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Secondary Metabolites from Two Species of Pulicaria and Their Cytotoxic Activity
Author(s) -
Triana Jorge,
López Mariana,
Pérez Francisco Javier,
León Francisco,
Quintana José,
Estévez Francisco,
Hernández Juan C.,
GonzálezPlatas Javier,
Brouard Ignacio,
Bermejo Jaime
Publication year - 2011
Publication title -
chemistry and biodiversity
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.427
H-Index - 70
eISSN - 1612-1880
pISSN - 1612-1872
DOI - 10.1002/cbdv.201000324
Subject(s) - sesquiterpene , chemistry , stereochemistry , flavonoid , cytotoxicity , asteraceae , cytotoxic t cell , terpene , biochemistry , in vitro , botany , biology , antioxidant
Abstract Two new compounds, the sesquiterpene (1 E ,5 E )‐8 β ‐acetoxy‐4 α ‐hydroxy‐7 β H‐germacra‐1(10),5‐dien‐14‐oic acid ( 2 ), and a nor‐sesquiterpene, (5 E )‐8 β ‐acetoxy‐4 α ‐hydroxy‐7 βH ‐germacr‐5‐en‐10‐one ( 3 ), were isolated from Pulicaria canariensis ssp. lanata , along with ten known compounds, including the flavonoid 5,3′‐dihydroxy‐3,7,4′‐trimethoxyflavone ( 4 ). From Pulicaria burchardii , we isolated seven known compounds; the physical and spectroscopic data of the triterpenoid 3 β ‐hydroxytaraxaster‐20‐en‐30‐al ( 1 ) are reported. The structures of compounds 1 – 3 were determined on the basis of HR‐MS, and 1D‐ and 2D‐NMR studies. The structure of 2 was corroborated by X‐ray crystal diffraction. Cell viability experiments revealed that the semisynthetic flavonoid 4b was the most cytotoxic compound against human leukemia cells, and the cytotoxicity was caused by induction of apoptosis, as determined by microscopy of nuclear changes.