A new diketopiperazine, cyclo-(4-S-hydroxy-R-proline-R-isoleucine), from an Australian specimen of the sponge Stelletta sp

Mar Drugs. 2011;9(11):2469-2478. doi: 10.3390/md9112469. Epub 2011 Nov 22.

Abstract

While investigating the cytotoxic activity of the methanol extract of an Australian marine sponge Stelletta sp. (Demospongiae), a new diketopiperazine, cyclo-(4-S-hydroxy-R-proline-R-isoleucine) (1), was isolated together with the known bengamides; A (2), F (3), N (4), Y (5), and bengazoles; Z (6), C(4) (7) and C(6) (8). The isolation and structure elucidation of the diketopiperazine (1), together with the activity of 1-8 against a panel of human and mammalian cell lines are discussed.

Keywords: Stelletta; anti-cancer activity; bengamide; bengazole; cyclo-(4-S-hydroxy-R-proline-R-isoleucine); diketopiperazine (DKP).

MeSH terms

  • Animals
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / isolation & purification
  • Antineoplastic Agents / pharmacology
  • Australia
  • Azepines / chemistry
  • Azepines / isolation & purification
  • Azepines / pharmacology*
  • Cell Line
  • Cell Line, Tumor
  • Diketopiperazines / chemistry
  • Diketopiperazines / isolation & purification
  • Diketopiperazines / pharmacology*
  • Humans
  • Neoplasms / drug therapy
  • Neoplasms / pathology
  • Oxazoles / chemistry
  • Oxazoles / isolation & purification
  • Oxazoles / pharmacology*
  • Peptides, Cyclic / chemistry
  • Peptides, Cyclic / isolation & purification
  • Peptides, Cyclic / pharmacology*
  • Porifera / chemistry*

Substances

  • Antineoplastic Agents
  • Azepines
  • Diketopiperazines
  • Oxazoles
  • Peptides, Cyclic
  • cyclo-(4-S-hydroxy-R-proline-R-isoleucine)