title: Lajollamycins, nitro group-bearing spiro-β-lactone-γ-lactams obtained from a marine-derived Streptomyces sp.
abstract: Lajollamycins (1-4), each of which bears a spiro-β-lactone-γ-lactam ring and a nitro-tetraene moiety, were obtained from a marine-derived Streptomyces strain isolated from the southern area of Jeju Island, Republic of Korea. The planar structures of the lajollamycins were elucidated on the basis of spectroscopic analyses by NMR, UV, IR, and MS. The absolute configuration of lajollamycin (1), the planar structure of which has been previously reported, was determined using J-based configuration analysis based on (1)H-(1)H and (1)H-(13)C coupling constants, as well as ROESY correlations, followed by the modified Mosher's method. The absolute configurations of lajollamycins B-D (2-4) were established by comparing their CD spectra with that of 1. The lajollamycins exhibited moderate inhibitory activity toward Candida albicans isocitrate lyase.
authors.affiliation: Natural Products Research Institute, College of Pharmacy, Seoul National University , 1 Gwanak-ro, Gwanak-gu, Seoul 151-742, Republic of Korea.
authors.forename: Keebeom
authors.initials: K
authors.lastname: Ko
authors.forename: So-Hyoung
authors.initials: SH
authors.lastname: Lee
authors.forename: Seong-Hwan
authors.initials: SH
authors.lastname: Kim
authors.forename: Eun-Hee
authors.initials: EH
authors.lastname: Kim
authors.forename: Ki-Bong
authors.initials: KB
authors.lastname: Oh
authors.forename: Jongheon
authors.initials: J
authors.lastname: Shin
authors.forename: Dong-Chan
authors.initials: DC
authors.lastname: Oh
mesh_terms: D002176:Candida albicans / Q000187:drug effects / Q000201:enzymology; D002942:Circular Dichroism; D007522:Isocitrate Lyase / Q000037:antagonists & inhibitors; D007769:Lactams / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D008386:Marine Biology; D015394:Molecular Structure; D056910:Republic of Korea; D013141:Spiro Compounds / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D013302:Streptomyces / Q000737:chemistry*; D047090:beta-Lactams / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology
chemical_list: D007769:Lactams; D013141:Spiro Compounds; D047090:beta-Lactams; C499026:lajollamycin; D007522:Isocitrate Lyase