Determination of Oleanolic, Betulinic and Ursolic Acid in Lamiaceae and Mass Spectral Fragmentation of Their Trimethylsilylated Derivatives

Razboršek, Maša Islamčević; Vončina, Darinka Brodnjak; Doleček, Valter; Vončina, Ernest

doi:10.1365/s10337-008-0533-6

Cited by 91 publications

(65 citation statements)

References 34 publications

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“…The contribution of terrestrial vascular plants to our samples is also evidenced by the presence of the triterpenoids betulin (lup-20(29)-ene-3β,28-diol), oleanolic (3β-hydroxyolean-12-en-28-oic) and ursolic (3β-hydroxyurs-12-en-28-oic) acids (Razboršek et al, 2008) as well as components of cuticular waxes (16,8-11-dihydroxyhexadecanoic, ω-hydroxyhexadecanoic, ω-hydroxyoleic and 18-hydroxyoctadec-9-enoic acids) (Kolattukudy, 1980) ( Fig. 3b).…”

Section: Terrestrial Vascular Plant Biomarkersmentioning

confidence: 90%

Seasonal survey of the composition and degradation state of particulate organic matter in the Rhône River using lipid tracers

et al. 2015

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Abstract. Lipid tracers including fatty acids, hydroxyacids, n-alkanols, sterols and triterpenoids were used to determine the origin and fate of suspended particulate organic matter (POM) collected in the Rhône River (France). This seasonal survey (April 2011 to May 2013) revealed a yearround strong terrestrial higher-plant contribution to the particulate organic matter (POM), with significant algal inputs observed in March and attributed to phytoplanktonic blooms likely dominated by diatoms. Major terrigenous contributors to our samples are gymnosperms, and more precisely their roots and stems, as evidenced by the presence of high proportions of ω-hydroxydocosanoic acid (a suberin biomarker). The high amounts of coprostanol detected clearly show that the Rhône River is significantly affected by sewage waters.Specific sterol degradation products were quantified and used to assess the part of biotic and abiotic degradation of POM within the river. Higher-plant-derived organic matter appears to be mainly affected by photo-oxidation and autoxidation (free radical oxidation), while organic matter of mammal or human origin, evidenced by the presence of coprostanol, is clearly more prone to bacterial degradation. Despite the involvement of an intense autoxidation-inducing homolytic cleavage of peroxy bonds, a significant proportion of hydroperoxides is still intact in higher plant debris. These compounds could affect the degradation of terrestrial material by inducing an intense autoxidation upon its arrival at sea.

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Section: Terrestrial Vascular Plant Biomarkersmentioning

confidence: 90%

Seasonal survey of the composition and degradation state of particulate organic matter in the Rhône River using lipid tracers

et al. 2015

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“…[14][15][16] In this case, characteristic fragment ions obtained from high-mass-resolution-ToF-SIMS mass spectra have been assigned, taking into account the mass spectral fragmentation pattern of the corresponding trimethylsilylated triterpenic acids obtained under electron impact conditions. The main fragment ion signals are present at m/z = 456.34 (molecular ion), Fig.…”

Section: Resultsmentioning

confidence: 99%

Oleanolic and ursolic acid in dammar and mastic resin: isomer discrimination by using ToF‐SIMS and multivariate statistics

Tortora

Biocca

Sotgiu

et al. 2016

Surface & Interface Analysis

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dTriterpenoid resins, such as dammar resin and mastic resin, are natural products used as protective varnishes on paintings. Dammar resin consists of a large amount of triterpenoid molecules including two triterpenic acids: oleanolic acid and ursolic acid. Similarly, mastic resin is a complex blend of terpenoids but containing oleanolic acid. In this paper, high-mass-resolution time-of-flight secondary ion mass spectrometry (ToF-SIMS) has been used to characterize the fragmentation patterns of oleanolic acid and ursolic acid. The hypothesized fragmentation pathways for these triterpenic acids have also been discussed. In order to distinguish between these two structural isomers, principal component analysis (PCA) has been adopted. This multivariate statistical analysis technique permits to identify the characteristic fragments and discriminates between very similar mass spectra. In addition, dammar resin and mastic resin have been characterized. A selection of characteristic peaks from ursolic and oleanolic acids mass spectra has been used to build a dataset for a multivariate analysis to compare triterpenoid resins and triterpenic acids. The results of PCA have revealed that mastic resin is strictly related to oleanolic acid, whereas dammar resin is differentiated by ursolic acid fragments. This study confirms that, in the cultural heritage field, the time-of-flight secondary ion mass spectrometry technique combined with PCA can be a powerful tool to investigate the chemical composition of organic compounds with very complex composition.

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“…The derivatization of the compound was carried out according to standard method [11]. In brief, 0.2µg of purified compounds were derivatized by adding 100µL of silylation reagent N-methyl-N-trimethyl silyl tri-fluoro acetamide (MSTFA) and 50µL of pyridine.…”

Section: Derivatization Of Purified Compoundmentioning

confidence: 99%

“…The structural elucidation of ursolic acid (UA) and oleanolic (OA) isomers were carried out by comparison of experimental values from GC-MS with previously reported values [11].…”

Section: Identification By Gc-mmentioning

confidence: 99%

Apoptosis Induction by Cestrum parqui L’Hér. leaves on HL-60 Cell Line: Identification of Active Phytomolecules

Chenni¹,

Torres²,

Estévez³

et al. 2015

IJCR

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IntroductionCancer, one of the leading causes of human death, has attracted more attention due to the complexity of etiology, diagnosis and treatment [1]. In recent years, chemotherapeutic management against various types of cancer including leukemia has been increased rapidly though some times cancer cells resistance against chemotherapy [2,3]. In this respect, search for effective anticancer agent that inhibit the proliferation of the cells as well as inhibit the resistance nature of the cancer cells and induce differentiation of the monocytes is an ongoing challenge. Therefore to find out anticancer agent with multi-target efficacies, attention has been focused on plant products as the plant products have been used as remedies for several human diseases including cancer from ancient times with lower side effects [4]. The reasons for using them that they contain variety of chemical compounds usually secondary metabolites with therapeutic values [5]. Cestrum parqui is belonging to the family Solanaceae, usually known as "green or Chilean cestrum" in Tunisia, are rich in various secondary metabolites such as saponins, polyhydroxylated terpenes (C13 norisoprenoids, sesquiterpenes, spirostanes and pseudosapogenins) and ent-kaurene glycosides (parquin and carboxyparquin) [6][7][8]. Several scientific reports demonstrate that C. parqui exhibits a wide spectrum of pharmacological activity when administered systemically or in isolated organ preparations. For example, it is used to treat headache, rheumatic pain, scabies, dermatosis, diarrhaea and metrorraghia [7]. The plant is also used in Chilean folk Abstract Background: In our time, there is an urgent need to discover natural anticancer products without toxic side's effects. Objective: The present study was conducted to investigate the anticancer activity of the methanolic extract of Cestrum parqui leaves as well as identification of the active compounds in this concern. Materials and Methods: Eight column chromatographic fractions were tested against human leukaemia cell line (HL-60) and the cell viability was measured by dimethylthiazol tetrazolium assay. Studies of apoptosis, cell cycle and DNA fragmentation were carried out following the standard protocol. Effective fractions were analysed by high performance liquid chromatography-ultra violet, HPLC-evaporative light scattering detector and preparative-HPLC. Finally the active compounds were identified by gas chromatography coupled to mass spectrometry. Results: Out of eight, fraction II showed remarkable inhibition on the growth of HL-60 cell line and fraction I showed moderate activity on such inhibition. Mechanisms of the inhibition were identified as cell cycle arrestation and apoptosis induction by the said fractions. Chromatographic and mass spectrometric analysis of the fraction II indicated the presence of oleanolic and ursolic acids as biologically active compounds. Conclusion: This study is the first investigation that shows Cestrum parqui has anticancer activity and the responsible compounds are olea...

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Determination of Oleanolic, Betulinic and Ursolic Acid in Lamiaceae and Mass Spectral Fragmentation of Their Trimethylsilylated Derivatives

Cited by 91 publications

References 34 publications

Seasonal survey of the composition and degradation state of particulate organic matter in the Rhône River using lipid tracers

Seasonal survey of the composition and degradation state of particulate organic matter in the Rhône River using lipid tracers

Oleanolic and ursolic acid in dammar and mastic resin: isomer discrimination by using ToF‐SIMS and multivariate statistics

Apoptosis Induction by Cestrum parqui L’Hér. leaves on HL-60 Cell Line: Identification of Active Phytomolecules

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