A new indole glycoside from Kitasatospora sp. MG372-hF19 carrying a 6-deoxy-α-l-talopyranose moiety

Small cell lung cancer (SCLC) is a severe malignancy with early and widespread metastasis, and novel therapeutic drugs are needed. To identify cytotoxic natural compounds against SCLC, we screened libraries of microbial fermentation broths using several lung cancer cell lines. We found that the acti...

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Bibliographic Details
Published in:Journal of antibiotics 2020-03, Vol.73 (3), p.167-170
Main Authors: Kohda, Yasuko, Sakamoto, Shuichi, Otsuka, Yasunari, Sawa, Ryuichi, Kubota, Yumiko, Igarashi, Masayuki, Muramatsu, Hideyuki, Iijima, Masatomi, Kawada, Manabu
Format: Article
Language:English
Subjects:
631/154/1435
631/67/1612
631/92/349
Bacteriology
Biomedical and Life Sciences
Bioorganic Chemistry
Brief Communication
Fermentation
Glycosides
Ionization
Ions
Life Sciences
Lung cancer
Mass spectrometry
Medicinal Chemistry
Microbiology
Organic Chemistry
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Summary:Small cell lung cancer (SCLC) is a severe malignancy with early and widespread metastasis, and novel therapeutic drugs are needed. To identify cytotoxic natural compounds against SCLC, we screened libraries of microbial fermentation broths using several lung cancer cell lines. We found that the actinomycete strain MG372-hF19 produces a compound that has not been isolated from natural sources but previously chemically synthesized, 6-chloro-1 H -indole-3-carboxaldehyde ( 1 ), and an entirely new compound, named 6-deoxy-α- L -talopyranose 1-(6-chloro-1 H -indole-3-carboxylate) ( 2 ), together with leptomycins. The molecular formulas of the compounds were established as C 9 H 6 ClNO and C 15 H 16 ClNO 6 , respectively, via high-resolution electrospray ionization mass spectrometry, and their structures were determined using detailed NMR. Absolute configurational analysis of the sugar unit of compound 2 revealed that the compound incorporates the rare deoxyhexose 6-deoxy-α- L -talopyranose. Both compounds exhibited weak growth-inhibiting activities against human lung cancer cell lines.
ISSN:0021-8820
1881-1469
DOI:10.1038/s41429-019-0258-9