Vermistatin

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Vermistatin
Vermistatin Structure.svg
Names
Preferred IUPAC name
(3R)-4,6-Dimethoxy-3-{4-oxo-6-[(1E)-prop-1-en-1-yl]-4H-pyran-3-yl}-2-benzofuran-1(3H)-one
Other names
5-(4,6-Dimethoxyphthalidyl)-2-propenyl-4H-pyran-4-one
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
PubChem CID
UNII
  • 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
    Key: YORFGPDHNOBVBM-BDUNBXCCSA-N
  • InChI=1/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
    Key: YORFGPDHNOBVBM-BDUNBXCCBS
  • C/C=C/C1=CC(=O)C(=CO1)[C@H]2C3=C(C=C(C=C3C(=O)O2)OC)OC
Properties
C18H16O6
Molar mass 328.320 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Vermistatin is an organic compound and a metabolite of mine-dwelling Penicillium vermiculatum found in Berkeley Pit Lake, Butte, Montana. [1] Penisimplicissin is a vermistatin analog with anticancer activity. [2]

Related Research Articles

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Penicillium rubens is a species of fungus in the genus Penicillium and was the first species known to produce the antibiotic penicillin. It was first described by Philibert Melchior Joseph Ehi Biourge in 1923. For the discovery of penicillin from this species Alexander Fleming shared the Nobel Prize in Physiology or Medicine in 1945. The original penicillin-producing type has been variously identified as Penicillium rubrum, P. notatum, and P. chrysogenum among others, but genomic comparison and phylogenetic analysis in 2011 resolved that it is P. rubens. It is the best source of penicillins and produces benzylpenicillin (G), phenoxymethylpenicillin (V) and octanoylpenicillin (K). It also produces other important bioactive compounds such as andrastin, chrysogine, fungisporin, roquefortine, and sorbicillins.

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Penicillium pinophilum is a species of fungus in the genus Penicillium which was isolated from a radio set in Papua New Guinea. Penicillium pinophilum produces 3-O-methylfunicone and mycophenolic acid

Penicillium solitum is an anamorphic, mesophilic, salinity-tolerant, and psychrotolerant species of fungus in the genus Penicillium. It is known to produce various compounds including polygalacturonase, compactin, cyclopenin, cyclopenol, cyclopeptin, dehydrocompactin, dihydrocyclopeptin, palitantin, solistatin, solistatinol, viridicatin, viridicatol.

References

  1. Fuska, J; Uhrín, D; Proksa, B; Votický, Z; Ruppeldt, J (1986). "The structure of vermistatin, a new metabolite from Penicillium vermiculatum". The Journal of Antibiotics. 39 (11): 1605–8. doi: 10.7164/antibiotics.39.1605 . PMID   3793630.
  2. Stierle AA, Stierle DB, Girtsman T (2012). "Caspase-1 inhibitors from an extremophilic fungus that target specific leukemia cell lines". J Nat Prod. 75 (3): 344–50. doi:10.1021/np200414c. PMC   3330824 . PMID   22295871.