Tunicyclin A, the first plant tricyclic ring cycloheptapeptide from Psammosilene tunicoides

Org Lett. 2009 Mar 5;11(5):1131-3. doi: 10.1021/ol8029577.

Abstract

A novel cycloheptapeptide, tunicyclin A, with a unique tricyclic ring cyclopeptide skeleton, was isolated from Psammosilene tunicoides. Its structure was elucidated by extensive NMR and MS analysis. Biogenetically, tunicyclin A might be derived from cyclo-(Pro(1)-Ser(2)-(gamma-keto-delta-aldehedyl-Glu(3))-Leu(4)-Val(5)-Gly(6)-Ser(7)) via two steps of nucleophilic addition.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amino Acid Sequence
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / isolation & purification*
  • Antineoplastic Agents / pharmacology
  • Caryophyllaceae / chemistry*
  • Doxorubicin / pharmacology
  • Drug Screening Assays, Antitumor
  • Drugs, Chinese Herbal / chemistry
  • Drugs, Chinese Herbal / isolation & purification*
  • Drugs, Chinese Herbal / pharmacology
  • HL-60 Cells
  • Humans
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Peptides, Cyclic / chemistry
  • Peptides, Cyclic / isolation & purification*
  • Peptides, Cyclic / pharmacology

Substances

  • Antineoplastic Agents
  • Drugs, Chinese Herbal
  • Peptides, Cyclic
  • tunicyclin A
  • Doxorubicin