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Withania somnifera (Ashwagandha) is a plant of the Solanaceae family. It has been widely used as a remedy for a variety of ailments in India and Nepal. The plant has also been used as a controlling agent for dental diseases. The aim of the present study was to evaluate the activity of the methanol extract of W. somnifera against the physiological ability of cariogenic biofilms and to identify the components of the extract. To determine the activity of the extract, assays for sucrose-dependent bacterial adherence, glycolytic acid production, acid tolerance, and extracellular polysaccharide formation were performed using Streptococcus mutans biofilms. The viability change of S. mutans biofilms cells was also determined. A phytochemical analysis of the extract was performed using TLC and LC/MS/MS. The extract showed inhibitory effects on sucrose-dependent bacterial adherence (≥ 100 μg/ml), glycolytic acid production (≥ 300 μg/ml), acid tolerance (≥ 300 μg/ml), and extracellular polysaccharide formation (≥ 300 μg/ml) of S. mutans biofilms. However, the extract did not alter the viability of S. mutans biofilms cells in all concentrations tested. Based on the phytochemical analysis, the activity of the extract may be related to the presence of alkaloids, anthrones, coumarines, anthraquinones, terpenoids, flavonoids, and steroid lactones (withanolide A, withaferin A, withanolide B, withanoside IV, and 12-deoxy withastramonolide). These data indicate that W. somnifera may be a potential agent for restraining the physiological ability of cariogenic biofilms.

The effort to maintain cannabinoid and terpene levels in harvested medicinal cannabis inflorescence is crucial, as many studies demonstrated a significant concentration decrease in these compounds during the drying, curing, and storage steps. These stages are critical for the preparation and preservation of medicinal cannabis for end-use, and any decline in cannabinoid and terpene content could potentially reduce the therapeutic efficacy of the product. Consequently, in the present study, we determined the efficacy of pre-harvest hexanoic acid treatment alongside four months of post-harvest vacuum storage in prolonging the shelf life of high THCA cannabis inflorescence. Our findings indicate that hexanoic acid treatment led to elevated concentrations of certain cannabinoids and terpenes on the day of harvest and subsequent to the drying and curing processes. Furthermore, the combination of hexanoic acid treatment and vacuum storage yielded the longest shelf life and the highest cannabinoid and mono-terpene content as compared to all other groups studied. Specifically, the major cannabinoid's—(-)-Δ9-trans-tetrahydrocannabinolic acid (THCA)—concentration decreased by 4–23% during the four months of storage with the lowest reduction observed following hexanoic acid pre-harvest treatment and post-harvest vacuum storage. Hexanoic acid spray application displayed a more pronounced impact on mono-terpene preservation than storage under vacuum without hexanoic acid treatment. Conversely, sesqui-terpenes were observed to be less prone to degradation than mono-terpenes over an extended storage duration. In summation, appropriate pre-harvest treatment coupled with optimized storage conditions can significantly extend the shelf life of cannabis inflorescence and preserve high active compound concentration over an extended time period. [ABSTRACT FROM AUTHOR]

Proteinogenic amino acids react with O,O-diterpenyl dithiophosphoric acids to give alkylammonium dithiophosphates possessing pronounced antibacterial activity. [ABSTRACT FROM AUTHOR]

This study was planned to develop a simple high-performance thin-layer chromatography method for qualitative and quantitative estimation of 3-acetyl-11-keto-β-boswellic acid (AKBBA), β-boswellic acid (BBA), 3-oxo-tirucallic acid (TCA) and serratol (SRT) with HPTLC-ESI-MS/MS for characterization in Boswellia serrata Roxb. oleo gum resin extract. The method was developed with hexane-ethyl acetate-toluene-chloroform-formic acid as mobile phase. R F values observed for AKBBA, BBA, TCA and SRT were 0.42, 0.39, 0.53 and 0.72, respectively. The method was validated according to International Council for Harmonisation guidelines. The concentration range for linearity was 100–500 ng/band for AKBBA and 200–700 ng/band for the other three markers with r 2 > 0.99. The method resulted in good recoveries as 101.56, 100.68, 98.64 and 103.26%. The limit of detection was noticed as 25 , 37, 54 and 38 ng/band, with a limit of quantification as 76, 114, 116 and 115 ng/band, for AKBBA, BBA, TCA and SRT, respectively. The four markers were identified and confirmed in B. serrata extract using TLC-MS by indirect profiling by LC-ESI-MS/MS and were identified as terpenoids, TCA and cembranoids: AKBBA (mass/charge (m/z) = 513.00), BBA (m/z  = 455.40), 3-oxo-tirucallic acid (m/z  = 455.70) and SRT (m/z  = 291.25), respectively. [ABSTRACT FROM AUTHOR]

Arylphosphonodithioic acid esters derived from monoterpenyl alcohols react with pyridoxine and seven-membered pyridoxine acetonide to form pyridoxinium O-terpenyl arylphosphonodithioates which showed a high antibacterial activity against Bacillus cereus. [ABSTRACT FROM AUTHOR]

San-Bai Decoction (SBD) is a classic whitening prescription originally recorded in the 'Introduction to Medicine' of the Ming Dynasty. SBD has been known for invigorating Qi and blood, promoting spleen and stomach, whitening skin, and fading melasma. However, its pharmacodynamic material basis and specific mechanism remain unclear. The aim of this study is to clarify the pharmacodynamic material basis of SBD and its mechanism of removing melasma. The positive and negative ion mass spectrum data of SBD extract were collected by UHPLC-Q-Exactive Orbitrap MS/MS, imported into Compound Discoverer (CD) 3.1 software, matched through the online database, and manually checked. Finally, the in vitro chemical components of SBD were classified. Similarly, the mass spectrum data of SBD in the serum of normal rats and melasma model rats were also analyzed by CD 3.1 software. The in vitro identified Compound file of SBD was imported into the Expected Compounds and the Generate Expected Compounds project was selected. The SBD compounds were then chosen under the Compound Section. All phase I and II reaction types related to SBD components were selected, and the metabolic platform of CD 3.1 software was utilized to process the results and obtain possible metabolites. The metabolites were scored and products with high scores were subsequently screened. According to literature comparison, the final metabolites of SBD in both normal rats and melasma model rats were determined and comprehensively analyzed. The Melasma model rats were constructed through intramuscular injection of progesterone and ultraviolet radiation B (UVB) irradiation. The preventing and treating effect of SBD on melasma were evaluated by regulating inflammation, epidermal collagen content, and oxidative stress. Additionally, the effect of SBD on the Phosphatidylinositol 3-kinase (PI3K)/Protein kinase B (Akt)/Glycogen synthase kinase 3β (GSK3β) pathway was investigated through Western blot (WB) to explore its underlying mechanism on whitening and removing melasma efficacy. Ultimately, 94 components were identified in SBD, including 41 flavonoids, 27 organic acids, and 9 glycosides, 3 terpenoids, 2 amides, 2 aldehydes, 1 phenylpropanoid and 9 other compounds. In the blood of normal rat group, a total of 24 prototype components and 61 metabolites were identified. Similarly, there were19 prototype components and 44 metabolites identified from the blood of melasma model rats. Pharmacodynamic experiment results indicated that SBD effectively reduced the incidence of melasma, prevent the loss of epidermal collagen, and elevate the activity of superoxide dismutase and decrease the malondialdehyde content in both liver and skin. Interestingly, the WB results demonstrated that SBD effectively activated PI3K/Akt/GSK3β pathway, and down-regulated the expression of melanin-related proteins. For the first time, the components of SBD extracts, and its prototype components and metabolites in the blood of normal rats and melasma model rats were successfully identified by high-resolution liquid chromatography-mass spectrometry with CD software. Additionally, the differences of in vivo components of SBD between normal rats and melasma model rats were analyzed. The preventive and therapeutic effect of SBD on melasma was verified in the melasma model rats induced by progesterone and UVB irradiation, and its mechanism was related to activating PI3K/Akt/GSK3β pathway and downregulating the expression of melanin-related proteins. These results provide an experimental foundation for further research on the pharmacodynamic substance basis and pharmacodynamic mechanism of SBD, as well as developing new anti-melasma formula with SBD. [Display omitted] • UHPLC-Q-Exactive Orbitrap mass spectrometry was employed to analyze the constituents of San-Bai Decoction (SBD) extract and its prototype components and metabolites in the blood of normal rats and melasma model rats. • The preventive and therapeutic effect of SBD on melasma was verified in the melasma model rats. • The mechanism of SBD on melasma was related to activating PI3K/Akt/GSK3β pathway. [ABSTRACT FROM AUTHOR]

This study aimed to screen microorganisms capable of removing ginkgolic acids (GAs) from Ginkgo biloba leaf. Given the presence of long alkyl side chains in GAs, the study first focused on screening microorganisms that could utilize long-chain alkanes (n-tridecane, n-pentadecane, and n-heptadecane) and further studying their GAs degradation abilities. The results showed that the degradation rates of GAs by the two bacteria strains (identified as Pantoea sp.) were about 50 %, and the degradation rates of GAs by the nine fungal strains (identified as Fusarium sp.) were about 95 %. Meanwhile, Lactiplantibacillus plantarum was also found to exhibit a robust capacity for degrading GAs. Through further optimization of the medium components and fermentation conditions, Lactiplantibacillus plantarum achieved a degradation rate of 81.581 % for total GAs after 72 hours of cultivation. Notably, this process did not significantly impact flavonoids and terpene lactones present in Ginkgo biloba extract (EGb), which are essential for its therapeutic properties. Additionally, the results demonstrated that the hydrophobicity of GAs significantly influenced the degradation efficiency of GAs by Lactiplantibacillus plantarum. This study highlights the potential industrial application value of Lactiplantibacillus plantarum in the production of ginkgo products with low GAs content, thereby enhancing the safety and efficacy of this widely used medicinal plant. • Two strains of bacteria and nine strains of fungi screened from the soil could degrade GAs. • Lactiplantibacillus plantarum commonly used in food industry has good ability to degrade GAs. • Lactiplantibacillus plantarum has no significant effect on flavonoids and other active ingredients in EGb. • The structure of GAs had great influence on the degradation effect of GAs by Lactiplantibacillus plantarum. [ABSTRACT FROM AUTHOR]

Introduction. In order to solve the growing demand for Muscat sparkling wines, some of the Muscat grapes used for the production of liqueur wines should be used as a raw material for sparkling wines. The technology of preparing young sparkling wines has a shorter production cycle. Science-based selection of the yeast race makes it possible to obtain young sparkling wines with a clear and bright Muscat aroma. Study objects and method. The research featured young sparkling wines from White Muscat grapes, produced using different yeasts races. The research involved both standard and modified methods of enochemical analysis. Results and discussion. The LALVIN QA-23 and Odesskiy Cherniy-SD-13 yeast races demonstrated a more active fermentation of Muscat white wort. The Sevastopolskaya 23 sample had in a slower fermentation, which promoted a greater accumulation of bound forms of carbon dioxide (16%). It contained the smallest amount of residual sugars (2 g/dm3) and thriable acids (6 g/dm3) and the largest amount of polyphenols (103 mg/dm3) and amine nitrogen (91 mg/dm3). Two samples accumulated a sufficient amount of free terpenes: 1.16 mg/dm3 for LALVIN QA-23 and 1.13 mg/dm3 for Sevastopolskaya 23. The degustation scores were quite high: LALVIN QA-23 received 9.03 points and Odesskiy Cherniy-SD-13 – 9.02 points, while Sevastopolskaya 23 scored 9.00 points. The LALVIN QA-23 sample proved to have the most pronounced varietal aroma, whereas the Odesskiy Cherniy-SD-13 sample possessed a more complex aromatic complex. Conclusion. The LALVIN QA-23 and Sevastopolskaya 23 yeast races were found suitable for bottle champagnization of young Muscat sparkling wines. They accumulated a sufficient amount of terpene alcohols. The samples had a clear Muscat aroma, harmonious taste, and good typical properties. The new method makes it possible to produce high quality sparkling wines in the harvest year.

Two new triterpenoids, 3β-hydroxytirucall-7,25-dien-24-one (1) and 3β-acetoxytirucall-7,23,25-triene (2), along with one new sesquiterpenoid, alloaromadendrane-12α,14β-dioic acid (3), were isolated from the vines and leaves of Chonemorpha megacalyx Pierre. Their structures were established on the basis of extensive spectroscopic data. [ABSTRACT FROM AUTHOR]

The identity of Lecanora ecorticata has been uncertain due to conflicting reports of the presence of zeorin and the loss of the holotype. Phylogenetic analysis suggests that the species probably belongs in Ramalinaceae, where it is the first leprose species reported. Zeorin was found to be absent in recently collected material of L. ecorticata, including specimens from the type locality, and the report of zeorin in the lost holotype is considered to be due to contamination. A new genus, Lithocalla, is erected to accommodate L. ecorticata and a second closely related species, that occurs in the Falkland Islands, is newly combined as Lithocalla malouina. A lectotype is selected for L. ecorticata. Lithocalla is characterized by a leprose thallus containing usnic acid with fatty acids and terpenoids, but no zeorin; ascomata and conidiomata are unknown. [ABSTRACT FROM AUTHOR]

The profiles of volatile compounds of Macedonian dry fermented sausage were determined by gas chromatography-mass spectrometry (GC–MS) using a solid- -phase microextraction (SPME). A total of 103 volatile compounds were identified and consisted of 12 acids, 16 ketones, 21 terpenes, 20 alcohols, 9 esters, 13 hydrocarbons and 12 miscellaneous. The analysis of the main volatile aromatic components proved that 62% of the compounds that were detected on the first days are terpenes and their content increased to 69 and 80% on days eight and fifteen, respectively. The 50% of the total concentration of volatile components results to be concentrated on the last day (15th) of ripening. They have the highest amounts of concentration of acids (57%), ketones (68%) and terpenes (56%) from the total concentration. There was a significant difference between the various periods of fermentation and there can be differences in the manufacture production stages. Macedonian dry sausages contain high levels of spicy terpenes, which could play an important role in the general flavour notes of this meat product.

The identity of Lecanora ecorticata has been uncertain due to conflicting reports of the presence of zeorin and the loss of the holotype. Phylogenetic analysis suggests that the species probably belongs in Ramalinaceae, where it is the first leprose species reported. Zeorin was found to be absent in recently collected material of L. ecorticata, including specimens from the type locality, and the report of zeorin in the lost holotype is considered to be due to contamination. A new genus, Lithocalla, is erected to accommodate L. ecorticata and a second closely related species, that occurs in the Falkland Islands, is newly combined as Lithocalla malouina. A lectotype is selected for L. ecorticata. Lithocalla is characterized by a leprose thallus containing usnic acid with fatty acids and terpenoids, but no zeorin; ascomata and conidiomata are unknown. [ABSTRACT FROM AUTHOR]

The emissions of BVOCs from oilseed rape (Brassica napus), both when the plant is exposed to clean air and when it is fumigated with ozone at environmentally-relevant mixing ratios (ca. 135 ppbv), were measured under controlled laboratory conditions. Emissions of BVOCs were recorded from combined leaf and root chambers using a recently developed Selective Reagent Ionisation—Time of Flight—Mass Spectrometer (SRI-ToF-MS) enabling BVOC detection with high time and mass resolution, together with the ability to identify certain molecular functionality. Emissions of BVOCs from below-ground were found to be dominated by sulfur compounds including methanethiol, dimethyl disulfide and dimethyl sulfide, and these emissions did not change following fumigation of the plant with ozone. Emissions from above-ground plant organs exposed to clean air were dominated by methanol, monoterpenes, 4-oxopentanal and methanethiol. Ozone fumigation of the plants caused a rapid decrease in monoterpene and sesquiterpene concentrations in the leaf chamber and increased concentrations of ca. 20 oxygenated species, almost doubling the total carbon lost by the plant leaves as volatiles. The drop in sesquiterpenes concentrations was attributed to ozonolysis occurring to a major extent on the leaf surface. The drop in monoterpene concentrations was attributed to gas phase reactions with OH radicals deriving from ozonolysis reactions. As plant-emitted terpenoids have been shown to play a role in plant-plant and plant-insect signalling, the rapid loss of these species in the air surrounding the plants during photochemical pollution episodes may have a significant impact on plant-plant and plant-insect communications. [ABSTRACT FROM AUTHOR]

Background and Purpose. The aim of this study was to evaluate the radiosensitizing effect of oleanolic acid (OA) on C6 rat glioma and the changes in tumor biology during radiosensitization therapy on 18F-fluoromisonidazole (18F-FMISO) positron emission tomography/computed tomography (PET/CT). Methods. The radiosensitizing effect of OA on C6 tumors was assessed in vivo by measuring the tumor inhibitory rate and rat survival time. Meanwhile, rats with C6 tumors were imaged with 18F-FMISO PET/CT during radiosensitization therapy. Tumor-to-muscle ratio (TMR) of 18F-FMISO maximum uptake was calculated by region of interest analysis. Changes in tumor biology after therapy were assessed with immunohistochemical staining. 18F-FMISO uptake was analyzed in relation to expression of tumor biomarkers including hypoxia-inducible factor (HIF)-1α, glucose transporter (Glut-1), the proliferation antigen Ki67, tumor suppressor P53, and microvessel density (MVD). Results. The results showed that OA combined with radiation inhibited the growth rates of tumors and prolonged the survival period of tumor-bearing rats effectively (χ2 = 12.5, p < 0.01). 18F-FMISO PET/CT indicated decreases in hypoxia after radiosensitization therapy. Statistical differences were observed in TMR of the irradiation group and OA combined with irradiation group (t = 3.32, p < 0.05). HIF-1α, Glut-1, Ki67, P53, and MVD expressions in tumors were downregulated by OA combined with radiation as well as with radiation alone. Additionally, there was a significant positive linear correlation between TMR and HIF-1α, Glut-1, Ki67, P53, and MVD. Conclusions. These results suggest that OA has a radiosensitizing effect on C6 tumors in terms of tumor volume inhibition, survival extension, and multiple poor prognosis biological markers downregulation. 18F-FMISO PET/CT can be of value for tumor biology noninvasive capture and radiosensitization response evaluation. [ABSTRACT FROM AUTHOR]

Oxidation products of α-pinene represent a fraction of organic matter in the environmental aerosol. α-pinene is one of most abundant monoterpenes released in the atmosphere by plants, located typically in boreal, temperate and tropical forests. This primary compound reacts with atmospheric oxidants, such as O 3 , O 2 , OH radicals and NO x , through the major tropospheric degradation pathway for many monoterpenes under typical atmospheric condition. Although several studies identified a series of by-products deriving from the α-pinene photo-oxidation in the atmosphere, such as pinic and cis-pinonic acid, the knowledge of the mechanism of this process is partially still lacking. Thus, the investigation of the distribution of these acids in the different size aerosol particles provides additional information on this regard. The aim of this study is twofold. First, we aim to improve the existing analytical methods for the determination of pinic and cis-pinonic acid in aerosol samples, especially in terms of analytical sensitivity and limits of detection (LOD) and quantification (LOQ). We even attempted to increase the knowledge of the α-pinene photo-oxidation processes by analysing, for the first time, the particle-size distribution up to nanoparticle level of pinic and cis-pinonic acid. The analysis of aerosol samples was carried out via high-performance liquid chromatography coupled to a triple quadrupole mass spectrometer. The instrumental LOD values of cis-pinonic and pinic acid are 1.6 and 1.2 ng L −1 while LOQ values are 5.4 and 4.1 ng L −1 , respectively. Samples were collected by MOUDI II™ cascade impactor with twelve cut-sizes, from March to May 2016 in the urban area of Mestre-Venice (Italy). The range concentrations in the aerosol samples were from 0.1 to 0.9 ng m −3 for cis-pinonic acid and from 0.1 to 0.8 ng m −3 for pinic acid. [ABSTRACT FROM AUTHOR]

Two new abscisic acid-type sesquiterpenes (1,2), and one new ansamycin (3), together with four known ansamycins, namely ansacarbamitocins4–7, were isolated from the fermentation extract ofAmycolatopsis albaDSM 44262. The structures of the new compounds were elucidated to be (E)-3-methyl-5-(2,6,6-trimethyl-3-oxocyclohex-1-enyl)pent-2-enoic acid (1) and (E)-3-methyl-5-(2,6,6-trimethyl-4-oxocyclohex-2-enyl)pent-2-enoic acid (2), and 9-O-methylansacarbamitocin A1 (3), on the basis of comprehensive analysis of spectroscopic data, respectively. The antimicrobial activities were also evaluated for all seven compounds. [ABSTRACT FROM AUTHOR]

Antrodia camphorata is a fungus that is endemic to Taiwan, and its fruiting body has been used as a folk medicine for the prevention or treatment of diverse diseases. The present study is aimed at investigating the antimelanogenesis and antioxidation effect of the ethanolic extract of Antrodia camphorata fruiting body (EE-AC), as well as its antiproliferation effects in B16-F0 melanoma cells. Regarding antimelanogenic effects, EE-AC had effective cupric ions reducing capacity and expressed more potent inhibitory effect than kojic acid on mushroom tyrosinase activity. Moreover, EE-AC significantly inhibited cellular tyrosinase activity and the melanin content in B16-F0 cells at 12.5 μg/mL concentration without cell toxicities. Regarding antioxidant effects, EE-AC exhibited potent DPPH radical- and SOD-like-scavenging activities. Regarding antiproliferative effects, EE-AC exhibited a selective cytotoxic effect and markedly inhibited the migration ability of B16-F0 cells. EE-AC increased the population of B16-F0 cells at sub-G1 phase of the cell cycle. EE-AC also caused the increase of early apoptotic cells and chromatin condensation, which indicated the apoptotic effects in B16-F0 cells. We demonstrated that EE-AC possessed antimelanogenic, antioxidant and anti-skin cancer actions. The results would contribute to the development and application of cosmetics, healthy food and pharmaceuticals. [ABSTRACT FROM AUTHOR]

Triterpenoids are the most representative group of phytochemicals, as they comprise more than 20,000 recognized molecules. These compounds are biosynthesized in plants via squalene cyclization, a C30 hydrocarbon that is considered to be the precursor of all steroids. Due to their low hydrophilicity, triterpenes were considered to be inactive for a long period of time; however, evidence regarding their wide range of pharmacological activities is emerging, and elegant studies have highlighted these activities. Several triterpenic skeletons have been described, including some that have presented with pentacyclic features, such as oleanolic and ursolic acids. These compounds have displayed incontestable biological activity, such as antibacterial, antiviral, and antiprotozoal effects, which were not included in a single review until now. Thus, the present review investigates the potential use of these triterpenes against human pathogens, including their mechanisms of action, via in vivo studies, and the future perspectives about the use of compounds for human or even animal health are also discussed. [ABSTRACT FROM AUTHOR]

We developed a sensitive and rapid method for determination of ferulic acid, caffeic acid, vanillic acid, and paeoniflorin in rat plasma based on ultra high performance liquid chromatography coupled with tandem mass spectrometry (UHPLC-MS/MS). The separation of the four compounds was carried out on an AcQuity UHPLC™ BEH column using a mobile phase consisting of acetonitrile and water (containing 0.1% formic acid). Electrospray ionization in positive and negative ion mode and multiple reaction monitoring was used to identify and quantify active components. All calibration curves gave good linearity (r > 0.991) over the concentration range from 4.24-2875 ngmL-1 for all components. The precision of the in vivo study was evaluated by intraday and interday assays and the percentages of RSD were all within 10.6%. The recovery ranged from 60.2 to 77.9%. The method was successfully applied to pharmacokinetic study of all three aromatic acids and one monoterpene in rat plasma. Furthermore, we compared the pharmacokinetics profile of the four compounds in normal and primary dysmenorrhea rats' plasma following oral administration of Shaofu Zhuyu decoction (SFZYD) and its ethanol supernatant extract (SFE). [ABSTRACT FROM AUTHOR]

The existence of two chemotypes of Pinus pinaster, on the basis of the chemical composition of the resin acids in their needles, is known. An investigation was performed on 54 samples of needles of Spanish Pinus pinaster to study the differences between these chemotypes on the basis of monoterpene, sesquiterpene, neutral diterpene, fatty acid, and resin acid composition. One-hundred and twelve compounds were identified by GC-FID and GC-MS. Statistical analysis of the results established the existence of two groups or chemotypes, in the ratio of 5:1. In one chemotype, total acid compounds were more abundant than neutral compounds, whereas in the other the concentrations of both neutral and acid compounds were similar. Distinction of the chemotypes was based on the presence/absence of a sesquiterpene (germacrene d-4-ol acetate), neutral diterpenes (8(14),13(15)-abietadiene, anticopalol, an isomer of anticopalol, and pimarol), fatty acids (10-octadecenoic, 14-hydroxy-10-octadecenoic, and 13-hydroxy-9-octadenoic acids and an unidentified fatty acid), and resin acids (levopimaric + palustric, eperuic, and anticopalic acids, and three isomers of anticopalic acid); and on the different relative percentages of other compounds of these types. This study gives a wide view of the composition of the needles of Pinus pinaster, improving the differentiation of chemotypes on the basis of terpene and acid composition. [ABSTRACT FROM AUTHOR]

Duboscic acid (1), a triterpenoid with a unique carbon backbone, was isolated from Duboscia macrocarpaBocq. It is the first member of a new class of triterpenoids, for which the name “dubosane” is proposed. Duboscic acid has a potent α-glucosidase inhibition, and its structure was unambiguously deduced by a single-crystal X-ray diffraction study. [ABSTRACT FROM AUTHOR]

A new (2α,3β)-23-sulphonyl-2,3-dihydroxyurs-12-en-28-oic acid O-α-l-rhamnopyranosyl-(1→4)-O-β-d-glucopyranosyl-(1→6)-O-β-d-glucopyranosyl ester (1) together with eighteen known compounds were isolated from Centella erecta (L.f.) Fern. Their structures were elucidated mainly by NMR and HRESIMS, as well as on comparison with the reported data. [Copyright &y& Elsevier]

Abstract: Description of the first synthesis of (+)-makassaric acid, an important kinase MK2 inhibitor. The key step was a Barton/McCombie radical deoxygenation. [Copyright &y& Elsevier]

Ganoderic acids (GAs), a kind of highly oxygenated lanostane-type triterpenoids, are important bioactive constituents of the famous medicinal mushroom Ganoderma lucidum. They have received wide attention in recent years due to extraordinarily pharmacological functions. Submerged fermentation of G. lucidum is viewed as a promising technology for production of GAs, and substantial efforts have been devoted to process development for enhancing GA production in the last decade. This article reviews recent publication about fermentative production of GAs and their potential applications, especially the progresses toward manipulation of fermentation conditions and bioprocessing strategies are summarized. The biosynthetic pathway of GAs is also outlined. [ABSTRACT FROM AUTHOR]

Two new scopadulane diterpenoids, termed Scopadulcic acids D (1, SDD) and E (2, SDE), together with two known analogues (3 and 4) were isolated from Scoparia dulcis. Their structures were elucidated by comprehensive spectroscopic analysis. The absolute configurations of 1 and 2 were determined by calculated electronic circular dichroism (ECD). Meanwhile, X-ray crystallographic analysis was applied to determine the absolute configuration of 1. All compounds were tested for their effect on attenuating palmitate-induced viability at the concentrations of 25 and 50 μM. The results showed that they significantly attenuated the palmitate-induced viability in MIN6 cells. [Display omitted] [ABSTRACT FROM AUTHOR]

Abstract: Proposed method of hydrodistillation–adsorption (HDA) on activated carbon and hydrodistillation (HD) with solvent trap were compared for the isolation of water-soluble, non-soluble and high volatile compounds, such as acids, monoterpenes, isothiocyanates and others from carob (Certonia siliqua L.), rosemary (Rosmarinus officinalis L.) and rocket (Eruca sativa L.). Isolated volatiles were analyzed by GC and GC/MS. The main advantages of HDA method over ubiquitous HD method were higher yields of volatile compounds and their simultaneous separation in three fractions that enabled more detail analyses. This method is particularly suitable for the isolation and analysis of the plant volatiles with high amounts of water-soluble compounds. In distinction from previously published adsorption of remaining volatile compounds from distillation water on activated carbon, this method offers simultaneous hydrodistillation and adsorption in the same apparatus. [Copyright &y& Elsevier]

The first phytochemical investigation on stems of Mitrephora thoreliiled to the isolation of three new lignanamides, thoreliamides A–C 1–3, and a new sesquiterpenoid, thorelinin 4, together with ten known compounds. The structures of the new compounds were established on the basis of extensive spectroscopic analyses. Thoreliamide C is the first trimer derived from cinnamic acid amide units. [ABSTRACT FROM AUTHOR]

Abstract: Selenocyclization with the use of the monoterpene diselenides from menthane, carane and pinane groups has been studied. The conditions for asymmetric selenocyclization have been optimized. It has been established that the best enantiomeric excesses were obtained in the case of selenocyclization for the unsubstituted alkyl diselenides with (+)-dineomenthyl diselenide. The results of the selenocyclization of the (+)-dineomenthyl diselenide with the unsaturated alcohols and acids are presented. [Copyright &y& Elsevier]

Two new diterpenes and ent-15α-hydroxykaur-16-en-19-oic acid 11,12-acetonide (3), together with 23 known compounds were isolated from the dried aerial parts of Nouelia insignis Franch. The structures of new compounds were determined to be ent-14β,15α-dihydroxykaur-16-en-19-oic acid (1), ent-14β-hydroxy-15-oxokaur-16-en-19-oic acid (2) on the basis of spectral and chemical evidence. The structure of ent-11α,16α-epoxy-15α-hydroxy-16S-kaur-19-oic acid (4) was confirmed by X-ray crystallographic analysis. [ABSTRACT FROM AUTHOR]

The review discusses recent advances in the field of acid-catalyzed intra- and intermolecular transformations of pinane terpenoids and their oxygen-containing derivatives. [ABSTRACT FROM AUTHOR]

Abstract: Two new abietane diterpenes cordioic acid and cordifolic acid were isolated from the methanolic extract of Cordia latifolia stem bark. The structures of these diterpenes were elucidated using spectroscopic techniques. To the best of our knowledge, this is the first instance of isolation of diterpenoids from this source. Furthermore, cordifolic acid is a rare 2,3-seco-abietane suggestive of its biogenesis from 3-keto-analogue. [Copyright &y& Elsevier]

Abstract: Two novel ent-isocopalane diterpenes, coelodiol ( 1 ) and coeloic acid ( 2 ), the latter characterized by an unique oxidative degradation of ring A, have been isolated from the Indonesian sponge Coelocarteria cfr. singaporensis. The stereostructure of these metabolites has been established through interpretation of NMR data and application of the exciton chirality CD method. Coelodiol ( 1 ) and coeloic acids ( 2 ) were found to inhibit the growth of MKN-45 cell line (human gastric adenocarcinoma). [Copyright &y& Elsevier]

Transformations of diepoxy derivatives of caryophyllene, a widely spread natural sesquiterpene, were studied in various acidic media under conditions of both homogeneous and heterogeneous catalysis. A number of previously unknown compounds were isolated. The experimental data were compared with the results of computer simulation of the most probable transformation pathways using molecular-mechanics and quantum-chemical methods. [ABSTRACT FROM AUTHOR]

Microbial degradation of geraniol, a natural monoterpene alcohol, was studied using a Rhodococcus sp. strain GR3 isolated from soil. The bioconversion product was identified as geranic acid [(2 E )-3,7-dimethylocta-2,6-dienoic acid] and its structure was established by 1H-NMR, Fourier-transform IR spectrometry and GC-MS. The optimum temperature for this bioconversion was found to be 30 °C, and the reaction proceeds to a saturation with a time constant of 12.5 h. No appreciable degradation of product was observed using this bacterium. [ABSTRACT FROM AUTHOR]

For the determination of pentacyclic triterpenes of the boswellic acid family in human plasma a novel sensitive method was developed combining serial extraction on diatomaceous earth and graphitized carbon black followed by reversed phase high-performance liquid chromatography (HPLC) and photodiode array detection. The overall average extraction yield of 12 different pentacyclic triterpenic acids was approximately 66%. The calibration graphs were linear with coefficients of correlation for all compounds greater than 0.999. The overall within-day and between-day coefficients of variation (CV) for the 12 pentacyclic triterpenic acids were 5.6 and 6.8%, respectively. This HPLC procedure delivers the analytical sensitivity, precision and accuracy required for clinical pharmacokinetic and therapeutic studies. [Copyright &y& Elsevier]

The rearrangement of α-pinene to camphene in an acidic environment, a reaction widely used on an industrial scale, has been studied by use of DFT/DZP theoretical methods. p-Menthadienes were rationalized as the main products of the proton catalyzed reaction whereby camphene is the main product if a catalyst providing a taylor made environment is present. Tricyclene, bornylene and α-fenchene are shown to be byproducts. [Copyright &y& Elsevier]

The importance of natural raw materials has grown recently because of their ready availability, renewable nature, biocompatibility and controllable degradability. One such group of plant-derived substances includes the triterpenoid acids, terpenic compounds consisting of six isoprene units, a carboxyl group and other functional groups producing various isomers. Most can be easily extracted from different parts of the plant and modified successfully. By themselves or as aglycones (genins) of triterpene saponins, they have potentially useful pharmaceutical activity. This review focuses on the supramolecular properties of triterpenoid acids with regard to their subsequent use as biocompatible nanocarriers. The review also considers the current list of pentacyclic triterpene acids for which molecular self-assembly has been confirmed without the need for structural modification. [Display omitted] • Supramolecular properties of pentacyclic triterpenoid acids. • Natural compounds potentially useful as biocompatible nanocarriers. • Molecular self-assembly in aqueous solvents without structural modification. [ABSTRACT FROM AUTHOR]