Journal
JOURNAL OF NATURAL PRODUCTS
Volume 84, Issue 3, Pages 724-737Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.jnatprod.0c01217
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Funding
- Regional Council of Campania Region
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Nine new limonoids were isolated from Guarea guidonia and Cedrela odorata, including three A2,B,D-seco-type limonoids, a mexicanolide, three nomilin-type limonoids, and two limonol derivatives. Among them, chisomicine D demonstrated the highest affinity as a type of client-selective Hsp90 inhibitor through biochemical and cellular assays, and molecular docking. The study also utilized a DFT/NMR procedure to define the relative configurations of certain limonoids.
Nine new limonoids (1-9) were isolated from the stem bark of Guarea guidonia (1-4) and Cedrela odorata (5-9). Their structures were elucidated using 1D and 2D NMR and MS data and chemical methods as three A2,B,D-seco-type limonoids (1-3), a mexicanolide (4), three nomilin-type (5-7) limonoids, and two limonol derivatives (8 and 9). A DFT/NMR procedure was used to define the relative configurations of 1 and 3. A surface plasmon resonance approach was used to screen the Hsp90 binding capability of the limonoids, and the A2,B,D-seco-type limonoid 8-hydro-(8S*,9S*)-dihydroxy-14,15-en-chisomicine A, named chisomicine D (1), demonstrated the highest affinity. By means of mass spectrometry data, biochemical and cellular assays, and molecular docking, 1 was found as a type of client-selective Hsp90 inhibitor binding to the C-terminus domain of the chaperone.
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