6,8-Di-O-methylcitreoisocoumarin

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6,8-Di-O-methylcitreoisocoumarin
Category Others
Catalog number BBF-04378
CAS 908098-80-6
Molecular Weight 306.31
Molecular Formula C16H18O6
Purity ≥98%

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Description

6,8-Di-O-methylcitreoisocoumarin is produced from Trichoderma sp. HPQJ-34.

Specification

Synonyms 3-(2-Hydroxy-4-oxopentyl)-6,8-dimethoxy-1H-isochromen-1-one; 3-(4-Oxo-2-hydroxypentyl)-6,8-dimethoxy-1H-2-benzopyran-1-one; 1H-2-Benzopyran-1-one, 3-(2-hydroxy-4-oxopentyl)-6,8-dimethoxy-
Storage Store at 2-8°C
IUPAC Name 3-(2-hydroxy-4-oxopentyl)-6,8-dimethoxyisochromen-1-one
Canonical SMILES CC(=O)CC(CC1=CC2=CC(=CC(=C2C(=O)O1)OC)OC)O
InChI InChI=1S/C16H18O6/c1-9(17)4-11(18)7-13-6-10-5-12(20-2)8-14(21-3)15(10)16(19)22-13/h5-6,8,11,18H,4,7H2,1-3H3
InChI Key JEVUJHJOJYCWTP-UHFFFAOYSA-N

Properties

Appearance Powder
Boiling Point 512.5±50.0°C at 760 mmHg
Density 1.2±0.1 g/cm3

Reference Reading

1. Asperopiperazines A and B: Antimicrobial and Cytotoxic Dipeptides from a Tunicate-Derived Fungus Aspergillus sp. DY001
Diaa T A Youssef, Lamiaa A Shaala, Grégory Genta-Jouve Mar Drugs. 2022 Jul 10;20(7):451. doi: 10.3390/md20070451.
Investigation of the cytotoxic fractions of the ethyl acetate extract of the fermentation broth of the tunicate-derived Aspergillus sp. DY001 afforded two new dipeptides, asperopiperazines A and B (1 and 2), along with the previously reported compounds (+)-citreoisocoumarin (3) and (-)-6,8-di-O-methylcitreoisocoumarin (4). Analyses of the 1D and 2D NMR spectroscopic data of the compounds supported their structural assignments. Asperopiperazine A (1) is a cyclic dipeptide of leucine and phenylalanine moieties, which are substituted with an N-methyl and an N-acetyl group, respectively. On the other hand, asperopiperazine B (2) is a cyclic dipeptide of proline and phenylalanine moieties with a hydroxyl group at C-2 of the proline part. The absolute configuration of the amino acid moieties in 1 and 2 were determined by Marfey's analyses and DFT NMR chemical shift calculations, leading to their assignment as cyclo(l-NMe-Leu-l-NAc-Phe) and cyclo(d-6-OH-Pro-l-Phe), respectively. Asperopiperazines A and B displayed higher antimicrobial effects against Escherichia coli and Staphylococcus aureus than Candida albicans. Furthermore, compounds 1-4 displayed variable growth inhibitory effects towards HCT 116 and MDA-MB-231 cells, with asperopiperazine A as the most active one towards HCT 116.

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