Biosynthesis of Staurosporine, 1. ¹H- and ¹³C-nmr Assignments

Abstract

Complete and unambiguous assignments of the 1H- and 13C-nmr spectra of the potent antitumor antibiotic staurosporine have been accomplished using a combination of one- and two-dimensional nmr techniques, including one-bond and long-range heteronuclear multiple-quantum coherence spectroscopy (HMQC). Staurosporine was found to be highly cytotoxic in the KB and P-388 assays but was inactive in the microtubulin assembly assay.

Cloning, Characterization and Heterologous Expression of the Indolocarbazole Biosynthetic Gene Cluster from Marine-Derived Streptomyces sanyensis FMA

“…The identity of the predominant ICZ compound, STA, produced by strain FMA was confirmed by MS and 1 H NMR analysis, which were identical to those previously reported [30] (Figure S4 and Figure S5, Supplementary Materials). The two compounds produced by spcI mutant were isolated, and their structures were determined by MS, 1 H NMR, 13 C NMR, 1 H– 1 H COSY, HSQC and HMBC (for two) data (Figure S6, Figure S7, Figure S8, Figure S9, Figure S10, Figure S11, Figure S12, Figure S13, Figure S14, Supplementary Materials).…”

Structure Elucidation and Anticancer Activity of 7-Oxostaurosporine Derivatives from the Brazilian Endemic Tunicate Eudistoma vannamei

“…Each of the protons in 1 and 2 were assigned using a combination of chemical shift data and coupling constants from the 1 H NMR spectrum (Table 1) and correlations from a COSY spectrum (Figure 2). Analysis of the chemical shift and coupling constant data indicated that the glycosidic unit matched that in staurosporine [22,23,24,25]. An HSQC experiment enabled the assignments of each methine, methylene and methyl carbon (Table 1).…”

“…Subsequent HMBC data facilitated the assignment of the remaining carbons (Table 1) with the exception of C-4c, C-5, C-7 and C-7a, which were interpreted by comparison with the literature [22,23,24,25]. Further long range correlations observed in the HMBC spectrum (Figure 2) provided definitive proof for the connectivity and thereby confirmed the structural assignment of 1 and 2 as 2-hydroxy-7-oxostaurosporine and 3-hydroxy-7-oxostaurosporine, respectively.…”

A new 16-membered tetraene macrolide JBIR-100 from a newly identified Streptomyces species

“…Compound 198a was isolated as white powder from fraction V using column chromatography on silica gel, followed by PTLC and finally purified on Sephadex Only one compound with this formula has been obtained from microorganisms so far: staurosporine (198a) [303] . This assumption was confirmed indeed by the from Streptomyces staurosporeus Awaya (AM-2282) [304] and subsequently from several other actinomycetes.…”