Beauveriolide I | CAS#154491-55-1 | Lipid droplet formation inhibitor

MedKoo Cat#: 463455 | Name: Beauveriolide I

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Description:

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

Beauveriolide I 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 I also inhibits acyl-coenzyme A:cholesterol acyltransferase (ACAT) activity in mouse macrophage membranes.

Chemical Structure

Beauveriolide I

CAS#154491-55-1

Theoretical Analysis

MedKoo Cat#: 463455

Name: Beauveriolide I

CAS#: 154491-55-1

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

Price and Availability

Size	Price	Availability	Quantity
1mg	USD 950.00	2 Weeks

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Synonym

Beauveriolide I;

IUPAC/Chemical Name

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

InChi Key

ZKSLFHXTWGEITF-JIORRVSTSA-N

InChi Code

InChI=1S/C27H41N3O5/c1-6-7-11-18(4)23-16-24(31)29-21(15-20-12-9-8-10-13-20)26(33)28-19(5)25(32)30-22(14-17(2)3)27(34)35-23/h8-10,12-13,17-19,21-23H,6-7,11,14-16H2,1-5H3,(H,28,33)(H,29,31)(H,30,32)/t18-,19-,21-,22+,23-/m0/s1

SMILES Code

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

Appearance

Solid powder

Purity

>95% (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: Yin Y, Chen B, Song S, Li B, Yang X, Wang C. Production of Diverse Beauveriolide Analogs in Closely Related Fungi: a Rare Case of Fungal Chemodiversity. mSphere. 2020 Sep 2;5(5):e00667-20. doi: 10.1128/mSphere.00667-20. PMID: 32878933; PMCID: PMC7471007. 2: Ohshiro T, Imuta S, Hijikuro I, Yagyu H, Takahashi T, Doi T, Ishibashi S, Tomoda H. The Anti-atherogenic Activity of Beauveriolide Derivative BVD327, a Sterol O-Acyltransferase 2-Selective Inhibitor, in Apolipoprotein E Knockout Mice. Biol Pharm Bull. 2020;43(6):951-958. doi: 10.1248/bpb.b19-00913. PMID: 32475917. 3: 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. 4: 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. 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: Tuan NN, Ngan NT, Kuo PC, Hung HY, Lan TN, Thanh NT, Xuan DTT, Thang TD, Wu TS. Characterization of Cyclodepsipeptides from the Mycelium of Isariajaponica from Vietnam. Nat Prod Commun. 2017 Mar;12(3):377-378. PMID: 30549889. 7: 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. 8: Xu YJ, Luo F, Gao Q, Shang Y, Wang C. Metabolomics reveals insect metabolic responses associated with fungal infection. Anal Bioanal Chem. 2015 Jun;407(16):4815-21. doi: 10.1007/s00216-015-8648-8. Epub 2015 Apr 21. PMID: 25895944. 9: 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. 10: 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. 11: 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. 12: 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. 13: 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. 14: 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. 15: 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. 16: 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. 17: 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. 18: Ohshiro T, Namatame I, Nagai K, Sekiguchi T, Doi T, Takahashi T, Akasaka K, Rudel LL, Tomoda H, Omura S. Absolute stereochemistry of fungal beauveriolide III and ACAT inhibitory activity of four stereoisomers. J Org Chem. 2006 Sep 29;71(20):7643-9. doi: 10.1021/jo0611667. Erratum in: J Org Chem. 2006 Nov 24;71(24):9252. PMID: 16995669. 19: Nagai K, Doi T, Sekiguchi T, Namatame I, Sunazuka T, Tomoda H, Omura S, Takahashi T. Synthesis and biological evaluation of a beauveriolide analogue library. J Comb Chem. 2006 Jan-Feb;8(1):103-9. doi: 10.1021/cc050084d. PMID: 16398560. 20: Matsuda D, Namatame I, Tomoda H, Kobayashi S, Zocher R, Kleinkauf H, Omura S. New beauveriolides produced by amino acid-supplemented fermentation of Beauveria sp. FO-6979. J Antibiot (Tokyo). 2004 Jan;57(1):1-9. doi: 10.7164/antibiotics.57.1. PMID: 15032479.