Roseabol A, a New Peptaibol from the Fungus Clonostachys rosea

A new 11 amino acid linear peptide named roseabol A (1) and the known compound 13-oxo-trans-9,10-epoxy-11(E)-octadecenoic acid (2) were isolated from the fungus Clonostachys rosea. Combined NMR and MS analysis revealed that roseabol A (1) contained amino acid residues characteristic of the peptaibol...

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Published inMolecules (Basel, Switzerland) Vol. 26; no. 12; p. 3594
Main Authors Kim, Chang-Kwon, Krumpe, Lauren R. H., Smith, Emily, Henrich, Curtis J., Brownell, Isaac, Wendt, Karen L., Cichewicz, Robert H., O’Keefe, Barry R., Gustafson, Kirk R.
Format Journal Article
LanguageEnglish
Published Basel MDPI AG 11.06.2021
MDPI
Subjects
Alzheimer's disease
Amino acid sequence
Amino acids
Carbon
Clonostachys rosea
Fungi
Hydroxyproline
Merkel cell carcinoma
Metabolites
Nucleotide sequence
peptaibol
Peptides
Skin cancer
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Abstract A new 11 amino acid linear peptide named roseabol A (1) and the known compound 13-oxo-trans-9,10-epoxy-11(E)-octadecenoic acid (2) were isolated from the fungus Clonostachys rosea. Combined NMR and MS analysis revealed that roseabol A (1) contained amino acid residues characteristic of the peptaibol family of peptides such as isovaline, α-aminoisobutyric acid, hydroxyproline, leucinol, and an N-terminal isovaleric acid moiety. The amino acid sequence was established by a combination of NMR studies and tandem MS fragmentation analyses, and the absolute configurations of the constituent amino acids of 1 were determined by the advanced Marfey’s method. Compound 2 showed inhibitory activity against Merkel cell carcinoma, a rare and difficult-to-treat type of skin cancer, with an IC50 value of 16.5 μM.
AbstractList A new 11 amino acid linear peptide named roseabol A (1) and the known compound 13-oxo-trans-9,10-epoxy-11(E)-octadecenoic acid (2) were isolated from the fungus Clonostachys rosea. Combined NMR and MS analysis revealed that roseabol A (1) contained amino acid residues characteristic of the peptaibol family of peptides such as isovaline, α-aminoisobutyric acid, hydroxyproline, leucinol, and an N-terminal isovaleric acid moiety. The amino acid sequence was established by a combination of NMR studies and tandem MS fragmentation analyses, and the absolute configurations of the constituent amino acids of 1 were determined by the advanced Marfey’s method. Compound 2 showed inhibitory activity against Merkel cell carcinoma, a rare and difficult-to-treat type of skin cancer, with an IC50 value of 16.5 μM.
A new 11 amino acid linear peptide named roseabol A ( 1 ) and the known compound 13-oxo- trans -9,10-epoxy-11( E )-octadecenoic acid ( 2 ) were isolated from the fungus Clonostachys rosea . Combined NMR and MS analysis revealed that roseabol A ( 1 ) contained amino acid residues characteristic of the peptaibol family of peptides such as isovaline, α -aminoisobutyric acid, hydroxyproline, leucinol, and an N -terminal isovaleric acid moiety. The amino acid sequence was established by a combination of NMR studies and tandem MS fragmentation analyses, and the absolute configurations of the constituent amino acids of 1 were determined by the advanced Marfey’s method. Compound 2 showed inhibitory activity against Merkel cell carcinoma, a rare and difficult-to-treat type of skin cancer, with an IC 50 value of 16.5 μM.
Author Wendt, Karen L.
Henrich, Curtis J.
Smith, Emily
O’Keefe, Barry R.
Kim, Chang-Kwon
Brownell, Isaac
Krumpe, Lauren R. H.
Gustafson, Kirk R.
Cichewicz, Robert H.
AuthorAffiliation 1 Molecular Targets Program, Center for Cancer Research, National Cancer Institute, Frederick, MD 21702, USA; kck100639@gmail.com (C.-K.K.); haughl@mail.nih.gov (L.R.H.K.); emily.smith2@nih.gov (E.S.); curtis.henrich2@nih.gov (C.J.H.); okeefeba@mail.nih.gov (B.R.O.)
2 Basic Science Program, Frederick National Laboratory for Cancer Research, Frederick, MD 21702, USA
4 Natural Products Discovery Group, Department of Chemistry and Biochemistry, University of Oklahoma, Norman, OK 73019, USA; klwendt@ou.edu (K.L.W.); rhcichewicz@ou.edu (R.H.C.)
5 Natural Products Branch, Developmental Therapeutics Program, Division of Cancer Treatment and Diagnosis, National Cancer Institute, Frederick, MD 21701, USA
3 Dermatology Branch, National Institute of Arthritis and Musculoskeletal and Skin Diseases, Bethesda, MD 20893, USA; isaac.brownell@nih.gov
AuthorAffiliation_xml – name: 3 Dermatology Branch, National Institute of Arthritis and Musculoskeletal and Skin Diseases, Bethesda, MD 20893, USA; isaac.brownell@nih.gov
– name: 1 Molecular Targets Program, Center for Cancer Research, National Cancer Institute, Frederick, MD 21702, USA; kck100639@gmail.com (C.-K.K.); haughl@mail.nih.gov (L.R.H.K.); emily.smith2@nih.gov (E.S.); curtis.henrich2@nih.gov (C.J.H.); okeefeba@mail.nih.gov (B.R.O.)
– name: 4 Natural Products Discovery Group, Department of Chemistry and Biochemistry, University of Oklahoma, Norman, OK 73019, USA; klwendt@ou.edu (K.L.W.); rhcichewicz@ou.edu (R.H.C.)
– name: 2 Basic Science Program, Frederick National Laboratory for Cancer Research, Frederick, MD 21702, USA
– name: 5 Natural Products Branch, Developmental Therapeutics Program, Division of Cancer Treatment and Diagnosis, National Cancer Institute, Frederick, MD 21701, USA
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crossref_primary_10_1007_s11030_024_10815_x
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    fullname: Lin
– volume: 31
  start-page: 1348
  year: 2014
  ident: ref_2
  article-title: New insights into the echinocandins and other fungal non-ribosomal peptides and peptaibiotics
  publication-title: Nat. Prod. Rep.
  doi: 10.1039/C4NP00046C
  contributor:
    fullname: Bills
SSID ssj0021415
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Snippet A new 11 amino acid linear peptide named roseabol A (1) and the known compound 13-oxo-trans-9,10-epoxy-11(E)-octadecenoic acid (2) were isolated from the...
A new 11 amino acid linear peptide named roseabol A ( 1 ) and the known compound 13-oxo- trans -9,10-epoxy-11( E )-octadecenoic acid ( 2 ) were isolated from...
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StartPage 3594
SubjectTerms Alzheimer's disease
Amino acid sequence
Amino acids
Carbon
Clonostachys rosea
Fungi
Hydroxyproline
Merkel cell carcinoma
Metabolites
Nucleotide sequence
peptaibol
Peptides
Skin cancer
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Title Roseabol A, a New Peptaibol from the Fungus Clonostachys rosea
URI https://www.proquest.com/docview/2545012247
https://search.proquest.com/docview/2548394961
https://pubmed.ncbi.nlm.nih.gov/PMC8231123
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Volume 26
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