Lateritin
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MedKoo CAT#: 598428

CAS#: 65454-13-9

Description: Lateritin is An Acyl-CoA:cholesterol acyltransferase (ACAT) inhibitor and a platelet aggregation inhibitor isolated from the mycelial cake of Gibberella lateritium; bassiatin is the (3S,6R) isomer.


Chemical Structure

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Lateritin
CAS# 65454-13-9

Theoretical Analysis

MedKoo Cat#: 598428
Name: Lateritin
CAS#: 65454-13-9
Chemical Formula: C15H19NO3
Exact Mass: 261.1365
Molecular Weight: 261.31
Elemental Analysis: C, 68.94; H, 7.33; N, 5.36; O, 18.37

Price and Availability

Size Price Availability Quantity
50.0mg USD 450.0 2 Weeks
100.0mg USD 750.0 2 Weeks
200.0mg USD 1250.0 2 Weeks
500.0mg USD 2850.0 2 Weeks
1.0g USD 3850.0 2 Weeks
2.0g USD 6450.0 2 Weeks
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Related CAS #: 65454-13-9    

Synonym: Lateritin; Bassiatin;

IUPAC/Chemical Name: 3-benzyl-6-isopropyl-4-methylmorpholine-2,5-dione

InChi Key: YOKBTBNVNCFOBF-UHFFFAOYSA-N

InChi Code: InChI=1S/C15H19NO3/c1-10(2)13-14(17)16(3)12(15(18)19-13)9-11-7-5-4-6-8-11/h4-8,10,12-13H,9H2,1-3H3

SMILES Code: O=C(OC1C(C)C)C(CC2=CC=CC=C2)N(C)C1=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 261.31 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: Pettit RK, Pettit GR, Xu JP, Weber CA, Richert LA. Isolation of human cancer cell growth inhibitory, antimicrobial lateritin from a mixed fungal culture. Planta Med. 2010 Mar;76(5):500-1. doi: 10.1055/s-0029-1240617. Epub 2009 Nov 25. PubMed PMID: 19941263.

2: Hasumi K, Shinohara C, Iwanaga T, Endo A. Lateritin, a new inhibitor of acyl-CoA:cholesterol acyltransferase produced by Gibberella lateritium IFO 7188. J Antibiot (Tokyo). 1993 Dec;46(12):1782-7. PubMed PMID: 8294234.

3: Meng L, Tao H, Dong G, Yang T, Zhang W, Zhu W, Huang C. ERK1/2 and Akt pathway activated during (3R,6R)-bassiatin(1)-induced apoptosis in MCF-7 cells. Cell Biol Int. 2012 Apr 1;36(4):345-8. doi: 10.1042/CBI20110388. PubMed PMID: 22150072.

4: Meng L, Feng B, Tao H, Yang T, Meng Y, Zhu W, Huang C. A novel antioestrogen agent (3R,6R)-bassiatin inhibits cell proliferation and cell cycle progression by repressing cyclin D1 expression in 17β-oestradiol-treated MCF-7 cells. Cell Biol Int. 2011 Jun;35(6):599-605. doi: 10.1042/CBI20100765. PubMed PMID: 21241249.

5: Kagamizono T, Nishino E, Matsumoto K, Kawashima A, Kishimoto M, Sakai N, He BM, Chen ZX, Adachi T, Morimoto S, et al. Bassiatin, a new platelet aggregation inhibitor produced by Beauveria bassiana K-717. J Antibiot (Tokyo). 1995 Dec;48(12):1407-12. PubMed PMID: 8557595.

6: Tang CY, Chen YW, Jow GM, Chou CJ, Jeng CJ. Beauvericin activates Ca2+-activated Cl- currents and induces cell deaths in Xenopus oocytes via influx of extracellular Ca2+. Chem Res Toxicol. 2005 May;18(5):825-33. PubMed PMID: 15892576.

7: Oh H, Kim T, Oh GS, Pae HO, Hong KH, Chai KY, Kwon TO, Chung HT, Lee HS. (3R,6R)-4-methyl-6-(1-methylethyl)-3-phenylmethyl-perhydro-1,4-oxazine-2,5-dione: an apoptosis-inducer from the fruiting bodies of Isaria japonica. Planta Med. 2002 Apr;68(4):345-8. PubMed PMID: 11988860.

8: Hughes AB, Sleebs MM. Total synthesis of bassiatin and its stereoisomers: novel divergent behavior of substrates in Mitsunobu cyclizations. J Org Chem. 2005 Apr 15;70(8):3079-88. PubMed PMID: 15822967.

9: Jow GM, Chou CJ, Chen BF, Tsai JH. Beauvericin induces cytotoxic effects in human acute lymphoblastic leukemia cells through cytochrome c release, caspase 3 activation: the causative role of calcium. Cancer Lett. 2004 Dec 28;216(2):165-73. PubMed PMID: 15533592.

10: Huang LH, Chen YX, Yu JC, Yuan J, Li HJ, Ma WZ, Watanapokasin R, Hu KC, Niaz SI, Yang DP, Lan WJ. Secondary Metabolites from the Marine-Derived Fungus Dichotomomyces sp. L-8 and Their Cytotoxic Activity. Molecules. 2017 Mar 11;22(3). pii: E444. doi: 10.3390/molecules22030444. PubMed PMID: 28287456.

11: Kamagate M, Assadi AA, Kone T, Giraudet S, Coulibaly L, Hanna K. Use of laterite as a sustainable catalyst for removal of fluoroquinolone antibiotics from contaminated water. Chemosphere. 2018 Mar;195:847-853. doi: 10.1016/j.chemosphere.2017.12.165. Epub 2017 Dec 26. PubMed PMID: 29289913.