Streptocinnamides A and B, Depsipeptides from Streptomyces sp. KMM 9044

Abstract

The bacterium Streptomyces sp. KMM 9044 from a sample of marine sediment collected in the northwestern part of the Sea of Japan produces highly chlorinated depsiheptapeptides streptocinnamides A (1) and B (2), representatives of a new structural group of antibiotics. The structures of 1 and 2 were determined using nuclear magnetic resonance and mass spectrometry studies and confirmed by a series of chemical transformations. Streptocinnamide A potently inhibits Micrococcus sp. KMM 1467, Arthrobacter sp. ATCC 21022, and Mycobacterium smegmatis MC2 155.

Marine natural products

“…yielded chlorinated depsiheptapeptides, streptocinnamides A 117 and B 118 . 32 that each contain m , m -dichloro- p -hydroxy- cis -α-methoxycinnamic acid as well as two rare amino acids, 3-hydroxy-4-chlorovaline and 4-acetoxy-5-methyl-proline. Streptocinnamide A showed potent antibacterial activity against Micrococcus sp.…”

A Survey of Recently Discovered Naturally Occurring Organohalogen Compounds

“…The former is highly potent toward strains of Micrococcus, Arthrobacter, and Mycobacterium smegmatis (MIC 4, 20, and 300 ng/mL, respectively). 108 A single methyl group on the upper proline residue in 247 is the only difference between the two depsipeptides. 108 The structure of forazoline A (249) from the marine-derived Actinomadura sp.…”

“…108 A single methyl group on the upper proline residue in 247 is the only difference between the two depsipeptides. 108 The structure of forazoline A (249) from the marine-derived Actinomadura sp. described earlier 109 has been revised to that shown.…”

“…KMM 9044 from a Sea of Japan sediment afforded streptocinnamides A ( 247 ) and B ( 248 ). The former is highly potent toward strains of Micrococcus , Arthrobacter , and Mycobacterium smegmatis (MIC 4, 20, and 300 ng/mL, respectively) . A single methyl group on the upper proline residue in 247 is the only difference between the two depsipeptides .…”

Phaeosphamides A and B, Cytotoxic Cyclodecadepsipeptides from the Mangrove-Derived Fungus Phaeosphaeriopsis sp. S296

“…Cyclic depsipeptides are a class of cyclopeptides in which one or more amide groups were replaced by lactone bond in the core ring, exhibiting a wide range of biological effects, such as cytotoxic, antimicrobial, antimalarial, and anti-HIV activities [ 1 , 2 , 3 , 4 ]. The structural variety of the peptides is attributed to the incorporation of distinct amino acid residues and hydroxylated carboxylic acids, in addition to unusual amino acid residues and various chemical modifications [ 5 , 6 , 7 ].…”