Ochracin
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| Category | Antibiotics |
| Catalog number | BBF-02615 |
| CAS | 17397-85-2 |
| Molecular Weight | 178.18 |
| Molecular Formula | C10H10O3 |
| Purity | 95% |
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Description
Ochracin has weak anti-Staphylococcus aureus effect.
Specification
| Synonyms | Mellein; 3,4-Dihydro-8-hydroxy-3-methylisocoumarin; Antibiotic AO-2; Antibiotic BV-1 |
| IUPAC Name | 8-hydroxy-3-methyl-3,4-dihydroisochromen-1-one |
| Canonical SMILES | CC1CC2=C(C(=CC=C2)O)C(=O)O1 |
| InChI | InChI=1S/C10H10O3/c1-6-5-7-3-2-4-8(11)9(7)10(12)13-6/h2-4,6,11H,5H2,1H3 |
| InChI Key | KWILGNNWGSNMPA-UHFFFAOYSA-N |
Properties
| Appearance | Colorless Columnar Crystals |
| Antibiotic Activity Spectrum | Gram-positive bacteria |
| Boiling Point | 392.7°C at 760 mmHg |
| Melting Point | 58-58.5°C |
| Density | 1.252 g/cm3 |
Reference Reading
1. Identification of Mellein as a Pathogenic Substance of Botryosphaeria dothidea by UPLC-MS/MS Analysis and Phytotoxic Bioassay
Yuanze Li, Zheng Gai, Caixia Wang, Pingliang Li, Baohua Li J Agric Food Chem. 2021 Aug 4;69(30):8471-8481. doi: 10.1021/acs.jafc.1c03249. Epub 2021 Jul 24.
Botryosphaeria dothidea is a pathogenic fungus that can cause apple ring rot, a destructive apple disease in China. There have been reports on its molecular pathogenesis, but the pathogenic substances still remain unknown. In the present study, instrument analysis including UPLC-high-resolution mass spectrometry (HRMS) and nuclear magnetic resonance showed that B. dothidea fermentation broth contained (R)-(-)-mellein, a well-known fungal enantiomer of mellein. For further confirmation, a UPLC-MS/MS method for the determination of mellein was developed and validated. By this method, mellein was found to also exist in B. dothidea-infected apple fruits and branches with concentration ranges of 0.14-0.94 and 5.88-80.29 mg/kg, respectively. The concentration in fruits reached a peak at 48 h after pathogen inoculation, while a sustained concentration increase was achieved within 11 days for branches. Simultaneously, it was evident that there was a relation between disease spot expansion and mellein production kinetics in apple tissue. Phytotoxic bioassay showed that mellein could cause discoloration and death of apple leaves and browning in stems. Therefore, we confirmed that mellein was one of the pathogenic substances of B. dothidea. The present study provided additional data for the research on the pathogenesis of this pathogen.
2. Isolation, purification and structural elucidation of Mellein from endophytic fungus Lasiodiplodia theobromae strain (SJF-1) and its broad-spectrum antimicrobial and pharmacological properties
M Saraswathi, S H Meshram, B Siva, S Misra, K Suresh Babu Lett Appl Microbiol. 2022 Dec;75(6):1475-1485. doi: 10.1111/lam.13813. Epub 2022 Aug 31.
In an on-going investigation of bioactive metabolites producing potential endophytic fungi, the strain Lasiodiplodia theobromae (SJF-1) was isolated from a medicinal plant Syzygium cumini. The cultural, morphological and molecular identification was done with the SJF-1 strain. The obtained gene sequence was deposited in NCBI with accession number MG 938644. The methanolic extract of SJF-1 strain possessed one major bioactive fraction, and it was purified by column chromatography. Further, it was identified as Mellein by various spectroscopic studies (1 H, 13 C, DEPT-135°, FT-IR, ESI-HR-MS and 2D NMR). Biologically, Mellein showed potent anti-Xanthomonas activity with minimum inhibitory concentration (MIC) values ranging from 1·9 to 62·5 μg ml-1 against 11 Xanthomonas strains, a broad-spectrum antimicrobial activity with MIC 7·8-31·25 μg ml-1 and 1·9-31·25 μg ml-1 towards both bacterial and fungal strains, respectively. The scanning electron microscope analysis proved the antimicrobial efficacy of a Mellein by rupturing the cell walls of Xanthomonas sp. Molecular docking studies further supported that the Mellein showed good binding interactions with the proteins of Xanthomonas sp. to reduce pathogenicity. Further, in silico pharmacological studies showed that this metabolite exhibited high gastrointestinal absorption properties and promising oral drug bioavailability. We report, anti-Xanthomonas, in silico docking and pharmacological studies of Mellein from (SJF-1) strain for the first time.
3. Melleins-Intriguing Natural Compounds
Pierluigi Reveglia, Marco Masi, Antonio Evidente Biomolecules. 2020 May 15;10(5):772. doi: 10.3390/biom10050772.
Melleins are 3,4-dihydroisocoumarins mainly produced by fungi, but also by plants, insects and bacteria. These specialized metabolites play important roles in the life cycles of the producers and they are involved in many biochemical and ecological processes. This review outlines the isolation and chemical and biological characterizations of natural-occurring melleins from the first report of (R)-mellein in 1933 to the most recent advances in their characterization in 2019. In addition, the pathways that could be involved in mellein biosynthesis are discussed, along with the enzymes and genes involved.
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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 ╳
