A new antitumor antibiotic, awamycin.

Umezawa, Iwao; Oka, Hiroyuki; Komiyama, Kanki; Hagiwara, Keiko; Tomisaka, Shigeru; Miyano, Tetsuji

doi:10.7164/antibiotics.36.1144

Cited by 8 publications

(1 citation statement)

References 5 publications

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“…Furthermore, compounds 5-15, awamycin and rubradirin are all red, and have UV chromophores that typically extend past 500 nm. 33,34 We postulate that the UV absorption characteristics of these molecules may be the cause for the large specific rotations. (21), which is typically co-administered with proguanil in the treatment of P. falciparum infections.…”

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confidence: 99%

Synthesis and antimalarial evaluation of a screening library based on a tetrahydroanthraquinone natural product scaffold

Choomuenwai

Andrews

Davis

2012

Bioorganic & Medicinal Chemistry

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As part of a research program aimed at discovering new antimalarial leads from Australian macrofungi a unique fungi-derived prefractionated library was screened against a chloroquine-sensitive Plasmodium falciparum line (3D7) using a radiometric growth inhibition assay. A library fraction derived from a Cortinarius species displayed promising antimalarial activity. UV-guided fractionation on the CH(2)Cl(2)/MeOH extract from this fungus resulted in the isolation of four known compounds: (1S,3R)-austrocortirubin (1), (1S,3S)-austrocortirubin (2), 1-deoxyaustrocortirubin (3), and austrocortinin (4). Compound 2 was used as a natural product scaffold in the parallel solution-phase synthesis of a small library of N-substituted tetrahydroanthraquinones (5-15). All compounds (1-15) were tested in vitro against P. falciparum 3D7 parasites and (1S,3S)-austrocortirubin (2), the major fungal constituent, was shown to be the most active compound with an IC(50) of 1.9 μM. This compound displayed moderate cytotoxicity against neonatal foreskin fibroblast (NFF) cells with an IC(50) of 15.6 μM.

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confidence: 99%

Synthesis and antimalarial evaluation of a screening library based on a tetrahydroanthraquinone natural product scaffold

Choomuenwai

Andrews

Davis

2012

Bioorganic & Medicinal Chemistry

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Miscellaneous quinones

Thomson¹

1997

Naturally Occurring Quinones IV

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Two sulfur-containing ansamycin antibiotics fromStreptomyces albolongus

et al. 1986

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Two sulfur-containing ansamycin antibiotics were isolated from the culture broth of Streptomyces albolongus C-46366; the major one was identical with awamycin and the minor one was a new ansamycin antibiotic, ansathiazin. Their structures were elucidated from their reactions and spectroscopic analyses. These antibiotics were active against gram-positive bacteria, acid-fast bacteria and a protozoan.

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A new antitumor antibiotic, awamycin.

Cited by 8 publications

References 5 publications

Synthesis and antimalarial evaluation of a screening library based on a tetrahydroanthraquinone natural product scaffold

Synthesis and antimalarial evaluation of a screening library based on a tetrahydroanthraquinone natural product scaffold

Miscellaneous quinones

Two sulfur-containing ansamycin antibiotics fromStreptomyces albolongus

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