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    Hydrangenone, a New Isoprenoid with an Unprecedented Skeleton from Salvia hydrangea
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    Department of Phytochemistry, Medicinal Plants and Drugs Research Institute, Shahid Beheshti University, G. C., Evin, Tehran, Iran, Chemistry and Chemical Engineering Research Center of Iran, Tehran, Iran, Division of Pharmaceutical Biology, University of Basel, Klingelbergstrasse 50, 4056 Basel, Switzerland, Department of Chemistry, Shahid Beheshti University, G. C., Evin, Tehran, Iran, and Swiss Tropical and Public Health Institute, Socinstrasse 57, CH-4002 Basel, Switzerland
    [email protected]
    †Department of Phytochemistry, Shahid Beheshti University.
    ‡Chemistry and Chemical Engineering Research Center of Iran.
    §University of Basel.
    ∥Department of Chemistry, Shahid Beheshti University.
    ⊥Swiss Tropical and Public Health Institute.
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    Organic Letters

    Cite this: Org. Lett. 2012, 14, 1, 166–169
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    https://doi.org/10.1021/ol202953b
    Published December 1, 2011
    Copyright © 2011 American Chemical Society
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    Abstract

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    Hydrangenone, a new heptacyclic isoprenoid with a 6/7/6/5/5 membered carbon ring skeleton, was isolated from the aerial parts of Salvia hydrangea. The structure was established by extensive NMR spectroscopic methods. The relative and absolute configuration of 1 was assigned by NOESY and X-ray crystallographic analysis and by comparison of experimental and calculated electronic circular dichroism (ECD) spectra. Compound 1 showed in vitro antiplasmodial activity, with an IC50 value of 1.4 μM against P. falciparum. A plausible biosynthetic pathway of 1 was also proposed.

    Copyright © 2011 American Chemical Society

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    Experimental procedure, 1D and 2D NMR spectra, and X-ray data (CIF file) of hydrangenone (1). This material is available free of charge via the Internet at http://pubs.acs.org.

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    Organic Letters

    Cite this: Org. Lett. 2012, 14, 1, 166–169
    Click to copy citationCitation copied!
    https://doi.org/10.1021/ol202953b
    Published December 1, 2011
    Copyright © 2011 American Chemical Society
    Request reuse permissions

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