virus type 2 activity of casuarinin from the bark of Terminalia arjuna Linn. Antiviral Res. 2002 Sep;55(3):447-55. doi: 10.1016/s0166-3542(02)00077-3. PMID: 12206882.
9: Yamada H, Wakamori S, Hirokane T, Ikeuchi K, Matsumoto S. Structural Revisions in Natural Ellagitannins. Molecules. 2018 Jul 30;23(8):1901. doi: 10.3390/molecules23081901. PMID: 30061530; PMCID: PMC6222896.
10: Souza-Moreira TM, Severi JA, Lee K, Preechasuth K, Santos E, Gow NA, Munro CA, Vilegas W, Pietro RC. Anti-Candida targets and cytotoxicity of casuarinin isolated from Plinia cauliflora leaves in a bioactivity-guided study. Molecules. 2013 Jul 9;18(7):8095-108. doi: 10.3390/molecules18078095. PMID: 23839114; PMCID: PMC6269720.
