Structures of new 18-membered macrolides FD-891 and FD-892.

Abstract

Structures of FD-891 and FD-892 were determined by extensive NMRspectral analysis as shown in Fig. 1. They belong to such 18-memberedmacrolides as concanamycins and virustomycin.In the course of our screening program for low molecular substances inducing morphological changes of HL-60, new 18-membered macrolides FD-891 and FD-892 were discovered in the fermentation broth of Streptomyce graminofaciens A-88901}. They belong to such 18-membered antibiotics as concanamycins2'3) and virustomycin4'5). Their biological properties are similar to those of 18-membered antibiotics1}. Their structures were determined by extensive NMRanalysis as shown in Fig. 1. This paper deals with their structural elucidation. Results and DiscussionStructure of FD-891 The physico-chemical properties of FD-891 are shown in Table 1. The UVspectrum of FD-891 showed the absorption at 270 nm due to a diene system conjugated with a carbonyl group. The bands at 3400 and

Phytotoxin produced by Streptomyces sp. causing potato russet scab in Japan

“…1), which was isolated as a cytocidal compound for in vitro tumor cell lines (Seki-Asano et al 1994a, 1994bEguchi et al 2002Eguchi et al , 2004. A comparison of the retention time and UV spectrum in ODS-HPLC and of the 1 H-NMR spectrum of the phytotoxin with those of an authentic sample confirmed that the phytotoxin was FD-891.…”

The Total Synthesis and Biological Properties of the Cytotoxic Macrolide FD‐891 and Its Non‐Natural (Z)‐C12 Isomer

“…[4] Macrolide FD-891, structurally related to the concanamycins even though it lacks a hemiketal moiety, was isolated in 1994 by a Japanese group from the fermentation broth of S. graminofaciens A-8890. [5] It shows cytotoxic activity against several tumour cell lines and, in addition, has been found to potently prevent both perforin-and Fasl-dependent CTlmediated killing pathways. In contrast to the structurally related concanamycin A, however, it is unable to inhibit vaAbstract: A total, stereoselective synthesis of the naturally occurring, cytotoxic macrolide FD-891 and of its nonnatural (Z)-C12 isomer is described.…”

Cloning and Characterization of the Biosynthetic Gene Cluster of 16‐Membered Macrolide Antibiotic FD‐891: Involvement of a Dual Functional Cytochrome P450 Monooxygenase Catalyzing Epoxidation and Hydroxylation

“…The same PCR also afforded a probable concanamycin PKS gene (77 % identity to ConE), [36] which was anticipated to be amplified because this strain reportedly produces concanamycin. [37] Three other KS genes were also amplified, indicating that this strain has the potential to produce unidentified polyketides.…”