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=CC=CC(O)=C2C(=O)O1
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 |
|---|---|---|
| Antimalarial halorosellinic acid from the marine fungus Halorosellinia oceanica. | 2001 Aug 6 |
|
| Three new dihydroisocoumarins from the Greek endemic species Scorzonera cretica. | 2001 Dec |
|
| Circumdatin G, a new alkaloid from the fungus Aspergillus ochraceus. | 2001 Jan |
|
| 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 Dec |
|
| Synthesis of pyran and pyranone natural products. | 2004 May 31 |
|
| Weed growth inhibitors from Aspergillus fischeri TISTR 3272. | 2007 Dec |
|
| The isolation of secondary metabolites and in vitro potent anti-cancer activity of clerodermic acid from Enicosanthum membranifolium. | 2007 Jun 1 |
|
| Use of solid phase microextraction (SPME) for profiling the volatile metabolites produced by Glomerella cingulata. | 2008 |
|
| E-2-ethylhexenal, E-2-ethyl-2-hexenol, mellein, and 4-hydroxymellein in Camponotus species from Brunei. | 2008 Feb |
|
| Microsphaeropsisin A, a new sesquiterpenoid isolated from the mangrove endophytic fungus (No. DZ39). | 2009 |
|
| Developmental toxicity of Ochratoxin A in rat embryo midbrain micromass cultures. | 2009 Jan |
|
| Composition and electrophysiological activity of constituents identified in male wing gland secretion of the bumblebee parasite Aphomia sociella. | 2009 Jan |
|
| Bioactive metabolites produced by Penicillium sp. 1 and sp. 2, two endophytes associated with Alibertia macrophylla (Rubiaceae). | 2009 Nov-Dec |
|
| Effects of ochratoxin a on livestock production. | 2010 Jul |
|
| Chemical, physical and biological approaches to prevent ochratoxin induced toxicoses in humans and animals. | 2010 Jul |
|
| Biotransformation of bioactive (-)-mellein by a marine isolate of bacterium Stappia sp. | 2010 Jun |
|
| Biodegradation of ochratoxin a for food and feed decontamination. | 2010 May |
|
| [Study on the second metabolisms from fungus HS-1 Epicoccum spp. from the sea cucumber in Yellow Sea]. | 2010 Oct |
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
Fri Dec 15 18:05:41 GMT 2023
by
admin
on
Fri Dec 15 18:05:41 GMT 2023
|
| Record UNII |
Y30Y67M5SV
|
| Record Status |
Validated (UNII)
|
| Record Version |
|
-
Download
| Name | Type | Language | ||
|---|---|---|---|---|
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Common Name | English |
| Code System | Code | Type | Description | ||
|---|---|---|---|---|---|
|
38760
Created by
admin on Fri Dec 15 18:05:41 GMT 2023 , Edited by admin on Fri Dec 15 18:05:41 GMT 2023
|
PRIMARY | |||
|
MELLEIN
Created by
admin on Fri Dec 15 18:05:41 GMT 2023 , Edited by admin on Fri Dec 15 18:05:41 GMT 2023
|
PRIMARY | |||
|
480-33-1
Created by
admin on Fri Dec 15 18:05:41 GMT 2023 , Edited by admin on Fri Dec 15 18:05:41 GMT 2023
|
PRIMARY | |||
|
Y30Y67M5SV
Created by
admin on Fri Dec 15 18:05:41 GMT 2023 , Edited by admin on Fri Dec 15 18:05:41 GMT 2023
|
PRIMARY | |||
|
114679
Created by
admin on Fri Dec 15 18:05:41 GMT 2023 , Edited by admin on Fri Dec 15 18:05:41 GMT 2023
|
PRIMARY |