Saquayamycin D

Saquayamycin D

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Category Antibiotics
Catalog number BBF-02881
CAS 99260-71-6
Molecular Weight 822.85
Molecular Formula C43H50O16

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Description

It is produced by the strain of Str. nodosus MH190-16F3. It has antimicrobial effect, but it has weaker effect against gram-negative bacteria. It has inhibitory effect on leukemia P388 cells and adriamycin-resistant P388 cells.

Specification

Synonyms Benz[a]anthracene-1,7,12(2H)-trione, 9-[[2',3-anhydro]-2,6-dideoxy-4-O-(3,6-dideoxy-a-L-erythro-hexopyranos-4-ulos-1-yl)-b-D-arabino-hexopyranosyl]-3,4,4a,12b-tetrahydro-4a,8,12b-trihydroxy-3-methyl-3-[[(2S,5S,6S)-tetrahydro-6-methyl-5-[[(2R,6S)-tetrahydro-6-methyl-5-oxo-2H-pyran-2-yl]oxy]-2H-pyran-2-yl]oxy]-, (3R,4aR,12bS)-; Benz[a]anthracene-1,7,12(2H)-trione, 9-[[2',3-anhydro]-2,6-dideoxy-4-O-(3,6-dideoxy-a-L-erythro-hexopyranos-4-ulos-1-yl)-b-D-arabino-hexopyranosyl]-3,4,4a,12b-tetrahydro-4a,8,12b-trihydroxy-3-methyl-3-[[tetrahydro-6-methyl-5-[(tetrahydro-6-methyl-5-oxo-2H-pyran-2-yl)oxy]-2H-pyran-2-yl]oxy]-, [2S-[2a(3S*,4aS*,12bR*),5b(2S*,6R*),6b]]-
IUPAC Name (3R,4aR,12bS)-9-((2S,4aS,5aR,7R,9R,9aR,10aR)-2,9-dimethyl-3-oxooctahydro-2H,7H-dipyrano[2,3-b:4',3'-e][1,4]dioxin-7-yl)-4a,8,12b-trihydroxy-3-methyl-3-(((2S,5S,6S)-6-methyl-5-(((2R,6S)-6-methyl-5-oxotetrahydro-2H-pyran-2-yl)oxy)tetrahydro-2H-pyran-2-yl)oxy)-3,4,4a,12b-tetrahydrotetraphene-1,7,12(2H)-trione

Properties

Appearance Orange Powder
Antibiotic Activity Spectrum Gram-negative bacteria; Neoplastics (Tumor)
Melting Point 152-155°C
Solubility Soluble in Methanol, Chloroform

Reference Reading

1. Saquayamycins, new aquayamycin-group antibiotics
T Uchida, M Imoto, Y Watanabe, K Miura, T Dobashi, N Matsuda, T Sawa, H Naganawa, M Hamada, T Takeuchi J Antibiot (Tokyo). 1985 Sep;38(9):1171-81. doi: 10.7164/antibiotics.38.1171.
From the culture broth of Streptomyces nodosus MH190-16F3, four new antibiotics have been isolated, and named saquayamycins A, B, C and D. The compounds are glycosides of aquayamycin, and among aquayamycin-group antibiotics they are most closely related to P-1894B (vineomycin A1). All saquayamycins act on Gram-positive bacteria and inhibit the growth of adriamycin-sensitive and adriamycin-resistant P388 leukemia cells.

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