Comprehensive Analysis of Secondary Metabolites in <i>Usnea longissima</i> (Lichenized Ascomycetes, Parmeliaceae) Using UPLC-ESI-QTOF-MS/MS and Pro-Apoptotic Activity of Barbatic Acid

Considering the importance of ultra-performance liquid chromatography-electrospray ionization-quadrupole time of flight-tandem mass spectrometry (UPLC-ESI-QTOF-MS/MS) hyphenated techniques for analysis of secondary metabolites from crude extracts, the present study was aimed at identification of sec...

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Main Authors: S. Divya Reddy, Bandi Siva, Katragunta Kumar, V. S. Phani Babu, Vemireddy Sravanthi, Joel Boustie, V. Lakshma Nayak, Ashok K Tiwari, CH. V. Rao, B. Sridhar, P. Shashikala, K. Suresh Babu
Format: Article
Language:English
Published: MDPI AG 2019-06-01
Series:Molecules
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Online Access:https://www.mdpi.com/1420-3049/24/12/2270
Description
Summary:Considering the importance of ultra-performance liquid chromatography-electrospray ionization-quadrupole time of flight-tandem mass spectrometry (UPLC-ESI-QTOF-MS/MS) hyphenated techniques for analysis of secondary metabolites from crude extracts, the present study was aimed at identification of secondary metabolites in acetone extract of the lichen <i>Usnea longissima</i>. From our study, 19 compounds were tentatively identified through comparison of exact molecular masses from their MS/MS spectra, mass fragmentation studies and comparison with literature data. In addition, potent cytotoxic activity of <i>U. longissima</i> extract prompted us to isolate four compounds, 18<i>R</i>-hydroxy-dihydroalloprotolichesterinic acid (<b>19</b>), neuropogolic acid (<b>20</b>), barbatic acid (<b>21</b>)<b>,</b> and usnic acid (<b>22</b>) from this extract which were adequately identified through mass spectrometry and NMR spectroscopy. All four compounds displayed cytotoxic activity. Barbatic acid (<b>21</b>) manifested doxorubicin equivalent activity against A549 lung cancer cell line with IC<sub>50</sub> of 1.78 &#181;M and strong G0/G1 accumulation of cells. Poly ADP-ribose polymerase (PARP) cleavage confirmed that it induced cytotoxic activity via apoptosis. Finally, our work has discerned the depside, barbatic acid (<b>21</b>) from crude extract as a candidate anti-cancer molecule, which induces cell death by stepping up apoptosis.
ISSN:1420-3049