MELLEIN

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

Structure Search

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

HIDE SMILES / InChI

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

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/28398744
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.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Hepatitis C virus 22 Target ID: CHEMBL379 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19060918	Inhibitor 8297
Genome polyprotein 4 Target ID: CHEMBL1293305 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11170686	Inhibitor 8297		35.0 µM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Hepatitis C 42 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19060918	Primary		Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
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	15000247
Synthesis of pyran and pyranone natural products.	2004 May 31	18007449
Use of solid phase microextraction (SPME) for profiling the volatile metabolites produced by Glomerella cingulata.	2008	18838830
Microsphaeropsisin A, a new sesquiterpenoid isolated from the mangrove endophytic fungus (No. DZ39).	2009	19851922
Bioactive metabolites produced by Penicillium sp. 1 and sp. 2, two endophytes associated with Alibertia macrophylla (Rubiaceae).	2009 Nov-Dec	20158153
Effects of ochratoxin a on livestock production.	2010 Jul	22069661
Chemical, physical and biological approaches to prevent ochratoxin induced toxicoses in humans and animals.	2010 Jul	22069658
Biotransformation of bioactive (-)-mellein by a marine isolate of bacterium Stappia sp.	2010 Jun	20622496
Biodegradation of ochratoxin a for food and feed decontamination.	2010 May	22069627
[Study on the second metabolisms from fungus HS-1 Epicoccum spp. from the sea cucumber in Yellow Sea].	2010 Oct	21355195

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Unknown

In Vitro Use Guide

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 `Fri Dec 15 18:05:41 UTC 2023` Edited by `admin` on `Fri Dec 15 18:05:41 UTC 2023`
Record UNII	Y30Y67M5SV
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

MELLEIN

Common Name

English

1H-2-BENZOPYRAN-1-ONE, 3,4-DIHYDRO-8-HYDROXY-3-METHYL-, (3R)-

Systematic Name

English

(R)-(-)-MELLEIN

Common Name

English

OCHRACIN

Common Name

English

Code System Code Type Description

CHEBI

38760