Pentacyclic triterpenes are secondary plant metabolites widespread in fruit peel, leaves and stem bark. In particular the lupane-, oleanane-, and ursane triterpenes display various pharmacological effects while being devoid of prominent toxicity. Therefore, these triterpenes are promising leading compounds for the development of new multi-targeting bioactive agents. Screening of 39 plant materials identified triterpene rich (> 0.1% dry matter) plant parts. Plant materials with high triterpene concentrations were then used to obtain dry extracts by accelerated solvent extraction resulting in a triterpene content of 50 - 90%. Depending on the plant material, betulin (birch bark), betulinic acid (plane bark), oleanolic acid (olive leaves, olive pomace, mistletoe sprouts, clove flowers), ursolic acid (apple pomace) or an equal mixture of the three triterpene acids (rosemary leaves) are the main components of these dry extracts. They are quantitatively characterised plant extracts supplying a high concentration of actives and therefore can be used for development of phytopharmaceutical formulations.

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Pentacyclic triterpene distribution in various plants - rich sources for a new group of multi-potent plant extracts.

Pentacyclic triterpenes are naturally found in a great variety of fruits, vegetables and medicinal plants and are therefore part of the human diet. The beneficial health effects of edible and medicinal plants have partly been associated with their triterpene content, but the in vivo efficacy in humans depends on many factors, including absorption and metabolism. This review presents an overview of in vitro and in vivo studies that were carried out to determine the bioavailability of pentacyclic triterpenes and highlights the efforts that have been performed to improve the dissolution properties and absorption of these compounds. As plant matrices play a critical role in triterpene bioaccessibility, this review covers literature data on the bioavailability of pentacyclic triterpenes ingested either from foods and medicinal plants or in their free form.

https://www.mdpi.com/1420-3049/22/3/400/pdf

Pentacyclic Triterpene Bioavailability: An Overview of In Vitro and In Vivo Studies

Ursolic acid is a very important compound due to its biological potential as an anti-inflammatory, trypanocidal, antirheumatic, antiviral, antioxidant and antitumoral agent. This study presents the HPLC analysis of ursolic acid (UA) content in eight different Ocimum species: O. americanum L., O. basilicum L, O. basilicum var purpurascens Benth, O. basilicum var. minimum L, O. gratissimum L, O. micranthum Willd, O. selloi Benth. and O. tenuiflorum L. grown in Northeastern Brazil. In these Ocimum species, UA was detected in different yields, with O. tenuiflorum showing the highest content (2.02%). This yield is very significant when compared with other sources of UA.

https://www.mdpi.com/1420-3049/13/10/2482/pdf

Variation of ursolic acid content in eight Ocimum species from northeastern Brazil.

Recent developments on the extraction and application of ursolic acid. A review.

Quinoa is a pseudocereal from South America that has received increased interest around the world because it is a good source of different nutrients and rich in antioxidant compounds. Thus, this study has focused on the effects of different agronomic variables, such as irrigation and salinity, on the phenolic and saponin profiles of quinoa. It was observed that irrigation with 25% of full water restitution, with and without the addition of salt, was associated with increases in free phenolic compounds of 23.16 and 26.27%, respectively. In contrast, bound phenolic compounds were not affected by environmental stresses. Saponins decreased if samples were exposed to drought and saline regimens. In situations of severe water deficit, the saponins content decreased 45%, and 50% when a salt stress was added. The results suggest that irrigation and salinity may regulate the production of bioactive compounds in quinoa, influencing its nutritional and industrial values.

Phenolic compounds and saponins in quinoa samples (Chenopodium quinoa Willd.) grown under different saline and nonsaline irrigation regimens.

Phytochemical investigations of different species of Lamiaceae family (rosemary-Rosmarinus officinalis L., sage-Salvia officinalis L., winter savory-Satureja montana L., clary sage-Salvia sclarea L. and sticky sage-Salvia glutinosa L.), using gas chromatography and mass spectrometry (GC-MS) were performed. The studies were focused on oleanolic, betulinic and ursolic acid. Since oleanolic and ursolic acid are position isomers with very similar structures, the difficulties in their separation and identification have been reported by several authors. However, both compounds can be well distinguished by order of elution during gas chromatography and by intensities of the fragment ion signals in their mass spectra, where the retro-Diels-Alder reaction was primarily observed. A combination of ultrasonic extraction, solid phase extraction, size exclusion chromatography, trimethylsilylation, and GC-MS resulted in simultaneous separation, identification and quantification of the mentioned compounds. The compounds have been identified by retention time and comparison of mass spectra with those of pure standards. The mass spectral fragmentation behavior of all three derivatised acids was investigated. The obtained characteristic fragment patterns are discussed in the presented work. Good linearity over the concentration range 1–50 mg L−1 for all three compounds was confirmed. The correlation coefficients (r 2 ) were in the range of 0.9980–0.9983. Quantitative analyses of different Lamiaceae extracts showed that the oleanolic acid content ranged from 0.09 to 0.9% dry weight, content of betulinic acid ranged from traces to 0.6%, and that of ursolic acid varied from 0.09 to 1.6% dry weight.

Ernest Voncina

Papers

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

Thermolysis on aluminum oxides chemisorbed 2,4,6-trichlorophenol as example for the fly ASH mediated surface catalysis reaction in PCDD/PCDF formation