Phytochemical study of the Balkan endemic J. tzar-ferdinandii Davidov allowed the identification of twenty-two components. β-Amyrin, lupeol, taraxasterol and Ψ-taraxasterol and their 3-O-acetates and 3-O-palmitates were identified by GC/MS. Six closely related sesquiterpene lactones and four flavones were isolated from the chloroform extract using column chromatography, and their structural identification was performed by spectral analyses. All isolated compounds are described for the first time in Jurinea species. The inhibitory potential of the total chloroform extract, fractions containing triterpenes, flavonoids and sesquiterpene lactones as well as individual compounds against a bacterial lipase from Candida rugosa (CRL) and a lipase from porcine pancrease (PPL) was evaluated. The half maximal inhibitory constants (IC50) for the two enzymes were in the range of 28–150 μg/mL. The strongest inhibitory activity was found for the total chloroform extract (29±1 μg/mL and 39±1 μg/mL for CRL and PPL, respectively.). Among the individual compounds, onopordopicrin was found to be the most potent inhibitor for CRL and PPL with IC50 values of 32±1 μg/mL and 36±1 μg/mL, respectively.
SusannaA., Garcia-JacasN., HidalgoO., VilatersanaR., GarnatjeT. (2006) The Cardueae (Compositae) revisited: Insights from its, trnL-trnF, and matK nuclear and chloroplast DNA analysis. Annals of the Missouri Botanical Garden, 93, 150–171.
2.
StoyanovN., StefanovB., KitanovB. (1967) Flora of Bulgaria, 4th ed., Vol. 2, Nauka i Izkustvo, Sofia, Bulgaria, 1119–1120 (In Bulgarian).
3.
AssyovB., PetrovaA., DimitrovD., VassilevR. (2006) Conspectus of the Bulgarian vascular flora: Distribution maps and floristic elements, AssyovB., and PetrovaA. (eds). Bulgarian Biodiversity Foundation, Sofia, Bulgaria, 224–225 (In Bulgarian).
4.
SinghP., SinghR., SatibN. (2016) A Review of Genus: Jurinea.International Journal of Life-Sciences Scientific Research, 2, 23–30.
5.
(a) TodorovaM., OgnyanovI. (1996) Pentacyclic triterpenes in roots of Jurinea albicaulis.Fitoterapia, 67, 383–383; (b) Mikolajczak KL, Smith CR. (1967) Pentacyclic triterpenes of Jurinea anatolica and Jurinea consanguinea fruit. Lipids, 2, 127-132.
6.
KönyeR., RessÁE, SólyomváryA., TóthG., DarcsiA., KomjátiB., HorváthP., NoszálB., Molnár-PerlI., BéniS., BoldizsárI. (2016) Enzyme-hydrolyzed Fruit of Jurinea mollis: a rich source of (-)-(8R,8'R)-arctigenin. Natural Product Communications, 11, 1459–1462.
7.
ÖztürkH., KolakU., MericC. (2011) Antioxidant, anticholinesterase and antibacterial activities of Jurinea consanguinea DC. Records of Natural Products, 5, 43–51.
8.
SinghP., SinghR., SatiN., SatiP.O., KumarN. (2015) Antioxidant and Antibacterial Activity of Jurinea dolomiaea Boiss Extracts. International Journal of Life-Sciences Scientific Research, 1, 74–78.
9.
TaherkhaniM., RustaiyanA. (2016) Investigation of in vitro cytotoxic, mutagenic and anti-mutagenic effects of shirazolide extracted from Jurinea leptoloba.Natural Product Research, 30, 2743–2746.
SaleemM. (2009) Lupeol, a novel anti-inflammatory and anti-cancer dietary triterpene. Cancer Letters, 285, 109–115.
12.
ChaturvediD. (2011) Sesquiterpene lactones: Structural diversity and their biological activities Opportunity. Challenge and Scope of Natural Products in Medicinal Chemistry, 313–334.
13.
HofbauerK., NicholsonJ., BossO. (2007) The obesity epidemic: current and future pharmacological treatments. Annual Review of Pharmacology and Toxicology, 47, 565–592.
14.
PadwalR., LiS.K., LauD.C.W. (2003) Long-term pharmacotherapy for overweight and obesity: a systematic review and meta-analysis of randomized controlled trials. International Journal of Obesity, 27, 1437–1446.
15.
PfallerM., DiekemaD., ColomboA., KibblerC., NgK., GibbsD., NewellV. (2006) Candida rugosa, an emerging fungal pathogen with resistance to azoles: geographic and temporal trends from the ARTEMIS DISK antifungal surveillance program. Journal of Clinical Microbiology, 44, 3578–3582.
16.
Braga-SilvaL., SantosA. (2011) Aspartic protease inhibitors as potential anti-Candida albicans drugs: impacts on fungal biology, virulence and pathogenesis, Current Medicinal Chemistry, 18, 2401–2419.
17.
BirariR.B., BhutaniK.K. (2007) Pancreatic lipase inhibitors from natural sources: unexplored potential. Drug Discovery Today, 12, 879–889.
18.
de la GarzaA.L., MilagroF.I., BoqueN., CampiónJ., MartínezJ.A. (2011) Natural inhibitors of pancreatic lipase as new players in obesity treatment. Planta Medica, 77, 773–785.
19.
SeyedanA., AlshawshM.A., AlshaggaM.A., KooshaS., MohamedZ. (2015) Medicinal plants and their inhibitory activities against pancreatic lipase: A review. Evidence-Based Complementary and Alternative Medicine, Article ID 973143, doi:10.1155/2015/973143.
20.
BudzikiewiczH., WilsonJ.M., DjerassiC. (1963) Mass spectrometry in structural and stereochemical problems. XXXII. Pentacyclic triterpenes. Journal of American Chemical Society, 85, 3688–3699.
21.
DrozdzB., HolubM., SamekZ., HeroutV., SormF. (1968) On terpenes. CXCII. The constitution and absolute configuration of onopordopicrine – a sesquiterpenic lactone. Collection of Czechoslovak Chemical Communications, 33, 1730–1737.
22.
RustaiyanA., AhmadiB., JakupovicJ., BohlmannF. (1986) Sesquiterpene lactones and eudesmane derivatives from Onopordon carmanicum.Phytochemistry, 25, 1659–1662.
23.
FortunaA.M., RiscalaE.C., CatalanC.A.N., GedrisT.E., HerzW. (2001) Sesquiterpene lactones from Centaurea tweediei.Biochemical Systematics and Ecology, 29, 967–971.
24.
SkaltsaH., DiamantoL., PanagouleasC., GeorgiadouE., GarciaB., SokovicM. (2000) Sesquiterpene lactones from Centaurea thessala and Centaurea attica. Antifungal activity. Phytochemistry, 55, 903–908.
25.
RustaijanA., NazariansL., BohlmannF. (1979) Two new elemanolides from Onopordon leptolepis.Phytochemistry, 18, 879–880.
26.
PatiG., KhareA.B., HuangK-F, LinF-M. (2015) Bioactive chemical constituents from the leaves of Lantana Camara L. Indian Journal of Chemistry, 54B, 691–697.
27.
DengY-R, SongA-X, WangH-Q. (2004) Chemical Components of Seriphidium santolium Poljak. Journal of the Chinese Chemical Society, 51, 629–636.
28.
ZaterH., HuetJ., FontaineV., BenayacheS., StévignyC., DuezP., BenayacheF. (2016) Chemical constituents, cytotoxic, antifungal and antimicrobial properties of Centaurea diluta Ait. subsp. algeriensis (Coss. & Dur.) Maire. Asian Pacific Journal of Tropical Medicine, 9, 554–561.
29.
Osei-SafoD., ChamaM.A., Addae-MensahI., WaibelR. (2009) Hispidulin and other constituents of Scoparia dulcis Linn. Journal of Science and Technology, 29, 7–15.
30.
BrunoM., MaggioA., RosselliS., SafderM., BanchevaS. (2011) Metabolites of the genus Onopordum (Asteraceae): Chemistry and biological Properties. Current Organic Chemistry, 15, 888–927.
31.
BrunoM., BanchevaS., RosseliS., MaggioA. (2013) Sesquiterpenoids in subtribe Centaureinae (Cass.) Dumort (tribe Cardueae, Asteraceae): Distribution, 13C NMR spectral data and biological properties. Phytochemistry, 95, 19–93.
32.
FormisanoC., RiganoD., SenatoreF., BanchevaS., MaggioA., RosselliS., BrunoM. (2012) Flavonoids in Subtribe Centaureinae (Cass.) Dumort. (Tribe Cardueae, Asteraceae): Distribution and 13C-NMR spectral data. Chemistry and Biodiversity, 9, 2096–2158.
33.
HochuliE., KupferE., MaurerR., MeisterW., MercadalY., SchmidtK. (1987) Lipstatin, an inhibitor of pancreatic lipase, produced by Streptomyces toxytricini II. Chemistry and structure elucidation. The Journal of Antibiotics, 40, 1086–1091.
34.
WeibelE.K., HadvaryP., HochuliE., KupferE., LengsfeldH. (1987) Lipstatin, an inhibitor of pancreatic lipase, produced by Streptomyces toxytricini I. Producing organism, fermentation, isolation and biological activity. The Journal of Antibiotics, 40, 1081–1085.
35.
LuyenN.T., TramL.H., HanhT.T.H., BinhP.T., DangN.H., MinhC.V. (2013) Inhibitors of α-glucosidase, α-amylase and lipase from Chrysanthemum morifolium.Phytochemistry Letters, 6, 322–325.
