Biosynthesis of prodiginines. ¹³C resonance assignments and enrichment patterns in nonyl-, cyclononyl-, methylcyclodecyl-, and butylcycloheptylprodiginine produced by actinomycete cultures supplemented with ¹³C-labeled acetate and ¹⁵N-labeled nitrate

Abstract

. Can. J Chem. 56, 11 55 (1978). Resonances in the 13C nmr spectra of nonylprodiginine, cyclononylprodiginine, methylcyclodecylprodiginine, and butylcycloheptylprodiginine were assigned using information from the literature, from high resolution spectra and double irradiation experiments, and from ' 3 C -1 5 N~~~p l i n g~ observed in samples of nonylprodiginine enriched with I5N. Supplementation of cultures with sodium [I-13C]-and [1,2-13C]acetate gave I3C-enriched prodiginines and the labeling patterns were established from 13C nmr spectra. These indicated that rings A and B were formed in a similar manner to rings A and B in prodigiosin and other prodiginine pigments. Ring C and ihe C2-alkyl substituent were derived in part from acetate units that were condensed in a linear 12-or 14-carbon chain. The same pattern of acetate assembly has been found in all actinomycete prodiginines examined.

Overproduction and biological activity of prodigiosin-like pigments from recombinant fusant of endophytic marine Streptomyces species

“…The red extract was subjected to column chromatography on a silica gel (60-120 mesh; Merck) column eluted with MeOH in CHCl 3 . Fractions eluted with 0.1 MeOH in CHCl 3 were found to be pure red fractions and had an absorbance maximum at 540 nm in acidic CHCl 3 , confirming published values for known prodigiosin analogs purified from Actinomycetes (Gerber et al 1978;Gerber 1975;Liu et al 2005;Tsao et al 2005). Thus combined and evaporated to yield PLPs (40 g L -1 ) as major ingredients of the producing fusant NRCF69.…”

“…BA18591 and Streptomyces griseoviridis respectively, can also be considered as members of the prodigiosin family (Gerber et al 1978;Hayakawa et al 1992;Kojiri et al 1993). Although as with many secondary metabolites, the true physiological and ecological functions of PLPs in the producer organisms remains unclear; these tripyrrole molecules have received renewed attention owing to reported immunosuppressive, anticancer antifungal, antibacterial, antiprotozoal, antimalarial and trypanolytic activities (Demain 1995;Pérez-Tomás et al 2003;Zhang et al 2005).…”

A twist of nature – the significance of atropisomers in biological systems

“…84 One such member of this family was extracted from the pigment of several Streptomyces species in 1975 by the Gerber group using chromatographic techniques, and initially assigned the structure 39 ( Figure 12) using mass spectral, UV-vis, and NMR analysis. 85 A revision of this structure to 40 (Figure 12) came three years later by the same author, 86 though confusion surrounding the correct structure and atropisomeric potential of the natural product remained, 87,88 until relatively recent studies put any ambiguities to rest and confirmed the correct general structure as 40. 89,90 It was in a study by Challis et al in 2010 that NOESY correlations of the HCl salts of extracted streptorubin B allowed for assignment of the major naturally occurring product as being the anticonfiguration with regards to the positioning of the C7ʹ n-butyl group relative to rings A and B, with the syn configuration only present in minor amounts.…”

Bioprospecting Anticancer Compounds from the Marine-Derived Actinobacteria Actinomadura sp. Collected at the Saint Peter and Saint Paul Archipelago (Brazil)

“…Fr. C (97.7 mg) was subjected to successive silica gel column chromatograpies eluted with n-hexane/EtOAc gradients to yield cyclononylprodigiosin 10,12 (2,33.0 mg). Fr.…”

“…Fr. F (15.0 mg) was further purified by HPLC using a semipreparative C 18 column with an isocratic mobile phase of CH 3 CN:H 2 O (9:1) to give nonylprodigiosin 10,12 (3,4.0 mg, t R 10.8 min). …”