Beauveriolide III | CAS#221111-70-2 | Lipid droplet formation inhibitor

MedKoo Cat#: 463369 | Name: Beauveriolide III

Description:

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

Beauveriolide III is a cyclodepsipeptide that has been found in Beauveria and an inhibitor of lipid droplet formation. It inhibits lipid droplet formation when used at concentrations of 3 and 10 µM, as well as inhibits cholesterol synthesis, in primary mouse peritoneal macrophages. Beauveriolide III also inhibits acyl-coenzyme A:cholesterol acyltransferase (ACAT) activity in mouse macrophage membranes. Beauveriolide III reduces the size of aortic atherosclerotic lesions in Ldlr-/- and ApoE-/- mouse models of atherosclerosis.

Chemical Structure

Beauveriolide III

CAS#221111-70-2

Theoretical Analysis

MedKoo Cat#: 463369

Name: Beauveriolide III

CAS#: 221111-70-2

Chemical Formula: C27H41N3O5

Exact Mass: 487.3046

Molecular Weight: 487.64

Elemental Analysis: C, 66.50; H, 8.48; N, 8.62; O, 16.40

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Synonym

Beauveriolide III;

IUPAC/Chemical Name

(3R,6S,9S,13S)-9-benzyl-3-((S)-sec-butyl)-13-((S)-hexan-2-yl)-6-methyl-1-oxa-4,7,10-triazacyclotridecane-2,5,8,11-tetraone

InChi Key

VEELKRGSLCNVAR-QVZGIDAOSA-N

InChi Code

InChI=1S/C27H41N3O5/c1-6-8-12-18(4)22-16-23(31)29-21(15-20-13-10-9-11-14-20)26(33)28-19(5)25(32)30-24(17(3)7-2)27(34)35-22/h9-11,13-14,17-19,21-22,24H,6-8,12,15-16H2,1-5H3,(H,28,33)(H,29,31)(H,30,32)/t17-,18-,19-,21-,22-,24+/m0/s1

SMILES Code

O=C(N[C@H]1CC2=CC=CC=C2)C[C@@]([H])([C@H](CCCC)C)OC([C@@]([H])([C@H](CC)C)NC([C@H](C)NC1=O)=O)=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

2934.99.9001

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 487.64 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.

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: Qasim M, Islam SU, Islam W, Noman A, Khan KA, Hafeez M, Hussain D, Dash CK, Bamisile BS, Akutse KS, Rizwan M, Nisar MS, Jan S, Wang L. Characterization of mycotoxins from entomopathogenic fungi (Cordyceps fumosorosea) and their toxic effects to the development of asian citrus psyllid reared on healthy and diseased citrus plants. Toxicon. 2020 Oct 12;188:39-47. doi: 10.1016/j.toxicon.2020.10.012. Epub ahead of print. PMID: 33058930. 2: Wang X, Gao YL, Zhang ML, Zhang HD, Huang JZ, Li L. Genome mining and biosynthesis of the Acyl-CoA:cholesterol acyltransferase inhibitor beauveriolide I and III in Cordyceps militaris. J Biotechnol. 2020 Feb 10;309:85-91. doi: 10.1016/j.jbiotec.2020.01.002. Epub 2020 Jan 8. PMID: 31926180. 3: Šimčíková D, Tůma P, Jegorov A Jr, Šimek P, Heneberg P. Rapid methods for the separation of natural mixtures of beauverolides, cholesterol acyltransferase inhibitors, isolated from the fungus Isaria fumosorosea. J Sep Sci. 2020 Mar;43(5):962-969. doi: 10.1002/jssc.201901084. Epub 2020 Jan 1. PMID: 31833157. 4: Weng Q, Zhang X, Chen W, Hu Q. Secondary Metabolites and the Risks of Isaria fumosorosea and Isaria farinosa. Molecules. 2019 Feb 13;24(4):664. doi: 10.3390/molecules24040664. PMID: 30781844; PMCID: PMC6412548. 5: Ohshiro T, Kobayashi K, Ohba M, Matsuda D, Rudel LL, Takahashi T, Doi T, Tomoda H. Selective inhibition of sterolO-acyltransferase 1 isozyme by beauveriolide III in intact cells. Sci Rep. 2017 Jun 23;7(1):4163. doi: 10.1038/s41598-017-04177-8. PMID: 28646165; PMCID: PMC5482845. 6: Masuda Y, Aoyama K, Yoshida M, Kobayashi K, Ohshiro T, Tomoda H, Doi T. Design, Synthesis, and Biological Evaluation of Beauveriolide Analogues Bearing Photoreactive Amino Acids. Chem Pharm Bull (Tokyo). 2016 Jul 1;64(7):754-65. doi: 10.1248/cpb.c16-00095. Epub 2016 Mar 26. PMID: 27020600. 7: Madariaga-Mazón A, González-Andradeb M, Toriello C, Navarro-Barranco H, Mata R. Potent anti-calmodulin activity of cyclotetradepsipeptides isolated from Isaria fumosorosea using a newly designed biosensor. Nat Prod Commun. 2015 Jan;10(1):113-6. PMID: 25920232. 8: Luo F, Li S, Chen L, Zhang W, Wang B, Huang B, Hu F. [Identification of spore germination and virulence related biomarkers from Beauveria bassiana using an LC-MS-based metabolomic technique]. Wei Sheng Wu Xue Bao. 2014 Jan 4;54(1):33-41. Chinese. PMID: 24783852. 9: de Bekker C, Smith PB, Patterson AD, Hughes DP. Metabolomics reveals the heterogeneous secretome of two entomopathogenic fungi to ex vivo cultured insect tissues. PLoS One. 2013 Aug 5;8(8):e70609. doi: 10.1371/journal.pone.0070609. PMID: 23940603; PMCID: PMC3734240. 10: Kavan D, Kuzma M, Lemr K, Schug KA, Havlicek V. CYCLONE--a utility for de novo sequencing of microbial cyclic peptides. J Am Soc Mass Spectrom. 2013 Aug;24(8):1177-84. doi: 10.1007/s13361-013-0652-7. Epub 2013 May 24. PMID: 23702710. 11: Zhang D, Li S, Lu R, Li K, Luo F, Peng F, Hu F. [Influence of incubation time on metabolites in mycelia of Paecilomyces militaris]. Wei Sheng Wu Xue Bao. 2012 Dec 4;52(12):1477-88. Chinese. PMID: 23457797. 12: Huang HJ, Jian YR, Chen CY. Traditional Chinese medicine application in HIV: an in silico study. J Biomol Struct Dyn. 2014;32(1):1-12. doi: 10.1080/07391102.2012.745168. Epub 2012 Dec 20. PMID: 23252879. 13: Nakaya S, Mizuno S, Ishigami H, Yamakawa Y, Kawagishi H, Ushimaru T. New rapid screening method for anti-aging compounds using budding yeast and identification of beauveriolide I as a potent active compound. Biosci Biotechnol Biochem. 2012;76(6):1226-8. doi: 10.1271/bbb.110872. Epub 2012 Jun 7. PMID: 22790951. 14: Doi T, Muraoka T, Ohshiro T, Matsuda D, Yoshida M, Takahashi T, Omura S, Tomoda H. Conformationally restricted analog and biotin-labeled probe based on beauveriolide III. Bioorg Med Chem Lett. 2012 Jan 1;22(1):696-9. doi: 10.1016/j.bmcl.2011.10.045. Epub 2011 Oct 21. PMID: 22079027. 15: Witter DP, Chen Y, Rogel JK, Boldt GE, Wentworth P Jr. The natural products beauveriolide I and III: a new class of beta-amyloid-lowering compounds. Chembiochem. 2009 May 25;10(8):1344-7. doi: 10.1002/cbic.200900139. PMID: 19396893; PMCID: PMC2812801. 16: Ohshiro T, Matsuda D, Nagai K, Doi T, Sunazuka T, Takahashi T, Rudel LL, Omura S, Tomoda H. The selectivity of beauveriolide derivatives in inhibition toward the two isozymes of acyl-CoA: cholesterol acyltransferase. Chem Pharm Bull (Tokyo). 2009 Apr;57(4):377-81. doi: 10.1248/cpb.57.377. PMID: 19336931. 17: Nagai K, Doi T, Ohshiro T, Sunazuka T, Tomoda H, Takahashi T, Omura S. Synthesis and biological evaluation of a focused library of beauveriolides. Bioorg Med Chem Lett. 2008 Aug 1;18(15):4397-400. doi: 10.1016/j.bmcl.2008.06.054. Epub 2008 Jun 20. PMID: 18620856. 18: Tomoda H, Doi T. Discovery and combinatorial synthesis of fungal metabolites beauveriolides, novel antiatherosclerotic agents. Acc Chem Res. 2008 Jan;41(1):32-9. doi: 10.1021/ar700117b. Epub 2007 Sep 6. PMID: 17803269. 19: Tomoda H, Omura S. Potential therapeutics for obesity and atherosclerosis: inhibitors of neutral lipid metabolism from microorganisms. Pharmacol Ther. 2007 Sep;115(3):375-89. doi: 10.1016/j.pharmthera.2007.05.008. Epub 2007 May 31. PMID: 17614133. 20: Ohshiro T, Rudel LL, Omura S, Tomoda H. Selectivity of microbial acyl-CoA: cholesterol acyltransferase inhibitors toward isozymes. J Antibiot (Tokyo). 2007 Jan;60(1):43-51. doi: 10.1038/ja.2007.6. PMID: 17390588.