Diaporthin
* Please be kindly noted products are not for therapeutic use. We do not sell to patients.
| Category | Antibiotics |
| Catalog number | BBF-01375 |
| CAS | 10532-39-5 |
| Molecular Weight | 250.25 |
| Molecular Formula | C13H14O5 |
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Description
Diaporthin is produced by the strain of Endothia parasitica ETH-M-156. It has the ability of anti-gram-positive bacteria, lattice spore, and yeast.
Specification
| Synonyms | (S)-8-Hydroxy-3-(2-hydroxypropyl)-6-methoxy-1H-2-benzopyran-1-one |
| IUPAC Name | 8-hydroxy-3-[(2S)-2-hydroxypropyl]-6-methoxyisochromen-1-one |
| Canonical SMILES | CC(CC1=CC2=CC(=CC(=C2C(=O)O1)O)OC)O |
| InChI | InChI=1S/C13H14O5/c1-7(14)3-10-5-8-4-9(17-2)6-11(15)12(8)13(16)18-10/h4-7,14-15H,3H2,1-2H3/t7-/m0/s1 |
| InChI Key | ORLHWDAVUBPRKN-ZETCQYMHSA-N |
Properties
| Appearance | Acicular Crystalline |
| Antibiotic Activity Spectrum | Gram-positive bacteria; yeast |
| Melting Point | 83-85°C |
Reference Reading
1. Chromone and isocoumarin derivatives from the endophytic fungus Xylomelasma sp. Samif07, and their antibacterial and antioxidant activities
Daowan Lai, Jing Li, Siji Zhao, Gan Gu, Xiao Gong, Peter Proksch, Ligang Zhou Nat Prod Res. 2021 Nov;35(22):4616-4620. doi: 10.1080/14786419.2019.1696333. Epub 2019 Nov 29.
Five chromone derivatives, including 2,6-dimethyl-5-methoxyl-7-hydroxylchromone (1), 6-hydroxymethyleugenin (2), 6-methoxymethyleugenin (3), chaetoquadrin D (4), and isoeugenitol (5), and three isocoumarin congeners, namely diaporthin (6), 8-hydroxy-6-methoxy-3-methylisocoumarin (7), and 6-methoxymellein (8), were isolated from the culture of the endophytic fungus Xylomelasma sp. Samif07 derived from the medicinal plant Salvia miltiorrhiza Bunge. Among them, compound 1 was a new natural product. Their structures were determined by spectroscopic methods and comparison with the literature. The isolated compounds were evaluated for their antibacterial and antioxidant activities. Compound 5 showed notable antitubercular activity against Mycobacterium tuberculosis with MIC value of 10.31 µg/mL, while compounds 1-3, and 5-7 displayed inhibitory activities against the other bacteria with MIC range of 25 ~ 100 µg/mL. Meanwhile, compound 6 showed potent hydroxyl radical-scavenging activity with EC50 value of 15.1 µg/mL, while compounds 5-7 showed certain ferric reducing ability.
2. Bioactive Secondary Metabolites from the Culture of the Mangrove-Derived Fungus Daldinia eschscholtzii HJ004
Hai-Xia Liao, Tai-Ming Shao, Rong-Qing Mei, Guo-Lei Huang, Xue-Ming Zhou, Cai-Juan Zheng, Chang-Yun Wang Mar Drugs. 2019 Dec 17;17(12):710. doi: 10.3390/md17120710.
Two new polyketides, 8-O-methylnodulisporin F (1) and nodulisporin H (2), two new naphthoquinones, 5-hydroxy-2-methoxy-6,7-dimethyl-1,4-naphthoquinone (3) and 5-hydroxy-2-methoxynaphtho[9-c]furan-1,4-dione (4), and a new naphthofuran 1,3,8-trimethoxynaphtho[9-c]furan (5), along with five known compounds 4-O-methyl eleutherol (6), 2-acetyl-7-methoxybenzofuran (7), (-)-orthosporin (8), diaporthin (9), and 6-hydroxymellein (10), were obtained from the EtOAc extract of the mangrove-derived fungus Daldinia eschscholtzii HJ004. The structures of the isolated compounds were elucidated by extensive NMR and MS analyses, while the absolute configurations of the stereogenic carbons were established based on experimental and calculated electronic circular dichroism spectra. Compounds 4 and 7 displayed a potent inhibitory activity against α-glucosidase with the IC50 values of 5.7 and 1.1 μg/mL, respectively. Compounds 1 and 2 showed a moderate antibacterial activity against Staphylococcus aureus, methicillin-resistant S. aureus (MRSA) and Bacillus cereus, with minimum inhibitory concentration (MIC) values ranging from 6.25 to 12.5 μg/mL. Compound 3 exhibited antibacterial activity against B. cereus with the MIC value of 12.5 μg/mL.
3. Brefeldin A from the Deep-Sea-Derived Fungus Fusarium sp. Targets on RIPK3 to Inhibit TNFα-Induced Necroptosis
Jia-Yi Shi, Chao-Feng Wang, Ming-Min Xie, You-Jia Hao, Ning Wang, Hua-Bin Ma, Xian-Wen Yang Chem Biodivers. 2022 Oct;19(10):e202200696. doi: 10.1002/cbdv.202200696. Epub 2022 Sep 16.
From the deep-sea-derived Fusarium sp. ZEN-48, four known compounds were obtained. Their structures were established by extensive analyses of the NMR, HR-ESI-MS, and the X-ray crystallographic data as brefeldin A (BFA, 1), brevianamide F (2), N-acetyltryptamine (3), and (+)-diaporthin (4). Although BFA was extensively investigated for its potent bioactivities, its role on TNFα-induced necroptosis was incompletely understood. In this study, BFA showed significant inhibition on TNFα-induced necroptosis by disrupting the necrosome formation and suppressing the phosphorylation of RIPK3 and MLKL (IC50 =0.5 μM). While, it had no effect on TNFα-induced NF-κB/MAPKs activation and apoptosis. The finding raised significant implications of BFA for necroptosis-related inflammatory disease therapy and new drug development from marine fungi.
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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 ╳
