Pholipomycin, a new member of phosphoglycolipid antibiotics. I. Taxonomy of producing organism and fermentation and isolation of pholipomycin.

Characterization of moenomycin antibiotic complex by multistage MALDI-IT/RTOF-MS and ESI-IT-MS

“…Chemically derived 6B-N-de(2-hydroxy-5-oxo-1-cyclopenten-1-yl)-moenomycin A has already been shown to be antibiotically active [47]. From structure-activity relationship analysis of the moenomycins [3, 7-9, 12, 25] and the activity of pholipomycin [23,29] and AC326-␣ [30] it can be concluded that the other three above mentioned substances are potent antibiotics as well. Furthermore, a moenomycin A carrying an oxygen in the moenocinol-group was found, which is most probably a chemical degradation product.…”

“…Although a more exact localization was not possible from the observed low-energy CID product ions, we assume that the unit C in this component carries a hydroxy-group in position 6. The presence of 6C-hydroxy-moenomycin A in the Flavomycin complex is also not completely surprising, taking into account the similarity of unit C to unit E, and the presence of a 2-(acetylamino)-2-deoxyglucopyranosyl group as unit C in the moenomycin-type antibiotics pholipomycin (6E-O-de-␤-Dglucopyranosyl-6C-hydroxy-moenomycin A) from Streptomyces lividoclavatus [23,29] and AC326-␣ from Actinomyces AC326 [30]. The latter is structurally identical to the proposed 6C-hydroxy-moenomycin A except that it possesses a cyclized moenocinol derivative.…”

“…The isoprenoidlike C 25 -alcohol [26], named moenocinol, seems to be required for the binding of the moenomycin antibiotics to the cytoplasmic membrane [27], whereas the units E, F, and H are concluded to form a polar binding epitope that is recognized by the donor binding site of the transglycosylases [3, 7-9, 19, 28]. In addition to the five known constituents of the Flavomycin complex, structurally related moenomycin-type antibiotics, including the prasinomycins, the diumycins (macarbomycins), ensanchomycin, prenomycin, teichomycin, pholipomycin, AC326-␣, 11837 RP, 8036 RP (quebemecin), and 19402 RP, have been found [3,23,29,30].…”

Bioactive oligosaccharide natural products

“…All nosokomycins lack the A ring common to other moenomycins and instead contain either a carboxylate or carbamate at this position. 55,56 Two additional structurally characterized members include pholipomycin [57][58][59][60] and AC326a 61 produced by S. lividoclavatus and the unidentied Actinomyces sp. AC326 respectively.…”

“…61 At least 25 potential moenomycin family members have been reported although the structures of most have yet to be fully elucidated. 56,58 A natural mixture of moenomycins (also known as bambermycins) marketed as Flavomycin® and Flavophospholipol have been used as animal growth promoters for at least forty years. [62][63][64] Despite their long use, no signicant resistance to moenomycins has been described.…”