Astepyrone

Astepyrone

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Astepyrone
Category Antibiotics
Catalog number BBF-00118
CAS 86925-92-0
Molecular Weight 200.19
Molecular Formula C9H12O5

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Description

Astepyrone is an antibiotic produced by Aspergillus terreus (IFO 4100). It has anti-ulcer effect.

Specification

IUPAC Name 2-hydroxy-4-methoxy-3-methyl-2,3,3a,7a-tetrahydrofuro[2,3-b]pyran-6-one
Canonical SMILES CC1C2C(OC1O)OC(=O)C=C2OC
InChI InChI=1S/C9H12O5/c1-4-7-5(12-2)3-6(10)13-9(7)14-8(4)11/h3-4,7-9,11H,1-2H3
InChI Key LJAOHLFTVVVALG-UHFFFAOYSA-N

Properties

Appearance Colorless Crystal
Melting Point 133-134°C

Reference Reading

1. Aromatic Polyketides from a Symbiotic Strain Aspergillus fumigatus D and Characterization of Their Biosynthetic Gene D8.t287
Yi Hua, Rui Pan, Xuelian Bai, Bin Wei, Jianwei Chen, Hong Wang, Huawei Zhang Mar Drugs. 2020 Jun 20;18(6):324. doi: 10.3390/md18060324.
The chemical investigation of one symbiotic strain, Aspergillus fumigatus D, from the coastal plant Edgeworthia chrysantha Lindl led to the isolation of eight compounds (1-8), which were respectively identified as rubrofusarin B (1), alternariol 9-O-methyl ether (2), fonsecinone D (3), asperpyrone A (4), asperpyrone D (5), fonsecinone B (6), fonsecinone A (7), and aurasperone A (8) by a combination of spectroscopic methods (1D NMR and ESI-MS) as well as by comparison with the literature data. An antimicrobial assay showed that these aromatic polyketides exhibited no remarkable inhibitory effect on Escherichia coli, Staphyloccocus aureus and Candida albicans. The genomic feature of strain D was analyzed, as well as its biosynthetic gene clusters, using antibiotics and Secondary Metabolite Analysis Shell 5.1.2 (antiSMASH). Plausible biosynthetic pathways for dimeric naphtho-γ-pyrones 3-8 were first proposed in this work. A non-reducing polyketide synthase (PKS) gene D8.t287 responsible for the biosynthesis of these aromatic polyketides 1-8 was identified and characterized by target gene knockout experiment and UPLC-MS analysis.
2. Asperpyrone, a rare α-pyrone metabolite produced by an endophytic fungus Aspergillus sp. isolated from Garicinia smeathmannii (Planch. & Triana) Oliv
Jean-Bosco Jouda, Emmanuel Mfotie Njoya, Ruland Tchuinkeu Nguengang, Virginie Flaure Tsague Tankeu, Hans-Georg Stammler, Yoshihito Shiono, Norbert Sewald, Alain Meli Lannang Nat Prod Res. 2023 Jan;37(1):8-15. doi: 10.1080/14786419.2021.1944139. Epub 2021 Jun 28.
A new α-pyrone, asperpyrone (1) and two known compounds, stigmasterol (2) and 7-hydroxy-3-(2,3-dihydroxybutyl)-1(3H)-Isobenzofuranone (3) were isolated from the solid rice culture of the endophytic fungus Aspergillus sp., an endophytic fungus isolated from the fresh inner tissue of the barks of Garicinia smeathmannii. Their structures were determined by extensive spectral analysis including 1 D and 2 D NMR, HRESIMS and single-crystal X-ray crystallographic analysis. Asperpyrone (1) was tested against an axenic culture of Entamoeba moshkovskii, but did not exhibit any significant amoebicidal activity.
3. Naphto-Γ-pyrones from the marine-derived fungus Aspergillus foetidus
Alexander S Antonov, Elena V Leshchenko, Olesya I Zhuravleva, Sergey A Dyshlovoy, Gunhild von Amsberg, Roman S Popov, Vladimir A Denisenko, Natalya N Kirichuk, Shamil Sh Afiyatullov Nat Prod Res. 2021 Jan;35(1):131-134. doi: 10.1080/14786419.2019.1610954. Epub 2019 Jun 26.
Nine naphto-γ-pyrones rubrofusarine B (1), TMC 256 A1 (2), fansecinones A (3) and B (4), aurasperones A (5), B (6) and F (7), dianhydro-aurasperone C (8) and asperpyrone B (9) were isolated from the marine-derived fungus Aspergillus foetidus KMM 4694. Their structures were established based on spectroscopic methods. The effect of the substances on viability and colony formation of human drug-resistant prostate cancer 22Rv1 cell was evaluated.

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