GC-MS analysis of penta- and tetra-cyclic triterpenes from resins ofPistacia species. Part I.Pistacia lentiscus var. Chia (original) (raw)
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Phytochemistry, 1978
Short Reports 815 acetylation and chromic acid/pyridium oxidation of the hydroxyl groups. The spectral data, the mps and the optical the plant material and the 'Deutsche Forschungsgemeinschaft' rotations of all compounds are in good agreement with those for supporting this work.
Rodriguésia
Crude non-volatile oleoresin from Burseraceae species (breu), a non-timber forest product of the Amazon, still lacks methods for its quality control even though its pharmacological activities have been associated to the major triterpenes α-amyrin (αAA), β-amyrin, α-amyrenone, β-amyrenone and lupeol (LU). Its chemical characterization has usually been determined by gas chromatography (GC) using columns with phases of low polarity, which are ineffective in the separation of αAA and LU. The present study aimed to develop a GC method to characterize and quantify triterpenes in commercial breu with good selectivity and resolution. Columns with phases of different polarity (DB-35, DB-1701, DB-17HT and DB-Innowax) were tested, and DB-17HT separated αAA and LU without signal suppression or high retention of other constituents. This column allowed the quantification of breu triterpenes using flame ionization detection and cholesterol as a reference standard. Good similarity between the calib...
Factors affecting the content of pentacyclic triterpenes in Centella asiatica raw materials
Pharmaceutical Biology, 2012
Context: Pentacyclic triterpenes, mainly, asiatic acid, madecassic acid, asiaticoside, and madecassoside are the active constituents of Centella asitica (L.) Urban. (Apiaceae). These compounds possess various pharmacological activities that have been shown to assist with wound healing and brain enrichment. Objective: Determination of these active pentacyclic triterpenes in extracts from the various parts of C. asiatica plants harvested at different times of the year and grown in different environments. Materials and methods: The separate plant parts selected were leaves, stolons, petioles, flowers, fruits, and nodes with roots. Dried powder from each part was extracted with ethanol by microwave-assisted extraction and subjected to determination of their content of the four pentacyclic triterpenes using a HPLC method. The effects of the places of cultivation as well as harvesting periods on the content of the four pentacyclic triterpenes in the extracts were also determined. Results and discussion: Among the various parts of C. asiatica, the leaves contained the highest amount of pentacyclic triterpenes with a total content of pentacyclic triterpenes of 19.5 mg/g dry powder. However, the contents of the pentacyclic triterpenes in C. asiatica varied according to the place of cultivation and the harvesting period. C. asiatica collected from Trang, Thailand gave the highest content of total pentacyclic triterpenes (37.2 mg/g dry powder) when harvested in March, while those collected from Songkhla, Thailand gave the highest value (37.4 mg/g dry powder) when collected in December. C. asiatica collected from Nakornsrithammarat and Ratchaburi, Thailand gave the lowest content of total pentacyclic triterpenes in all experimental harvesting periods.
Chemodiversity of Ursane- and Oleanane-Type Triterpenes in Amazonian Burseraceae Oleoresins
Chemistry & Biodiversity, 2013
The oleoresins exuded from species of the Burseraceae family present high potential due to their biological and pharmacological properties. The evaluation of the chemodiversity of the oleoresins of 23 Amazonian species of Burseraceae provided a profile of the principal constituents, viz., the ursane-type triterpenes a-amyrin (1), a-amyrenone (3), and brein (5) and the oleanane-type triterpenes b-amyrin (2), b-amyrenone (4), and maniladiol (6), and allowed to determine which of these species have the highest biotechnological potential and which ones are rich in other, potentially new, triterpenes or volatile compounds of interest for the cosmetics industry. The oleoresin compositions obtained by GC-FID and GC/MS analyses were submitted to principal component analysis (PCA) and hierarchical clustering on principal components (HCPC), which divided the 23 samples in five clusters. Protium giganteum and Trattinnickia peruviana, constituting the first cluster, presented high oleoresin contents of 3 and 4 (28.8 and 16.3% on average, resp.). The seven species of Burseraceae composing the second cluster were potential producers of new triterpenes and volatile compounds. Dacryodes hopkinsii and five Protium species (third cluster) presented average contents for all the triterpenes analyzed. The highest contents of 5 and 6 (averages of 3.9 and 5.4%, resp.) were observed in P. heptaphyllum ssp. ullei and T. glaziovii (fourth cluster). Finally, the six Protium species forming the fifth cluster showed high contents of 1 and 2 (48.0 and 19.9% on average, resp.). Moreover, this study allowed the description of the triterpene composition of 13 not previously investigated species.
Journal of The Brazilian Chemical Society, 2000
Various acid diterpenes of Copaifera cearensis Huber ex Ducke were isolated from the crude extract by flash Silica Gel/Potassium Hydroxide Chromatography. The main components were identified by GC-MS analyses. Further fractionation by reversed phase (RP) semi-preparative HPLC allowed isolation and identification of minor components and provided additional spectral data of those compounds. It was possible to detect the presence of eleven acid diterpenes in addition to a sesquiterpene acid. In addition to potassium hydroxide deposition on the silica surface, the presence of Si-OK residues, resulting from a cation exchange process, was established.
Planta Medica
Chios mastic gum is the resinous secretion obtained from the barks of the shrub Pistacia lentiscus var. Chia, which is endemic to the Greek island of Chios. Since antiquity, Chios mastic gum has found several uses as a phytotherapeutic remedy, primarily for the treatment of gastrointestinal disorders while recently, Chios mastic gum was also recognized by EMA as an herbal medicinal product with specific indications. Chios mastic gumʼs biological properties are attributed to triterpenes which comprise the major chemical group (approx. 70%) and notably isomasticadienonic acid and masticadienonic acid. However, due to their structural characteristics, the isolation thereof in high yield and purity is challenging and since they are not commercially available, pharmacological studies aiming to assess their biological properties are limited. In the present work, masticʼs phytochemical investigation by UPLC-HRMS is followed by the isolation and characterization of isomasticadienonic acid a...
Evaluation of seasonal changes of triterpenic acid contents inViscum albumfrom different host trees
Context: Viscum album L. (Loranthaceae) is a semi-parasitic plant used in pharmacy and medicine mostly for its hypotensive and anticancer activity. The effects may be related to the presence of triterpenic acids, such as betulinic (BA) and oleanolic (OA) acids. Objectives: In our investigations the content of triterpenic acids in V. album from different host trees depending on the season of harvest was determined. Material and methods: V. album herb was dried and extracted with ethyl acetate using ultrasound energy. The reversed phase HPLC-PDA method was used for the analysis of triterpenic acids. The structure of the target components was confirmed by mass spectrometry with an electrospray ionization source. Results: Diversity in the content of both compounds was noted; however, OA was the dominant triterpenic acid and the amount thereof was $10 times higher than that of BA. The analysis of changes in the amount of triterpenic acids during the spring-winter period revealed the highest content of OA in summer (from 6.84 to 13.65 mg/g). In turn, in the other seasons of harvest, the content was in the range of 4.41-9.83, 6.41-9.56 and 5.59-12.16 mg/g for spring, autumn and winter, respectively. In most cases, a similar tendency was observed for BA. Discussion and conclusion: In most cases, the highest amount of the investigated compounds was found in summer; thus, this period seems to be optimal for acquisition of plant material rich in triterpenic acids.