The cytochalasins, a new class of biologically active mould metabolites

Aldridge, David C.; Armstrong, J. J.; Speake, R. N.; Turner, W. B.

doi:10.1039/c19670000026

Cited by 64 publications

(63 citation statements)

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“…Cytochalasin C and D have been isolated from the entomopathogenic fungus M. anisopliae (Aldridge et al, 1967a; Aldridge and Turner, 1969). Like cytochalasin E and K, both cytochalasin C and D are derived from octaketide chain and contain a benzyl group originated from phenylalanine but lack the vinyl carbonate moeity (Figure 1).…”

Section: Resultsmentioning

confidence: 99%

Identification and engineering of the cytochalasin gene cluster from Aspergillus clavatus NRRL 1

Qiao

Chooi

Tang

2011

Metabolic Engineering

122

124

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Cytochalasins are a group of fungal secondary metabolites with diverse structures and bioactivities, including cytochalasin E produced by Aspergillus clavatus, which is a potent anti-angiogenic agent. Here, we report the identification and characterization of the cytochalasin gene cluster from A. clavatus NRRL 1. As a producer of cytochalasin E and K, the genome of A. clavatus was analyzed and the ~30 kb ccs gene cluster was identified based on the presence of a polyketide synthase-nonribosomal peptide synthetases (PKS-NRPS) and a putative Baeyer-Villiger monooxygenase (BVMO). Deletion of the central PKS-NRPS gene, ccsA, abolished the production of cytochalasin E and K, confirming the association between the natural products and the gene cluster. Based on bioinformatic analysis, a putative biosynthetic pathway is proposed. Furthermore, overexpression of the pathway specific regulator ccsR elevated the titer of cytochalasin E from 25 mg/L to 175 mg/L. Our results not only shed light on the biosynthesis of cytochalasins, but also provided genetic tools for increasing and engineering the production.

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Section: Resultsmentioning

confidence: 99%

Identification and engineering of the cytochalasin gene cluster from Aspergillus clavatus NRRL 1

Qiao

Chooi

Tang

2011

Metabolic Engineering

122

124

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“…In certain cases, the ring system can be oxidized to an unusual cyclic carbonate as observed for cytochalasin E ( 53 ). Depending on the amino acid incorporated in the isoindolone moiety, the cytochalasans can be further subdivided into cytochalasins [41] (phenylalanine), chaetoglobosins [45–46] (tryptophan), aspochalasins [47] (leucine), pyrichalasins [48] (tyrosine) or alachalasins [49–50] (alanine).…”

Section: Reviewmentioning

confidence: 99%

The chemistry of isoindole natural products

Speck¹,

Magauer²

2013

Beilstein J. Org. Chem.

296

163

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SummaryThis review highlights the chemical and biological aspects of natural products containing an oxidized or reduced isoindole skeleton. This motif is found in its intact or modified form in indolocarbazoles, macrocyclic polyketides (cytochalasan alkaloids), the aporhoeadane alkaloids, meroterpenoids from Stachybotrys species and anthraquinone-type alkaloids. Concerning their biological activity, molecular structure and synthesis, we have limited this review to the most inspiring examples. Within different congeners, we have selected a few members and discussed the synthetic routes in more detail. The putative biosynthetic pathways of the presented isoindole alkaloids are described as well.

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“…Rothweiler i Tamm 3 i godinu dana poslije Aldridge i sur. 4 izolirali su prva dva spoja iz skupine citohalazina, citohalazin B 7 i D 8 (slika 5). Citohalazini su skupina od dvadesetak citostatički aktivnih metabolita izoliranih iz gljivica, građeni od visokosupstituirane hidrogenirane izoindolinske jezgre kondenzirane na 11-ili 14-eročlani makrociklički prsten.…”

Section: Prirodni I Sintetski Derivati Izoindolinaunclassified

Derivati izoindolina, sinteza i biološka aktivnost. I. Prirodni i sintetski derivati izoindolina

Karminski‐Zamola¹

2014

Kem. Ind.

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The cytochalasins, a new class of biologically active mould metabolites

Cited by 64 publications

References 0 publications

Identification and engineering of the cytochalasin gene cluster from Aspergillus clavatus NRRL 1

Identification and engineering of the cytochalasin gene cluster from Aspergillus clavatus NRRL 1

The chemistry of isoindole natural products

Derivati izoindolina, sinteza i biološka aktivnost. I. Prirodni i sintetski derivati izoindolina

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