New cytotoxic cyclic peptides and dianthramide from Dianthus superbus

J Nat Prod. 2004 Sep;67(9):1522-7. doi: 10.1021/np040036v.

Abstract

Four new cyclic peptides, dianthins C-F (1-4), and a new dianthramide, 4-methoxydianthramide B (5), were isolated from the MeOH extract of the traditional Chinese medicinal plant Dianthus superbus. The sequences of cyclic peptides 1-4 were elucidated as cyclo(Gly(1)-Pro(2)-Phe(3)-Tyr(4)-Val(5)-Ile(6)-), cyclo(Gly(1)-Ser(2)-Leu(3)-Pro(4)-Pro(5)-Ile(6)-Phe(7)-), cyclo(Gly(1)-Pro(2)-Ile(3)-Ser(4)-Phe(5)-Val(6)-), and cyclo(Gly(1)-Pro(2)-Phe(3)-Val(4)-Phe(5)-) on the basis of ESI tandem mass fragmentation analysis, chemical evidence, and extensive 2D NMR methods. The conformation of compound 1 was established as an alpha-helix by CD analysis. Furthermore, compounds 3 and 5 showed cytotoxicities toward the Hep G2 cancer cell line with IC(50) values of 2.37 and 4.08, respectively.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amino Acid Sequence
  • Antineoplastic Agents, Phytogenic / chemistry
  • Antineoplastic Agents, Phytogenic / isolation & purification*
  • Antineoplastic Agents, Phytogenic / pharmacology
  • Circular Dichroism
  • Dianthus / chemistry*
  • Drug Screening Assays, Antitumor
  • Inhibitory Concentration 50
  • Peptides, Cyclic / chemistry
  • Peptides, Cyclic / isolation & purification*
  • Peptides, Cyclic / pharmacology
  • Plant Proteins / chemistry
  • Plant Proteins / isolation & purification*
  • Plant Proteins / pharmacology
  • Plants, Medicinal / chemistry*
  • Ribosome Inactivating Proteins, Type 1
  • Tumor Cells, Cultured

Substances

  • Antineoplastic Agents, Phytogenic
  • Peptides, Cyclic
  • Plant Proteins
  • Ribosome Inactivating Proteins, Type 1