Theopapuamide, a cyclic depsipeptide from a Papua New Guinea lithistid sponge Theonella swinhoei.
Theopapuamide (1), a new cytotoxic peptide, has been isolated from the lithistid sponge Theonella swinhoei from Papua New Guinea. The structure was established by analysis of NMR, mass spectrometry, and chemical methods. The undecapeptide (1) contains several unusual amino acid residues, of which the occurrence of beta-methoxyasparagine and 4-amino-5-methyl-2,3,5-trihydroxyhexanoic acid (Amtha) is unprecedented in natural peptides. Compound 1 also contains an amide-linked fatty acid moiety, 3-hydroxy-2,4,6-trimethyloctanoic acid (Htoa). Theopapuamide (1) was cytotoxic against CEM-TART and HCT-116 cell lines, with EC50 values of 0.5 and 0.9 microM, respectively.
Ratnayake
Anokha S
AS
Department of Medicinal Chemistry, Department of Biochemistry, and Department of Pharmacology and Toxicology, University of Utah, Salt Lake City, Utah 84112, USA.
Bugni
Tim S
TS
Feng
Xidong
X
Harper
Mary Kay
MK
Skalicky
Jack J
JJ
Mohammed
Kaleem A
KA
Andjelic
Cynthia D
CD
Barrows
Louis R
LR
Ireland
Chris M
CM
D000818:Animals; D000970:Antineoplastic Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D047630:Depsipeptides / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D004354:Drug Screening Assays, Antitumor; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D010219:Papua New Guinea; D047232:Theonella / Q000737:chemistry*
D000970:Antineoplastic Agents; D047630:Depsipeptides; C516618:theopapuamide