Beauveriolide III

Beauveriolide III

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Beauveriolide III
Category Antibiotics
Catalog number BBF-00274
CAS 221111-70-2
Molecular Weight 487.63
Molecular Formula C27H41N3O5

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Description

Beauveriolide III is produced by the strain of Beauveria sp. FO-6979. The effect of I and III can inhibit the formation of Lipid droplet. 10μmol/L can reduce the number and size of the cytolipid droplet in the macrophage but it is not cytotoxic to the macrophages.

Specification

Synonyms CHEMBL409855; SCHEMBL16174055
IUPAC Name (3R,6S,9S,13S)-9-benzyl-3-[(2S)-butan-2-yl]-13-[(2S)-hexan-2-yl]-6-methyl-1-oxa-4,7,10-triazacyclotridecane-2,5,8,11-tetrone
Canonical SMILES CCCCC(C)C1CC(=O)NC(C(=O)NC(C(=O)NC(C(=O)O1)C(C)CC)C)CC2=CC=CC=C2
InChI 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
InChI Key VEELKRGSLCNVAR-QVZGIDAOSA-N

Properties

Appearance White Powder
Melting Point 246-248 °C

Reference Reading

1. Conformationally restricted analog and biotin-labeled probe based on beauveriolide III
Hiroshi Tomoda, Daisuke Matsuda, Taichi Ohshiro, Takayuki Doi, Satoshi Omura, Masahito Yoshida, Terushige Muraoka, Takashi Takahashi Bioorg Med Chem Lett . 2012 Jan 1;22(1):696-9. doi: 10.1016/j.bmcl.2011.10.045.
A conformationally restricted oxazoline analog 7 was designed on the basis of a SAR study of beauveriolide III (2) and its analogs reported previously. Conformational analysis by molecular mechanics calculation suggested that the three side chains of 7 mostly occupy the same spaces as those of 2. The analog 7 was synthesized by peptide coupling of the d-cyclohexylglycine-containing ester 11 and d-Ser-containing dipeptide 12, macrolactamization, and cyclodehydration of 6 for the construction of an oxazoline ring. The bicyclic 7 exhibited potential inhibitory activity for cholesteryl ester synthesis similar to that by 2. These results revealed biologically important 3D spaces of the three side chains in inhibitory activity for cholesteryl ester synthesis. In addition, we accomplished the synthesis of a biotin-labeled probe 8 by copper-catalyzed (3+2) cycloaddition of a biotin-containing alkyne 16 and azido-containing beauveriolide analog 15 prepared from 6.
2. Absolute stereochemistry of fungal beauveriolide III and ACAT inhibitory activity of four stereoisomers
Hiroshi Tomoda, Takafumi Sekiguchi, Lawrence L Rudel, Kenichiro Nagai, Taichi Ohshiro, Takayuki Doi, Satoshi Omura, Kazuaki Akasaka, Ichiji Namatame, Takashi Takahashi J Org Chem . 2006 Sep 29;71(20):7643-9. doi: 10.1021/jo0611667.
Fungal beauveriolide III (BeauIII, 1b), a cyclodepsipeptide inhibiting acyl-CoA:cholesterol acyltransferase (ACAT) and showing antiatherogenic activity in mouse models, consists of L-Phe, L-Ala, D-allo-Ile, and 3-hydroxy-4-methyloctanoic acid (HMA) moieties, but the stereochemistry of the HMA part has not until now been fully defined. To determine it, four HMA stereoisomers were synthesized and labeled with (S)-(+)-2-(anthracene-2,3-dicarboximido)-1-propyl trifluoromethane sulfonate (AP-OTf), a chiral fluorescent reagent. The derivatives were separated by HPLC and compared with the natural HMA derivative, which was thereby identified as (3S,4S)HMA in BeauIII. Furthermore, the four beauveriolide III isomers ((3S,4S)BeauIII (23a), (3R,4R)BeauIII (23b), (3R,4S)BeauIII (23c), and (3S,4R)BeauIII (23d)) were synthesized, and it was shown that all the spectral data for 23a were identical with those for natural 1b. Isomers 23a and 23d showed potent inhibitory activity of lipid droplet accumulation in macrophages, while the other two isomers caused weak inhibition. Thus, the 3S configuration of BeauIII is important for this activity. Furthermore, 23a and 23d showed rather specific inhibition against the ACAT1 isozyme.
3. Genome mining and biosynthesis of the Acyl-CoA:cholesterol acyltransferase inhibitor beauveriolide I and III in Cordyceps militaris
Ming-Liang Zhang, Jian-Zhong Huang, Yang-Le Gao, Huai-Dong Zhang, Xue Wang, Li Li J Biotechnol . 2020 Feb 10;309:85-91. doi: 10.1016/j.jbiotec.2020.01.002.
Ascomycete fungi Cordyceps are widely used in traditional Chinese medicine, and numerous investigations have been carried out to uncover their biological activities. However, primary researches on the physiological effects of Cordyceps were committed using crude extracts. At present, there are only a few compounds which were comprehensively characterized from Cordyceps, partial owing to the low production. In order to scientifically take advantage of Cordyceps, we used the strategy of genome mining to discover bioactive compounds from Cordyceps militaris. We found the putative biosynthetic gene cluster of the acyl-CoA:cholesterol acyltransferase inhibitor beauveriolides in the genome of C. militaris, and produced the compounds by heterologous expression in Aspergillus nidulans. Production of beauveriolide I and III also was detected in both ferment mycelia and fruiting bodies of C. militaris. The possible biosynthetic pathway was proposed. Our studies unveil the active compounds of C. militaris against atherosclerosis and Alzheimer's disease and provide the enzyme resources for the biosynthesis of new cyclodepsipeptide molecules.

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It is commonly abbreviated as: C1V1 = C2V2

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Tip: Chemical formula is case sensitive. C22H30N4O c22h30n40
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