Vioxanthin
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| Category | Antibiotics |
| Catalog number | BBF-02513 |
| CAS | 15447-05-9 |
| Molecular Weight | 546.5 |
| Molecular Formula | C30H26O10 |
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Description
Vioxanthin is an antibiotic produced by Malbranchea pulchella var. sulfurea. It is active against gram-positive bacteria and bacteroides fragilis.
Specification
| Synonyms | Tf-26Vx |
| IUPAC Name | (3R)-8-[(3R)-9,10-dihydroxy-7-methoxy-3-methyl-1-oxo-3,4-dihydrobenzo[g]isochromen-8-yl]-9,10-dihydroxy-7-methoxy-3-methyl-3,4-dihydrobenzo[g]isochromen-1-one |
| Canonical SMILES | CC1CC2=C(C(=C3C(=C2)C=C(C(=C3O)C4=C(C5=C(C6=C(CC(OC6=O)C)C=C5C=C4OC)O)O)OC)O)C(=O)O1 |
| InChI | InChI=1S/C30H26O10/c1-11-5-13-7-15-9-17(37-3)23(27(33)19(15)25(31)21(13)29(35)39-11)24-18(38-4)10-16-8-14-6-12(2)40-30(36)22(14)26(32)20(16)28(24)34/h7-12,31-34H,5-6H2,1-4H3/t11-,12-/m1/s1 |
| InChI Key | CJKYODJTBJDEJI-VXGBXAGGSA-N |
Properties
| Appearance | Pale Yellow Crystal |
| Antibiotic Activity Spectrum | Gram-positive bacteria |
| Boiling Point | 764.7°C at 760 mmHg |
| Melting Point | 332°C (dec.) |
| Density | 1.463 g/cm3 |
| Solubility | Soluble in chloroform and DMF. |
Reference Reading
1. Diversity and Biosynthetic Potential of Fungi Isolated from St. John's Island, Singapore
Madhaiyan Munusamy, Kenneth Tan, Choy Eng Nge, Martin Muthee Gakuubi, Sharon Crasta, Yoganathan Kanagasundaram, Siew Bee Ng Int J Mol Sci. 2023 Jan 5;24(2):1033. doi: 10.3390/ijms24021033.
Adaptation to a wide variety of habitats allows fungi to develop unique abilities to produce diverse secondary metabolites with diverse bioactivities. In this study, 30 Ascomycetes fungi isolated from St. John's Island, Singapore were investigated for their general biosynthetic potential and their ability to produce antimicrobial secondary metabolites (SMs). All the 30 fungal isolates belong to the Phylum Ascomycota and are distributed into 6 orders and 18 genera with Order Hypocreales having the highest number of representative (37%). Screening for polyketide synthase (PKS) and nonribosomal peptide synthetase (NRPS) genes using degenerate PCR led to the identification of 23 polyketide synthases (PKSs) and 5 nonribosomal peptide synthetases (NRPSs) grouped into nine distinct clades based on their reduction capabilities. Some of the identified PKSs genes share high similarities between species and known reference genes, suggesting the possibility of conserved biosynthesis of closely related compounds from different fungi. Fungal extracts were tested for their antimicrobial activity against S. aureus, Methicillin-resistant S. aureus (MRSA), and Candida albicans. Bioassay-guided fractionation of the active constituents from two promising isolates resulted in the isolation of seven compounds: Penilumamides A, D, and E from strain F4335 and xanthomegnin, viomellein, pretrichodermamide C and vioxanthin from strain F7180. Vioxanthin exhibited the best antibacterial activity with IC50 values of 3.0 μM and 1.6 μM against S. aureus and MRSA respectively. Viomellein revealed weak antiproliferative activity against A549 cells with an IC50 of 42 μM. The results from this study give valuable insights into the diversity and biosynthetic potential of fungi from this unique habitat and forms a background for an in-depth analysis of the biosynthetic capability of selected strains of interest with the aim of discovering novel fungal natural products.
2. Diversity in Fungal Intermolecular Phenol Coupling of Polyketides: Regioselective Laccase-Based Systems
Leon Fürtges, Sebastian Obermaier, Wiebke Thiele, Silke Foegen, Michael Müller Chembiochem. 2019 Aug 1;20(15):1928-1932. doi: 10.1002/cbic.201900041. Epub 2019 Jul 8.
Polyketides form a structurally diverse and pharmaceutically important class of secondary metabolites. Both diversity and biological activity are largely facilitated by post-polyketide synthase tailoring including methylation, oxidation, reduction, glycosylation, and dimerization. Cytochrome P450 enzymes (CYPs), flavin-dependent monooxygenases (FMOs), and laccases are known to catalyze phenol coupling in the biosynthesis of polyketide dimers. Polyketide homodimers resulting from enzyme catalysis are often formed in a highly regio- and stereoselective manner, in contrast to analogous nonenzymatic dimerization. Although it is known that CYPs and FMOs are capable of selectively generating one of several putative isomers, hitherto described laccases depend on auxiliary proteins to achieve similar selectivity. Herein, regioselective phenol coupling catalyzed by a fungal laccase is demonstrated. The heterologously produced Av-VirL from Aspergillus viridinutans selectively generated the 6,6'-homodimer of (R)-semivioxanthin. Genome analysis is used to show that laccase-based phenol-coupling systems are widespread in fungi. Homologues of Av-VirL were identified in the putative biosynthetic gene clusters of vioxanthin, xanthomegnin, and xanthoepocin, and of the perylenequinones hypocrellin A, elsinochrome A, and cercosporin. These findings show that laccases are capable of selective phenol coupling in the absence of auxiliary proteins.
3. 1,3-Dioxepine and spiropyran derivatives of viomellein and other dimeric naphthopyranones from cultures of Aspergillus elegans KUFA0015 and their antibacterial activity
Decha Kumla, Emilia Sousa, Alessia Marengo, Tida Dethoup, José A Pereira, Luís Gales, Joana Freitas-Silva, Paulo M Costa, Sharad Mistry, Artur M S Silva, Anake Kijjoa Phytochemistry. 2021 Jan;181:112575. doi: 10.1016/j.phytochem.2020.112575. Epub 2020 Nov 6.
Two undescribed viomellein derivatives, xanthoelegansin and spiroxanthoelegansin, were isolated together with clavatol, sitosteanone, vioxanthin, xanthomegnin, viomellein, rubrosulphin, rubrosulphin diacetate, viopurpurin , ochratoxin A, ochratoxin A methyl ester, ochratoxin B and ochratoxin β, from cultures of the marine sponge-associated fungus Aspergillus elegans KUFA0015. The structures of the undescribed compounds were established based on an extensive analysis of 1D and 2D NMR spectra as well as HRMS data. The structure of xanthoelegansin and the absolute configuration of its stereogenic carbons were confirmed by X-ray analysis. The change in conformation of xanthoelegansin was interpreted using quantum mechanical theoretical calculation data in combination with the observation of the change of the proton signals of the 1,3-dioxepine ring in 1HNMR spectra at varying temperatures. The mechanisms of the formation of xanthoelegansin and spiroxanthoelegansin from viomellein were proposed. Clavatol, sitosteanone, vioxanthin, xanthomegnin, viomellein, xanthoelegansin, rubrosulphin, rubrosulphin diacetate, ochratoxin A, ochratoxin A methyl ester, ochratoxin B and ochratoxin β were assayed for their antibacterial activity against reference strains and multidrug-resistant isolates from the environment. The tested compounds were also evaluated for their capacity to inhibit biofilm formation in the reference strains.
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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 ╳
