ChemInform Abstract: CYCLIC PEPTIDES FROM PENICILLIUM ISLANDICUM. A REVIEW AND A REEVALUATION OF THE STRUCTURE OF ISLANDITOXIN

Ghosh, Anil C.; Ramgopal, Malathi

doi:10.1002/chin.198131312

Cited by 2 publications

(2 citation statements)

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“…Although both D-and L-β-Phe have been encountered from natural sources other than fungi, [14][15][16][17][18][19][20][21] to our knowledge, the only other fungal metabolite containing an L-β-Phe unit is the cyclic peptide cyclochlorotine, produced by Penicillium islandicum. 22,23 The above data reveal that the configuration at C-21 of structure 1 is opposite to that originally proposed for haenamindole. The literature proposal was based on the absence of a ROESY correlation between the two α-protons (H-21 and H-24) of the diketopiperazine unit.…”

Section: Resultsmentioning

confidence: 62%

Haenamindole and fumiquinazoline analogs from a fungicolous isolate of Penicillium lanosum

et al. 2016

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Three amino acid-derived compounds, haenamindole (1) and 2'-epi-fumiquinazolines C (2) and D (3), were isolated from cultures of a fungicolous isolate of Penicillium lanosum (MYC-1813=NRRL 66231). Compound 1 was also encountered in cultures of P. corylophilum (MYC-418=NRRL 28126). Structure elucidation of these metabolites was based mainly on high resolution mass spectrometry and NMR data analysis. Haenamindole (1) was found to be a recently reported diketopiperazine-type metabolite that incorporates an unusual β-Phe unit. Analysis of X-ray crystallographic data and the products of acid hydrolysis of 1 enabled a conclusive, slightly modified stereochemical assignment for haenamindole. Fumiquinazoline analog 2 is a new natural product, while related compound 3 has been previously reported only as a product of an in vitro enzymatic step and of a genetically engineered fungal culture. Compounds 1 and 3 showed antiinsectan activity against the fall armyworm Spodoptera frugiperda.

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Section: Resultsmentioning

confidence: 62%

Haenamindole and fumiquinazoline analogs from a fungicolous isolate of Penicillium lanosum

et al. 2016

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“…Asperphenamate (Phe + Phenylalaninol) (358) P. arenicota (McCorkindale et at., 1978a), P. brevicompactum (Bird and Campbell, 1982a,b) Cydopiamines A and B (isomers) (Trp+ Pro) (359, 360) P. aurantiogriseum, P. griseofutvum (Bond et at., 1979) HOH,cJN~" ;:::: (Marumo, 1959;Yoshioka et at., 1973;Ghosh and Ramgopal, 1980) purpurogenum (Sumiki and Miyao, 1952;Miyao, 1960;Studer, 1969) ~CH_NH-CO~ Amino acid configuration: *L; **0.…”

Section: Several Amino Acidsmentioning

confidence: 99%

Penicillium and Acremonium

Peberdy¹

1987

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v Foreword Biotechnology is a word that was originally coined to describe the new processes which could be derived from our ability to manipulate, in vitro, the genetic material common to all organisms. I t has now become a generic term encompassing all "applications" of living systems, including the more traditional fermentation and agricultural industries. Recombinant DNA technology has opened up new opportunities for the exploitation of microorganisms and animal and plant cells as producers or modifiers of chemical and biological products.This series of handbooks deals exclusively with microorganisms which are at the forefront of the new technologies and brings together in each of its volumes the background information necessary to appreciate the historical development of the organisms making up a particular genus, the degree to which molecular biology has opened up new opportunities, and the place they occupy in today's biotechnology industry. Our aim was to make this primarily a practical approach, with emphasis on methodology, combining for the first time information which has largely been spread across a wide literature base or only touched upon briefly in review articles. Each handbook should provide the reader with a source text, from which the importance of the genus to his or her work can be identified, and a practical guide to the handling and exploitation of the organisms included.It is perhaps apt that Volume I of the series should deal with a group of organisms involved in producing chemicals which have dominated the fermentation and pharmaceutical industries for the past forty years-the antibiotics. In terms of the degree to which molecular biology has made an impact on this genus to date, it is clear that the major rewards are still to come.

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ChemInform Abstract: CYCLIC PEPTIDES FROM PENICILLIUM ISLANDICUM. A REVIEW AND A REEVALUATION OF THE STRUCTURE OF ISLANDITOXIN

Abstract: Die toxischen Cyclopeptide Islanditoxin (I) und Cyclochlorotin (II) aus Penicillium Islandicum werden in ihrer Struktur sichergestellt.

Cited by 2 publications

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Haenamindole and fumiquinazoline analogs from a fungicolous isolate of Penicillium lanosum

Haenamindole and fumiquinazoline analogs from a fungicolous isolate of Penicillium lanosum

Penicillium and Acremonium

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