MedKoo Cat#: 596024 | Name: Clivorine

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Clivorine is an otonecine pyrrolizidine alkaloid from Ligularia species.

Chemical Structure

 Clivorine
Clivorine
CAS# 275806-81-0

Theoretical Analysis

MedKoo Cat#: 596024

Name: Clivorine

CAS#: 275806-81-0

Chemical Formula: C21H27NO7

Exact Mass: 405.1788

Molecular Weight: 405.44

Elemental Analysis: C, 62.21; H, 6.71; N, 3.45; O, 27.62

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Synonym
Clivorine; J1.344.443I; Clivorine (neutral);
IUPAC/Chemical Name
(1R,4Z,6S,7S,11Z)-6,7,14-trimethyl-3,8,17-trioxo-4-vinyl-2,9-dioxa-14-azabicyclo[9.5.1]heptadeca-4,11-dien-7-yl acetate
InChi Key
LIEIOJNANXUNDT-VKPCTYQGSA-N
InChi Code
InChI=1S/C21H27NO7/c1-6-15-11-13(2)21(4,29-14(3)23)20(26)27-12-16-7-9-22(5)10-8-17(18(16)24)28-19(15)25/h6-7,11,13,17H,1,8-10,12H2,2-5H3/b15-11-,16-7-/t13-,17+,21-/m0/s1
SMILES Code
O=C(/C(C=C)=C\[C@H](C)[C@@]1(OC(C)=O)C)O[C@](C2=O)([H])CCN(C)C/C=C2/COC1=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
>2 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
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 405.44 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.

Recalculate based on batch purity %
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: Liu W, Li X, Zhou B, Fang S, Ho W, Chen H, Liang H, Ye L, Tang J. Differential induction of apoptosis and autophagy by pyrrolizidine alkaloid clivorine in human hepatoma Huh-7.5 cells and its toxic implication. PLoS One. 2017 Jun 26;12(6):e0179379. doi: 10.1371/journal.pone.0179379. eCollection 2017. PubMed PMID: 28650983; PubMed Central PMCID: PMC5484491. 2: Xiong A, Yan AL, Bi CW, Lam KY, Chan GK, Lau KK, Dong TT, Lin H, Yang L, Wang Z, Tsim KW. Clivorine, an otonecine pyrrolizidine alkaloid from Ligularia species, impairs neuronal differentiation via NGF-induced signaling pathway in cultured PC12 cells. Phytomedicine. 2016 Aug 15;23(9):931-8. doi: 10.1016/j.phymed.2016.06.006. Epub 2016 Jun 10. PubMed PMID: 27387401. 3: Ji LL, Sheng YC, Zheng ZY, Shi L, Wang ZT. The involvement of p62-Keap1-Nrf2 antioxidative signaling pathway and JNK in the protection of natural flavonoid quercetin against hepatotoxicity. Free Radic Biol Med. 2015 Aug;85:12-23. doi: 10.1016/j.freeradbiomed.2015.03.035. Epub 2015 Apr 14. PubMed PMID: 25881548. 4: Ji L, Ma Y, Wang Z, Cai Z, Pang C, Wang Z. Quercetin prevents pyrrolizidine alkaloid clivorine-induced liver injury in mice by elevating body defense capacity. PLoS One. 2014 Jun 6;9(6):e98970. doi: 10.1371/journal.pone.0098970. eCollection 2014. PubMed PMID: 24905073; PubMed Central PMCID: PMC4048295. 5: Li YH, Kan WL, Li N, Lin G. Assessment of pyrrolizidine alkaloid-induced toxicity in an in vitro screening model. J Ethnopharmacol. 2013 Nov 25;150(2):560-7. doi: 10.1016/j.jep.2013.09.010. Epub 2013 Sep 14. PubMed PMID: 24045176. 6: Xia Q, Zhao Y, Von Tungeln LS, Doerge DR, Lin G, Cai L, Fu PP. Pyrrolizidine alkaloid-derived DNA adducts as a common biological biomarker of pyrrolizidine alkaloid-induced tumorigenicity. Chem Res Toxicol. 2013 Sep 16;26(9):1384-96. doi: 10.1021/tx400241c. Epub 2013 Aug 26. PubMed PMID: 23937665. 7: Liang Q, Sheng Y, Jiang P, Ji L, Xia Y, Min Y, Wang Z. The gender-dependent difference of liver GSH antioxidant system in mice and its influence on isoline-induced liver injury. Toxicology. 2011 Feb 4;280(1-2):61-9. doi: 10.1016/j.tox.2010.11.010. Epub 2010 Nov 30. PubMed PMID: 21126554. 8: Ji L, Liu T, Wang Z. Pyrrolizidine alkaloid clivorine induced oxidative injury on primary cultured rat hepatocytes. Hum Exp Toxicol. 2010 Apr;29(4):303-9. doi: 10.1177/0960327110361757. Epub 2010 Feb 9. PubMed PMID: 20144959. 9: Liang QN, Liu TY, Ji LL, Min Y, Xia YY. Pyrrolizidine alkaloid clivorine-induced oxidative stress injury in human normal liver L-02 cells. Drug Discov Ther. 2009 Dec;3(6):247-51. PubMed PMID: 22495657. 10: Ji L, Liu T, Chen Y, Wang Z. Protective mechanisms of N-acetyl-cysteine against pyrrolizidine alkaloid clivorine-induced hepatotoxicity. J Cell Biochem. 2009 Oct 1;108(2):424-32. doi: 10.1002/jcb.22269. PubMed PMID: 19623661. 11: Ji L, Liu T, Wang Z. Protection of epidermal growth factor against clivorine-induced mitochondrial-mediated apoptosis in hepatocytes. Environ Toxicol. 2010 Jun;25(3):304-9. doi: 10.1002/tox.20500. PubMed PMID: 19437449. 12: Ji L, Chen Y, Wang Z. Protection of S-adenosyl methionine against the toxicity of clivorine on hepatocytes. Environ Toxicol Pharmacol. 2008 Nov;26(3):331-5. doi: 10.1016/j.etap.2008.06.007. Epub 2008 Jul 9. PubMed PMID: 21791384. 13: Ji L, Chen Y, Liu T, Wang Z. Involvement of Bcl-xL degradation and mitochondrial-mediated apoptotic pathway in pyrrolizidine alkaloids-induced apoptosis in hepatocytes. Toxicol Appl Pharmacol. 2008 Sep 15;231(3):393-400. doi: 10.1016/j.taap.2008.05.015. Epub 2008 May 28. PubMed PMID: 18586292. 14: Xia Q, Yan J, Chou MW, Fu PP. Formation of DHP-derived DNA adducts from metabolic activation of the prototype heliotridine-type pyrrolizidine alkaloid, heliotrine. Toxicol Lett. 2008 May 5;178(2):77-82. doi: 10.1016/j.toxlet.2008.02.008. Epub 2008 Mar 4. PubMed PMID: 18395999. 15: Ji LL, Chen Y, Wang ZT. The toxic effect of pyrrolizidine alkaloid clivorine on the human embryonic kidney 293 cells and its primary mechanism. Exp Toxicol Pathol. 2008 Jun;60(1):87-93. doi: 10.1016/j.etp.2007.11.010. Epub 2008 Jan 30. PubMed PMID: 18249102. 16: Ji L, Chen Y, Wang Z. Intracellular glutathione plays important roles in pyrrolizidine alkaloid clivorine-induced toxicity on L-02 hepatocytes. Toxicol Mech Methods. 2008 Jan;18(8):661-4. doi: 10.1080/15376510802205726. PubMed PMID: 20020852. 17: Tang J, Akao T, Nakamura N, Wang ZT, Takagawa K, Sasahara M, Hattori M. In vitro metabolism of isoline, a pyrrolizidine alkaloid from Ligularia duciformis, by rodent liver microsomal esterase and enhanced hepatotoxicity by esterase inhibitors. Drug Metab Dispos. 2007 Oct;35(10):1832-9. Epub 2007 Jul 16. PubMed PMID: 17639025. 18: Lin G, Tang J, Liu XQ, Jiang Y, Zheng J. Deacetylclivorine: a gender-selective metabolite of clivorine formed in female Sprague-Dawley rat liver microsomes. Drug Metab Dispos. 2007 Apr;35(4):607-13. Epub 2007 Jan 19. PubMed PMID: 17237157. 19: Xia Q, Chou MW, Edgar JA, Doerge DR, Fu PP. Formation of DHP-derived DNA adducts from metabolic activation of the prototype heliotridine-type pyrrolizidine alkaloid, lasiocarpine. Cancer Lett. 2006 Jan 8;231(1):138-45. PubMed PMID: 16356839. 20: Ji LL, Zhang M, Sheng YC, Wang ZT. Pyrrolizidine alkaloid clivorine induces apoptosis in human normal liver L-02 cells and reduces the expression of p53 protein. Toxicol In Vitro. 2005 Feb;19(1):41-6. PubMed PMID: 15582354.