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1.
Sci Total Environ ; 912: 169216, 2024 Feb 20.
Article En | MEDLINE | ID: mdl-38092198

Nonpolar organic compounds (NPOCs) are found in atmospheric aerosols and have significant implications for environmental and human health. Although many studies have quantitatively estimated the sources of NPOCs in different cities, few have evaluated their main influencing factors (e.g., emissions and meteorological conditions) at relatively long (e.g., different seasons) and short timescales (e.g., several days during pollution episodes). A better understanding of this issue could optimise strategies for dealing with organic contamination in atmospheric particulate matter. NPOCs (including n-alkanes, PAHs and hopanes) in fine particulate matter (PM2.5) were sampled daily at Nanchang, China, from 1 November 2020 to 31 October 2021. Analyses of specific biomarkers and diagnostic ratios indicate that the NPOCs mainly had anthropogenic sources. The quantitative estimates of a positive matrix factorization model show that fossil fuel and biomass combustion were the main sources of n-alkanes (contributing 64.8 %), while vehicle exhaust was the main source of PAHs (47.0 %) and hopanes (52.3 %). Seasonally, the contributions from coal and/or biomass combustion were higher in autumn and winter (40.2-56.3 %) than in spring and summer (25.7-44.3 %), while contributions from natural plants, petroleum volatilization and vehicle exhaust were higher in spring and summer (14.7-63.5 %) than in autumn and winter (8.1-48.9 %). Redundancy analysis shows that increased emissions, especially from coal and/or biomass combustion, are the main cause of increases in NPOCs, during both annual sampling periods and winter pollution episodes. Over the year, higher temperature and longer sunshine hours correspond to lower NPOC concentrations. In winter pollution episodes, increases in temperature and relative humidity correspond to increases in NPOC concentrations. Our results suggest that controlling primary emissions, especially from coal and biomass combustion, may be an effective way to prevent increases in NPOC concentrations.


Air Pollutants , Polycyclic Aromatic Hydrocarbons , Humans , Air Pollutants/analysis , Seasons , Environmental Monitoring , Particulate Matter/analysis , China , Vehicle Emissions/analysis , Organic Chemicals/analysis , Coal/analysis , Aerosols/analysis , Polycyclic Aromatic Hydrocarbons/analysis , Pentacyclic Triterpenes/analysis , Alkanes/analysis
2.
Anal Sci ; 39(10): 1741-1756, 2023 Oct.
Article En | MEDLINE | ID: mdl-37386278

Boswellia serrata (B. serrata) is an important medicinal plant widely used as dietary supplements to provide a support for osteoarthritic and inflammatory diseases. The occurrence of triterpenes in leaves of B. serrata is very little or none. Therefore, the qualitative and quantitative determination of phytoconstituents (triterpenes and phenolics) present in the leaves of B. serrata is very much needed. The aim of this study was to develop an easy, rapid, efficient and simultaneous liquid chromatography-mass spectrometry (LC-MS/MS) method for the identification and quantification of the compounds present in the leaves extract of B. serrata. The purification of ethyl acetate extracts of B. serrata was performed by solid phase extraction method, followed by HPLC-ESI-MS/MS analysis. Chromatographic parameters of the analytical method included negative electrospray ionization (ESI-) with a flow of 0.5 mL/min in gradient mode consisting of acetonitrile (A) and water (B) containing 0.1% formic acid, at 20 °C. Total 19 compounds (13 triterpenes and 6 phenolic compounds) were separated, and simultaneously quantified using a validated LC-MS/MS method with high accuracy and sensitivity. Good linearity was obtained with r2 > 0.973 in the calibration range. The overall recoveries were in a range between 95.78 and 100.2% with relative standard deviations (RSD) below 5% for the entire procedure of matrix spiking experiments. Overall, there was no ion suppression from the matrix. The quantification data showed that the total amount of triterpenes and phenolic compounds in the leaves of B. serrata ethyl acetate extract samples ranged from 14.54 to 102.14 mg/g and 2.14 to 93.12 mg/g of dry extract, respectively. This work provides, for the first time, a chromatographic fingerprinting analysis on the leaves of B. serrata. A rapid, efficient, and simultaneous liquid chromatography-mass spectrometry (LC-MS/MS) method was developed and used for the both identification and quantification of triterpenes and phenolic compounds in the leaves extracts of B. serrata. The method established in this work can be used as quality-control method for other market formulations or dietary supplements containing leaf extract of B. serrata.


Boswellia , Triterpenes , Chromatography, Liquid/methods , Tandem Mass Spectrometry/methods , Boswellia/chemistry , Pentacyclic Triterpenes/analysis , Plant Extracts/chemistry , Chromatography, High Pressure Liquid/methods , Triterpenes/analysis
3.
Biomed Chromatogr ; 36(10): e5448, 2022 Oct.
Article En | MEDLINE | ID: mdl-35837756

The goal of the study was to determine how much lupeol was present in different Bauhinia acuminata samples. Lupeol was analyzed using a unique (verified) high-performance thin-layer chromatography (HPTLC) method. Separation of various compounds was achieved on silica gel (66 F 254) plates with toluene and methanol (99:1) as the mobile phase, followed by derivatization with Liebermann-Burchard reagent (r2 = 0.996). The proposed approach demonstrated a satisfactory linear relationship in the concentration range of 4-8 µg/mL. The limit of detection and limit of quantification were 63.84 ng/spot and 208.57 ng/spot, respectively. The proposed method was a simple and precise procedure that provided good resolution with other constituents of extracts. The validated HPTLC method described was simple, dependable, and practical and could be useful for standardizing and evaluating the quality of herbal material and formulations containing various Bauhinia species. The leaf, stem, unsaponified matter leaf, and stem petroleum ether extract had good amounts of lupeol (25.75, 38.25, 1.65, and 1.75, respectively). This research will be helpful for the quantitative determination of lupeol from herbal formulations as well as useful for further studies in this area.


Bauhinia , Chromatography, Thin Layer/methods , Pentacyclic Triterpenes/analysis , Plant Extracts/chemistry
4.
Sci Total Environ ; 839: 156273, 2022 Sep 15.
Article En | MEDLINE | ID: mdl-35643145

The behavior of emissions is an important concern of in-situ burning (ISB) of spilled oils. In particular, the heavy soot originated from ISB can negatively impact the atmospheric environment. To track the behavior of ISB soot, the conservative biomarkers, such as hopanes and steranes, can be potentially used. In this study, the stability of chemical fingerprints of hopanes and steranes in the ISB soot were investigated based on the burning of two different types of oils, including one ultra-light condensate (i.e., surrogate Sanchi condensate) and one heavy oil. The results indicate that the chromatographic patterns and diagnostic ratios of hopanes and steranes in the ISB soot emissions almost remain identical to their corresponding source oils, proving the various oil source identification of ISB soot can be realized. This work attempts to provide novel insights into the application of biomarkers in the management of ISB emissions.


Petroleum Pollution , Petroleum , Biomarkers/analysis , Oils , Pentacyclic Triterpenes/analysis , Petroleum/analysis , Petroleum Pollution/analysis , Soot/analysis
5.
J Nat Med ; 76(4): 842-848, 2022 Sep.
Article En | MEDLINE | ID: mdl-35488895

Three new pentacyclic triterpenes, trivially named sandkoetjapic acids A-C (1-3), have been isolated from the leaves extract of Sandoricum koetjape, along with the known triterpenes 3-oxo-olean-12-en-29-oic (4), bryonolic (5), and bryononic (6) acids. The structures of the new triterpenes were determined mainly by NMR spectroscopic and mass spectroscopic data. The isolation of these pentacyclic triterpenes in the plant's leaves is for the first time. Preliminary biological evaluation of 1-6 was done against eight receptor tyrosine kinases (RTKs), including EGFR, HER2, HER4 (epidermal growth factor receptor), IGF1R, InsR (insulin receptor), KDR (kinase insert domain receptor), and PDGFRα/-ß (platelet-derived growth factor receptor), and their inhibitory properties against ß-lactamase. The results showed that none of them were active both as the inhibitors of these RTKs and ß-lactamase.


Meliaceae , Triterpenes , Meliaceae/chemistry , Molecular Structure , Pentacyclic Triterpenes/analysis , Plant Extracts/analysis , Plant Extracts/pharmacology , Plant Leaves/chemistry , Triterpenes/chemistry , beta-Lactamases/analysis
6.
Sci Rep ; 12(1): 2909, 2022 02 21.
Article En | MEDLINE | ID: mdl-35190633

A newly standardised extract of Centella asiatica (Centell-S) with better water solubility than the previous standardised extract of C. asiatica (ECa 233) was developed, and pharmacokinetic profiles of bioactive triterpenoids were investigated in beagle dogs. The test substances were administered via intravenous or oral administration with single and multiple doses for 7 days. The concentrations of major bioactive triterpenoids, including madecassoside, asiaticoside, madecassic acid, and asiatic acid, in biological samples were measured by liquid chromatography-tandem mass spectrometry. The dogs in this study showed good tolerability to all test substances, based on the physical appearance and blood chemistry 24 h after dosing. The major bioactive triterpenoids found in systemic blood circulation were madecassoside, asiaticoside, and asiatic acid; the concentration of these components ranged from 1 to 10,000 µg/L after intravenous administration of 1.0 mg/kg Centell-S. Oral administration of 10 and 20 mg/kg Centell-S generated approximately twofold higher plasma levels of both madecassoside and asiaticoside compared with equivalent doses of ECa 233. In addition, there was an accumulation of triterpenoid glycosides after multiple oral administrations of Centell-S for 7 days, while triterpenic acids showed little tendency for accumulation. Beagles had good tolerability to both standardised extracts of C. asiatica, and showed a similar pattern of bioactive triterpenoids to humans. Centell-S increased oral bioavailability of major triterpenoid glycosides and can be further developed into a phytopharmaceutical product.


Glycosides/pharmacokinetics , Plant Extracts/administration & dosage , Plant Extracts/pharmacokinetics , Triterpenes/pharmacokinetics , Water , Administration, Oral , Animals , Biological Availability , Centella/chemistry , Dogs , Glycosides/analysis , Pentacyclic Triterpenes/analysis , Pentacyclic Triterpenes/pharmacokinetics , Plant Extracts/chemistry , Solubility , Triterpenes/administration & dosage , Triterpenes/analysis , Triterpenes/chemistry
7.
Molecules ; 26(10)2021 May 17.
Article En | MEDLINE | ID: mdl-34067825

Lupeol, a natural lupane-type pentacyclic triterpene, possesses various pharmacological properties, and its production attracts attention. Significant quantities of lupeol are deposited on the castor aerial organ surface and are easily extractable as a predominant wax constituent. Thus, castor might be considered as a potential bioreactor for the production of lupeol. The lupeol biosynthesis pathway is well known, but how it is regulated remains largely unknown. Among large numbers of castor cultivars, we targeted one accession line (337) with high levels of lupeol on its stem surface and low levels thereof on its hypocotyl surface, implicating that lupeol synthesis is differentially regulated in the two organs. To explore the underlying mechanisms, we did comparative transcriptome analysis of the first internode of 337 stem and the upper hypocotyl. Our results show that large amounts of auxin-related genes are differentially expressed in both parts, implying some possible interactions between auxin and lupeol production. We also found that several auxin-responsive cis-elements are present in promoter regions of HMGR and LUS genes encoding two key enzymes involved in lupeol production. Furthermore, auxin treatments apparently induced the expression levels of RcHMGR and RcLUS. Furthermore, we observed that auxin treatment significantly increased lupeol contents, whereas inhibiting auxin transport led to an opposite phenotype. Our study reveals some relationships between hormone activity and lupeol synthesis and might provide a promising way for improving lupeol yields in castor.


Indoleacetic Acids/metabolism , Pentacyclic Triterpenes/metabolism , Ricinus/metabolism , Castor Oil/isolation & purification , Castor Oil/metabolism , Epidermis/metabolism , Gene Expression/genetics , Gene Expression Regulation, Plant/genetics , Indoleacetic Acids/analysis , Pentacyclic Triterpenes/analysis , Signal Transduction , Transcriptome/genetics
8.
Vet Parasitol ; 294: 109449, 2021 Jun.
Article En | MEDLINE | ID: mdl-33991727

Trypanosomosis and helminthosis, considered as part of neglected tropical diseases, are parasitic infections of public health importance, especially in Africa. Medicinal plants have been used in most parts of Africa, to treat these parasitic infections. The study aims to determine the anti-trypanosomal and anthelminthic properties of Tetrapleura tetraptera (fruit and stembark). The aqueous extracts of T. tetraptera fruit (TTFaq) and stembark (TTSaq), as well as ethanol extracts of T. tetraptera fruit (TTFe) and stembark (TTSe), were screened for their in vitro anti-trypanosomal and anthelminthic activities against T. b. brucei and Pheretima posthuma worms, respectively. Preliminary phytochemical screening of all extracts and gas chromatography-mass spectrometry (GC-MS) analysis of most active extracts were conducted. TTFaq exhibited anti-trypanosomal activity with IC50 of 18.18 µg/mL. TTSe and TTFe had moderate anti-trypanosomal activity with IC50 of 34.76 and 34.84 µg/mL, respectively. TTSaq had relatively low activity against the parasite with IC50 of 55.03 µg/mL. The SI of T. tetraptera extracts was between the range of 0.14-2.09. TTFaq showed dose-dependent activity causing paralysis and death of the adult worms at all concentrations. At the least concentration of 0.625 mg/mL, TTFaq induced paralysis and death after 101.88 ± 0.8 and 242.64 ± 0.38 min of exposure, respectively compared with the negative control (p < 0.0001). TTFe, TTSe and TTSaq caused paralysis of worms after 318.32 ± 0.74, 422.5 ± 0.72, 422.20 ± 0.55 min of exposure at minimum concentrations of 2.5, 10 and 5 mg/mL, respectively (p < 0.0001). However, no death was observed in worms treated with TTFe, TTSe and TTSaq at all test concentrations. In the presence of sub-minimal inhibitory concentration of the extracts, TTFaq potentiated the anthelminthic activity of albendazole whiles TTFe, TTSaq and TTSe inhibited the activity of albendazole. Phytochemical screening revealed the presence of saponins, triterpenoids, reducing sugars, flavonoids (absent in TTFe), steroids (absent in TTFaq) and tannins (absent in TTSe and TTFe) in the extracts. GC-MS revealed the presence of 9-octadecenamide and betulic acid in TTFaq. Hence, there was evidence provided here that Tetrapleura tetraptera may be effective. This gives credence to their folkloric use. However, further study might be necessary to ascertain safety use in both humans and animals.


Albendazole/chemistry , Anthelmintics/pharmacology , Phytochemicals/pharmacology , Plant Extracts/pharmacology , Tetrapleura/chemistry , Trypanocidal Agents/pharmacology , Trypanosoma brucei brucei/drug effects , Albendazole/pharmacology , Anthelmintics/chemistry , Ethanol , Fruit/chemistry , Gas Chromatography-Mass Spectrometry/veterinary , Oleic Acids/chemistry , Pentacyclic Triterpenes/analysis , Phytochemicals/chemistry , Plant Bark/chemistry , Plant Extracts/chemistry , Plant Stems/chemistry , Plants, Medicinal , Trypanocidal Agents/chemistry , Water , Betulinic Acid
9.
Molecules ; 26(5)2021 Mar 07.
Article En | MEDLINE | ID: mdl-33800018

Protium heptaphyllum (Aubl.) Marchand (PH) trees are endemic to the tropical region of South America, mostly Brazil. Antibacterial, antinociceptive, anti-inflammatory, anxiolytic, antidepressant and anti-hyperlipidemic/anti-hypercholesterolemic effects were reported for its resinous exudate Protiumheptaphyllum resin (PHR). This work aims to provide a qualitative and quantitative consistent chemical profiling of the major constituents of this resin and two extracts enriched in acid (acidic triterpene concentrated extract, ATCE) and neutral triterpenes (α and ß-amyrin concentrated extract, AMCE). GC-MS/GC-FID was used for volatile terpene fraction, a validated GC-MS method was developed for quantification of neutral α and ß-amyrin and HPLC-APCI HRMS2 was used for acidic triterpenes analysis. The chemical investigation reported 29 molecules, including 14 volatile terpenes, 6 neutral triterpenes and 11 acid triterpenes. The most abundant compounds were α-amyrin (251.28 g kg-1, 123.98 g kg-1 and 556.82 g kg-1 in PHR, ATCE and AMCE, respectively), ß-amyrin (172.66 g kg-1, 95.39 g kg-1 and 385.58 g kg-1 in PHR, ATCE and AMCE, respectively), 3-oxo-tirucalla-7,24-dien-21-oic acid (80.64 g kg-1, 157.10 g kg-1 and 15.31 g kg-1 in PHR, ATCE and AMCE, respectively) and 3α-hydroxy-tirucalla-8,24-dien-21-oic acid (77.71 g kg-1, 130.40 g kg-1 and 11.64 g kg-1 in PHR, ATCE and AMCE, respectively). Results showed specific enrichment of acidic and neutral triterpenoids in the two respective extracts.


Burseraceae/chemistry , Resins, Plant/chemistry , Volatile Organic Compounds/chemistry , Chromatography, High Pressure Liquid/methods , Gas Chromatography-Mass Spectrometry/methods , Pentacyclic Triterpenes/analysis , Plant Extracts/analysis , Plant Extracts/chemistry , Reproducibility of Results , Terpenes/analysis , Triterpenes/analysis , Triterpenes/chemistry
10.
Nat Prod Res ; 35(3): 503-507, 2021 Feb.
Article En | MEDLINE | ID: mdl-31282206

The lupeol detection in callus of Vernonanthura patens (Kunth) H. Rob. leaves is discussed. Leaf segments previously treated with sodium hypochlorite, ethanol, and distilled water were placed in MS basal medium (Murashige and Skoog) for 7 days. Next, callus induction were done in two complemented MS medium for 6 weeks. Then, callus propagation were performed in MS medium supplemented with 1.0 mg/L of benzylaminopurine (BAP) and 0.5 mg/L of 2,4-dichlorophenoxyacetic acid (2,4-D) for 50 days. Fresh callus were extracted every 10 days in an ultrasonic bath using ethyl acetate (1.0 g/10 mL). The identification was carried out by Gas Chromatography-Mass Spectrometry (GC-MS) using selected ion monitoring (SIM) acquisition mode with characteristic ions of lupeol. The results obtained indicate the occurrence of lupeol in callus extract after twenty days of proliferation. These findings could be use in subsequent scale-up studies for biomass production containing this active compound in order to replace conventional methods.


Asteraceae/cytology , Asteraceae/metabolism , Pentacyclic Triterpenes/analysis , Pentacyclic Triterpenes/metabolism , Plant Leaves/cytology , 2,4-Dichlorophenoxyacetic Acid/pharmacology , Benzyl Compounds/pharmacology , Culture Media/chemistry , Culture Media/pharmacology , Gas Chromatography-Mass Spectrometry , Plant Leaves/metabolism , Purines/pharmacology , Tissue Culture Techniques/methods
11.
Nat Prod Res ; 35(15): 2574-2578, 2021 Aug.
Article En | MEDLINE | ID: mdl-31674832

Leaf extracts from Eugenia punicifolia are rich in pentacyclic triterpenic acids (PTAs), especially barbinervic acid (BA), which is an important biomarker of the species. Dichloromethane extracts of E. punicifolia leaf samples harvested in Amazonian summer and winter seasons were analysed by infrared spectroscopy using ATR-FTIR technique aiming to evaluate barbinervic acid (BA) and its PTAs equivalent contents. A validated HPLC-DAD quantification method was also performed to compare the relationship between BA and PTAs contents in E. punicifolia extracts with ATR-FTIR technique. The use of ATR-FTIR allowed a rapid, efficient and environment-friendly quantification method for total PTAs equivalent content, showing a significant statistical difference (p< 0.05) in the production of these metabolites (38.66 µg/mL, summer; 13.62 µg/mL, winter). A mathematical correction factor between the HPLC-DAD and ATR-FTIR quantification methods was established.


Eugenia , Pentacyclic Triterpenes/chemistry , Plant Extracts/chemistry , Chromatography, High Pressure Liquid , Pentacyclic Triterpenes/analysis , Spectroscopy, Fourier Transform Infrared
12.
Phytomedicine ; 77: 153287, 2020 Oct.
Article En | MEDLINE | ID: mdl-32739573

BACKGROUND: Styrax, one of the most famous folk medicines, has been frequently used for the treatment of cardiovascular diseases and skin problems in Asia and Africa. It is unclear whether Styrax or Styrax-related herbal medicines may trigger clinically relevant herb-drug interactions. PURPOSE: This study was carried out to investigate the inhibitory effects of Styrax on human cytochrome P450 enzymes (CYPs) and to clarify whether this herb may modulate the pharmacokinetic behavior of the CYP-substrate drug warfarin when co-administered. STUDY DESIGN: The inhibitory effects of Styrax on CYPs were assayed in human liver microsomes (HLM), while the pharmacokinetic interactions between Styrax and warfarin were investigated in rats. The bioactive constituents in Styrax with strong CYP3A inhibitory activity were identified and their inhibitory mechanisms were carefully investigated. METHODS: The inhibitory effects of Styrax on human CYPs were assayed in vitro, while the pharmacokinetic interactions between Styrax and warfarin were studied in rats. Fingerprinting analysis of Styrax coupled with LC-TOF-MS/MS profiling and CYP inhibition assays were used to identify the constituents with strong CYP3A inhibitory activity. The inhibitory mechanism of oleanonic acid (the most potent CYP3A inhibitor occurring in Styrax) against CYP3A4 was investigated by a panel of inhibition kinetics analyses and in silico analysis. RESULTS: In vitro assays demonstrated that Styrax extract strongly inhibited human CYP3A and moderately inhibited six other tested human CYPs, as well as potently inhibited warfarin 10-hydroxylation in liver microsomes from both humans and rats. In vivo assays demonstrated that compared with warfarin given individually in rats, Styrax (100 mg/kg) significantly prolonged the plasma half-life of warfarin by 2.3-fold and increased the AUC(0-inf) of warfarin by 2.7-fold when this herb was co-administrated with warfarin (2 mg/kg) in rats. Two LC fractions were found with strong CYP3A inhibitory activity and the major constituents in these fractions were characterized by LC-TOF-MS/MS. Five pentacyclic triterpenoid acids (including epibetulinic acid, betulinic acid, betulonic acid, oleanonic acid and maslinic acid) present in Styrax were potent CYP3A inhibitors, and oleanonic acid was a competitive inhibitor against CYP3A-mediated testosterone 6ß-hydroxylation. CONCLUSION: Styrax and the pentacyclic triterpenoid acids occurring in this herb strongly modulate the pharmacokinetic behavior of warfarin via inhibition of CYP3A.


Herb-Drug Interactions , Microsomes, Liver/drug effects , Plant Extracts/pharmacokinetics , Styrax/chemistry , Warfarin/pharmacokinetics , Animals , Anticoagulants/pharmacokinetics , Chromatography, Reverse-Phase , Cytochrome P-450 CYP3A/metabolism , Cytochrome P-450 CYP3A Inhibitors/pharmacology , Cytochrome P-450 Enzyme Inhibitors/pharmacokinetics , Cytochrome P-450 Enzyme System/metabolism , Humans , Hydroxylation/drug effects , Male , Microsomes, Liver/metabolism , Pentacyclic Triterpenes/analysis , Pentacyclic Triterpenes/pharmacology , Plant Extracts/chemistry , Plants, Medicinal/chemistry , Rats, Sprague-Dawley , Tandem Mass Spectrometry , Triterpenes/analysis , Triterpenes/pharmacology , Betulinic Acid
13.
Biomolecules ; 10(4)2020 03 27.
Article En | MEDLINE | ID: mdl-32230928

Many biologically-active plant-derived compounds have therapeutic or chemopreventive effects. The use of plant in vitro cultures in conjunction with modern genetic engineering techniques allows greater amounts of valuable secondary metabolites to be obtained without interfering with the natural environment. This work presents the first findings concerning the acquisition of transgenic hairy roots of Senna obtusifolia overexpressing the gene encoding squalene synthase 1 from Panax ginseng (PgSS1) (SOPSS hairy loot lines) involved in terpenoid biosynthesis. Our results confirm that one of PgSS1-overexpressing hairy root line extracts (SOPSS2) possess a high cytotoxic effect against a human acute lymphoblastic leukemia (NALM6) cell line. Further analysis of the cell cycle, the expression of apoptosis-related genes (TP53, PUMA, NOXA, BAX) and the observed decrease in mitochondrial membrane potential also confirmed that the SOPSS2 hairy root extract displays the highest effects; similar results were also obtained for this extract combined with doxorubicin. The high cytotoxic activity, observed both alone or in combination with doxorubicin, may be due to the higher content of betulinic acid as determined by HPLC analysis. Our results suggest synergistic effects of tested extract (betulinic acid in greater amount) with doxorubicin which may be used in the future to develop new effective strategies of cancer chemosensitization.


Antineoplastic Agents, Phytogenic/pharmacology , Farnesyl-Diphosphate Farnesyltransferase/genetics , Panax/genetics , Precursor Cell Lymphoblastic Leukemia-Lymphoma/drug therapy , Senna Extract/pharmacology , Apoptosis/drug effects , Doxorubicin/pharmacology , Gene Expression Profiling , Gene Expression Regulation, Leukemic/drug effects , Green Fluorescent Proteins/genetics , Humans , Leukemia , Membrane Potential, Mitochondrial/drug effects , Pentacyclic Triterpenes/analysis , Plant Proteins/genetics , Plant Proteins/metabolism , Plant Roots/chemistry , Plant Roots/cytology , Plant Roots/genetics , Plants, Genetically Modified/genetics , Polymerase Chain Reaction , Precursor Cell Lymphoblastic Leukemia-Lymphoma/genetics , Precursor Cell Lymphoblastic Leukemia-Lymphoma/pathology , Senna Extract/chemistry , Senna Plant/genetics , Betulinic Acid
14.
Nat Prod Res ; 34(23): 3313-3319, 2020 Dec.
Article En | MEDLINE | ID: mdl-30810367

A new pentacyclic triterpenoid, 3-oxo-urs-11,13(18)-dien-28-oic acid (1), along with twelve known triterpenoids, α-amyrin (2), 19α-hydroxy-α-amyrin (3), triptohypol E (4), uvaol (5), 2α,3α-dihydroxyurs-11-en-13ß,28-olide (6), 3ß-hydroxyurs-11-en-13ß,28-olide (7), ursolic acid (8), asiatic acid (9), oleanolic acid (10), aegiceradienol (11), obtusalin (12) and betulinic acid (13) were isolated from the leaves of Rhododendron dauricum L. Their structures were established from spectroscopic data and comparison with reported values. Among them, compounds 3, 4, 6, 7 and 11 were isolated from the Ericaceae family for the first time. Compounds 2, 5, 9, 12 and 13 were obtained from R. dauricum for the first time. Additionally, compounds 6, 10 and 11 significantly inhibited the levels of NO in LPS-stimulated RAW 264.7 cells at 3 µM.


Anti-Inflammatory Agents, Non-Steroidal/pharmacology , Nitric Oxide/biosynthesis , Rhododendron/chemistry , Triterpenes/chemistry , Triterpenes/pharmacology , Animals , Anti-Inflammatory Agents, Non-Steroidal/chemistry , Drug Evaluation, Preclinical , Lipopolysaccharides/pharmacology , Mice , Molecular Structure , Nitric Oxide/antagonists & inhibitors , Oleanolic Acid/analysis , Pentacyclic Triterpenes/analysis , Plant Extracts/chemistry , Plant Leaves/chemistry , RAW 264.7 Cells , Triterpenes/analysis , Betulinic Acid , Ursolic Acid
15.
Nat Prod Res ; 34(3): 421-424, 2020 Feb.
Article En | MEDLINE | ID: mdl-30499332

Phytochemical investigation of the Jurinea macrocephala roots afforded six compounds namely ß-sitosterol (1), lupenone (2), physcion (3), ptiloepoxide (4), 20, 21α-epoxytaraxastan-3ß-ol (5) and chlorogenic acid (6). All the compounds were isolated for the first time in roots. The structures of the compounds were established by analysis of their spectroscopic (1H and 13C NMR) and spectrometric (MS) data, as well as by comparison of these with those reported in the literature. Metabolic profiling of chloroform and ethyl acetate fractions were also accomplished using NMR. In NMR analysis, ERETIC (electronic reference to access in-vivo concentration) 2 method was used for the quantification of identified metabolites. High quantity of chlorogenic acid (6, 130 mg/g) lupenone (2, 33.4 mg/g) and amyrins (α, ß) (170.6 mg/g) were detected in ethyl acetate and chloroform fractions. Further studies on the biological evaluation of phenolic-rich and chloroform fractions could be beneficial to explore its pharmaceutical potential.


Asteraceae/chemistry , Phytochemicals/analysis , Plant Extracts/chemistry , Plant Roots/chemistry , Chlorogenic Acid/analysis , Molecular Structure , Pentacyclic Triterpenes/analysis , Phytochemicals/isolation & purification , Sitosterols/analysis , Spectrum Analysis , Triterpenes/analysis
16.
Sci Rep ; 9(1): 18501, 2019 12 06.
Article En | MEDLINE | ID: mdl-31811217

The chemical composition of pentacyclic triterpenes was analysed using a 'Royal Gala' x 'Granny Smith' segregating population in 2013 and 2015, using apple peels extracted from mature fruit at harvest and after 12 weeks of cold storage. In 2013, 20 compound isoforms from nine unique compound classes were measured for both treatments. In 2015, 20 and 17 compound isoforms from eight unique compound classes were measured at harvest and after cold storage, respectively. In total, 68 quantitative trait loci (QTLs) were detected on 13 linkage groups (LG). Thirty two and 36 QTLs were detected for compounds measured at harvest and after cold storage, respectively. The apple chromosomes with the most QTLs were LG3, LG5, LG9 and LG17. The largest effect QTL was for trihydroxy-urs-12-ene-28-oic acid, located on LG5; this was measured in 2015 after storage, and was inherited from the 'Royal Gala' parent (24.9% of the phenotypic variation explained).


Fruit/chemistry , Malus/genetics , Pentacyclic Triterpenes/analysis , Quantitative Trait Loci , Chromosome Mapping , Crosses, Genetic , Genes, Plant , Genetic Linkage , Phenotype , Species Specificity
17.
Talanta ; 205: 120011, 2019 Dec 01.
Article En | MEDLINE | ID: mdl-31450389

A fast and simple analytical method was developed to fully understand the chemical diversity of pentacyclic triterpenes: lupane, oleanane and ursane type, using multiple neutral loss markers scanning combined with substructure recognition (MNLSR). This procedure was performed on ultra-high performance liquid chromatography coupled to electrospray ionization quadrupole Orbitrap high resolution mass spectrometry (UHPLC/ESI Q-Orbitrap). Hippophae rhamnoides was used as an example. This approach includes three systematic workflows: (i) targeted identification of 25 reference standards in order to deduce the mechanism of fragmentation in both positive and negative modes. (ii) statistical analysis for neutral loss markers and structural fragment markers of pentacyclic triterpenes by fragmentation mechanism information. (iii) untargeted identification using multiple neutral loss markers scanning technique to discover new compounds and then confirming structural characterization by structural fragment markers. This mass spectra data analysis approach was successful to identify and confirm 15 new compounds from Hippophae rhamnoides samples. This study extended the application of mass spectrometry to satisfy the requirements of high-throughput identification for pentacyclic triterpenes in new medicine or food resources and could help chemists rapidly discover novel similar substructure compounds from a complex matrix.


Hippophae/chemistry , Pentacyclic Triterpenes/analysis , Spectrometry, Mass, Electrospray Ionization/methods , Calibration , Chemical Fractionation/methods , Chromatography, High Pressure Liquid , Isomerism , Limit of Detection , Molecular Structure , Pentacyclic Triterpenes/chemistry , Pentacyclic Triterpenes/isolation & purification , Reproducibility of Results , Signal Processing, Computer-Assisted , Tandem Mass Spectrometry/methods , Triterpenes/analysis
18.
Geobiology ; 17(5): 551-563, 2019 09.
Article En | MEDLINE | ID: mdl-31325234

Bacteriohopanepolyols (BHPs) are pentacyclic triterpenoid lipids that contribute to the structural integrity and physiology of some bacteria. Because some BHPs originate from specific classes of bacteria, BHPs have potential as taxonomically and environmentally diagnostic biomarkers. For example, a stereoisomer of bacteriohopanetetrol (informally BHT II) has been associated with anaerobic ammonium oxidation (anammox) bacteria and suboxic to anoxic marine environments where anammox is active. As a result, the detection of BHT II in the sedimentary record and fluctuations in the relative abundance of BHT II may inform reconstructions of nitrogen cycling and ocean redox changes through the geological record. However, there are uncertainties concerning the sources of BHT II and whether or not BHT II is produced in abundance in non-marine environments, both of which are pertinent to interpretations of BHT II signatures in sediments. To address these questions, we investigate the BHP composition of benthic microbial mats from Lake Fryxell, Antarctica. Lake Fryxell is a perennially ice-covered lake with a sharp oxycline in a density-stabilized water column. We describe the diversity and abundance of BHPs in benthic microbial mats across a transect from oxic to anoxic conditions. Generally, BHP abundances and diversity vary with the morphologies of microbial mats, which were previously shown to reflect local environmental conditions, such as irradiance and oxygen and sulfide concentrations. BHT II was identified in mats that exist within oxic to anoxic portions of the lake. However, anammox bacteria have yet to be identified in Lake Fryxell. We examine our results in the context of BHPs as biomarkers in modern and ancient environments.


Bacteria/metabolism , Geologic Sediments/analysis , Lipids/analysis , Pentacyclic Triterpenes/analysis , Antarctic Regions , Bacteria/chemistry , Bacterial Physiological Phenomena , Lakes/chemistry , Polymers/analysis
19.
Molecules ; 24(11)2019 Jun 07.
Article En | MEDLINE | ID: mdl-31181656

Pentacyclic triterpenic acids from oleogum resins of Boswellia species are of considerable therapeutic interest. Yet, their pharmaceutical development is hampered by uncertainties regarding botanical identification and the complexity of triterpenic acid mixtures. Here, a highly sensitive, selective, and accurate method for the simultaneous quantification of eight boswellic and lupeolic acids by high-performance liquid chromatography with tandem mass spectrometry detection (HPLC-MS/MS) was developed. The method was applied to the comparative analysis of 41 oleogum resins of the species B. sacra, B. dalzielli, B. papyrifera, B. serrata, B. carterii, B. neglecta, B. rivae, B. frereana, and B. occulta. Multivariate statistical analysis of the data revealed differences in the triterpenic acid composition that could be assigned to distinct Boswellia species and to their geographic growth location. Extracts of the oleogum resins exhibited cytotoxicity against the human, treatment-resistant, metastatic breast cancer cell line MDA-MB-231. Extracts from B. sacra were the most potent ones with an average IC50 of 8.3 ± 0.6 µg/mL. The oleogum resin of the B. sacra was further fractionated to enrich different groups of substances. The cytotoxic efficacy against the cancer cells correlates positively with the contents of pentacyclic triterpenic acids in Boswellia extracts.


Antineoplastic Agents, Phytogenic/analysis , Boswellia/chemistry , Breast Neoplasms/drug therapy , Pentacyclic Triterpenes/analysis , Resins, Plant/analysis , Antineoplastic Agents, Phytogenic/pharmacology , Cell Line, Tumor , Cell Proliferation/drug effects , Cell Survival/drug effects , Chromatography, High Pressure Liquid , Drug Resistance, Neoplasm/drug effects , Female , Humans , Pentacyclic Triterpenes/pharmacology , Resins, Plant/pharmacology , Tandem Mass Spectrometry , Triterpenes/isolation & purification , Triterpenes/pharmacology
20.
J Chromatogr Sci ; 57(8): 688-696, 2019 Aug 16.
Article En | MEDLINE | ID: mdl-31251318

Tephrosia purpurea (L.) Pers., commonly known as "sarpunkha" and "wild indigo", is being used in traditional systems of medicine to treat liver disorders, spleen and kidney. In the present study, a validated High Performance Thin Layer Chromatography (HPTLC) method was established for the estimation of lupeol, ß-sitosterol and rotenone in various extracts of T. purpurea with the aim to see the effect of seasons on the quantity of aforesaid phytoconstituents. The plant material was collected in summer (April), rainy (August) and winter (December) during 2013-2014 from Lucknow, India. The method was validated in terms of precision, repeatability, specificity, sensitivity linearity and robustness. The method permits reliable quantification and showed good resolution on silica gel with toluene-ethyl acetate-formic acid (9:1:1 v/v/v) as mobile phase, and characteristic bands of ß-sitosterol, rotenone and lupeol were observed at Rf 0.38, 0.45 and 0.52, respectively. The content of aforesaid phytoconstituents varies from season to season and extract to extract. Our finding indicated that winter season (December) may not be appropriate for collection of T. purpurea for the preparation of therapeutic formulations because of the high content of rotenone, a known insecticide that is responsible for Parkinson's disease and associated with heart failure, fatty liver and liver necrosis.


Chromatography, Thin Layer/methods , Pentacyclic Triterpenes/analysis , Plant Extracts/analysis , Rotenone/analysis , Sitosterols/analysis , Tephrosia/chemistry , India , Seasons
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