Aaptodines A–D, Spiro Naphthyridine–Furooxazoloquinoline Hybrid Alkaloids from the Sponge Aaptos suberitoides

LC–MS-oriented fractionation of the sponge Aaptos suberitoides resulted in the isolation of four heptacyclic alkaloids, aaptodines A–D (1–4), which contain 9,10-dihydrofuro­[2,3-f]­[1,3]­oxazolo­[5,4-h]­quinolone and 7,8-dihydrocyclopenta­[de]­[1,6]­naphthyridine subunits with a spiro carbon atom. T...

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Veröffentlicht in:Organic letters 2020-11, Vol.22 (21), p.8215-8218
Hauptverfasser: Wang, Pianpian, Huang, Jian, Kurtán, Tibor, Mándi, Attila, Jia, Hongli, Cheng, Wei, Lin, Wenhan
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Sprache:eng
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Zusammenfassung:LC–MS-oriented fractionation of the sponge Aaptos suberitoides resulted in the isolation of four heptacyclic alkaloids, aaptodines A–D (1–4), which contain 9,10-dihydrofuro­[2,3-f]­[1,3]­oxazolo­[5,4-h]­quinolone and 7,8-dihydrocyclopenta­[de]­[1,6]­naphthyridine subunits with a spiro carbon atom. The structures were determined on the basis of NMR spectroscopic and single-crystal X-ray diffraction data analysis aided by electronic circular dichroism calculations and Mosher’s method. A biosynthetic pathway for the formation of aaptodines A–D is postulated. Aaptodine D exhibits potent inhibition against osteoclast formation.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.0c02645