Isariin
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| Category | Antibiotics |
| Catalog number | BBF-01880 |
| CAS | 10409-85-5 |
| Molecular Weight | 637.85 |
| Molecular Formula | C33H59N5O7 |
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Description
Isariin is originally isolated from Isaria felina.
Specification
| Synonyms | (R)-N-(N-(N-(N-(N-(3-hydroxy-1-oxododecyl)glycyl)-L-valyl)-D-leucyl)-L-alanyl)-L-Valine rho-lactone; Cyclo[L-alanyl-L-valyl-(3R)-3-hydroxydodecanoylglycyl-L-valyl-D-leucyl] |
| IUPAC Name | (3S,6S,9R,12S,19R)-6-methyl-9-(2-methylpropyl)-19-nonyl-3,12-di(propan-2-yl)-1-oxa-4,7,10,13,16-pentazacyclononadecane-2,5,8,11,14,17-hexone |
| Canonical SMILES | CCCCCCCCCC1CC(=O)NCC(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)O1)C(C)C)C)CC(C)C)C(C)C |
| InChI | InChI=1S/C33H59N5O7/c1-9-10-11-12-13-14-15-16-24-18-26(39)34-19-27(40)37-28(21(4)5)32(43)36-25(17-20(2)3)31(42)35-23(8)30(41)38-29(22(6)7)33(44)45-24/h20-25,28-29H,9-19H2,1-8H3,(H,34,39)(H,35,42)(H,36,43)(H,37,40)(H,38,41)/t23-,24+,25+,28-,29-/m0/s1 |
| InChI Key | KIJLRIARMCGDJZ-YSWCBTLJSA-N |
Properties
| Boiling Point | 946.4°C at 760 mmHg |
| Melting Point | 251°C |
| Density | 1.003 g/cm3 |
Reference Reading
1. Insecticidal cyclodepsipeptides from Beauveria felina
Aude Langenfeld, Alain Blond, Sabelle Gueye, Patrick Herson, Bastien Nay, Joëlle Dupont, Soizic Prado J Nat Prod. 2011 Apr 25;74(4):825-30. doi: 10.1021/np100890n. Epub 2011 Mar 25.
A novel cyclodepsipeptide, iso-isariin B (1), and the known isaridin E (2) were isolated from the entomopathogenic fungus Beauveria felina. Their structures were elucidated using MS/MS fragmentation and extensive 2D-heteronuclear NMR. The X-ray structure of isaridin E was obtained, showing two potent intramolecular H bonds and a type-VI turn with the HyLeu(1)-Pro(2) amide bond in a cis conformation. Iso-isariin B (1) was active against the pest-insect Sitophilus spp. with an LD(50) value of 10 μg/mL. This observation also gives some clues for ecological interpretation of cyclodepsipeptide production by B. felina.
2. Cyclodepsipeptides and other O-containing heterocyclic metabolites from Beauveria felina EN-135, a marine-derived entomopathogenic fungus
Feng-Yu Du, Xiao-Ming Li, Peng Zhang, Chun-Shun Li, Bin-Gui Wang Mar Drugs. 2014 May 13;12(5):2816-26. doi: 10.3390/md12052816.
Bioassay-guided fractionation of a culture extract of Beauveria felina EN-135, an entomopathogenic fungus isolated from a marine bryozoan, led to the isolation of a new cyclodepsipeptide, iso-isariin D (1); two new O-containing heterocyclic compounds that we have named felinones A and B (2 and 3); and four known cyclodepsipeptides (4-7). The structures were elucidated via spectroscopic analysis, and the absolute configurations of 1 and 2 were determined using single-crystal X-ray diffraction and CD, respectively. All isolated compounds were evaluated for antimicrobial activity and brine-shrimp (Artemia salina) lethality.
3. Genomics-driven discovery of a new cyclodepsipeptide from the guanophilic fungus Amphichorda guana
Min Liang, Hai-Ning Lyu, Zi-Ying Ma, Er-Wei Li, Lei Cai, Wen-Bing Yin Org Biomol Chem. 2021 Mar 11;19(9):1960-1964. doi: 10.1039/d1ob00100k.
Two potential non-ribosomal peptide synthetases (NRPSs) were identified in the genome of a guanophilic fungus Amphichorda guana by bioinformatics analysis and gene knockout experiments. Liquid chromatography coupled with mass spectrometry (LC-MS) guided isolation led to the discovery of a new cyclodepsipeptide isaridin H (1) and seven known analogs, desmethylisaridin E (2), isaridin E (3), isariin A (4), iso-isariin B (5), iso-isariin D (6), isariin E (7), and nodupetide (8). The absolute configuration of isaridin H (1) was achieved by Marfey's method. Isaridin H (1) showed significant antifungal activity against Botrytis cinerea and Alternaria solani.
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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 ╳
