title: Herbicidin congeners, undecose nucleosides from an organic extract of Streptomyces sp. L-9-10.
abstract: Four new undecose nucleosides (herbicidin congeners), three known herbicidins, and 9-(β-d-arabinofuranosyl)hypoxanthine (Ara-H) were isolated from the organic extract of a fermentation culture of Streptomyces sp. L-9-10 using proton NMR-guided fractionation. Their structures were elucidated on the basis of comprehensive 1D and 2D NMR and mass spectrometry analyses. These structures included 2'-O-demethylherbicidin F (1), 9'-deoxy-8',8'-dihydroxyherbicidin B (2), 9'-deoxy-8'-oxoherbicidin B (2a), and the 8'-epimer of herbicidin B (3). This is the first detailed assignment of proton and carbon chemical shifts for herbicidins A, B, and F. The isolated compounds were evaluated for cancer chemopreventive potential based on inhibition of tumor necrosis factor alpha (TNF-α)-induced nuclear factor-kappa B (NF-κB) activity.
authors.affiliation: Department of Pharmaceutical Sciences, The Daniel K. Inouye College of Pharmacy, University of Hawai'i at Hilo , 34 Rainbow Drive, Hilo, Hawaii 96720, United States.
authors.forename: Xingyun
authors.initials: X
authors.lastname: Chai
authors.forename: Ui Joung
authors.initials: UJ
authors.lastname: Youn
authors.forename: Dianqing
authors.initials: D
authors.lastname: Sun
authors.forename: Jingqiu
authors.initials: J
authors.lastname: Dai
authors.forename: Philip
authors.initials: P
authors.lastname: Williams
authors.forename: Tamara P
authors.initials: TP
authors.lastname: Kondratyuk
authors.forename: Robert P
authors.initials: RP
authors.lastname: Borris
authors.forename: Julian
authors.initials: J
authors.lastname: Davies
authors.forename: Ivan G
authors.initials: IG
authors.lastname: Villanueva
authors.forename: John M
authors.initials: JM
authors.lastname: Pezzuto
authors.forename: Leng Chee
authors.initials: LC
authors.lastname: Chang
mesh_terms: D001087:Arabinonucleosides / Q000737:chemistry / Q000302:isolation & purification; D006801:Humans; D015394:Molecular Structure; D016328:NF-kappa B; D019906:Nuclear Magnetic Resonance, Biomolecular; D011684:Purine Nucleosides / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D013302:Streptomyces / Q000737:chemistry*; D014409:Tumor Necrosis Factor-alpha
chemical_list: D001087:Arabinonucleosides; D016328:NF-kappa B; D011684:Purine Nucleosides; D014409:Tumor Necrosis Factor-alpha; C008099:hypoxanthine arabinoside; C013551:herbicidins