Verrucofortine
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| Category | Others |
| Catalog number | BBF-04573 |
| CAS | 113706-21-1 |
| Molecular Weight | 409.52 |
| Molecular Formula | C24H31N3O3 |
| Purity | >99% by HPLC |
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Description
A diketopiperazine alkaloid derived from tryptophan and leucine. It is a fungal metabolite isolated from penicillium verrucosum. It exhibits no apparent toxicity in mice even at high doses in vivo.
Specification
| Synonyms | Fructigenine B; Verrucosine; Verrucozine; (-)-Verrucofortine; (3S-(3alpha,5aalpha,10balpha,11abeta))-6-Acetyl-10b-(1,1-dimethyl-2-propenyl)-6,10b,11,11a-tetrahydro-3-(2-methylpropyl)-2H-pyrazino(1',2':1,5)pyrrolo(2,3-b)indole-1,4-(3H,5aH)-dione; (3S,5aR,10bR,11aS)-6-acetyl-10b-(1,1-dimethyl-2-propen-1-yl)-6,10b,11,11a-tetrahydro-3-(2-methylpropyl)-2H-pyrazino[1',2':1,5]pyrrolo[2,3-b]indole-1,4(3H,5aH)-dione |
| Storage | Store at -20°C |
| IUPAC Name | (1R,4S,7S,9R)-16-acetyl-9-(2-methylbut-3-en-2-yl)-4-(2-methylpropyl)-2,5,16-triazatetracyclo[7.7.0.02,7.010,15]hexadeca-10,12,14-triene-3,6-dione |
| Canonical SMILES | CC(C)CC1C(=O)N2C(CC3(C2N(C4=CC=CC=C43)C(=O)C)C(C)(C)C=C)C(=O)N1 |
| InChI | InChI=1S/C24H31N3O3/c1-7-23(5,6)24-13-19-20(29)25-17(12-14(2)3)21(30)27(19)22(24)26(15(4)28)18-11-9-8-10-16(18)24/h7-11,14,17,19,22H,1,12-13H2,2-6H3,(H,25,29)/t17-,19-,22-,24+/m0/s1 |
| InChI Key | BMRZKNPRSPWNNW-UNBWHIKDSA-N |
| Source | Penicillium sp. |
Properties
| Appearance | Solid |
| Boiling Point | 654.4°C at 760 mmHg |
| Melting Point | 261.08°C (Predicted) |
| Density | 1.21 g/cm3 |
| Solubility | Soluble in Ethanol, Methanol, DMF, DMSO; Poorly soluble in Water |
Reference Reading
1.Production of mycotoxins on artificially and naturally infested building materials.
Nielsen KF1, Gravesen S, Nielsen PA, Andersen B, Thrane U, Frisvad JC. Mycopathologia. 1999;145(1):43-56.
In this study, the ability to produce mycotoxins during growth on artificially infested building materials was investigated for Penicillium chrysogenum, Pen. polonicum, Pen. brevicompactum, Chaetomium spp., Aspergillus ustus, Asp. niger, Ulocladium spp., Alternaria spp., and Paecilomyces spp., all isolated from water-damaged building materials. Spores from the different isolates of the above mentioned species were inoculated on gypsum board with and without wallpaper and on chipboard with and without wallpaper. Fungal material was scraped off the materials, extracted, and analyzed using high performance liquid chromatography-diode array detection and thin layer chromatography. All six isolates of C. globosum produced the toxic chaetoglobosins A and C, at levels of up to 50 and 7 microg/cm2 respectively. The quantities of secondary metabolites produced by Penicillia were generally low, and no toxin production was detected from any of the five isolates of Pen.
2.Production of secondary metabolites by some terverticillate penicillia on carbohydrate-rich and meat substrates.
Núñez F1, Westphal CD, Bermúdez E, Asensio MA. J Food Prot. 2007 Dec;70(12):2829-36.
Most terverticillate penicillia isolated from dry-cured meat products are toxigenic, but their ability to produce hazardous metabolites on meat-based substrates is not well known. The production of extrolites by selected terverticillate penicillia isolated from dry-cured ham has been studied on carbohydrate-rich media (malt extract agar, Czapek yeast autolysate agar, rice extract agar, and rice), meat extract triolein salt agar, and ham slices. Chloroform extracts from the selected strains grown on malt extract agar were toxic for the brine shrimp (Artemia salina) larvae and VERO cells at a concentration of 2 mg/ml, but 0.02 mg/ml produced no toxic effect. Analysis by high-pressure liquid chromatography (HPLC) coupled with photodiode array detection (DAD) or with mass spectrometry (MS) and an atmospheric pressure chemical ionization (APCI) source revealed different biologically active metabolites: cyclopiazonic acid and rugulovasine A from Penicillium commune; verrucosidin, anacine, puberuline, verrucofortine, and viridicatols from Penicillium polonicum; arisugacin and viridicatols from Penicillium echinulatum; and compactin and viridicatols from Penicillium solitum.
3.Penicillium strains isolated from Slovak grape berries taxonomy assessment by secondary metabolite profile.
Santini A1, Mikušová P, Sulyok M, Krska R, Labuda R, Srobárová A. Mycotoxin Res. 2014 Nov;30(4):213-20. doi: 10.1007/s12550-014-0205-3. Epub 2014 Aug 12.
The secondary metabolite profiles of microfungi of the genus Penicillium isolated from samples of grape berries collected in two different phases during two vegetative seasons in Slovakia is described to assess the taxonomy. Three Slovak vine regions have been selected for this study, based on their climatic differences and national economic importance. Cultures of microfungi isolated from berries were incubated on different selective media for macro and micromorphology identification. The species Penicillium brevicompactum, Penicillium crustosum, Penicillium chrysogenum, Penicillium expansum, Penicillium palitans and Penicillium polonicum were identified according to growth and morphology. The related strains were found to produce a broad spectrum of fungal metabolites, including roquefortine C, chaetoglobosin A, penitrem A, cyclopeptin, cyclopenin, viridicatin, methylviridicatin, verrucofortine, secalonic acid D, cyclopiazonic acid, fumigaclavine and mycophenolic acid.
4.Penicyrones A and B, an epimeric pair of α-pyrone-type polyketides produced by the marine-derived Penicillium sp.
Bu YY1, Yamazaki H1, Takahashi O1, Kirikoshi R1, Ukai K1, Namikoshi M1. J Antibiot (Tokyo). 2016 Jan;69(1):57-61. doi: 10.1038/ja.2015.82. Epub 2015 Aug 5.
Two polyketides containing an α-pyrone unit, named penicyrones A (1) and B (2), were isolated from a culture broth of the marine-derived Penicillium sp. TPU1271 together with nine known compounds: verrucosidin (3), fructigenine A (4), verrucofortine (5), cyclo-(L-Trp-L-Phe) (6), cyclopenol (7), cyclopenin (8), penipratynolene (9), aspterric acid (10) and viridicatol (11). The structures of 1 and 2 were elucidated by analyzing the spectroscopic data of 1, 2 and their O-acetyl derivatives (1a and 2a). Compounds 1 and 2 were epimers of each other at the C-9 position. The absolute configurations of 1 and 2 were assigned on the basis of NOESY data for 1, 2, 1a and 2a, a conformational analysis and the identity of the biogenetic pathway with verrucosidin (3). The planar structure of penicyrones was found in the SciFinder as a compound in the commercial chemical libraries; however, the stereostructure and spectroscopic data were not available. Therefore, this is the first study on the isolation and structure elucidation, including the absolute configurations, of penicyrones A (1) and B (2) as fungal metabolites.
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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 ╳
