Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C10H10O3 |
| Molecular Weight | 178.1846 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 1 / 1 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
C[C@@H]1CC2=C(C(=O)O1)C(O)=CC=C2
InChI
InChIKey=KWILGNNWGSNMPA-ZCFIWIBFSA-N
InChI=1S/C10H10O3/c1-6-5-7-3-2-4-8(11)9(7)10(12)13-6/h2-4,6,11H,5H2,1H3/t6-/m1/s1
| Molecular Formula | C10H10O3 |
| Molecular Weight | 178.1846 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 1 / 1 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
DescriptionCurator's Comment: The description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/19060918 | https://www.ncbi.nlm.nih.gov/pubmed/11170686 | https://www.ncbi.nlm.nih.gov/pubmed/17363259 | https://www.ncbi.nlm.nih.gov/pubmed/25323623 | https://www.ncbi.nlm.nih.gov/pubmed/24752796
Curator's Comment: The description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/19060918 | https://www.ncbi.nlm.nih.gov/pubmed/11170686 | https://www.ncbi.nlm.nih.gov/pubmed/17363259 | https://www.ncbi.nlm.nih.gov/pubmed/25323623 | https://www.ncbi.nlm.nih.gov/pubmed/24752796
Mellein (3,4-dihydroisocoumarin) is a dihydroisocoumarin, a phenolic compound produced by Aspergillus ochraceus, with potent anti-hepatitis C virus protease activity. Mellein is a common metabolite in fungi and molds and particularly in endophytic fungi associated with higher plants. Occasionally, it has been isolated from some higher plants such as Ficus formosana (Moraceae) and Garcinia bancana (Clusiaceae) and also from marine organisms. On the other hand, it is particularly notable the presence of this compound in insects in which acts as a pheromone and as a defense substance. Mellein has been recognized for its antibacterial, phytotoxic, larvicide and fungicide activities, and also because it acts as an inhibitor of HCV protease enzyme and prostaglandin synthesis.
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| [Study on the second metabolisms from fungus HS-1 Epicoccum spp. from the sea cucumber in Yellow Sea]. | 2010-10 |
|
| Effects of ochratoxin a on livestock production. | 2010-07 |
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| Chemical, physical and biological approaches to prevent ochratoxin induced toxicoses in humans and animals. | 2010-07 |
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| Biotransformation of bioactive (-)-mellein by a marine isolate of bacterium Stappia sp. | 2010-06 |
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| Biodegradation of ochratoxin a for food and feed decontamination. | 2010-05 |
|
| Bioactive metabolites produced by Penicillium sp. 1 and sp. 2, two endophytes associated with Alibertia macrophylla (Rubiaceae). | 2010-02-18 |
|
| Developmental toxicity of Ochratoxin A in rat embryo midbrain micromass cultures. | 2009-01 |
|
| Composition and electrophysiological activity of constituents identified in male wing gland secretion of the bumblebee parasite Aphomia sociella. | 2009-01 |
|
| Microsphaeropsisin A, a new sesquiterpenoid isolated from the mangrove endophytic fungus (No. DZ39). | 2009 |
|
| E-2-ethylhexenal, E-2-ethyl-2-hexenol, mellein, and 4-hydroxymellein in Camponotus species from Brunei. | 2008-02 |
|
| Use of solid phase microextraction (SPME) for profiling the volatile metabolites produced by Glomerella cingulata. | 2008 |
|
| Weed growth inhibitors from Aspergillus fischeri TISTR 3272. | 2007-12 |
|
| The isolation of secondary metabolites and in vitro potent anti-cancer activity of clerodermic acid from Enicosanthum membranifolium. | 2007-06-01 |
|
| Synthesis of pyran and pyranone natural products. | 2004-05-31 |
|
| The North American mushroom competitor, Trichoderma aggressivum f. aggressivum, produces antifungal compounds in mushroom compost that inhibit mycelial growth of the commercial mushroom Agaricus bisporus. | 2003-12 |
|
| Three new dihydroisocoumarins from the Greek endemic species Scorzonera cretica. | 2001-12 |
|
| Biosynthesis of ochratoxins by Aspergillus ochraceus. | 2001-11 |
|
| Antimalarial halorosellinic acid from the marine fungus Halorosellinia oceanica. | 2001-08-06 |
|
| Circumdatin G, a new alkaloid from the fungus Aspergillus ochraceus. | 2001-01 |
Patents
Sample Use Guides
Mellein toxin was isolated from D. seriata isolate F-99.2. Three-week-old V. vinifera cv. Chardonnay calli were subcultured in MPM1 solid medium (with mellein at 25, 200 and 500 μg/ml. Calli were incubated at 28 °C in the dark using aMemmerto™ incubator. The toxicity of the extracellular compounds or mellein was assessed visually as the appearance of necrosis on the calli at 0, 1, 3 and 6 days, and calli were collected for defence gene expression analysis. Five calli (from five different Petri dishes) were collected for each condition and at each time.
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 19:02:24 GMT 2025
by
admin
on
Mon Mar 31 19:02:24 GMT 2025
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| Record UNII |
Y30Y67M5SV
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| Record Status |
Validated (UNII)
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| Record Version |
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38760
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MELLEIN
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480-33-1
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Y30Y67M5SV
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114679
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