Cryptosporiopsin
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| Category | Antibiotics |
| Catalog number | BBF-01087 |
| CAS | 25707-30-6 |
| Molecular Weight | 265.09 |
| Molecular Formula | C10H10Cl2O4 |
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Description
It is produced by the strain of Cryptosporiopsis sp. and Sporormia affinis. It has antibacterial activity to many kinds of basidiomycetes, algal fungi, ascomycetes and hemiplegia fungi that cause wood rot, and can inhibit spore germination of Phytophthora potatoes. It also has certain activity against gram-positive bacteria and negative bacteria.
Specification
| Synonyms | (+)-Cryptosporiopsin; 2-Cyclopentene-1-carboxylic acid, 5-dichloro-1-hydroxy-4-oxo-2-propenyl-, methyl ester, (E)-(1S,5S)-(+)- |
| IUPAC Name | methyl (1S,5S)-3,5-dichloro-1-hydroxy-4-oxo-2-[(E)-prop-1-enyl]cyclopent-2-ene-1-carboxylate |
| Canonical SMILES | CC=CC1=C(C(=O)C(C1(C(=O)OC)O)Cl)Cl |
| InChI | InChI=1S/C10H10Cl2O4/c1-3-4-5-6(11)7(13)8(12)10(5,15)9(14)16-2/h3-4,8,15H,1-2H3/b4-3+/t8-,10-/m1/s1 |
| InChI Key | VFXXEEUGYINLKM-KHSHYHJCSA-N |
Properties
| Appearance | Colorless Crystal |
| Antibiotic Activity Spectrum | Gram-positive bacteria; Gram-negative bacteria; Fungi |
| Boiling Point | 377.5 °C at 760 mmHg |
| Melting Point | 133-137 °C |
| Density | 1.44 g/cm3 |
| Solubility | Soluble in Ethanol, Chloroform |
Reference Reading
1. Zoosporicidal metabolites from an endophytic fungus Cryptosporiopsis sp. of Zanthoxylum leprieurii
Ferdinand Mouafo Talontsi, Petrea Facey, Michel D Kongue Tatong, M Tofazzal Islam, Holm Frauendorf, Siegfried Draeger, Andreas von Tiedemann, Hartmut Laatsch Phytochemistry. 2012 Nov;83:87-94. doi: 10.1016/j.phytochem.2012.06.006. Epub 2012 Aug 8.
Two polyketides, cryptosporiopsin A (1) and hydroxypropan-2',3'-diol orsellinate (3), and a natural cyclic pentapeptide (4), together with two known compounds were isolated from the culture of Cryptosporiopsis sp., an endophytic fungus from leaves and branches of Zanthoxylum leprieurii (Rutaceae). The structures of these metabolites were elucidated on the basis of their spectroscopic and spectrometric data. Cryptosporiopsin A and the other metabolites exhibited motility inhibitory and lytic activities against zoospores of the grapevine downy mildew pathogen Plasmopara viticola at 10-25μg/mL. In addition, the isolated compounds displayed potent inhibitory activity against mycelial growth of two other peronosporomycete phytopathogens, Pythium ultimum, Aphanomyces cochlioides and a basidiomycetous fungus Rhizoctonia solani. Weak cytotoxic activity on brine shrimp larvae was observed.
2. Natural Products of Picea Endophytes from the Acadian Forest
David R McMullin, Blake D Green, Natasha C Prince, Joey B Tanney, J David Miller J Nat Prod. 2017 May 26;80(5):1475-1483. doi: 10.1021/acs.jnatprod.6b01157. Epub 2017 Apr 11.
Endophytes of healthy needles were collected from Picea rubens (red spruce) and P. mariana (black spruce) in a survey of southeastern New Brunswick, Canada. Four endophyte strains were selected for further investigation based on the production of biologically active extracts from culture filtrates during screening as well as phylogenetic relationship to species known to produce natural products or taxonomic novelty. A novel endophyte within the family Rhytismataceae produced two new dihydropyrones (1 and 2) as major metabolites together with phthalides (3 and 4), isocoumarins (5 and 6), and tyrosol (7). Lachnum cf. pygmaeum synthesized a new chlorinated para-quinone, chloromycorrhizinone A (8), and the nematicidal compounds (1'Z)-dechloromycorrhizin A (9), mycorrhizin A (10), and chloromycorrhizin A (11). A new isocoumarin (12) and four related structures (13-16) were isolated from an undescribed taxon in the Mycosphaerellaceae. The known antifungal metabolites cryptosporiopsin (17), 5-hydroxycryptosporiopsin (18), (+)-cryptosporiopsinol (19), and mellein (20) were produced by Pezicula sporulosa. Phylogenetically diverse conifer endophytes from the Acadian forest continue to be a productive source of new biologically active natural products.
3. Early Oxidative Transformations During the Biosynthesis of Terrein and Related Natural Products
Lukas Kahlert, Darlon Bernardi, Maurice Hauser, Laura P Ióca, Roberto G S Berlinck, Elizabeth J Skellam, Russell J Cox Chemistry. 2021 Aug 16;27(46):11895-11903. doi: 10.1002/chem.202101447. Epub 2021 Jun 24.
The mycotoxin terrein is derived from the C10 -precursor 6-hydroxymellein (6-HM) via an oxidative ring contraction. Although the corresponding biosynthetic gene cluster (BGC) has been identified, details of the enzymatic oxidative transformations are lacking. Combining heterologous expression and in vitro studies we show that the flavin-dependent monooxygenase (FMO) TerC catalyzes the initial oxidative decarboxylation of 6-HM. The reactive intermediate is further hydroxylated by the second FMO TerD to yield a highly oxygenated aromatic species, but further reconstitution of the pathway was hampered. A related BGC was identified in the marine-derived Roussoella sp. DLM33 and confirmed by heterologous expression. These studies demonstrate that the biosynthetic pathways of terrein and related (polychlorinated) congeners diverge after oxidative decarboxylation of the lactone precursor that is catalyzed by a conserved FMO and further indicate that early dehydration of the side chain is an essential step.
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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 ╳
