The structures of novel antibiotics, saframycin B and C

Arai, Tadashi; Takahashi, Katsuhiro; Kubo, Akinori; Nakahara, Shinsuke; Sato, Sadao; Aiba, Kimie; Tamura, Chihiro

doi:10.1016/s0040-4039(01)93972-3

Cited by 56 publications

(32 citation statements)

References 6 publications

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“…[4][5][6][7][8] The antitumor activity of a novel antibiotic, saframycin A, with a unique structure consisting of a dimer of 6-methyl-7-methoxy-1,2,3,4-tetrahydroisoquinoline-5,8-dione, as the basic skeleton, has been reported . [9][10][11][12] In our studies on the microbial conversion of SA into antibiotics possessing antitumor spectra different from those of the parent compound (SA), reduction of the side chain carbonyl group of SA was observed.…”

mentioning

confidence: 99%

Microbial conversion of saframycin A to 25-dihydrosaframycin A and 21-decyano-25-dihydrosaframycin A (25-dihydrosaframycin B) and their biological activities.

Takahashi¹,

Yazawa²,

Kishi³

et al. 1982

J. Antibiot.

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25-Dihydrosaframycin A(AR1) and 21-decyano-25-dihydrosaframycinA(AR3) were produced by the microbial conversion of saframycin A(SA). Efficient conversion of SA to AR, and AR3 was observed with Rhodococcus amidophifus IFM 144. Though the antimicrobial activity of AR, was one tenth that of SA, the in vitro antitumor activity of AR1 was found to be equivalent to that of SA. In contrast, AR, was biologically less active.Microlial conversion has been studied extensively1~3) for many classes of organic compounds, namely alkaloids, antibiotics and steroids.For antitumor antibiotics, considerable attention has been given to the microbial reduction of carbonyl groups in relation to antitumor activities .4-8)The antitumor activity of a novel antibiotic, saframycin A, with a unique structure consisting of a dimer of 6-methyl-7-methoxy-1,2,3,4-tetrahydroisoquinoline-5,8-dione, as the basic skeleton, has been reported .9-12)In our studies on the microbial conversion of SA into antibiotics possessing antitumor spectra different from those of the parent compound (SA), reduction of the side chain carbonyl group of SA was observed.In this paper, we report our studies on the microbial conversion of SA to AR, and AR, and their biological properties. Materials and MethodsMicroorganisms and Cultivation Rhodococcus amidophih{s IFM 144 was maintained on slants of I % glycerol nutrient medium until used. The strain was grown in 500-ml Erlenmeyer flasks, each containing 100 ml of a medium consisting of: meat extract 1 %, peptone 1 %, yeast extract 1 %, NaCl 0.3 % (pH 7.2). After 48 hours incubation at 27°C on a rotary shaker at 250 rpm, the culture was centrifuged, washed and suspended in a small volume (23 ml) of 0.1 M phosphate buffer (pH 7.5).Microbial Conversion of Saframyicn A(SA) Two ml of the suspension was mixed with 2 ml of the 10% aqueous methanol solution of SA (0.5 mg/ ml) in a test tube and the mixture incubated at 37°C for 18 hours. The reaction mixture was centrifuged at 500 rpm, and the supernatant extracted with ethyl acetate. The ethyl acetate layer was concentrated in vacuo, and the residue extracted with 1 N HCl solution. After adjustment to pH 7.5 with conc.

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confidence: 99%

Microbial conversion of saframycin A to 25-dihydrosaframycin A and 21-decyano-25-dihydrosaframycin A (25-dihydrosaframycin B) and their biological activities.

Takahashi¹,

Yazawa²,

Kishi³

et al. 1982

J. Antibiot.

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“…5 (11-9) 2. 14.0 4.0 (7-6) 4.0 (7)(8) 20.0 (9)(10) 20.0(10-9) 8.0 (10-11) 8.0(11-10) 3.0(11-12) (1)(2) 13.1 (2-3) 3.9 (2-1) 3.9 (2-4) 13.1 9.2 (3-1) 2.3 (3)(4) 17. 3 (5-6) 12.0 (5-7) 3.9 17.3 3.1 (6)(7) 12.0 (7-5) 3.1 3.1 (7)(8) 20.0 (9)(10) 20.0 (10-9) 7.3 (10-11) 7.3 (11-10) 2.6(11-12) 2.6(12-11) …”

Section: Structure Of Saframycinsmentioning

confidence: 99%

“…4 (5-6) 12.1 (5-7) 2.5 (5-4) 16.4 3.6 (6-7) 12.1 3.6 21.9 (9)(10) 21.9(10-9) 7.3 (10-11) 7.3 (11-10) 3.6(11-12) 3.6 (12-11) The numbering system shown here is arbitrary and serves only as an aid in NMR spectral identification.…”

Section: Structure Of Saframycinsmentioning

confidence: 99%

Isolation and structural elucidation of new saframycins Y3, Yd-1, Yd-2, Ad-1, Y2b and Y2b-d.

et al. 1986

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“…Inspection of structural features of ecteinascidin-743 (ET-743; 21) and ecteinascidin-729 (ET-729; 22) from tunicate reveals similarities to saframycins A (23) and B (24) isolated from Streptomyces lavendula [44] and safracin isolated from Pseudomonas fluorescens [45] . Such observation represents one of several clues on the microbial origin of these chemicals [47] .…”

mentioning

confidence: 99%

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

Ueda¹,

Hashimoto²,

Yamamura³

et al. 2011

J Antibiot

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The structures of novel antibiotics, saframycin B and C

Cited by 56 publications

References 6 publications

Microbial conversion of saframycin A to 25-dihydrosaframycin A and 21-decyano-25-dihydrosaframycin A (25-dihydrosaframycin B) and their biological activities.

Microbial conversion of saframycin A to 25-dihydrosaframycin A and 21-decyano-25-dihydrosaframycin A (25-dihydrosaframycin B) and their biological activities.

Isolation and structural elucidation of new saframycins Y3, Yd-1, Yd-2, Ad-1, Y2b and Y2b-d.

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

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