Lantadene A

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

MedKoo CAT#: 598378

CAS#: 467-81-2

Description: Lantadene A is a toxic principle, triterpene acid from Lantana camara.


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Lantadene A is not in stock, may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 598378
Name: Lantadene A
CAS#: 467-81-2
Chemical Formula: C35H52O5
Exact Mass: 552.3815
Molecular Weight: 552.79
Elemental Analysis: C, 76.05; H, 9.48; O, 14.47


Synonym: Lantadene A; Rehmannic acid; HSDB 3503;

IUPAC/Chemical Name: (4R,4aS,6aS,6bR,8aR,12aR,12bR,14bS)-2,2,6a,6b,9,9,12a-heptamethyl-4-(((E)-2-methylbut-2-enoyl)oxy)-10-oxo-1,3,4,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-octadecahydropicene-4a(2H)-carboxylic acid

InChi Key: KCLIRHUTOPOHKJ-DSYIDUNCSA-N

InChi Code: InChI=1S/C35H52O5/c1-10-21(2)28(37)40-27-20-30(3,4)19-23-22-11-12-25-32(7)15-14-26(36)31(5,6)24(32)13-16-34(25,9)33(22,8)17-18-35(23,27)29(38)39/h10-11,23-25,27H,12-20H2,1-9H3,(H,38,39)/b21-10+/t23-,24-,25+,27+,32-,33+,34+,35-/m0/s1

SMILES Code: CC1(C)C(CC[C@]2(C)[C@@]3([H])CC=C4[C@]5([H])CC(C)(C)C[C@@H](OC(/C(C)=C/C)=O)[C@@](C(O)=O)5CC[C@](C)4[C@@](C)3CC[C@@]12[H])=O


Technical Data

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).

Harmonized System Code:
2934.99.03.00


References

1: Grace-Lynn C, Chen Y, Latha LY, Kanwar JR, Jothy SL, Vijayarathna S, Sasidharan S. Evaluation of the hepatoprotective Effects of Lantadene A, a pentacyclic triterpenoid of Lantana plants against acetaminophen-induced liver damage. Molecules. 2012 Nov 23;17(12):13937-47. doi: 10.3390/molecules171213937. Retraction in: Sasidharan S. Molecules. 2013;18(4):3839-40. PubMed PMID: 23178309.

2: Grace-Lynn C, Darah I, Chen Y, Latha LY, Jothy SL, Sasidharan S. In vitro antioxidant activity potential of lantadene A, a pentacyclic triterpenoid of Lantana plants. Molecules. 2012 Sep 19;17(9):11185-98. PubMed PMID: 22992785.

3: LOUW PG. Lantadene A, the active principle of Lantana camara L.; isolation of lantadene B, and the oxygen functions of lantadene A and lantadene B. Onderstepoort J Vet Sci Anim Ind. 1948 Mar;23(1-2):233-8. PubMed PMID: 18863442.

4: Sharma S, Sharma OP, Dawra RK, Bhat TK. Disposition of lantadene A, the pentacyclic triterpenoid hepatotoxin, orally administered to guinea pigs. Toxicol Lett. 1999 Mar 8;105(1):59-66. PubMed PMID: 10092057.

5: Singh A, Sharma OP, Dawra RK, Kanwar SS, Mahato SB. Biotransformation of lantadene A (22 beta-angeloyloxy-3-oxoolean-12-en-28-oic acid), the pentacyclic triterpenoid, by Alcaligenes faecalis. Biodegradation. 1999;10(5):373-81. PubMed PMID: 10870553.

6: Sharma OP, Dawra RK, Pattabhi V. Molecular structure, polymorphism, and toxicity of lantadene A, the pentacyclic triterpenoid from the hepatotoxic plant Lantana camara. J Biochem Toxicol. 1991 Spring;6(1):57-63. PubMed PMID: 1880789.

7: Sharma M, Sharma PD, Bansal MP, Singh J. Synthesis, cytotoxicity, and antitumor activity of lantadene-A congeners. Chem Biodivers. 2007 May;4(5):932-9. PubMed PMID: 17511006.

8: Sharma OP, Makkar HP, Dawra RK. Spectrophotometric determination of lantadene A, 22 beta-angeloyloxy-3-oxoolean-12-en-28-oic acid. Anal Biochem. 1983 Feb 1;128(2):474-7. PubMed PMID: 6846824.

9: Garcia AF, Medeiros HC, Maioli MA, Lima MC, Rocha BA, da Costa FB, Curti C, Groppo M, Mingatto FE. Comparative effects of lantadene A and its reduced metabolite on mitochondrial bioenergetics. Toxicon. 2010 Jun 15;55(7):1331-7. doi: 10.1016/j.toxicon.2010.02.004. Epub 2010 Feb 10. PubMed PMID: 20152851.

10: Sharma M, Rakhi A, Dalal N, Sharma N. Design, synthesis and evaluation of lantadene A congener with hydroxyl functionality in ring A as an antitumour agent. Nat Prod Res. 2011 Feb;25(4):387-96. doi: 10.1080/14786411003792173. Epub 2010 Jul 8. PubMed PMID: 20623424.

11: Singh A, Sharma OP, Kurade NP, Ojha S. Detoxification of lantana hepatotoxin, lantadene A, using Alcaligenes faecalis. J Appl Toxicol. 2001 May-Jun;21(3):225-8. PubMed PMID: 11404834.

12: Sharma OP, Dawra RK, Datta AK, Kanwar SS. Biodegradation of lantadene A, the pentacyclic triterpenoid hepatotoxin by Pseudomonas pickettii. Lett Appl Microbiol. 1997 Apr;24(4):229-32. PubMed PMID: 9134768.

13: Monika, Sharma A, Suthar SK, Aggarwal V, Lee HB, Sharma M. Synthesis of lantadene analogs with marked in vitro inhibition of lung adenocarcinoma and TNF-α induced nuclear factor-kappa B (NF-κB) activation. Bioorg Med Chem Lett. 2014 Aug 15;24(16):3814-8. doi: 10.1016/j.bmcl.2014.06.068. Epub 2014 Jun 28. PubMed PMID: 25027934.

14: Sharma OP, Dawra RK, Makkar HP. Isolation and partial purification of Lantana (Lantana camara L.) toxins. Toxicol Lett. 1987 Jul;37(2):165-72. PubMed PMID: 3603590.

15: Sharma OP, Makkar HP, Pal RN, Negi SS. Lantadene A content and toxicity of the lantana plant (Lantana camara, Linn.) to guinea pigs. Toxicon. 1980;18(4):485-8. PubMed PMID: 7210034.

16: Dong Y, Zhang M, Ling B. [Antifeeding effects of crude lantadene from Lantana camara on Plutella xylostella and Spodoptera litura larvae]. Ying Yong Sheng Tai Xue Bao. 2005 Dec;16(12):2361-4. Chinese. PubMed PMID: 16515188.

17: Parimoo HA, Sharma R, Patil RD, Sharma OP, Kumar P, Kumar N. Hepatoprotective effect of Ginkgo biloba leaf extract on lantadenes-induced hepatotoxicity in guinea pigs. Toxicon. 2014 Apr;81:1-12. doi: 10.1016/j.toxicon.2014.01.013. Epub 2014 Jan 25. PubMed PMID: 24472344.

18: Tailor NK, Jaiswal V, Lan SS, Lee HB, Sharma M. Synthesis, selective cancer cytotoxicity and mechanistic studies of novel analogs of lantadenes. Anticancer Agents Med Chem. 2013 Jul 1;13(6):957-66. PubMed PMID: 23293887.

19: Tailor NK, Boon HL, Sharma M. Synthesis and in vitro anticancer studies of novel C-2 arylidene congeners of lantadenes. Eur J Med Chem. 2013 Jun;64:285-91. doi: 10.1016/j.ejmech.2013.04.009. Epub 2013 Apr 10. PubMed PMID: 23644211.

20: Sharma OP, Dawra RK, Makkar HP. Toxicity of isolated Lantana (Lantana camara L) constituents to male and female guinea pigs. Vet Hum Toxicol. 1989 Feb;31(1):10-3. PubMed PMID: 2711601.