A new antiviral antibiotic SF-2140 produced by Actinomadura.

Itö, Tatsuo; Ohba, Kazunori; Koyama, Masato; Sezaki, Masaji; Tohyama, Hiroyoshi; Shomura, Takashi; Fukuyasu, Harumi; Kazuno, Yuzo; Niwa, Tomizo; Kojima, Michio; Niida, Taro

doi:10.7164/antibiotics.37.931

Cited by 22 publications

(9 citation statements)

References 4 publications

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“…Interestingly, in the crystal structure, the methyl uronate ring of compound 3 adopts a ' C4 (D) conformation. 2 Since the 'H NMR data for the di-0-acetyl derivatives of neosidomycin and SF-2140 are virtually identical with regard to the sugar units (the large values of J1t,2, and J4tax,5, being important pieces of data in the assignment of structure 2 to neosidomycin diacetate'), the later workers suggested that the structures of neosidomycin and its di-0-acetyl derivative should be revised to 5 and 6 respectively.2 It might be noted that since the absolute configuration of neosidomycin had not been determined, the original structure 1 ' and the revised suggestion 5 differ only in relative configuration at C-5'.…”

mentioning

confidence: 99%

Synthesis of the indole nucleoside antibiotics neosidomycin and SF-2140

Buchanan¹,

Stoddart²,

Wightman³

1994

J. Chem. Soc., Perkin Trans. 1

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The indole nucleoside antibiotics neosidomycin 5 and SF-2140 3 have been synthesized. Methyl 4deoxy-2,3-0-isopropylidene-a-~-/yxo-hexopyranoside 8 was converted into methyl 1 -chloro-l,4dideoxy-2,3-di-O-pivaloyl-~-~-/yxo-hexopyranuronate 33 in five steps. Silver(i) -catalysed coupling of compound 33 with 3-(cyanomethyl) indole 20 gave stereoselectively an a-nucleoside which was converted into methyl 1 -[3-(carbamoylmethyl) indol-1 -yl] -1.4-dideoxy-a-o-/yxo-hexopyranuronate (neosidomycin, 5). Coupling of compound 33 to 3-cyanomethyl-4-methoxyindole 23 by the sodium salt procedure, and subsequent deacylation, gave methyl 1 -(3-cyanomethyl-4-methoxyindol-1 -yl) -1,4-dideoxy-a-~-/yxo-hexopyranuronate (SF-21 40, 3). Neosidomycin, SF-21 40, and their 0acyl derivatives adopt a conformation which differs from that of 1 -(6-O-benzoyl-4-deoxy-2,3-0pivaloyl-~-~-/yxo-hexopyranosyl)-3-(cyanomethy1)indole 29, in which the methyl uronate grouping of the antibiotics is present at a lower oxidation level.

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mentioning

confidence: 99%

Synthesis of the indole nucleoside antibiotics neosidomycin and SF-2140

Buchanan¹,

Stoddart²,

Wightman³

1994

J. Chem. Soc., Perkin Trans. 1

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“…Antiviral antibiotic SF-2140 41 was obtained from the broth of Actinomadura albolutea (Nocardiaceae), which was isolated from soil. It showed antiviral and weak antibacterial activity against Gram-negative and Gram-positive bacteria (82,83). Two novel glycoconjugates, ethyl indole-3-lactate-O-β-D-glucopyranoside 42 and pmenth-1-ene-8,9-diol-9-β-D-glucopyranoside have been detected in Riesling wine (84).…”

Section: Indole Alkaloid Glycosidesmentioning

confidence: 99%

Astonishing diversity of natural surfactants: 6. Biologically active marine and terrestrial alkaloid glycosides

Dembitsky

2005

Lipids

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This review article presents 209 alkaloid glycosides isolated and identified from plants, microorganisms, and marine invertebrates that demonstrate different biological activities. They are of great interest, especially for the medicinal and/or pharmaceutical industries. These biologically active glycosides have good potential for future chemical preparation of compounds useful as antioxidants, anticancer, antimicrobial, and antibacterial agents. These glycosidic compounds have been subdivided into several groups, including: acridone; aporphine; benzoxazinoid; ergot; indole; enediyne alkaloidal antibiotics; glycosidic lupine alkaloids; piperidine, pyridine, pyrrolidine, and pyrrolizidine alkaloid glycosides; glycosidic quinoline and isoquinoline alkaloids; steroidal glycoalkaloids; and miscellaneous alkaloid glycosides.

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“…20 The total synthesis of three indole alkaloids 24, 25, and 26, isolated from two species of European Basidiomycetes (Tricholoma virgatum and T. sciodes), 21 has been achieved from 4-bromo-3-nitrotoluene (27) as a common starting material (Scheme 3). 22 The key reaction is the Bartoli indole synthesis of ortho-substituted nitro-aromatic compounds 27 and 28 with vinylmagnesium bromide (29).…”

Section: Non-tryptaminesmentioning

confidence: 99%

“…Two new indole nucleosides, kahakamides A (43a) and B (43b), have been isolated from the actinomycete Nocardiopsis dassonvillei, obtained from a shallow water sediment sample. 27 The N-glycosylindole structure is rare and only two related microbial metabolites, neosidomycin 28 and SF-2140, 29 Four novel indole-type glucosinolates, glucoisatisin (R) (44a), epiglucoisatisin (S ) (44b), 3Ј-hydroxyglucoisatisin (R) (45a), and 3Ј-hydroxyepiglucoisatisin (S ) (45b), have been isolated from the seeds of woad (Isatis tinctoria L.) together with six known glucosinolates. 30 Their structures were elucidated by spectroscopic analysis ( 1 H and 13 C NMR, COSY, HSQC, HMBC, and NOESY spectra).…”

Section: Indole Auxins and Phytoalexinsmentioning

confidence: 99%