Fagopyrin F fraction from Fagopyrum tataricum demonstrates photodynamic inactivation of skin infecting bacterium and squamous cell carcinoma (A431) cells.

Photodynamic therapy (PDT) stands out as a noteworthy development as an alternative targeted treatment against skin ailments. While PDT has advanced significantly, research into photo-activatable "Green drugs" derived from plants which are less toxic than the synthetic drugs has not kept pace. This study investigates the potential of Fagopyrin F Containing Fraction (FCF) derived from Fagopyrum tataricum in mediating PDT against Staphylococcus aureus and skin cancer cells (A431). FCF was isolated from the plant extract using thin-layer chromatography, followed by identification of the compound through high-performance liquid chromatography and high-resolution liquid chromatography-mass spectrometry. FCF was tested to determine its antibacterial and anticancer efficacy. Results revealed that FCF-mediated PDT exhibited potent action against S. aureus, significantly reducing bacterial viability (MIC 19.5 µg/100 µL). Moreover, FCF-mediated PDT showed good efficacy against A431 cells, resulting in a notable reduction in cell viability (IC50 29.08 µg/mL). Given the known association between S. aureus and squamous cell carcinoma (SCC), FCF shows the potential to effectively target and eradicate both SCC and the related S. aureus present within the lesions. In silico study reveals that Fagopyrin F effectively binds with the epidermal growth factor (EGFR), one among the highly expressed proteins in the A431 cells, with a binding energy of - 9.6 kcal/mol. The affinity of Fagopyrin F for EGFR on A431 cancer cells along with its cytotoxicity against skin cancer cells while safeguarding the normal cells (L929) plays a major part in the way it targets cancer cells. However, its safety, efficacy, and long-term advantages in treating skin conditions require more investigation, including in vivo investigations and clinical trials.

Dual SARS-CoV-2 and MERS-CoV inhibitors from Artemisia monosperma: isolation, structure elucidation, molecular modelling studies, and in vitro activities.

The COVID-19 pandemic has spread throughout the whole globe, so it is imperative that all available resources be used to treat this scourge. In reality, the development of new pharmaceuticals has mostly benefited from natural products. The widespread medicinal usage of species in the Asteraceae family is extensively researched. In this study, compounds isolated from methanolic extract of Artemisia monosperma Delile, a wild plant whose grows in Egypt's Sinai Peninsula. Three compounds, stigmasterol 3-O-ß-D-glucopyranoside 1, rhamnetin 3, and padmatin 6, were first isolated from this species. In addition, five previously reported compounds, arcapillin 2, jaceosidin 4, hispidulin 5, 7-O-methyleriodictyol 7, and eupatilin 8, were isolated. Applying molecular modelling simulations revealed two compounds, arcapillin 2 and rhamnetin 3 with the best docking interactions and energies within SARS-CoV-2 Mpro-binding site (-6.16, and -6.70 kcal mol-1, respectively). The top-docked compounds (2-3) were further evaluated for inhibitory concentrations (IC50), and half-maximal cytotoxicity (CC50) of both SARS-CoV-2 and MERS-CoV. Interestingly, arcapillin showed high antiviral activity towards SARS-CoV-2 and MERS-CoV, with IC50 values of 190.8 µg mL-1 and 16.58 µg mL-1, respectively. These findings may hold promise for further preclinical and clinical research, particularly on arcapillin itself or in collaboration with other drugs for COVID-19 treatment.

Sustainable cannabinoids purification through twin-column recycling chromatography and green solvents.

In the present study, twin-column recycling chromatography has been employed for the purification of a Cannabis extract by using a green solvent, ethanol, as the mobile phase. In particular, the complete removal of the psychoactive tetrahydrocannabinol (THC) from a Cannabis extract rich in cannabidiol (CBD) was achieved under continuous conditions. The performance of the method, in terms of compound purity, recovery, productivity and solvent consumption, was compared to that of traditional batch operations showing the potential of the twin-column recycling approach. The employment of a theoretical model to predict the band profiles of the two compounds during the recycling process has facilitated method development, thus further contributing to process sustainability by avoiding trial and error attempts or at least decreasing the number of steps significantly.

Purification of proanthocyanidins from nut seeds and study on its bactericidal mechanism against Streptococcus mutans.

AIM: The aim of this study was to purify proanthocyanidins from areca nut seeds (P-AN) and to investigate the bactericidal activity and mechanism of the purified products against Streptococcus mutans. METHODS AND RESULTS: Ultra-performance liquid chromatography tandem quadrupole time-of-flight mass spectrometry, Fourier transform infrared, Matrix-assisted laser desorption/ ionization time of flight mass spectrometry (MADLI-TOF-MS), and thiolysis experiment were used for P-AN chemical analysis. Time-kill analysis and glycolytic pH drop were used to evaluate the activity of S. mutans in vitro. Meanwhile, the investigation of the bacteriostatic mechanism included membrane protein, fluidity, permeability, and integrity tests. The results showed that P-AN was a kind of proanthocyanidin mainly composed of B-type proanthocyanidins and their polymers. Moreover, MADLI-TOF-MS and thiolysis experiments demonstrated that the degree of polymerization of P-AN was 13. The time-kill analysis showed that P-AN had strong bactericidal activity against S. mutans. P-AN at minimum inhibitory concentration (MIC) concentrations was able to induce S. mutans death, while complete lethality occurred at 2 MIC. Glycolysis test showed that P-AN significantly inhibited S. mutans acid production (P < .01). The morphological changes of S. mutans were observed by scanning electron microscopy and transmission electron microscopy experiments, which indicated that P-AN destroyed the cellular structure of S. mutans. At the same time, significant changes were observed in membrane proteins, fluidity, permeability, and integrity. CONCLUSION: P-AN can effectively inhibit the activity of S. mutans. P-AN can reduce the erosion of the tooth surface by the acid of S. mutans. P-AN could break the structure of the cell membrane protein of S. mutans. P-AN could destroy the integrity of membrane, resulting in the death of S. mutans.

Preparative separation of the constituents from Ginkgo biloba L. leaves by a combination of multi-stage solvent extraction and countercurrent chromatography.

In this study, we employed a combination approach for the preparative separation of constituents from Ginkgo biloba L. leaves. It involved multi-stage solvent extractions utilizing two-phase multi-solvent systems and countercurrent chromatography (CCC) separations using three different solvent systems. The n-heptane/ethyl acetate/water (1:1:2, v/v) and n-heptane/ethyl acetate/methanol/water (HepEMWat, 7:3:7:3, v/v) solvent systems were screened out as extraction systems. The polarities of the upper and lower phases in the multi-solvent systems were adjustable, enabling the effectively segmented separation of complex constituents in G. biloba L. The segmented products were subsequently directly utilized as samples and separated using CCC with the solvent systems acetate/n-butanol/water (4:1:5, v/v), HepEMWat (5:5:5:5, v/v), and HepEMWat (9:1:9:1, v/v), respectively. As a result, a total of 11 compounds were successfully isolated and identified from a 2 g methanol extract of G. biloba L through two-stage extraction and three CCC separation processes; among them, nine compounds exhibited high-performance liquid chromatography purity exceeding 85%.

Modeling the liquid-liquid chromatography separation of cannabinoids from hemp extracts.

The separation of cannabinoids from hemp materials is nowadays one of the most promising industrial applications of liquid-liquid chromatography (LLC). Despite various experimental research efforts to purify cannabinoids, there are currently few works on process modeling. Thus, this study aimed to explore a straightforward approach to model the LLC separation of cannabinoids from two hemp extracts with different compositions. The feed materials were simplified to mixtures of preselected key components (i.e., cannabidiol, tetrahydrocannabinol, cannabigerol, and cannabinol). The elution profiles of cannabinoids were simulated using the equilibrium-cell model with an empirical nonlinear correlation. The model parameters were derived from the elution profiles of single-solute pulse injections. For the validation of the proposed approach, LLC separations with the two hemp extracts were performed in descending mode with the solvent system composed of hexane/methanol/water 10/8/2 (v/v/v). The injected sample concentrations were gradually increased from 5 to 100 mg/mL. The results showed that the approach could describe reasonably well the elution behavior of the cannabinoids, with deviations of only 1-2 min between simulated and experimental elution times. However, to improve the prediction accuracy, the model parameters can be refitted to the elution profiles of 3-4 systematically selected pulse injections with specific hemp extracts.

Screening and isolation of quorum sensing inhibitors of Pseudomonas aeruginosa from Phellodendron amurense extracts using bio-affinity chromatography.

Drug-resistant bacterial infections pose a significant challenge in the field of bacterial disease treatment. Finding new antibacterial pathways and targets to combat drug-resistant bacteria is crucial. The bacterial quorum sensing (QS) system regulates the expression of bacterial virulence factors. Inhibiting bacterial QS and reducing bacterial virulence can achieve antibacterial therapeutic effects, making QS inhibition an effective strategy to control bacterial pathogenicity. This article mainly focused on the PqsA protein in the QS system of Pseudomonas aeruginosa. An affinity chromatography medium was developed using the SpyTag/SpyCatcher heteropeptide bond system. Berberine, which can interact with the PqsA target, was screened from Phellodendron amurense by affinity chromatography. We characterized its structure, verified its inhibitory activity on P. aeruginosa, and preliminarily analyzed its mechanism using molecular docking technology. This method can also be widely applied to the immobilization of various protein targets and the effective screening of active substances.

Copaifera spp. oleoresins and two isolated compounds (ent-kaurenoic and ent-polyalthic acid) inhibit Toxoplasma gondii growth in vitro.

Toxoplasmosis affects about one-third of the world's population. The disease treatment methods pose several side effects and do not efficiently eliminate the parasite, making the search for new therapeutic approaches necessary. We aimed to assess the anti-Toxoplasma gondii activity of four Copaifera oleoresins (ORs) and two isolated diterpene acids, named ent-kaurenoic and ent-polyalthic acid. We used HeLa cells as an experimental model of toxoplasmosis. Uninfected and infected HeLa cells were submitted to the treatments, and the parasite intracellular proliferation, cytokine levels and ROS production were measured. Also, tachyzoites were pre-treated and the parasite invasion was determined. Finally, an in silico analysis was performed to identify potential parasite targets. Our data show that the non-cytotoxic concentrations of ORs and diterpene acids controlled the invasion and proliferation of T. gondii in HeLa cells, thus highlighting the possible direct action on parasites. In addition, some compounds tested controlled parasite proliferation in an irreversible manner. An additional and non-exclusive mechanism of action involves the modulation of host cell components, by affecting the upregulation of the IL-6. Additionally, molecular docking suggested that ent-polyalthic acid has a high affinity for the active site of the TgCDPK1 protein. Copaifera ORs have great antiparasitic activity against T. gondii, and this effect can be partially explained by the presence of the isolated compounds ent-kaurenoic and ent-polyalthic acid.

Subcritical Water Extraction of Undaria pinnatifida: Comparative Study of the Chemical Properties and Biological Activities across Different Parts.

The subcritical water extraction of Undaria pinnatifida (blade, sporophyll, and root) was evaluated to determine its chemical properties and biological activities. The extraction was conducted at 180 °C and 3 MPa. Root extracts exhibited the highest phenolic content (43.32 ± 0.19 mg phloroglucinol/g) and flavonoid content (31.54 ± 1.63 mg quercetin/g). Sporophyll extracts had the highest total sugar, reducing sugar, and protein content, with 97.35 ± 4.23 mg glucose/g, 56.44 ± 3.10 mg glucose/g, and 84.93 ± 2.82 mg bovine serum albumin (BSA)/g, respectively. The sporophyll contained the highest fucose (41.99%) and mannose (10.37%), whereas the blade had the highest galactose (48.57%) and glucose (17.27%) content. Sporophyll had the highest sulfate content (7.76%). Key compounds included sorbitol, glycerol, L-fucose, and palmitic acid. Root extracts contained the highest antioxidant activity, with IC50 values of 1.51 mg/mL (DPPH), 3.31 mg/mL (ABTS+), and 2.23 mg/mL (FRAP). The root extract exhibited significant α-glucosidase inhibitory activity with an IC50 of 5.07 mg/mL, indicating strong antidiabetic potential. The blade extract showed notable antihypertensive activity with an IC50 of 0.62 mg/mL. Hence, subcritical water extraction to obtain bioactive compounds from U. pinnatifida, supporting their use in functional foods, cosmetics, and pharmaceuticals is highlighted. This study uniquely demonstrates the variation in bioactive compound composition and bioactivities across different parts of U. pinnatifida, providing deeper insights. Significant correlations between chemical properties and biological activities emphasize the use of U. pinnatifida extracts for chronic conditions.

Ephedra intermedia Schrenk & C. A. Mey Methanol Extract: Nanoencapsulation by Mini-Emulsion Polymerization and its Release Trend under Simulated Conditions of the Human Body.

In this research, the extract of Ephedra intermedia Schrenk & C.A.Mey. was encapsulated using the mini-emulsion polymerization method based on methyl methacrylate polymers with a nanometer size. The encapsulated extract was characterized using different analytical techniques. Furthermore, the loading efficiency and release of the plant extract were examined. FT-IR spectroscopy confirmed the formation of an expectational product. The TEM and SEM imaging showed a spherical morphology for the prepared encapsulated extract. The average size of poly-methyl-methacrylate nanoparticles containing Ephedra extract was found to be approximately 47 nm. The extract loading efficiency and encapsulation efficiency test demonstrated a dose-depending behavior on E. intermedia extract for both analyses, which is highly advantageous for traversing biological barriers. The release assay shows a controlled release for the extract at phosphate buffer solution (PBS). A 38 % release was calculated after 36 hours. The results obtained from the present study reveal that encapsulating the plant extract is a suitable alternative to control and increase their medicinal properties.

Therapeutic Potential of Cornus Genus: Navigating Phytochemistry, Pharmacology, Clinical Studies, and Advanced Delivery Approaches.

The genus Cornus (Cornaceae) plants are widely distributed in Europe, southwest Asia, North America, and the mountains of Central America, South America, and East Africa. Cornus plants exhibit antimicrobial, antioxidative, antiproliferative, cytotoxic, antidiabetic, anti-inflammatory, neuroprotective and immunomodulatory activities. These plants are exploited to possess various phytoconstituents such as triterpenoids, iridoids, anthocyanins, tannins and flavonoids. Pharmacological research and clinical investigations on various Cornus species have advanced significantly in recent years. Over the past few decades, a significant amount of focus has also been made into developing new delivery systems for Cornus mas and Cornus officinalis. This review focuses on the morphological traits, ethnopharmacology, phytochemistry, pharmacological activities and clinical studies on extracts and active constituents from plants of Cornus genus. The review also highlights recent novel delivery systems for Cornus mas and Cornus officinalis extracts to promote sustained and targeted delivery in diverse disorders. The overwhelming body of research supports the idea that plants from the genus Cornus have therapeutic potential and can be investigated in the future for treatingseveral ailments.

Origanum Grosii Extracts as Novel Eco-Friendly Corrosion Inhibitors for Mild Steel In HCl Medium.

Two green inhibitors extracted from an endemic species (Origanum grosii (Og)) using two solvents of different polarity (water and ethanol), OgW (aqueous extract) and OgE (ethanolic extract), were used for the anticorrosion of mild steel (M steel) in a 1 M HCl medium. Anticorrosive performance of OgW and OgE was assessed using standard electrochemical techniques, EIS/PDP measurements, weight loss method and SEM/EDX surface analysis. The results show that OgW achieves a maximum inhibition efficiency of 92 % and that the extract in aqueous medium (more polar) is more efficient than the extract in ethanolic medium (less polar). Both extracts act as mixed inhibitors and their corrosion process is predominantly governed by a charge transfer. Concentration and temperature effect was studied and shown that they are two antagonistic parameters for the evolution of inhibitory effectiveness of both OgW and OgE. The adsorption isotherms of the two inhibitors OgE and OgW obey to the Langmuir adsorption model. Moreover, the examination of SEM images and EDX spectra support a deposit of both extracts on the metal surface by an adsorption phenomenon. Besides, theoretical approach of the molecular structures of the major compounds M-OgW and M-OgE and inhibition efficiency was examined via DFT calculations and molecular dynamics simulations and it was consistent with the experimental findings.

Distribution, Chemical Constituents and Biological Properties of Genus Malaxis.

The genus Malaxis (family Orchidaceae), comprises nearly 183 species available across the globe. The plants of this genus have long been employed in traditional medical practices because of their numerous biological properties, like the treatment of infertility, hemostasis, burning sensation, bleeding diathesis, fever, diarrhea, dysentery, febrifuge, tuberculosis, etc. Various reports highlight their phytochemical composition and biological activities. However, there is a lack of systematic review on the distribution, phytochemistry, and biological properties of this genus. Hence, this study aims to conduct a thorough and critical review of Malaxis species, covering data published from 1965 to 2022 with nearly 90 articles. Also, it examines different bioactive compounds, their chemistry, and pharmacotherapeutics as well as their traditional uses. A total of 189 unique compounds, including the oil constituents were recorded from Malaxis species. The highest active ingredients were obtained from Malaxis acuminata (103) followed by Malaxis muscifera (49) and Malaxis rheedei (33). In conclusion, this review offers an overview of the current state of knowledge on Malaxis species and highlights prospects for future research projects on them. Additionally, it recommends the promotion of domestication studies for rare medicinal orchids like Malaxis and the prompt implementation of conservation measures.

Combretum micranthum G. Don (Combretaceae): A Review on Traditional Uses, Phytochemistry, Pharmacology and Toxicology.

Combretum micranthum (Combretaceae) is a medicinal plant widely known and used in Africa to treat a variety of conditions such as diabetes, fever, coughs, bronchitis, diarrhea, pain, malaria and liver disorders, among others. Due to its wide traditional use, in this review, published scientific reports on its composition and pharmacological properties were explored by conducting a literature search of databases. To date, 155 organic compounds including 34 flavonoids, 16 phenolic acids, 14 alkaloids, 15 fatty acids, 14 terpenoids/steroids, 24 amino acids, 8 carbohydrate substances and 30 other organic compounds have been identified from this plant. In addition to these organic compounds, 6 minerals (potassium nitrate, calcium, magnesium, potassium, sodium, iron and zinc) have also been reported. In vitro and in vivo studies have shown that these phytochemicals and plant extracts have a wide range of pharmacological potential, including antibacterial, antiviral, antioxidant, antidiabetic, anti-inflammatory, analgesic, antihypertensive, nephroprotective, hepatoprotective, anxiolytic, anti-cholinesterase and antidiarrheal activities. Additionally, no harmful effects have been revealed through studies. Thus, this study could constitute a valuable reference for the valorization of C. micranthum in the pharmaceutical industry.

A Review on the Traditional Applications, Phytochemistry, and Pharmacology of the Genus Physochlaina G. Don.

Physochlaina is a genus of flowering plants belonging to the family Solanaceae and consists of 10 species distributed in various Asian countries. The species of the genus have been traditionally used to cure a variety of illnesses due to their highly valuable medicinal properties, including cancer, asthma, cough, weakness, stomachache, diarrhea, swelling, spasms, toothache, boils, ulcers, rheumatic pain, chronic bronchitis, gastric problems, abdominal pain, palpitation, and insomnia. The species have gained significant attention due to their remarkable ethnopharmacological and ethnomedicinal significance. The researchers have isolated so far 71 biologically active secondary metabolites from different Physochlaina species, which include flavonoids, alkaloids, coumarins, phenolic acids, iridoids, and sterols. These compounds exhibit diverse biological activities, such as antibacterial, anti-oxidant, anti-inflammatory, cytotoxic, and anticancer properties. The present review has been compiled with the intention of providing a comprehensive overview of the botany, distribution, traditional uses, phytochemical profile, and biological activities of the genus Physochlaina for future exploration of plant-based drugs and therapeutic approaches. The present review contributes to understanding the significant pharmacological potential of Physochlaina species and unraveling their chemical composition, highlighting their relevance in developing therapeutic agents. Till date, numerous pharmacological properties and isolated phytochemicals of Physochlaina species that support the species traditional and ethnobotanical history have been documented in a number of scientific publications. However, greater emphasis should be paid to in vivo investigations on various extracts and their phytoconstituents as well as mechanistic analysis to help drug developers better understand how to use Physochlaina species as significant therapeutic resources for herbal formulations using various techniques.

A Review on Traditional Uses, Phytochemistry, Pharmacology and Clinical Application of Tinospora sinensis (Lour.) Merr.

Tinospora sinensis (T. sinensis), whose Tibetan name is "Lezhe", as a traditional medicine, is widely distributed in China, India and Sri Lanka. It is used for the treatment of rheumatic arthralgia, sciatica, lumbar muscle strain and bruises. Research over the previous decades indicated that T. sinensis mainly contains terpenes, lignans, alkaloids, phenol glycosides and other chemical components. A wide range of pharmacologic activities such as anti-inflammatory, analgesic, immunosuppressive, anti-aging, anti-radiation, anti-leishmania and liver protection have been reported. However, the scholar's research on the pharmacodynamic material basis of T. sinensis is relatively weak. Data regarding many aspects such as links between the traditional uses and bioactivities, pharmacokinetics, and quality control standard of active compositions is still limited and need more attention. This review reports a total of 241 compounds, the ethnopharmacology and clinical application of T. sinensis, covering the literature which were searched by multiple databases including Web of Science, PubMed, Google Scholar, Science Direct, CNKI and other literature sources from 1996 to date, with a view to provide a systematic and insightful reference and lays a foundation and inspiration for the application and further in-depth research of T. sinensis resources.

The First Comprehensive Chemical Profiling of Vachellia gummifera (Willd.) Kyal. & Boatwr., a Plant with Medicinal Value.

Vachellia gummifera (Willd.) Kyal. & Boatwr. is a medicinal plant endemic to Morocco that has no documented studies on its chemical composition. In this study, the chemical composition of the water/methanol (4 : 1) extracts of air-dried leaf and stem samples of Moroccan V. gummifera was determined using UHPLC-MS and NMR. In total, over 100 metabolites were identified in our study. Pinitol was the major compound in both the leaf and stem extracts, being significantly more abundant in the former. Asparagine and 3-hydroxyheteroendrin were the second most abundant compounds in the stem and leaf extracts, respectively, though both compounds were present in each tissue. The other compounds included flavonoids based on quercetin, and phenolic derivatives. Eucomic acid, only identified in the stems and was the major aromatic compound distinguishing the leaf and stem profiles. Quercetin 3-O-(6''-O-malonyl)-ß-D-glucopyranoside was identified as the major flavonoid in the leaves but was also present in the stems. Other malonylated derivatives that were all flavonol glycosides based on myricetin, kaempferol, and isorhamnetin in addition to quercetin were also identified. This is the first report of eucomic acid and malonylated compounds in Vachellia species. This report provides valuable insights into the chemotaxonomic significance of the Vachellia genus.

Baccharoides anthelmintica (L.) Moench: A Review on Ethnomedicinal, Phytochemical, Pharmacological and Toxicological Profile.

Baccharoides anthelmintica (L.) Moench is a popular medicinal plant with a long history of use in several traditional remedies to cure a variety of diseases including; its effect on the central nervous system, gastrointestinal tract, metabolism, kidneys, gynecology, skin diseases, and general health. The present review aims to provide the latest, organized information on toxicological, pharmacological, phytochemical, and ethnomedicinal applications of Baccharoides anthelmintica. For this; several well-known searchable websites (search engines) like; Web of Science, Google Scholar, Scopus-Elsevier, Taylor & Francis, Springer, and DOAJ, were used to empirically investigate the knowledge of this useful medicinal plant. Based on previous studies, the pharmacological action of B. anthelmintica is due to various secondary metabolites including alkaloids, terpenoids, lignans, steroids, and other phytoconstituents. Hence, the present study recorded 225 phytochemicals obtained from different parts of the plant, where the steroids and derivatives (48), terpenes and sesquiterpenes (46), flavonoids and derivatives (41), fatty acids and derivatives (40), phenolic acids (12), triterpenes (11), chalcones (06), diterpenes (01) and miscellaneous (20) were reported. The present review also covered the pharmacological importance, including antioxidant, antimicrobial, antiparasitic, antidiabetic, hypolipidemic action, liver disease, anticancer potential, anti-HIV, antiosteoporotic action, antitoxic action, skin disorder, wound healing and immunomodulatory activity, systemic infection, and treatment of neurodegenerative diseases etc. The review concluded that B. anthelmintica has several pharmacological activities, which were due to the presence of secondary metabolites present in it, and thus indicates the importance of medicinal value of this plant. Hence, B. anthelmintica may be a good source for developing a lead molecule in the process of new drug discovery and development. More study is required to determine the pharmacokinetics, mechanism of action, long-term toxicology testing, safe dosage, and possible interactions with other herbs/drugs.

Three New Polyphenol Derivatives from the Fruits of Macaranga Monandra and their Antioxidant Potential.

Phytochemical investigation of the methanol extract from the fruits of Macaranga monandra (Euphorbiaceae Muell. et Arg.) afforded one new geranylated 1',2'-dihydrophenanthrene and two new flavonoid derivatives, named macamondrin (1), macamondrione A (2) and B (3) respectively. The structures of these compounds were elucidated mainly by NMR, mass spectral data and in comparison with data from the literature. Along with compounds 1-3, nine known compounds among which oleanolic acid (4); daucosterol (5); 3ß-acetoxy-11α,12α-epoxytaraxerol (6); 3,3',4-tri-O-methylellagic acid (7); 3,3',4,4'-tetra-O-methylellagic acid (8); 4'-O-methyl-6-isoprenylapigenin (9); 4'-O-methyl-8 isoprenylkaempférol (10); 4'-O-methyl-6-isoprénylkaempférol (11); 6-isoprénylkaempférol (12), were also isolated. Crude extracts as well as isolated compounds were evaluated for their antioxidant activity using the ABTS, DPPH and FRAP methods. It appears that the 50 % radical scavenging concentrations ranging from 6.26 to 11.7 µg/ml on the ABTS radical, from 1.77 to 48.22 µg/ml on the DPPH radical, and from 1.54 to 67.97 µg/ml with the FRAP method. For the compounds tested, very good antioxidant activities were observed, which clearly shows that these molecules can have an anti oxidative stress potentiel.

Four Unidentified Compounds Isolated from the Stem Barks of Aphanamixis polystachya and Their NO Production Inhibition in LPS Activated RAW 264.7 Cells.

Phytochemical study on the methanol extract of the stem barks of Aphanamixis polystachya led to the isolation of four previously undescribed (1-4) and ten known compounds (5-14). Their chemical structures were elucidated to be 11-methoxysawaranospiroride C (1), 6α,9S,10,13-tetrahydroxymegastigmane-3-one (2), 11-hydroxyaphanamixin B (3), (2Z,6E,13E)-2,6,13-triene-11,15-dihydroxyphytanic acid (4), cinnacasside D (5), cinnacasside E (6), vilsonol F (7), (3S,5R,6S,7E,9R)-3,5,6,9-tetrahydroxy-7-en-megastigmane (8), (3S,5R,6R,7E,9R)-3,6,9,10-tetrahydroxy-7-en-megastigmane (9), citroside A (10), threo-1-(3,4,5-trimethoxyphenyl)-1,2,3-propanetriol (11), 3,4,5-trimethoxyphenyl-1-O-ß-D-glucopyranoside (12), p-coumaric acid (13), ferulic acid (14) by HR-ESI-MS, ECD, 1D-, and 2D-NMR spectra. Compounds 1, 3, 4, and 9 showed NO production inhibitory activity in LPS activated RAW 264.7 cells with IC50 values of 42.0, 67.9, 20.5, and 78.6 µM, respectively, while the remaining compounds were inactive with IC50 values over 100 µM.