Vernolepin

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

MedKoo CAT#: 558716

CAS#: 18542-37-5

Description: Vernolepin is a natural reversible plant growth inhibitor.

Chemical Structure

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Vernolepin
CAS# 18542-37-5
Instruction

Theoretical Analysis

MedKoo Cat#: 558716
Name: Vernolepin
CAS#: 18542-37-5
Chemical Formula: C15H16O5
Exact Mass: 276.10
Molecular Weight: 276.290
Elemental Analysis: C, 65.21; H, 5.84; O, 28.95

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

Request quote for custom synthesis

Synonym: Vernolepin

IUPAC/Chemical Name: (3aR,4S,5aR,9aR,9bR)-5a-Ethenyl-4-hydroxy-3,9-dimethylidene-3a,4,5,6,9a,9b-hexahydrofuro[2,3-f]isochromene-2,8-dione

InChi Key: IFYQXAXVZGMFNW-MVIRXUPPSA-N

InChi Code: InChI=1S/C15H16O5/c1-4-15-5-9(16)10-7(2)14(18)20-12(10)11(15)8(3)13(17)19-6-15/h4,9-12,16H,1-3,5-6H2/t9-,10+,11+,12-,15+/m0/s1

SMILES Code: O=C(O1)C([C@@]2([H])[C@@]1([H])[C@@]3([H])C(C(OC[C@@]3(C=C)C[C@@H]2O)=O)=C)=C

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

More Info:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 276.29 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
Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: Thongnest S, Chawengrum P, Keeratichamroen S, Lirdprapamongkol K, Eurtivong C, Boonsombat J, Kittakoop P, Svasti J, Ruchirawat S. Vernodalidimer L, a sesquiterpene lactone dimer from Vernonia extensa and anti-tumor effects of vernodalin, vernolepin, and vernolide on HepG2 liver cancer cells. Bioorg Chem. 2019 Aug 16;92:103197. doi: 10.1016/j.bioorg.2019.103197. [Epub ahead of print] PubMed PMID: 31445193.

2: Kimani NM, Backhaus S, Matasyoh JC, Kaiser M, Herrmann FC, Schmidt TJ, Langer K. Preparation of Sesquiterpene Lactone-Loaded PLA Nanoparticles and Evaluation of Their Antitrypanosomal Activity. Molecules. 2019 Jun 4;24(11). pii: E2110. doi: 10.3390/molecules24112110. PubMed PMID: 31167374; PubMed Central PMCID: PMC6600441.

3: Kimani NM, Matasyoh JC, Kaiser M, Brun R, Schmidt TJ. Anti-Trypanosomatid Elemanolide Sesquiterpene Lactones from Vernonia lasiopus O. Hoffm. Molecules. 2017 Apr 8;22(4). pii: E597. doi: 10.3390/molecules22040597. PubMed PMID: 28397756; PubMed Central PMCID: PMC6154322.

4: Bach SM, Díaz FR, Bach H, Catalán CA. A facile and efficient four-step enantioselective synthesis of (+)-vernolepin from (+)-minimolide, the major germacranolide of Mikania minima. Nat Prod Commun. 2011 Apr;6(4):433-8. PubMed PMID: 21560754.

5: Barrero AF, Oltra JE, Alvarez M, Rosales A. Synthesis of (+)-8-deoxyvernolepin and its 11,13-dihydroderivative. A novel reaction initiated by sulfene elimination leads to the 2-Oxa-cis-decalin skeleton. J Org Chem. 2002 Aug 9;67(16):5461-9. PubMed PMID: 12153243.

6: Jakupovic J, Baruah RN, Thi TV, Bohlmann F, Msonthi JD, Schmeda-Hirschmann G. New Vernolepin Derivatives from Vernonia glabra and Glaucolides from Vernonia scorpioides. Planta Med. 1985 Oct;51(5):378-80. PubMed PMID: 17342587.

7: Laekeman GM, De Clerck F, Vlietinck AJ, Herman AG. Vernolepin: an antiplatelet compound of natural origin. Naunyn Schmiedebergs Arch Pharmacol. 1985 Oct;331(1):108-13. PubMed PMID: 3934564.

8: Arrick BA, Griffo W, Cohn Z, Nathan C. Hydrogen peroxide from cellular metabolism of cystine. A requirement for lysis of murine tumor cells by vernolepin, a glutathione-depleting antineoplastic. J Clin Invest. 1985 Aug;76(2):567-74. PubMed PMID: 3928682; PubMed Central PMCID: PMC423862.

9: Arrick BA, Nathan CF. Glutathione metabolism as a determinant of therapeutic efficacy: a review. Cancer Res. 1984 Oct;44(10):4224-32. Review. PubMed PMID: 6380705.

10: Laekeman GM, Mertens J, Totté J, Bult H, Vlietinck AJ, Herman AG. Isolation and pharmacological characterization of vernolepin. J Nat Prod. 1983 Mar-Apr;46(2):161-9. PubMed PMID: 6410002.

11: Arrick BA, Nathan CF, Cohn ZA. Inhibition of glutathione synthesis augments lysis of murine tumor cells by sulfhydryl-reactive antineoplastics. J Clin Invest. 1983 Feb;71(2):258-67. PubMed PMID: 6401768; PubMed Central PMCID: PMC436864.

12: Laekeman GM, De Clerck F, Herman AG, Totté J, Vlietinck A. Vernolepin and platelet aggregation: further studies on the mechanism of action. Arch Int Pharmacodyn Ther. 1982 Dec;260(2):284-6. PubMed PMID: 7165431.

13: Laekeman GM, Mertens J, Totte J, Bult H, Vlietinck A, Herman AG. Vernolepin and platelet aggregation. Arch Int Pharmacodyn Ther. 1982 Mar;256(1):175-6. PubMed PMID: 7092416.

14: Grieco PA, Nishizawa M, Oguri T, Burke SD, Marinovic N. Sesquiterpene lactones: total synthesis of (+/-)-vernolepin and (+/-)-vernomenin. J Am Chem Soc. 1977 Aug 17;99(17):5773-80. PubMed PMID: 886122.

15: Grieco PA, Noguez JA, Masaki Y. (+/-)-Deoxyvernolepin. A cytotoxic vernolepin prototype. J Org Chem. 1977 Feb 4;42(3):495-501. PubMed PMID: 264534.

16: Grieco PA, Noguez JA, Masaki Y, Hiroi Y, Nishizawa M, Rosowsky A, Oppenheim S, Lazarus H. Synthesis of mono- and bifunctional alpha-methylene lactone systems as potential tumor inhibitors. J Med Chem. 1977 Jan;20(1):71-6. PubMed PMID: 264567.

17: Wege PM, Clark RD, Heathcock CH. Synthesis of sesquiterpene antitumor lactones. 6. cis-8a-Vinyloctahydro-3H-2-benzopyran-3,7-dione, a precursor to vernolepin. J Org Chem. 1976 Sep 17;41(19):3144-8. PubMed PMID: 966107.

18: Lantz CH, Larner J. In vivo studies on the mechanism of action of the tumor inhibitor vernolepin in the Walker 256 carcinosarcoma. Cancer Biochem Biophys. 1976 Aug;1(5):229-38. PubMed PMID: 975025.

19: Danishefsky S, Kitahara T, Schuda PF, Etheredge SJ. Letter: A remarkable epoxide opening. An expeditious synthesis of vernolepin and vernomenin. J Am Chem Soc. 1976 May 12;98(10):3028-30. PubMed PMID: 1262633.

20: Clark RD, Heathcock CH. Synthesis of a cytotoxic vernolepin prototype. Ozonization of silyloxyalkenes. J Org Chem. 1976 Apr 16;41(8):1396-403. PubMed PMID: 1263006.