An Antitumor Antibiotic Produced by Penicillium Stipitatum Thom; Its Identity With Duclauxin

Kuhr, I.; Fuska, J.; Sedmera, Petr; Podojil, M.; Vokoun, J.; Ванек, З.

doi:10.7164/antibiotics.26.535

Cited by 33 publications

(22 citation statements)

References 5 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…16 Flasks were inoculated with 1 mL of G, spores of P. herquei (Figure 1). 16 Flasks were inoculated with 1 mL of G, spores of P. herquei (Figure 1).…”

Section: Resultsmentioning

confidence: 99%

See 1 more Smart Citation

Properties and Cost Effective Method for Production of the Antitumor Agent Duclauxin from Sporulating Penicillium herquei

Bryant

Cutler

Jacyno

1993

Journal of Pharmaceutical Sciences

View full text Add to dashboard Cite

Duclauxin, an antitumor agent, was isolated from sporulating Penicillium herquei (ATCC34665) grown on a medium of peanut hulls supplemented with potato starch solution (termed "Gostar"). The medium was inoculated with a sporulating subculture of P. herquei established on a 2% potato starch slurry supplemented with mineral salts. The P. herquei grew as well on Gostar as on an enriched medium. Duclauxin was isolated in crystalline form from Gostar-grown P. herquei. Comparison of costs of duclauxin obtained from inexpensive Gostar versus costly enriched media indicated that Gostar reduces production expenses. Duclauxin was not effective as an antibiotic against certain species of gram-positive and gram-negative bacteria, fungi, and viruses, but a concentration-dependent inhibition of wheat coleoptile growth was observed. Duclauxin was characterized by melting point, optical rotation, IR and NMR spectroscopy, MS and X-ray diffraction.

show abstract

“…16 Flasks were inoculated with 1 mL of G, spores of P. herquei (Figure 1). 16 Flasks were inoculated with 1 mL of G, spores of P. herquei (Figure 1).…”

Section: Resultsmentioning

confidence: 99%

“…16 Physical Analyses-The melting point (mp) was measured on a Kofler block (hot-stage microscope apparatus) and is uncorrected. 16 Physical Analyses-The melting point (mp) was measured on a Kofler block (hot-stage microscope apparatus) and is uncorrected.…”

Section: Extraction Of Duclauxin From P Herquei Grown On Gostarmentioning

confidence: 99%

Properties and Cost Effective Method for Production of the Antitumor Agent Duclauxin from Sporulating Penicillium herquei

Bryant

Cutler

Jacyno

1993

Journal of Pharmaceutical Sciences

View full text Add to dashboard Cite

show abstract

“…[3][4][5][6] This strain was previously studied by Cox et al for the biosynthesis of tropolones. 7 A recent study of Penicillium mangini by Huang and coworkers led to the structure revision of duclauxin (8) and derivatives, correcting a long-standing misrepresentation of the absolute configuration of C-9′.…”

mentioning

confidence: 99%

Antimicrobial Oligophenalenone Dimers from the Soil Fungus Talaromyces stipitatus

et al. 2016

View full text Add to dashboard Cite

New polyketide-derived oligophenalenone dimers, 9a-epi-bacillisporin E (1) and bacillisporins F−H (2−5), along with the known bacillisporin A (6), were isolated from the fungus Talaromyces stipitatus. Their structures and absolute configurations were determined on the basis of spectroscopic analyses, electronic circular dichroism, and GIAO NMR shift calculation followed by DP4 analysis. The antimicrobial activity of these compounds was evaluated against a panel of human pathogenic bacteria. Among them, bacillisporin H (5) exhibited antimicrobial activity together with modest cytotoxicity against HeLa cells.

show abstract

“…Duclauxin is a heptacyclic molecule containing an isocoumarin and a dihydroisocoumarin group. The compound is produced by several Penicillium species (Shibata, Ogihara, Tokutake & Tanaka, 1965;Kuhr et al, 1973;Bryant, Cutler & Jacyno, 1993a) and it is an effective agent against numerous tumor cell types (Fuskova, Proksa & Fuska, 1977;Kawai & Nozawa, 1982;Shiojiri, Kawai, Kato, Ogihara & Nozawa, 1983;Kovac, Bohmerova & Fuska, 1978;Kawai et al, 1985;Bryant, Cutler & Jacyno, 1993b). Duclauxin prevents ATP synthesis by inhibiting mitochondrial respiration.…”

Section: Commentmentioning

confidence: 99%

Duclauxin Ethyl Acetate Solvate, 2C29H22O11.C4H8O2

Bryant¹,

Cutler²,

Burla³

et al. 1995

Acta Crystallogr C

View full text Add to dashboard Cite

Duclauxin, [8R-(8a,8afl,15afl,15ba,16S*)]-16-(acetyloxy)-8a, 15a-dihydro-4,1 l-dihydroxy-8a-methoxy-6,9-dimethyl-7H-8,15b-methano-1H,3H, 12H-benzo-[de]cyclohepta[ 1,2-g: 3,4, 5-d'e']bis[2]benzopyran-3,7,-12,15(8H)-tetrone, cocrystallized with ethyl acetate solvent (2:1). Duclauxin, an antitumor agent, when isolated from Penicillium herquei displays an unusually low melting point (469-471 K) compared with duclauxin from P. duclauxii or P. stipitatum (503 and 508-509 K, respectively), even though all spectral characterizations of duclauxin from these three sources indicate identical substances. The X-ray structural analysis of duclauxin from P. herquei reveals the presence of an ethyl acetate molecule, which is a likely explanation for the abnormal melting point. The duclauxin molecular structure consists of two largely planar halves which are held by the remaining atoms into an approximate open clam-shell configuration. Significant intramolecular hydrogen bonding is observed between the phenolic hydroxyl groups and lactonic carbonyl O atoms; the only significant intermolecular hydrogen bonding is between the ketonic 0(3) atom of one duclauxin molecule to the phenolic 0(6) atom in the other. There are no especially close intermolecular contacts between ethyl acetate and either of the duclauxin molecules.

show abstract

An Antitumor Antibiotic Produced by Penicillium Stipitatum Thom; Its Identity With Duclauxin

Cited by 33 publications

References 5 publications

Properties and Cost Effective Method for Production of the Antitumor Agent Duclauxin from Sporulating Penicillium herquei

Properties and Cost Effective Method for Production of the Antitumor Agent Duclauxin from Sporulating Penicillium herquei

Antimicrobial Oligophenalenone Dimers from the Soil Fungus Talaromyces stipitatus

Duclauxin Ethyl Acetate Solvate, 2C29H22O11.C4H8O2

Contact Info

Product

Resources

About