Ulleungamides A and B, Modified α,β-Dehydropipecolic Acid Containing Cyclic Depsipeptides from Streptomyces sp. KCB13F003.
Two novel cyclic depsipeptides, ulleungamides A (1) and B (2), were isolated from cultures of terrestrial Streptomyces sp. Their structures were determined by analyses of spectroscopic data and various chemical transformations, including modified Mosher's method, advanced Marfey's method, PGME, GITC derivatizations, and Snatzke's method. Ulleungamides were determined to be a new class of peptides bearing unprecedented units, such as 5-hydroxy-6-methyl-2,3-dehydropipecolic acid, 4,5-dihydroxy-6-methyl-2,3-dehydropipecolic acid, and amino-linked 2-isopropylsuccinic acid. Ulleungamide A displayed growth inhibitory activity against Staphylococcus aureus and Salmonella typhimurium without cytotoxicity.
‡Department of Biomolecular Science, University of Science and Technology, Daejeon 305-333, Korea.
Sangkeun
S
Son
‡Department of Biomolecular Science, University of Science and Technology, Daejeon 305-333, Korea.
Sung-Kyun
SK
Ko
‡Department of Biomolecular Science, University of Science and Technology, Daejeon 305-333, Korea.
Mina
M
Jang
Jae Kyoung
JK
Lee
In-Ja
IJ
Ryoo
§Microbial Resources Center, Korea Research Institute of Bioscience and Biotechnology, Daejeon 306-809, Korea.
Jung-Sook
JS
Lee
Kyung Ho
KH
Lee
‡Department of Biomolecular Science, University of Science and Technology, Daejeon 305-333, Korea.
Nak-Kyun
NK
Soung
⊥College of Pharmacy, Wonkwang University, Iksan 570-749, Korea.
Hyuncheol
H
Oh
‡Department of Biomolecular Science, University of Science and Technology, Daejeon 305-333, Korea.
Young-Soo
YS
Hong
‡Department of Biomolecular Science, University of Science and Technology, Daejeon 305-333, Korea.
Bo Yeon
BY
Kim
‡Department of Biomolecular Science, University of Science and Technology, Daejeon 305-333, Korea.
Jae-Hyuk
JH
Jang
‡Department of Biomolecular Science, University of Science and Technology, Daejeon 305-333, Korea.
Jong Seog
JS
Ahn
D047630:Depsipeptides / Q000737:chemistry / Q000145:classification / Q000302:isolation & purification* / Q000494:pharmacology; D004354:Drug Screening Assays, Antitumor; D006367:HeLa Cells; D006801:Humans; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D010875:Pipecolic Acids / Q000737:chemistry*; D012486:Salmonella typhimurium / Q000187:drug effects; D013211:Staphylococcus aureus / Q000187:drug effects; D013237:Stereoisomerism; D013302:Streptomyces / Q000737:chemistry*
D047630:Depsipeptides; D010875:Pipecolic Acids; C000603265:ulleungamide A; C000603266:ulleungamide B; C100914:4,5-dehydropipecolic acid