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.


Chemical Structure

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Lantadene A
CAS# 467-81-2

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

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.

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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

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: 2934.99.03.00

Preparing Stock Solutions

The following data is based on the product molecular weight 552.79 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

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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.