Andrastin C
* Please be kindly noted products are not for therapeutic use. We do not sell to patients.
| Category | Enzyme inhibitors |
| Catalog number | BBF-00465 |
| CAS | |
| Molecular Weight | 472.61 |
| Molecular Formula | C28H40O6 |
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Description
It is produced by the strain of Penicillum sp. FO-3929. It can inhibit PFTase. IC50 is 13.3 μmol/L.
Specification
| IUPAC Name | methyl (3S,5S,8S,9S,10R,13R,14R)-3-acetoxy-17-hydroxy-4,4,8,10,12,13,16-heptamethyl-15-oxo-1,2,3,4,5,6,7,8,9,10,13,15-dodecahydro-14H-cyclopenta[a]phenanthrene-14-carboxylate |
| Canonical SMILES | CC1=CC2C3(CCC(C(C3CCC2(C4(C1(C(=C(C4=O)C)[O-])C)C(=O)OC)C)(C)C)OC(=O)C)C |
| InChI | InChI=1S/C28H40O6/c1-15-14-19-25(6)12-11-20(34-17(3)29)24(4,5)18(25)10-13-26(19,7)28(23(32)33-9)22(31)16(2)21(30)27(15,28)8/h14,18-20,30H,10-13H2,1-9H3/p-1/t18-,19+,20+,25-,26+,27+,28-/m1/s1 |
| InChI Key | AWMJEDMVXAOTQZ-QUQNHZJXSA-M |
Properties
| Appearance | White Powder |
| Melting Point | 115-120 °C |
| Solubility | Soluble in Methanol |
Reference Reading
1. Cytochrome P450 for Citreohybridonol Synthesis: Oxidative Derivatization of the Andrastin Scaffold
Yudai Matsuda, Zhiyang Quan, Takaaki Mitsuhashi, Chang Li, Ikuro Abe Org Lett. 2016 Jan 15;18(2):296-9. doi: 10.1021/acs.orglett.5b03465. Epub 2016 Jan 5.
A biosynthetic gene cluster similar to that for andrastin A (1) was discovered in Emericella variecolor NBRC 32302. Ctr-P450, a cytochrome P450 uniquely present in the cluster, was coexpressed with the andrastin A biosynthetic genes, leading to the production of the antifeedant agent citreohybridonol (4), along with four new andrastin derivatives. The results revealed the unusual multifunctionality of Ctr-P450 and indicated that this approach can be applied for further natural product diversification.
2. Metabolomic and Transcriptomic Comparison of Solid-State and Submerged Fermentation of Penicillium expansum KACC 40815
Hyang Yeon Kim, Do Yeon Heo, Hye Min Park, Digar Singh, Choong Hwan Lee PLoS One. 2016 Feb 10;11(2):e0149012. doi: 10.1371/journal.pone.0149012. eCollection 2016.
Penicillium spp. are known to harbor a wide array of secondary metabolites with cryptic bioactivities. However, the metabolomics of these species is not well-understood in terms of different fermentation models and conditions. The present study involved metabolomics profiling and transcriptomic analysis of Penicillium expansum 40815 under solid-state fermentation (SSF) and submerged fermentation (SmF). Metabolite profiling was carried out using ultra-performance liquid chromatography quadruple time-of-flight mass spectrometry with multivariate analysis, followed by transcriptomic analyses of differentially expressed genes. In principal component analysis, the metabolite profiling data was studied under different experimental sets, including SSF and SmF. The significantly different metabolites such as polyketide metabolites (agonodepside B, rotiorin, verrucosidin, and ochrephilone) and corresponding gene transcripts (polyketide synthase, aromatic prenyltransferase, and terpenoid synthase) were primarily detected under SmF conditions. In contrast, the meroterpenoid compounds (andrastin A and C) and their genes transcripts were exclusively detected under SSF conditions. We demonstrated that the metabolite production and its corresponding gene expression levels in P. expansum 40815 were significantly influenced by the varying growth parameters and the immediate environment. This study further provides a foundation to produce specific metabolites by regulating fermentation conditions.
3. Toward the total synthesis of (±)-andrastin C
Rei Okamoto, Kazutaka Takeda, Hidetoshi Tokuyama, Masataka Ihara, Masahiro Toyota J Org Chem. 2013 Jan 4;78(1):93-103. doi: 10.1021/jo301948h. Epub 2012 Nov 15.
An efficient approach to generate a fully functionalized cyclopenta[a]phenanthrene 34, the basic carbon framework of andrastin C (1c), is described. The present synthetic route features a stereoselective intramolecular Diels-Alder reaction of triene 12 and an intramolecular carbonyl ene reaction of 3-phenanthrenyl-2-(methoxymethoxy)propanal 31.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
