Caryophyllene Sesquiterpenes from Pulicaria vulgarisGaertn.: Isolation, Structure Determination, Bioactivity and Structure−Activity Relationship

Abstract

A new caryophyllene, named pulicaryenne A (1), along with four other known caryophyllene derivatives (2, 3, 4 and 5) were isolated from the ethyl acetate extract of aerial parts of Pulicaria vulgaris GAERTN. (Asteraceae). All compounds were isolated for the first time from this species. Compound 2 was identified as a new epimer of a known caryophyllene derivative isolated previously from P. dysenterica. Their structures were established by spectroscopic means including NMR analysis (1D-and 2D-NMR) and ESI-TOF-MS. All compounds were evaluated for their anticholinesterase, antityrosinase and cytotoxic activities against two human cell lines (A549 and HeLa). Results showed that compound 5 exhibited the highest cytotoxic effect against A549 and anticholinesterase activity with IC 50 values of 8.50 � 0.75 and 6.45 � 0.09 μg/mL, respectively. Furthermore, compound 5 showed also an interesting antityrosinase activity with percent inhibition value of 79.0 � 2.5 % at 50 μg/mL. The bioactivity and drug likeness scores of the isolated compounds 1-5 were calculated using Molinspiration software and discussed. These results may suggest that the five caryophyllene derivatives endowed with good biological properties, which could be used as bioactive alternatives in pharmaceutical preparations.

Potentiation of Low-Dose Doxorubicin Cytotoxicity by Affecting P-Glycoprotein through Caryophyllane Sesquiterpenes in HepG2 Cells: an in Vitro and in Silico Study

“…Caryophyllane sesquiterpenes are natural phytochemicals widely occurring in terrestrial plants and plant-associated fungal species [32][33][34][35][36][37], and are present in marine environments as secondary metabolites from the resident living organisms and microbes [38][39][40][41].…”

Constituents of Pulicaria inuloides and Cytotoxic Activities of Two Methoxylated Flavonols

“…The structure of compound 2 was established based on the analysis of its spectral data (1D- and 2D-NMR, specific rotation measurement). The remaining compounds were identified by the direct comparison of their spectral data ( 1 H NMR, specific rotation, UV spectra) to those found in the literature [ 7 , 30 , 31 , 32 , 33 , 34 , 35 , 36 , 37 , 38 , 39 , 40 ].…”

“…(1 S ,9 R )-14-Acetoxycaryophyll-5(6)-en-7-one ( 3 ) has been described as a metabolite of P. scabra [ 31 ], P. arabica [ 32 ], and P. dysenterica [ 33 ]. Zardi-Bergaoui et al [ 7 ] from fresh aerial parts of P. vulgaris isolated (1 S ,9 R )-5 β -hydroxycaryophylla-2(15),6(14)-dien-7-one as a new compound named pulicaryenne A. The 1 H NMR spectrum of the compound was identical to that of 7 .…”

“…(Asteraceae, Inuleae-Inulinae) comprises over 80 species that are native to Europe, Asia, and Africa [ 1 ]. Only about one-third of them have been phytochemically investigated so far [ 2 , 3 , 4 , 5 , 6 , 7 , 8 , 9 , 10 , 11 ]. Numerous species are endemic to the Mediterranean Basin, and only two: P. dysenterica (L.) Bernh.…”

Plant Terpenoids as the Promising Source of Cholinesterase Inhibitors for Anti-AD Therapy

“…For instance, compound ( 71 ) exhibited a stronger AChE inhibitory effect than compound ( 68 ). The finding could be explained by the absence of the asymmetric center C-6 in compound ( 71 ) and its replacement by the endocylic double bond Δ 5,6 through the inversion of the configuration at C-11 [ 45 ].…”