Main Triterpenoid Research Articles

Organic Tracers from Asphalt in Propolis Produced by Urban Honey Bees, Apis mellifera Linn.

Propolis is a gummy material produced by honey bees to protect their hives and currently has drawn the attention of researchers due to its broad clinical use. It has been reported, based only on observations, that honey bees also collect other non-vegetation substances such as paint or asphalt/tar to make propolis. Therefore, propolis samples were collected from bee hives in Riyadh and Al-Bahah, a natural area, Saudi Arabia to determine their compositional characteristics and possible sources of the neutral organic compounds. The samples were extracted with hexane and analyzed by gas chromatography-mass spectrometry. The results showed that the major compounds were n-alkanes, n-alkenes, methyl n-alkanoates, long chain wax esters, triterpenoids and hopanes. The n-alkanes (ranging from C17 to C40) were significant with relative concentrations varying from 23.8 to 56.8% (mean = 44.9+9.4%) of the total extracts. Their odd carbon preference index (CPI) ranged from 3.6 to 7.7, with a maximum concentration at heptacosane indicating inputs from higher plant vegetation wax. The relative concentrations of the n-alkenes varied from 23.8 to 41.19% (mean = 35.6+5.1%), with CPI = 12.4-31.4, range from C25 to C35 and maximum at tritriacontane. Methyl n-alkanoates, ranged from C12 to C26 as acids, with concentrations from 3.11 to 33.2% (mean = 9.6+9.5%). Long chain wax esters and triterpenoids were minor. The main triterpenoids were α- and β-amyrins, amyrones and amyryl acetates. The presence of hopanes in some total extracts (up to 12.5%) indicated that the bees also collected petroleum derivatives from vicinal asphalt and used that as an additional ingredient to make propolis. Therefore, caution should be taken when considering the chemical compositions of propolis as potential sources of natural products for biological and pharmacological applications. Moreover, beekeepers should be aware of the proper source of propolis in the flight range of their bee colonies.

Optimization of Extraction Conditions and Phytochemical Screening of Root Extract of Synadenium glaucescens Pax

Optimization of extraction conditions and phytochemical screening of the root bark of Synadenium glaucescens were carried out in a stepwise manner in order to obtain the highest yields and the constituents of the extracts. Sequential extraction using Soxhlet method was performed using dichloromethane, hexane and petroleum ether, respectively, each followed by ethanol. Extraction conditions included: running time of 2 to 6 hours, temperature at 25 oC to 95 oC and particle size ranging from 0.4mm to >3mm diameter. Phytochemical screening was done using derivatisation techniques, gas chromatography-mass spectrometry and high performance liquid chromatography. Extraction with dichloromethane followed by ethanol resulted in a higher yield by 25%, within 4 hrs of extraction, particle size of 1mm, at temperatures of 30 oC for dichloromethane and 75 oC for ethanol. Fatty acid analysis indicated absence of free fatty acids in both Dichloromethane and ethanolic extracts. Silylation and Thin Layer Chromatography indicated the presence of non hindered and hindered functionality and the presence of triterpenoids in the dichloromethane extract. Phytochemical screening of the dichloromethane extracts indicated that it is composed of two main triterpenoids that best matched with Lanosterol (42%) and Cycloartenol (31%). Other minor compounds identified through chromatographic analysis were phytol, ergostadiol, hentriacontane, sitastirol aceate, lupeol and hopenone. The ethanolic extracts indicated the presence of polyphenolic compounds.

Fast analysis of triterpenoids in Ganoderma lucidum spores by ultra‐performance liquid chromatography coupled with triple quadrupole mass spectrometry

A rapid and reliable method was established for simultaneous determination of main triterpenoids in Ganoderma lucidum spores using ultra-high-performance liquid chromatography coupled with triple quadrupole mass spectrometry (UPLC-TQ-MS). The established method was validated in terms of linearity, sensitivity, precision, accuracy and stability, and was successfully applied to determine the contents of 10 main triterpenoids in different batches of G. lucidum spores. The analysis results showed that moderate levels of triterpenoids were found in G. lucidum spores. In addition, a MS full scan with a daughter ion scan experiment was performed to identify the potential derivatives of triterpenoids present in G. lucidum spores. As a result, a total of 22 triterpenoids from different G. lucidum spores were unequivocally or tentatively identified via comparisons with authentic standards and literatures. This method provides both qualitative and quantitative results without the need for repetitive UPLC-MS analyses, thereby increasing efficiency and productivity, making it suitable for high-throughput applications.

Triterpenoid profile of flower and leaf cuticular waxes of heather Calluna vulgaris

Analysis of the main triterpenoid profile of chloroform-soluble cuticular waxes of heather flowers and leaves by GC–MS revealed the following composition: five triterpene acids – betulinic, oleanolic, ursolic, 3-oxo-olean-12-en-28-oic and 3-oxo-ursan-12-en-28-oic; eight monohydroxyalcohols – α-amyrin, β-amyrin, cycloartanol, 24-methylenecycloartanol, friedelinol, germanicol, lupeol and taraxasterol; three dihydroxyalcohols – betulin, erythrodiol and uvaol; two aldehydes – oleanolic and ursolic; four ketones – α-amyrenone, 4-epi-friedelin, friedelin and taraxerone and seven steroids – campesterol, cholesterol, sitostanol, sitosterol, stigmasterol, stigmasta-3,5-dien-7-one and stigmastane-3,6-dione. Triterpenoids accounted for 20% and 65% by mass of flower and leaf waxes, respectively, which suggest that heather leaves represent a very promising source of these compounds. Ursolic acid was the principal triterpenoid in the cuticular wax of both organs, whereas among the neutral triterpenes, friedelin and uvaol were the most abundant in flowers and leaves, respectively. This report provides the first thorough overview of the triterpenoid composition of cuticular waxes of heather.

Preparative isolation of triterpenoids from Ganoderma lucidum by counter-current chromatography combined with pH-zone-refining

Ganoderma lucidum is a famous fungus. The triterpenoids are the main bioactive components and exhibit various pharmacological activities. However, the scarcity of the pure triterpenoid has greatly restrained the modern research of G. lucidum. The present paper first describes a convenient method to separate the main triterpenoids from G. lucidum using counter-current chromatography (CCC) technique. Ganoderic acid C6 (38mg), E (76mg), F (32mg) were successfully separated from the crude extract in 1day with the HPLC purity of above 90% using stepwise CCC. Ganoderic acid G (36mg), A (64mg), B (25mg), D (28mg) and ganoderenic acid D (11mg) were separated in 2days with the HPLC purity of above 90% using a combination of stepwise CCC and pH-zone-refining CCC. The method presented in the paper is much quicker and easier than the previous methods.

In vivo Antithrombotic and Antiplatelet Activities of a Quantified Acanthopanax sessiliflorus Fruit Extract

Aim To investigate the in vivo antithrombotic and antiplatelet activities and triterpenoid saponin contents of ethanol extract of Acanthopanax sessiliflorus fruits (ASF EtOH). Methods In the present work a quantified ASF EtOH was selected to determine its in vivo antithrombotic activity in a rat arteriovenous shunt thrombosis model and its inhibitory effect on adenosine diphosphate (ADP)-induced platelet aggregation using a platelet aggregometer. Ten triterpenoid saponin contents of the extract of the fruits were determined by a validated ultra-performance liquid chromatography-tandem mass spectrometry (UPLC-MS/MS) method. Total triterpenoid saponin content was also determined according to the colorimetric method by ultraviolet-visible spectrophotometer. Results After ASF EtOH (125, 250, 500 and 1 000 mg·kg −1/d) was orally administered to rats for 15 d, the in vivo antithrombotic activity on rats was in a concentration-dependant manner showing a significant linear relationship for ASF EtOH ( P < 0.05). Meanwhile, ASF EtOH significantly ( P < 0.05) inhibited ADP-induced platelet aggregation in vivo on rats. The inhibitions of (16.3 ± 4.7)%, (28.6 ± 4.1)%, (47.9 ± 4.0)% and (61.3 ± 6.6)% were reached for ASF EtOH at doses of 125, 250, 500 and 1 000 mg(kg −1 body weight (bw) respectively, compared to an inhibition of (55.4 ± 7.5)% for the positive control aspirin (27 mg(kg −1/d). The contents of the main triterpenoid saponins 22 α-hydroxychiisanoside, momordin Ib and chiisanogenin were (3 755 ± 51.3), (2 461 ± 73.0) and (1 114 ± 75.4) μg·g −1 dry fruit respectively. The amount of total triterpenoid saponins in ASF EtOH was (30.6 ± 0.6) mg of ginsenoside Re equivalents (GRE)/g. Conclusion These experimental results suggest that ASF EtOH has both in vivo antithrombotic and antiplatelet activities.

NMR‐based metabonomic approach on the toxicological effects of a Cimicifuga triterpenoid

Cimicifugae Rhizoma, a well-known botanical dietary supplement, has been the subject of intense interest due to its potential application for alleviating menopausal symptom. Although there are clinic data that the Cimicifuga extract should have hepatotoxicity, no evidence on the main chemical components has been reported. Cimicidol-3-O-β -d-xyloside (CX) is one of the main triterpenoids of the rhizome. This work studies the toxicological effects of CX after oral administration (50 mg kg(-1) per day) over a 7-day period in female SD rats using metabonomic analyses of (1) H NMR spectra of urine, serum and liver tissue extracts. Histopathological studies of liver and analyses of blood biochemical parameter, such as alanine aminotransferase, aspartate aminotransferase, alkaline phosphatase, blood urea nitrogen and creatinine revealed that CX had no negative impacts on liver and kidney. However, the metabolic signature of (1) H NMR-based urinalysis of daily samples displayed an increment in the levels of taurine, trimethylamine-N-oxide (TMAO), betaine and acetate. Elevated serum levels of creatinine, glucose, alanine, TMAO and betaine and lower levels of lactate were observed. Metabolic profiling on aqueous soluble extracts of liver showed simultaneously increases in succinate, glycogen, choline, glycerophosphorylcholine, TMAO and betaine levels and reduction in valine, glucose and lactate levels. Nevertheless, no changes in any metabonomic level were found in lipid-soluble extracts of liver. These findings indicate that CX has a slight toxicity in liver and kidney via disturbance of the metabolisms of energy and amino acids. The present study provides a reasonable explanation for the clinical hepatotoxicity of Cimicifuga extract.

Anti-tumor activity of triterpenoid-rich extract from bamboo shavings (Caulis bamfusae in Taeniam)

Bamboo shavings are a kind of Chinese traditional medicine, which have been certificated as a material of functional food by the Ministry of Health in China. The anti-tumor activities of a triterpenoid-rich extract of bamboo shavings (EBS) and its main component, friedelin were evaluated in the present study. It was proved that EBS could inhibit the growth of P388 and A549 cancer cell lines effectively by SRB and MTT assay. Meanwhile, EBS had notable inhibitory effect on the sarcoma-loaded mice S180 model, which led to a depressed trend of tumor weight, compared to cyclophosphamide. Furthermore, the anti-tumor activity of friedelin monomer, a main triterpenoid separated from EBS, was tested by MTT assay and results showed that friedelin displayed rather strong anti-tumor activities on the proliferation of four cancer lines, A375, L929, Hela and THP-1, with a time-dose relationship compared to de-methylcantharidin, respectively. Therefore, it is suggested that EBS has a great potential to be applied in functional food for its anti-tumor activity, in which friedelin was one of the most important active factors.

Pentacyclic Triterpenoids from Olive Fruit and Leaf

This work establishes a new procedure for the extraction and analysis of pentacyclic triterpenes, with which fruits and leaves from three Spanish olive cultivars ("Picual", "Hojiblanca", and "Arbequina") has been studied. The leaf contains important amounts of oleanolic acid (3.0-3.5% DW), followed by significant concentrations of maslinic acid and minor levels of ursolic acid, erythrodiol, and uvaol. The abundance and profile of triterpenoids change during the leaf ontogeny. In the fruit, triterpenes are exclusively located in the epicarp at concentrations 30-fold lower than that in the leaf. Maslinic acid is the main triterpenoid, only accompanied of oleanolic acid. Along the ripening the levels of these triterpenes decreased. All the analyzed leaves and fruits come from the same agricultural estate, with identical climate and culturing conditions. For this reason, the found differences could majorly be attributable to the genetic factors of the olive cultivars.

Simultaneous quantification of three major triterpenoids in radix asteris by high‐performance liquid chromatography with evaporative light scattering detection

Radix asteris, with triterpenoids as its main pharmacological effective compounds, has been widely used for moistening the lung, dispersing phlegm and relieving cough. Quantification of the triterpenoids is important for the quality control of Radix asteris. To establish a high-performance liquid chromatography method with evaporative light scattering detection for simultaneous determination of three major triterpenoids, shionone, friedelin and epi-friedelinol, in Radix asteris. The optimal chromatographic conditions were achieved on an RP(18) column with gradient elution by acetonitrile and 0.05% acetic acid in 22 min with ELSD set at an evaporating temperature of 40 degrees C. Validation of the method included tests of linearity, sensitivity, precision, repeatability, stability and accuracy. All calibration curves showed good linear regression (r(2) > 0.9991) within test ranges. The established method showed good precision and accuracy with overall intra-day and inter-day variations of 1.61-2.97 and 1.74-2.42%, respectively, and overall recoveries of 97.35-101.13% for the three compounds analysed. The method developed was successfully applied to quantify the main triterpenoids in 14 Radix asteris samples.

Determination and Quantitation of Five Cucurbitane Triterpenoids in Momordica charantia by Reversed-Phase High-Performance Liquid Chromatography with Evaporative Light Scattering Detection

A simple and specific analytical method for the quantitative determination of five cucurbitane-type triterpenoids isolated from the fruit of Momordica charantia is developed. The triterpenoids present in the fruits of Momordica charantia are separated with an acetonitrile (0.1% acetic acid)-water (0.1% acetic acid)-methanol (0.1% acetic acid) gradient at a flow rate of 0.5 mL/min. The high-performance liquid chromatography separation was performed on a Phenomenex C18 reversed-phase column. By using an evaporative light scattering detector, the main triterpenoids of Momordica charantia could be detected at levels as low as 10 microg/mL. The method was validated for precision, repeatability, and accuracy. The relative standard deviation was between 0.6-4.4%. The method was sensitive, quick, and accurate for the determination of main triterpenes and saponins in Momordica charantia, and can be used for quality control of Momordica charantia and its related dietary supplements.

Simultaneous quantitation of three major triterpenoid glycosides in Centella asiatica extracts by high performance liquid chromatography with evaporative light scattering detection

A high-performance liquid chromatography method with evaporative light scattering detection was established for simultaneous determination of three major triterpenoid glycosides, i.e. asiaticoside, madecassoside and asiaticoside-B, in Centella asiatica extracts. The optimal chromatographic conditions were achieved on a COSMOSIL 5C(18)-MS-II column by constant elution with water (0.01% trifluoroacetic acid, v/v) and acetonitrile (1.0% methyl tert-butyl ether, 0.01% trifluoroacetic acid, v/v) (78:22) as mobile phase at a flow rate of 1.0 mL/min; the column temperature was 30 degrees C. The evaporative light scattering detector was set at an evaporating temperature of 40 degrees C and nitrogen gas pressure of 3.5 bar. The validation of the method included tests of linearity, sensitivity, precision, repeatability, stability and accuracy. All calibration curves showed good linear regression (r(2) > 0.9993) within test ranges. The established method showed good precision and accuracy with overall intra-day and inter-day variations of 1.73-3.06 and 3.89%-4.92%, respectively, and overall recoveries of 97.63-99.39% for the three compounds analyzed. The method developed was successfully applied to quantify the main triterpenoid glycosides in Centella asiatica extracts from different companies.

Anti‐fatigue activity of a triterpenoid‐rich extract from Chinese bamboo shavings (Caulis bamfusae in taeniam)

The anti-fatigue activity of a pentacyclic triterpenoid extract from bamboo shavings (EBS) from the bark of bamboo (Bambusa tuldoides Munro), was evaluated in BALB/c mice. EBS, isolated by the supercritical CO(2) fluid extraction (SFE) technique, was given to mice at concentrations of 0.04 (low-dose group), 0.08 (middle-dose group) and 0.25 g/kg body weight (high-dose group). The anti-fatigue activity of EBS was estimated by the change in body weight, weight-loaded swimming test and climbing test, and corresponding parameters including serum urea nitrogen, hepatic glycogen and blood lactic acid were measured. The results showed that an appropriate level of EBS could prolong the weight-loaded swimming and climbing time, and had an active effect on the serum urea nitrogen, hepatic glycogen and blood lactic acid level in BALB/c mice, which significantly embodied the anti-fatigue activity of EBS. Overall, it is predicted that EBS, being a composition mainly containing a group of pentacyclic triterpenoids, and its main triterpenoid components have great potential for application in relevant fields for its anti-fatigue activity.

The effect of erythrodiol-3-acetate on the expressions of matrix metalloproteinase-1 and type-1 procollagen caused by ultraviolet irradiated cultured primary old aged human skin fibroblasts

Methanol and aqueous extracts of Styrax japonica used traditionally for the treatments of skin elastic materials were screened in vitro for the matrix metalloproteinase (MMP)-1 inhibitor actions. The methylene chloride soluble fraction of methanol extract from the stems of S. japonica showed significant MMP-1 inhibition in primary old aged human skin fibroblasts caused by ultraviolet (UV) irradiation. Main triterpenoids were isolated by repeated column chromatography. Among them, the triterpenoid erythrodiol-3-acetate reduced the expression of MMP-1 and induced the expression of type-1 procollagen at the protein levels in a dose-dependent manner caused by UV irradiated cultured old aged human skin fibroblasts. Taken together, our results suggest that erythrodiol-3-acetate plays an important role in the skin aging process caused by UV irradiation.

Variation in birch bark secondary chemistry between and within clones: implications for herbivory by hares

We studied the variation in bark chemistry between and within 19 European white birch (Betula pendula) clones and its implications to resistance to the mountain hare (Lepus timidus). We used one‐year‐old clonal plantlets originating from randomly selected naturally regenerated parental trees. The same clones were used in both chemical analyses and in feeding experiments. The condensed tannins were analysed by an acid butanol assay, other phenolic components by HPLC‐DAD, and triterpenoid components by HPLC‐MS. The resistance to hare was tested in open‐field feeding experiment. The main phenolic compounds in birch bark were catechin derivatives, rhododendrin, platyphylloside, and condensed tannins, and the main triterpenoids were papyriferic acid and pendulic acid. Most of the variation in the concentrations of the studied compounds was found between clones for the studied phenolics and large variation for triterpenoid components were found both between clones and among plantlets within the same clone. Hares clearly selected among the studied clones. Our results suggest that birch bark chemistry play an important role in resistance to herbivory by hare. The total triterpenoids and total flavonoid‐aglycones showed significant negative correlation with hare feeding. It seems that a genetic basis for bark chemistry and birch resistance is strong. Such a high variation in secondary chemistry both between clones and within individual clones indicates that European white birch populations have a good resistance towards variable environmental conditions and varying pressures from herbivory.

Intraperitoneal administration of Senegae Radix extract and its main component, senegin-II, affects lipid metabolism in normal and hyperlipidemic mice.

The hypolipidemic effect of Senegae Radix, i.e. "Senega," was investigated in normal and hyperlipidemic mice. The n-butanol fraction of the methanol extract of Senegae Radix (SN) (5 mg/kg) significantly reduced the blood triglyceride level of normal mice 7 h after intraperitoneal administration (p < 0.05) and also significantly reduced the blood triglyceride level of cholesterol-fed mice under similar conditions (p < 0.05). SN (5 mg/kg) also reduced the blood triglyceride and cholesterol levels after repeated administration to cholesterol-fed mice. SN also decreased the blood triglyceride level in Triton-induced hyperlipidemia. It is suggested that this fraction contains one or more hypolipidemic components including the main triterpenoid glycoside, senegin-II, which significantly reduces the levels of blood triglycerides in normal mice.

Bryonolic acid production in hairy roots of Trichosanthes kirilowii Max. var Japonica Kitam. Transformed with Agrobacterium rhizogenes and its cytotoxic activity.

The hairy roots of Trichosanthes kirilowii Max, var. japonica Kitam. were induced by Agrobacterium rhizogenes (TCC 15834) on sterile shoots. The axenic culture of hairy roots proliferated 30 to 60-fold based on the initial fresh weight after three weeks of culture in Murashige & Skoog liquid media. Bryonolic acid as the main triterpenoid was isolated in a high yield, together with chondrillasterol from the hairy roots of this plant. Bryonolic acid showed strong inhibition of the growth of B-16 melanoma cells.

Absolute Stereochemistry of Raspacionin, the Main Triterpenoid from the Marine Sponge Raspaciona aculeata

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTAbsolute Stereochemistry of Raspacionin, the Main Triterpenoid from the Marine Sponge Raspaciona aculeataGuido Cimino, Rosangela de A. Epifanio, Anna Madaio, Raffaella Puliti, and Enrico TrivelloneCite this: J. Nat. Prod. 1993, 56, 9, 1622–1626Publication Date (Print):September 1, 1993Publication History Published online1 July 2004Published inissue 1 September 1993https://doi.org/10.1021/np50099a028RIGHTS & PERMISSIONSArticle Views95Altmetric-Citations5LEARN ABOUT THESE METRICSArticle Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated. Share Add toView InAdd Full Text with ReferenceAdd Description ExportRISCitationCitation and abstractCitation and referencesMore Options Share onFacebookTwitterWechatLinked InReddit PDF (298 KB) Get e-Alerts Get e-Alerts

Comparative study on the strain-specific triterpenoid components of Ganoderma lucidum

The examination of strain-specific triterpenoid components pattern was made in three strains of Ganoderma lucidum; Sekishi, Shishi, Kokushi (all Japanese names). Comparative examination on triterpenoid patterns of strains of Ganoderma lucidum by HPLC revealed that Sekishi and Shishi have similar ganoderic acid derivatives, but Kokushi has no ganoderic acid derivatives. Ganoderic acid V 1, isolated as a main triterpenoid component of Shishi, is a new ganoderic acid derivative: (24 E)-3β,20ξ-dihydroxy-7,11,15-trioxo-5α-lanosta-8,24-dien-26-oic acid.

Fern constituents. Onoceroid,.ALPHA.-onoceradiene,serratene and onoceranoxide,isolated from Lemmaphyllum microphyllum varieties.

α-Onoceradiene (I) and serratene (IV) were isolated and identified from a Polypodiaceous fern, Lemmaphyllum microphyllum var. microphyllum, while a new compound, onoceranoxide (VII), was obtained from var. obovatum as a main triterpenoid and its structure was established.