Vermistatin
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| Category | Antibiotics |
| Catalog number | BBF-05562 |
| CAS | 72669-21-7 |
| Molecular Weight | 328.32 |
| Molecular Formula | C18H16O6 |
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Description
It is a new metabolite from mine-dwelling Penicillium vermiculatum. It is an antibiotic with cytotoxic effects.
Specification
| Synonyms | (R,E)-4,6-dimethoxy-3-(4-oxo-6-(prop-1-en-1-yl)-4H-pyran-3-yl)isobenzofuran-1(3H)-one; Fijiensin; (-)-Fijiensin; NSC 656107; 1(3H)-Isobenzofuranone, 4,6-dimethoxy-3-(4-oxo-6-(1-propenyl)-4H-pyran-3-yl)-, (R)-; 5-(4,6-Dimethoxy-3R-phthalidy)-2-(1E)-propenyl-4H-pyran-4-one |
| Storage | Store at RT |
| IUPAC Name | (3R)-4,6-dimethoxy-3-[4-oxo-6-[(E)-prop-1-enyl]pyran-3-yl]-3H-2-benzofuran-1-one |
| Canonical SMILES | CC=CC1=CC(=O)C(=CO1)C2C3=C(C=C(C=C3OC)OC)C(=O)O2 |
| InChI | InChI=1S/C18H16O6/c1-4-5-10-7-14(19)13(9-23-10)17-16-12(18(20)24-17)6-11(21-2)8-15(16)22-3/h4-9,17H,1-3H3/b5-4+/t17-/m0/s1 |
| InChI Key | YORFGPDHNOBVBM-BDUNBXCCSA-N |
Properties
| Appearance | Solid |
| Boiling Point | 580.7°C at 760 mmHg |
| Density | 1.367 g/cm3 |
Reference Reading
1. New polyketides from the basidiomycetous fungus Pholiota sp
Jie Lin, Rui-Yun Huo, Lin Hou, Shan Jiang, Shu-Lin Wang, Yan-Ling Deng, Ling Liu J Asian Nat Prod Res. 2022 Oct 17;1-9. doi: 10.1080/10286020.2022.2132481. Online ahead of print.
Two new polyketides, pholiotones B and C (1 and 2), and four known compounds, trichodermatide D (3), vermistatin (4), dehydroaltenuene A (5) and terpestacin (6) were isolated from the crude extract of Pholiota sp. Their structures were identified by NMR and MS spectroscopic data. The absolute configurations of compounds 1 and 2 were elucidated by modified Mosher's method, electronic circular dichroism (ECD) calculations and 13C NMR calculations as well as DP4+ probability analyses. All the compounds were evaluated for their antifungal and cytotoxicity.
2. Vermistatin derivatives with α-glucosidase inhibitory activity from the mangrove endophytic fungus Penicillium sp. HN29-3B1
Yayue Liu, Guoping Xia, Hanxiang Li, Lin Ma, Bo Ding, Yongjun Lu, Lei He, Xuekui Xia, Zhigang She Planta Med. 2014 Jul;80(11):912-7. doi: 10.1055/s-0034-1382859. Epub 2014 Aug 12.
Three new vermistatin derivatives, 6-demethylpenisimplicissin (1), 5'-hydroxypenisimplicissin (2), and 2''-epihydroxydihydrovermistatin (3), along with five known vermistatin analogues, methoxyvermistatin (4), vermistatin (5), 6-demethylvermistatin (6), hydroxyvermistatin (7), and penisimplicissin (8), were isolated from the culture of the mangrove endophytic fungus Penicillium sp. HN29-3B1 from Cerbera manghas. Their structures were elucidated mainly by nuclear magnetic resonance spectroscopy. The absolute configurations of compounds 1 and 2 were deduced on the basis of circular dichroism data. The absolute structures of compounds 3 and 5 were confirmed by a single-crystal X-ray diffraction experiment using Cu Kα radiation. In the bioactivity assay, compounds 1 and 3 exhibited α-glucosidase inhibitory activity with IC50 values of 9.5 ± 1.2 and 8.0 ± 1.5 µM, respectively. The plausible biosynthetic pathways for all compounds are discussed.
3. Eurothiocin A and B, sulfur-containing benzofurans from a soft coral-derived fungus Eurotium rubrum SH-823
Zhaoming Liu, Guoping Xia, Senhua Chen, Yayue Liu, Hanxiang Li, Zhigang She Mar Drugs. 2014 Jun 20;12(6):3669-80. doi: 10.3390/md12063669.
Two new sulfur-containing benzofuran derivatives, eurothiocin A and B (1 and 2), along with five known compounds, zinniol (3), butyrolactone I (4), aspernolide D (5), vermistatin (6), and methoxyvermistatin (7), were isolated from the cultures of Eurotium rubrum SH-823, a fungus obtained from a Sarcophyton sp. soft coral collected from the South China Sea. The new compounds (1 and 2) share a methyl thiolester moiety, which is quite rare among natural secondary metabolites. The structures of these metabolites were assigned on the basis of detailed spectroscopic analysis. The absolute configurations of 1 and 2 were determined by comparison of the experimental and calculated electronic circular dichroism (ECD) data. Compounds 1 and 2 exhibited more potent inhibitory effects against α-glucosidase activity than the clinical α-glucosidase inhibitor acarbose. Further mechanistic analysis showed that both of them exhibited competitive inhibition characteristics.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
