Classification Term: 170316
Azaphilones (ontology term: 8b6028b0353c2b38efdd816fc9e4234f)
found 500 associated metabolites at sub_class
metabolite taxonomy ontology rank level.
Ancestor: Chromanes
Child Taxonomies: There is no child term of current ontology term.
Ascochitine
Causes brown rot in broad bean
8-Hydroxy-3,4,5-trimethyl-6-oxo-4,6-dihydro-3H-isochromene-7-carboxylic acid
Epicocconone
Monascin
Monascin is an organic heterotricyclic compound that is 3a,4,8,9a-tetrahydro-2H-furo[3,2-g][2]benzopyran-2,9(3H)-dione that is substituted at positions 3, 6, and 9a by hexanoyl, (1E)-prop-1-en-1-yl and methyl groups, respectively (the 3S,3aR,9aR diastereoisomer). One of the azaphilonoid pigments in extracts of Monascus pilosus-fermented rice (red-mould rice), it is a potent inhibitor of carcinogenesis measured against chemical- or UV-initiated, phorbol-promoted mouse skin tumours. It has a role as an antineoplastic agent, a PPARgamma agonist, an antilipemic drug and a fungal metabolite. It is an organic heterotricyclic compound, a gamma-lactone, an alpha,beta-unsaturated ketone and a polyketide. Monascin is a natural product found in Monascus kaoliang, Monascus purpureus, and Monascus pilosus with data available. An organic heterotricyclic compound that is 3a,4,8,9a-tetrahydro-2H-furo[3,2-g][2]benzopyran-2,9(3H)-dione that is substituted at positions 3, 6, and 9a by hexanoyl, (1E)-prop-1-en-1-yl and methyl groups, respectively (the 3S,3aR,9aR diastereoisomer). One of the azaphilonoid pigments in extracts of Monascus pilosus-fermented rice (red-mould rice), it is a potent inhibitor of carcinogenesis measured against chemical- or UV-initiated, phorbol-promoted mouse skin tumours.
asperfuranone
A member of the class of 2-benzofurans that is 6,7-dihydro-2-benzofuran-4(5H)-one that is substituted at positions 5 and 6 by hydroxy groups, at position 5 by a methyl group and at position 1 by a (2E,4E,6S)-4,6-dimethylocta-2,4-dienoyl group (the 5S,6R-diastereoisomer). A polyketide that was first obtained from the fungus Aspergillus nidulans by using a genomic mining approach.
Chaetoviridin C
An azaphilone that is 9,9a-dihydro-6H-furo[2,3-h]isochromene-6,8(6aH)-dione substituted by a chloro group at position 5, a 3-hydroxy-2-methylbutanoyl group at position 9, a methyl group at position 6a and a 3-methylpent-1-en-1yl group at position 3. It has been isolated from Chaetomium globosum.
comazaphilone D
An azaphilone that is 5,6,7,8-tetrahydro-1H-isochromene substituted by a hydroxy and methyl group at position 7, an oxo group at position 8, a prop-1-en-1-yl group at position 3 and a (2,4-dihydroxy-6-methylbenzoyl)oxy group at position 6.Isolated from Penicillium commune, it exhibits antibacterial and antineoplastic activities.
comazaphilone A
An azaphilone that is 5,6,7,8-tetrahydro-1H-isochromene substituted by a hydroxy group at position 6, a methyl group at position 7, an oxo group at position 8, a propyl group at position 3 and a (4-hydroxy-2-methoxy-6-methylbenzoyl)oxy group at position 7. It has been isolated from Penicillium commune.
comazaphilone F
An azaphilone that is 5,6,7,8-tetrahydro-1H-isochromene substituted by a hydroxy group and a methyl group at position 7, an oxo group at position 8, a propyl group at position 3 and a (3,4-dihydroxy-2-methoxy-6-methylbenzoyl)oxy group at position 6. Isolated from Penicillium commune, it exhibits antibacterial and antineoplastic activities.
(7R,8S)-7,8-dihydroxy-3,7-dimethyl-6-oxo-8H-isochromene-5-carbaldehyde
Harziphilone
A member of the class of isochromanes that is 1,5,6,7-tetrahydro-8H-isochromen-8-one substituted by hydroxy groups at positions 6 and 7, a methyl group at position 7 and a penta-1,3-dien-1-yl moiety at position 3. Isolated from the fermentation broth of Trichoderma harzianum, it exhibits anti-HIV activity.
Purpurquinone A
An azaphilone that is 1H-isochromene-6,8(7H,8aH)-dione substituted by a prop-1-en-1-yl group at position 3, hydroxy groups at positions 1 and 8a, a methyl group at position 7 and a (2,4-dihydroxy-6-methylbenzoyl)oxy group at position 7. It has been isolated from Penicillium purpurogenum.
Rotiorinol A
An azaphilone that is 9,9a-dihydro-2H-furo[3,2-g]isochromen-2-one substituted by an acetyl group at position 3, a hydroxy group at position 9, a 3,5-dimethylhepta-1,3-dien-1-yl group at position 6 and a methyl group at position 9a. It has been isolated from Chaetomium cupreum and exhibits antifungal activity.
Purpurquinone B
An azaphilone that is 1H-isochromene-6,8(7H,8aH)-dione substituted by a prop-1-en-1-yl group at position 3, hydroxy groups at positions 1 and 8a, a methyl group at position 7 and a (3,4,6-trihydroxy-2-methylbenzoyl)oxy group at position 7. It has been isolated from Penicillium purpurogenum.
Purpurquinone C
An azaphilone that is 1H-isochromene-6,8(7H,8aH)-dione substituted by a prop-1-en-1-yl group at position 3, a hydroxy group at position 8a, a methyl group at position 7 and a (2,4-dihydroxy-6-methylbenzoyl)oxy group at position 7. It has been isolated from Penicillium purpurogenum.
epi-isochromophilone II
An azaphilone that is 7,8-dihydro-6H-isochromen-6-one substituted by a chloro group at position 5, a 3,5-dimethylhepta-1,3-dien-1-yl group at position 3, a hydroxy group at position 7, a methyl group at position 7 and a 2-oxopropyl group at position 8. Isolated from Chaetomium cupreum, it exhibits antifungal activity.
chaetomugilin A
An azaphilone isolated from Chaetomium globosum and has been shown to exhibit inhibitory activity against the brine shrimp (Artemia salina) and Mucor miehei.
7,8-dihydroxy-3,5,7-trimethyl-8,8a-dihydro-1H-isochromen-6-one
Chaetoviridin H
An azaphilone that is 6H-furo[2,3-h]isochromene-6,8(6aH)-dione substituted by a 3-hydroxy-2-methylbutanoyl group at position 9, a methyl group at position 6a and a 3-methylpent-1-en-1yl group at position 3. It has been isolated from Chaetomium globosum.
longirostrerone C
An azaphilone that is 9,9a-dihydro-6H-furo[2,3-h]isochromene-6,8(6aH)-dione substituted by a 6-methyl-2-oxocyclohex-3-en-1-yl group at position 3, a methyl group at position 6a and a 4,6,8-trimethyldeca-2,4-dienoyl group at position 9. Isolated from Chaetomium longirostre, it exhibits cytotoxic and antimalarial activities.
Chaetoviridin G
An azaphilone that is 9,9a-dihydro-6H-furo[2,3-h]isochromene-6,8(6aH)-dione substituted by a chloro group at position 5, a methyl group at position 6a, a 2-methylbut-2-enoyl group at position 9 and a 3-methylpent-1-en-1-yl group at position 3. It has been isolated from Chaetomium globosum.
Longirostrerone B
An azaphilone that is 7,8-dihydro-6H-isochromen-6-one substituted by a hydroxy group at position 7, a 4-hydroxy-2-methyl-6-oxocyclohexyl group at position 3, a methyl group at position 7 and a 5,7,9-trimethyl-2-oxoundeca-3,5-dien-1-yl group at position 8. Isolated from Chaetomium longirostre, it exhibits cytotoxic and antimalarial activities.