Bastadin 20 and bastadin O-sulfate esters from Ianthella basta: novel modulators of the Ry1R FKBP12 receptor complex

J Nat Prod. 1996 Dec;59(12):1121-7. doi: 10.1021/np960507g.

Abstract

New compounds bastadin 20 (9), 15,34-O-disulfatobastadin 7 (10), and 10-O-sulfatobastadin 3 (11) were isolated from Ianthella basta collected in Exmouth Gulf, Western Australia. Compounds 10 and 11 exhibited moderate differential activity as SR Ca2+ channel agonists (EC50 13.6 and 100 microM, respectively) of the Ry1R FKBP12 complex, while the potency of 9 was almost half that of 10 (EC50 20.6 microM). The problem of dereplication of bastadins was addressed using 1H-NMR "fingerprinting" of MeO signals in the corresponding permethyl bastadin derivatives.

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.
  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Animals
  • Calcium Channel Agonists / chemistry*
  • Calcium Channel Agonists / pharmacology
  • Calcium Channels / drug effects
  • Calcium Channels / metabolism*
  • Cell Line
  • Halogenated Diphenyl Ethers
  • Magnetic Resonance Spectroscopy
  • Muscle Proteins / drug effects
  • Muscle Proteins / metabolism*
  • Peptides, Cyclic / chemistry*
  • Peptides, Cyclic / pharmacology
  • Phenyl Ethers / chemistry*
  • Phenyl Ethers / pharmacology
  • Porifera / chemistry*
  • Ryanodine Receptor Calcium Release Channel
  • Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization

Substances

  • 10-O-sulfatobastadin 3
  • 15,34-O-disulfatobastadin 7
  • Calcium Channel Agonists
  • Calcium Channels
  • Halogenated Diphenyl Ethers
  • Muscle Proteins
  • Peptides, Cyclic
  • Phenyl Ethers
  • Ryanodine Receptor Calcium Release Channel
  • bastadin 20