Characterization of l-Digitoxosyl-phenanthroviridin from Streptomyces venezuelae ISP5230

Abstract

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The expansive library of jadomycins

“…L-Digitoxosylated phenanthroviridin (49) was isolated recently when Robertson and co-workers were investigating the incorporation of L-lysine. 32 The authors proposed that apparent instability of the L-lysine jadomycin analogue, congruent with previous reports, 15 led to a breakdown product 49.…”

“…At the time of publication, over forty-five of the described jadomycins have been evaluated for biological activity, including various cancer cytotoxicity assays [7][8][9][10]13,15,[17][18][19][20]25,[32][33][34][35] and antimicrobial panels. 6,20,33,34 Jadomycins have been implicated in the inhibition of aurora kinase B 10,54 and topoisomerases.…”

Streptomyces venezuelae NRRL B-65442: genome sequence of a model strain used to study morphological differentiation in filamentous actinobacteria

“…The S. venezuelae strain used at the John Innes Centre (JIC) was obtained from Diversa Corporation (San Diego, USA) in 2003 and described as strain ATCC 10712; the company had in turn obtained it from the Vining laboratory (Doull et al., 1985 ). In addition to chloramphenicol (Fernández-Martínez et al., 2014 ), this strain also produces the polyketide antibiotic jadomycin B (Doull et al., 1993 , 1994 ; Jakeman et al., 2006 ), which also has antitumour activity (Hall et al., 2015 ), and its congeners (Robertson et al., 2015 ), as well as the biaryl polyketide venemycin (Thanapipatsiri et al., 2016 ), the non-ribosomal peptide watasemycin (Inahashi et al., 2017 ), the γ-aminobutyrate-derived gaburedins (Sidda et al., 2013 ), and the indole arcyriaflavin (Mervyn Bibb, unpublished data); it also has the potential to produce a novel lanthipeptide, venezuelin (Goto et al., 2010 ). At the same time, Diversa Corporation also kindly provided a genome sequence of the strain that had been obtained by whole-genome shotgun Sanger sequencing (GenBank Accession No.…”

Total Synthesis of Phenanthroviridin Aglycon and Its Analog

“…Moreover, aglycon 1 exhibited antibacterial activity against Staphylococcus aureus ATCC 29213 with a MIC value of 0.25 μg/mL [2] . In 2015, the novel glycoside, L ‐digitoxosyl‐phenanthroviridin ( 3 ), was isolated from Streptomyces venezuelae ISP5230 [3] . Glycoside 3 showed cytotoxic activity against the National Cancer Institute (NCI) 60 human tumor cell line screen compared to jadomycin antibiotics that have a unique 8 H ‐benzo[ b ]oxazolo[3,2‐ f ]phenanthridine skeleton incorporating an amino acid unit in the 1,3‐oxazolidin‐5‐one ring [3] .…”

“…[2] In 2015, the novel glycoside, L -digitoxosyl-phenanthroviridin (3), was isolated from Streptomyces venezuelae ISP5230. [3] Glycoside 3 showed cytotoxic activity against the National Cancer Institute (NCI) 60 human tumor cell line screen compared to jadomycin antibiotics that have a unique 8H-benzo[b]oxazolo[3,2-f]phenanthridine skeleton incorporating an amino acid unit in the 1,3-oxazolidin-5one ring. [3] As an example of jadomycin antibiotics, jadomycin B (4) is also shown in Figure 1.…”