Globunoids A-D, undescribed bichalconoid and biflavanoids with α-glucosidase and α-amylase inhibitory activities from Knema globularia stems.

A bichalconoid, globunoid A (1) and three biflavanones, globunoids B-D (2-4), previously undescribed, were isolated from the stems of Knema globularia, along with fourteen known analogues 5-18. The chemical structures of 1-4 were elucidated by the comprehensive spectroscopic analysis including UV, IR, HRESIMS, and NMR; the absolute configurations were determined based on their NOESY data, DP4+ statistical analysis, and ECD calculation. Up to now, compounds 2 and 3 represent the first 3,3″-linked biflavanone structures. Among the isolated compounds, 2, 3, and 2,3-dihydrocalodenin B (6) potently inhibited α-glucosidase and α-amylase activities, with IC50 values in the range 1.1-7.5 µM. Furthermore, the most active compound 6 was found to be a non-competitive inhibitor against these two enzymes.

A chromosome-level reference genome of an aromatic medicinal plant Adenosma buchneroides.

Adenosma buchneroides Bonati, belonging to the genus Adenosum (Plantaginaceae), is an aromatic medicinal plant and utilized in traditional Chinese medicine. It has been widely used as plant-based repellents to prevent vector-borne diseases. However, the lack of a reference genome limits the study of conservation management and molecular biology of A. buchneroides. Here, we generated a chromosome-level de novo genome assembly of A. buchneroides which is a high-quality chromosome-scale assembly of aromatic medicinal plant in Plantaginaceae. The genome has a total length of 442.84 Mb with scaffold N50 of 27.98 Mb and 95.55% of the genome assigned to 14 chromosomes. BUSCO assessment yielded a completeness score of 97.2%. Furthermore, we predicted 24,367 protein-coding genes, and 95.79% of them was functionally annotated. The chromosome-scale genome of A. buchneroides will be a significant resource for understanding the genetic basis and evolution of active components biosynthesis, which will facilitate further study and exploit of A. buchneroides.

Phytochemical Analysis and Evaluation of the Antioxidant, Antiproliferative, Antibacterial, and Antibiofilm Effects of Globularia alypum (L.) Leaves.

Globularia alypum L. (GA) is a Mediterranean plant of the Globulariaceae family which is widely used in traditional Tunisian medicine. The main goal of this study was to evaluate the phytochemical composition, antioxidant, antibacterial, and antibiofilm activities, and the antiproliferative potential of different extracts of this plant. The identification and the quantification of the different constituents of extracts were determined using gas chromatography-mass spectrometry (GC-MS). The antioxidant activities were evaluated using spectrophotometric methods and chemical tests. The antiproliferative study was based on the use of colorectal cancer SW620 cells, including an antibacterial assessment with the microdilution method and analysis of the antibiofilm effects via the crystal violet assay. All extracts presented several components, mainly sesquiterpenes, hydrocarbon, and oxygenated monoterpenes. The results revealed that the maceration extract had the most important antioxidant effect (IC50 = 0.04 and 0.15 mg/mL), followed by the sonication extract (IC50 = 0.18 and 0.28 mg/mL). However, the sonication extract demonstrated significant antiproliferative (IC50 = 20 µg/mL), antibacterial (MIC = 6.25 mg/mLand MBC > 25 mg/mL), and antibiofilm (35.78% at 25 mg/mL) properties against S. aureus. The results achieved confirm the important role of this plant as a source of therapeutic activities.

Genome assembly of the pioneer species Plantago major L. (Plantaginaceae) provides insight into its global distribution and adaptation to metal-contaminated soil.

Plantago is a major genus belonging to the Plantaginaceae family and is used in herbal medicine, functional food, and pastures. Several Plantago species are also characterized by their global distribution, but the mechanism underpinning this is not known. Here, we present a high-quality, chromosome-level genome assembly of Plantago major L., a species of Plantago, by incorporating Oxford Nanopore sequencing and Hi-C technologies. The genome assembly size was approximately 671.27 Mb with a contig N50 length of 31.30 Mb. 31,654 protein-coding genes were identified from the genome. Evolutionary analysis showed that P. major diverged from other Lamiales species at ~62.18 Mya and experienced two rounds of WGD events. Notably, many gene families related to plant acclimation and adaptation expanded. We also found that many polyphenol biosynthesis genes showed high expression patterns in roots. Some amino acid biosynthesis genes, such as those involved in histidine synthesis, were highly induced under metal (Ni) stress that led to the accumulation of corresponding metabolites. These results suggest persuasive arguments for the global distribution of P. major through multiscale analysis. Decoding the P. major genome provides a valuable genomic resource for research on dissecting biological function, molecular evolution, taxonomy, and breeding.

Globularia arabica Methanolic Leaf Extract Has Higher Efficacy on Burn Wound Healing in Diabetic Rats Compared to Malva slyvestries Methanolic Leaf Extract.

This study aimed to see how effective Globularia arabica and Malva slyvestries-based cream formulations were at healing scald burn wounds in rats. Depending on ointment, preparations of 1%, 5%, and 10% w/w were created. For comparison, an ointment base and a regular burn cream composed soframycine were utilized. Rats introduced a burn by solidifying equipment at 100°C on a 14-mm2 shaved dorsal region. A deep second-degree burn was created, and the percentage of wound contraction was measured over the next 15 days. The rats were euthanized on days 8 and 15, and histological slides were prepared using hematoxylin and eosin staining. Compared to the control group, there was a substantial increase in wound contraction and a significant decrease in the duration of epithelialization in the based ointment-treated groups. However, as paralleled to Globularia arabica, significant (P < .05) results were observed with 10% Globularia arabica cream, whereas Malva slyverstries indicate minimal healing. Soframycine causes a substantial increase in wound contraction (P < .05). Soframycine cream with 10% Globularia arabica therapy resulted in practically complete re-epithelialization and re-structuring of wound tissue on histological examination, whereas Malva slyversries treatment resulted in low epithelization during treatment days. The findings suggest that Globularia arabica-based cream has the wound-healing capability.

A review on the traditional uses, phytochemistry, and pharmacology of the genus Veronicastrum (Plantaginaceae).

ETHNOPHARMACOLOGICAL RELEVANCE: Veronicastrum Heist. ex Fabr. (Plantaginaceae) is a multifunctional plant in China and other parts of the continent. It has traditionally been used in the treatment of ascites, edema, blood stasis, pain relief, chronic nephritis injury, fever, cough, headache, arthritis, dysentery, rheumatism, pleural effusion, liver damage, and other disorders. Although research has confirmed that the genus Veronicastrum contain many active compounds, no review of its traditional uses, phytochemistry or pharmacology has been conducted to date. AIM: This review aims to systematically evaluate the traditional uses, phytochemistry, and pharmacology of the genus Veronicastrum, discuss its medicinal potential, modern scientific research, and the relationship between them, and put forward some suggestions to promote further development and utilization of Veronicastrum. MATERIALS AND METHODS: The traditional uses, phytochemical and pharmacological data related to the genus Veronicastrum from 1955 to date was compiled by surveying the ethnomedicinal books and published papers, and searching the online databases including Google Scholar, China National Knowledge Infrastructure (CNKI), Science Direct, Web of Science and World Flora Online. RESULTS: Species of the genus Veronicastrum are widely used in folkloric medicine and some of their uses have been confirmed in modern pharmacological activities. A total of 89 chemical constituents have been isolated from the genus Veronicastrum, including flavonoids, carbohydrates, iridoids, terpenoids, phytosterols, phenolic acids, and other constituents. Among the compounds isolated, iridoids, flavonoids, and terpenoids are responsible for the biological activities of this genus with significant pharmacological activities both in vitro and in vivo. The extracts and compounds isolated from this genus have been reported to contain a wide range of pharmacological activities such as immunosuppressive, antioxidant, anti-cancer, anti-inflammatory, gastro protective, and antimicrobial activity. CONCLUSION: The genus Veronicastrum is not only a great herbal remedy, but also has numerous bioactive chemicals with potential for new drug discovery. In the literature, phytochemical investigations have been undertaken on five species. Detailed scientific research is still needed to fully understand this genus. Furthermore, its bioactive chemicals' structure-activity connection, in vivo activity, and mechanism of action ought to be investigated further.

Chemical profiling of Dizygostemon riparius (Plantaginaceae) plant extracts and its application against larvae of Aedes aegypti L. (diptera: culicidae).

Dengue fever is a reemerging disease of global concern among health authorities due to its high rate of proliferation. In 2019, Brazil registered its second-highest dengue mortality rate since 1998, with approximately 754 deaths and 1.5 million probable cases. Brazilian Ministry of Health prevention and control strategies for Aedes include insecticides, eradication of breeding sites, and awareness campaigns. However, as new mosquito variants resistant to conventional insecticides emerge, there is an increasing demand for effective environment-friendly plant extracts and natural substances against adult mosquitos and/or larvae of Aedes aegypti L. with no negative impacts on human health. This study aimed to investigate the larvicidal activity of Dizygostemon riparius extracts and analyze its chemical profile for the first time. Dizygostemon is a Plantaginaceae bytipic genus and D. riparius is an aromatic plant recently identified in Maranhão, Brazil. The essential oil from its lilac morphotype already exhibited larvicidal potential against Aedes albopictus, but the still limited data on this new plant species require further chemical and biological studies on other species, such as Aedes aegypti. Ethyl acetate and methanol crude leaf extracts yielded, respectively, 17.60 and 25.96%. High-performance liquid chromatography (HPLC) with UV detection coupled with electrospray ionization mass spectrometry (HPLC-UV-ESI-IT/MS) analyses confirmed the presence of polymethoxyflavones and coumarins, such as isorhamnetin 3-galactoside-7-rhamnoside, 5,7-dihydroxy-3-(3-hydroxy-4,5-dimethoxyphenyl)-6-methoxy-4-benzopyrone and 3',5-dihydroxy-4',6,7-trimethoxyflavone. Ethyl acetate extract presented the best performance in larvicide bioassays (LC50 = 542.2 ± 11.5 µg.mL-1). Our results highlight the chemical and biological potential of this new species found in the cerrado of eastern Maranhão and open perspectives for future studies focusing on isolating and identifying other active secondary metabolites of Dizygostemon riparius.

In vitro and in vivo wound healing activities of Globularia arabica leaf methanolic extract in diabetic rats.

AIM: This study assessed the effects of topical application of the plant Globularia arabica extract on the diabetic rate of wound closure. METHODS: The effect of methanol extracts of G. arabica leaf extract on pro-inflammatory and anti-inflammatory cytokines, as well as the rate of wound contraction, hydroxyproline, and collagen content, was examined using an excision model of wound repair in male rats. RESULTS: The healing pattern was also highly related to using 10% plant extract and significantly, (p-values <0.025) increased wound contraction and increased hydroxyproline and collagen expression in both non-diabetic and diabetic rats, demonstrating that G. arabica extract possesses potent wound healing capacity. During the early wound healing phase, IL-6 levels were found to be upregulated by G. arabica treatment. Increased wound contraction augmented hydroxyproline and collagen content, supporting the early wound healing exhibited by G. arabica. One of the ways for speeding wound healing may be the induction of cytokine production. The result of our study shows that the fibroblast cell line treated with 20 µg/ml methanolic extract of G. arabica significantly (p-values <0.035) increases the cell migration that indicated the high wound healing activity. CONCLUSION: Results suggest that G. arabica may be useful in the topical management of wound healing.

Antibacterial and antibiofilm activity of Lagotis brachystachya extract against extended-spectrum ß-lactamases-producing Escherichia coli from broiler chickens.

Lagotis brachystachya Maxim (L. brachystachya) is an herb widely used in traditional Tibetan medicine. In the present study, the antibacterial activity of L. brachystachya extract to extended-spectrum-lactamases (ESBLs)-producing E. coli was determined by Kirby-Bauer disc diffusion, minimum inhibitory concentrations (MICs) and minimum bactericidal concentrations (MBCs) methods as well as time-kill curve assay. Meanwhile, the biofilm inhibition and eradication effects of L. brachystachya extract on the ESBLs-producing E. coli were evaluated by crystal violet staining, and further confirmed by confocal laser scanning microscope (CLSM) and scanning electron microscopy (SEM). The results indicated that L. brachystachya extract exhibited moderate antibacterial activity, with diameter of inhibition zones varying from 15.4 to 20.3 mm, and the MIC and MBC values were 6.25 to 25 mg/mL and 12.5 to 100 mg/mL, respectively. Time-kill curve showed that 4 × MIC level of L. brachystachya extract concentration of was able to kill 99.9% of ESBLs-producing E. coli after 16 h treatment. The biofilm inhibition rate and eradication rate for the ESBLs-producing E. coli were 35.66 to 79.91% and 22.18 to 56.21% at MIC level of extract concentration, respectively. CLSM images showed that the biofilm became thinner as the ESBLs-producing E. coli isolate exposed to L. brachystachya extract with a concentration-dependent manner from 1/4 × MIC to MIC compared with the control isolate. SEM images indicated that L. brachystachya extract at 1/2 × MIC and MIC levels could evidently inhibit the biofilm formation or eradicate the mature biofilms. The effect of L. brachystachya highlights its potential of antibacterial and antibiofilm activities against the ESBLs-producing E. coli.

Anti-obesity, anti-hyperglycaemic, anti-antipyretic and analgesic activities of Globularia alypum extracts.

OBJECTIVES: The aim of this study is to evaluate the anti-obesity, anti-hyperglycaemic, analgesic and antipyretic activities of Globularia alypum (GA). MATERIALS AND METHODS: GA methanol and water extracts (GAME, GAWE) were administered to high-fat-high-glucose diet (HFFD) rats. RESULTS: This study showed that GAME exhibited the highest antioxidant, anti-α-amylase and anti-lipase activities, with half inhibitory concentration (IC50) values 0.067, 1.05 and 2.97 mg/ml respectively. In HFFD rats, the administration of GAME inhibited lipase activity by 36, 37 and 30% in the intestine, pancreas and serum, respectively, reduced body weight by 17.7% and modulated lipid profile. In addition, administration of GAME to HFFD-rats decreased α-amylase activity, improved glucose level and protected liver function. Furthermore, the administration of GA extracts to rats revealed antipyretic (reduction in writhing by 64%) and analgesic (decrease of temperature by 1.11 °C) activities. CONCLUSION: This study showed that GA extracts exhibited an anti-obesity, anti-hyperglycaemia, anti-pyretic and analgesic activities.

A new diarylhexane and two new diarylpropanols from the roots of Knema globularia.

A new diarylhexane, kneglobularone B (1) and two new diarylpropanols, kneglobularols A - B (2 - 3) along with seven known compounds (4 - 10) were isolated and characterized from the roots of Knema globularia. It is the first time to find arylpropyl quinone (4) and isoflavone (8) in Myristicaceae family. In addition, 5 was found for the first time in Knema genus. Their structures were elucidated by UV, IR, MS, 1 D and 2 D NMR techniques. Compound 4 exhibited strong cytotoxicity against the NCI - H187 and MCF - 7 cell lines with IC50 values of 3.08 and 6.68 µg/mL, respectively.

In vitro phytochemical and anticancer activity of Misopates orontium L. and Dicliptera bupleuroides Nees.

In the present study phytochemical analysis and anticancer activity of Misopates orontium L. and Dicliptera bupleuroides Nees was carried out. Methanolic extracts of M. orontium and D. bupleuroides were selected for phytochemical analysis. The present analysis showed the presence of phytochemical such as carbohydrates, proteins, tannins, glycosides, alkaloids, saponins, phenols and flavonoids in M. orontium and D. bupleuroides. Anticancer assays including MTT, Alamar Blue (AB), Neutral Red (NR) and lactate dehydrogenase (LDH) were employed on whole herb methanolic extract and all other fractions of both plants to calculate the % age of cell viability and cell cytotoxicity. The percentage of cell viability was highly significant in all anticancer assays for all fractions. Therefore, ethyl acetate and aqueous fractions showed the excellent profile in evaluation of cytotoxicity in each assay. All above findings indicated that the whole herb of both selected plants have strong anticancer activity.

A review of the aromatic genus Adenosma: Geographical distribution, traditional uses, phytochemistry and biological activities.

ETHNOPHARMACOLOGICAL RELEVANCE: The strongly scented genus Adenosma R. Brown (Plantaginaceae) comprises between 26 and 29 species with mainly southeast Asian distributions. Several species are used traditionally, mostly in Asian countries, for medicinal purposes including the treatment of colds and tumors, as well as stomach, liver, and skin disorders. Some species are also used as insecticides and/or insect repellents against mosquitoes or fleas. AIM OF THE REVIEW: Although the potential health benefits of Adenosma spp. are not yet well-known or well-studied in modern medicine, the aim of the present review is to provide a critical appraisal of the current state of knowledge regarding the geographical distribution, traditional uses, phytochemistry, phytochemicals and biological properties of Adenosma spp. MATERIALS AND METHODS: Electronic databases (Web of Science, Science Direct, Google Scholar, Scifinder, Microsoft Academic, eFloras), Biodiversity Heritage Library (BHL), and the China National Knowledge Infrastructure (CNKI), were searched using the key words "Adenosma", "", "", "", "nhân tran", as well as the scientific names of the species, and a library search was also conducted for articles and books related to the subject published in English, Chinese or Vietnamese, as well as Ph.D. theses and M.Sc. dissertations published before April 2020. RESULTS: Adenosma spp. is traditionally used to treat gastrointestinal disorders, hepatitis, colds, and skin problems. Phenolic acids, flavonoids, and terpenoids constitute the main phytochemicals in these plants. Several evaluations based on bioassays have demonstrated biological activity for Adenosma spp., including antidiabetic, anticancer, and insecticidal activities; extracts and isolated compounds have also shown effective biological activity. However, current research has focused only on a few species, and on limited geographical regions, mainly in China and Vietnam. More and broader ethnopharmacological studies are therefore needed to provide further evidence of the health benefits of these plants. CONCLUSIONS: Adenosma spp. are plants rich in essential oils, particularly terpenoids, and the crude extracts have valuable bioactive properties. Certain lines of research based on cell lines and animal models show the potential value in different areas of health management. Further investigation into the traditional knowledge in southeast Asian and Pacific island regions, as well as the into the toxicity and identity of the bioactive compounds and their mechanisms of action is necessary.

Plantaginis Semen polysaccharides ameliorate renal damage through regulating NLRP3 inflammasome in gouty nephropathy rats.

Gouty nephropathy (GN) is considered to be a prevalent renal disease and is an inflammatory event mainly induced by MSU crystals. Plantaginis Semen is a traditional Chinese herb that has been used in the treatment of gout, gouty arthritis and GN, but the mechanism and ingredients have been unclear. In this study, we explored and evaluated the preliminary structural characterizations of Plantaginis Semen polysaccharides (PSPs) and the activity of protecting against renal damage in GN rats. Three polysaccharide fractions, PSP-D, PSP-H and PSP-S, were sequentially extracted by different processes from the seed of Plantago asiatica L. The Fourier transform infrared spectral (FTIR) results showed that there were significant differences between PSP-S and the other two polysaccharides (PSP-D and PSP-H). PSP-D and PSP-H have pyrene monomers and linkages of ß-glycosides in their structures, and PSP-S has furanoside in the molecular structure. The scanning electron microscope (SEM) images of three polysaccharides showed that PSP-D has a smooth surface and a small curve, PSP-H is block-like and uneven in magnitude, whereas PSP-S is sea-tent-like and its surface is very distinct from the others. Main components and molar ratios are also different. Rats were randomly divided into six groups (n1/6 8 per group): the control group, model group, positive group, and three treatment groups (PSP-D, PSP-H and PSP-S). For all groups except the control group, rats were intragastrically administered the adenine suspension (50 mg kg-1 d-1) and fed with a high-yeast diet (15 g kg-1 d-1) for 28 days. On the 9th day, the control group and the model group were administered normal saline at the same time. Treatment groups were individually given corresponding drugs for 20 days. We found that PSPs could prevent renal damage, including decreasing the inflammatory response and regulating the (NOD)-like receptor protein 3 (NLRP3) protein in renal tissue. The underlying mechanism was related to NLRP3 inflammasome signal pathways, and it could take effect through the down-regulation of the protein expression levels of NLRP3, ASC and caspase-1 and inhibit the release of downstream inflammatory factors. PSPs are promising polysaccharides that could protect against renal injury through ameliorating renal inflammation in GN rats. Plantaginis Semen polysaccharides are potential functional food ingredients or pharmacological agents for treating GN in clinical practice.

Phytochemical Investigation and Antioxidant Activity of Globularia alypum L.

The Moroccan flora is rich in medicinal plants that are commonly used in folk medicine for the treatment of various diseases. The present study was designed to investigate the total phenolic and flavonoid contents, as well as the antioxidant properties of leaves extracts from Globularia alypum L. colected from the Taza region in northeast Morocco. Additionally, the individual phenolics and volatiles of the extracts were also evaluated. The organic extracts of this plant were obtained by Soxhlet extraction using two different solvents, namely ethyl acetate and chloroform. The antioxidant capacity of leaves extracts was measured using DPPH, ABTS and FRAP assays; the phenolic profile was determined by HPLC-DAD/ESI-MS analysis, whereas the volatile composition was elucidated by GC-MS. The ethyl acetate extract analysis showed a total of 20 phenolic compounds and the determination of phenolic contents showed a significant value of 56.5 ± 0.61 µg GAE/mg of extract in comparison with the chloroform extract (18.9 ± 0.48 µg GAE/mg of extract). Also, the determination of the flavonoid contents revealed that the ethyl acetate extract contained the highest value (30.2 ± 0.55 µg CE/mg of extract) in comparison with the chloroform extract (18.0 ± 0.36 µg CE/mg of extract). Concerning the antioxidant properties, interesting values were attained for the ethyl acetate extract which exhibited higher antioxidant activity, namely IC50 = 12.3 ± 3.83 µg/mL and IC50 = 37.0 ± 2.45 µg/mL for the DPPH and ABTS assays, respectively, whereas a value of 531.1 ± 17.08 (mg AAE/g DW) was obtained for the FRAP assay. Concerning the volatile profile, a total of 73 compounds were positively detected and among them n-hexadecanoic acid (13.5%) was the most abundant one. The results achieved confirm the important role of this plant as a source of natural antioxidants.

Two new phenylpropanoid glycosides from Lagotis brachystachya Maxim and their Xanthione Oxidase inhibitions.

Two new phenylpropanoid glycosides lagotiside C and D, along with 11 known compounds were isolated from the whole plant of Lagotis brachystachya Maxim. The structures of lagotiside C and D was elucidated on the basis of spectroscopic data analysis. Moreover, all isolated components were evalued for the inhibition on Xanthione Oxidase (XOD) activity in vitro. Results indicated that all the compounds exhibited inhibitory effects on XOD with inhibition ratio in the range of 6.35%-83.69%, which suggested that Lagotis brachystachya could be served as an XOD inhibitor.

Carbohydrate saving or biomass maintenance: which is the main determinant of the plant's long-term submergence tolerance?

It is hypothesized that plant submergence tolerance could be assessed from the decline of plant biomass due to submergence, as biomass integrates all eco-physiological processes leading to fitness. An alternative hypothesis stated that the consumption rate of carbohydrate is essential in differing tolerance to submergence. In the present study, the responses of biomass, biomass allocation, and carbohydrate content to simulated long-term winter submergence were assessed in four tolerant and four sensitive perennials. The four tolerant perennials occur in a newly established riparian ecosystem created by The Three Gorges Dam, China. They had 100% survival after 120 days' simulated submergence, and had full photosynthesis recovery after 30 days' re-aeration, and the photosynthetic rate was positively related to the growth during the recovery period. Tolerant perennials were characterized by higher carbohydrate levels, compared with the four sensitive perennials (0% survival) at the end of submergence. Additionally, by using a method which simulates posterior estimates, and bootstraps the confidence interval for the difference between strata means, it was found that the biomass response to post-hypoxia, rather than that to submergence, could be a reliable indicator to assess submergence tolerance. Interestingly, the differences of changes in carbohydrate content between tolerant and sensitive perennials during submergence were significant, which were distinct from the biomass response, supporting the hypothesis that tolerant perennials could sacrifice non-vital components of biomass to prioritize the saving of carbohydrates for later recovery. Our study provides some insight into the underlying mechanism(s) of perennials' tolerance to submergence in ecosystems such as temperate wetland and reservoir riparian.

Composition and Larvicidal Activity of the Oil of Dizygostemon riparius (Plantaginaceae), a New Aromatic Species Occurring in Maranhão, Brazil.

Dizygostemon riparius (Plantaginaceae) is a new aromatic herbaceous species occurring in Maranhão State, Brazil. It is used as flavorings to remove domestic animal parasites and preventing mosquitoes. GC and GC/MS were used to analyze its essential oil, and a larvicidal bioassay was performed against Aedes albopictus larvae, a vector of arboviruses in Brazil. endo-Fenchyl acetate, endo-fenchol, (E)-caryophyllene, and caryophyllene oxide were the oil's primary constituents, totalizing 88.0 %. The two morphotypes of D. riparius, with purple and white flowers, did not present a significant difference in the oils' composition. From a chemotaxonomic point of view, D. riparius oil showed some similarities with other oils of Plantaginaceae, suggesting (E)-caryophyllene and caryophyllene oxide as possible chemical markers. The oil larvicidal action displayed the lowest and highest mortality percentage at 50 mg/L (2.0 %) and 600 mg/L (88.0 %). The fenchyl acetate and fenchol standards showed a lower and higher mortality percentage at a concentration of 300 mg/L (42.0 % and 26.0 %) and 900 mg/L (96.0 % and 98.0 %), respectively. The present study results with the D. riparius oil point to a new bioproduct with significant larvicidal activity.

Anticancer Activity of Novel Plant Extracts and Compounds from Adenosma bracteosum (Bonati) in Human Lung and Liver Cancer Cells.

Cancer is the second leading cause of death globally, and despite the advances in drug development, it is still necessary to develop new plant-derived medicines. Compared with using conventional chemical drugs to decrease the side effects induced by chemotherapy, natural herbal medicines have many advantages. The present study aimed to discover the potential cytotoxicity of ethanol extract and its derived fractions (chloroform, ethyl acetate, butanol, and aqueous) of Adenosma bracteosum Bonati. (A. bracteosum) on human large cell lung carcinoma (NCI-H460) and hepatocellular carcinoma (HepG2). Among these fractions, the chloroform showed significant activity in the inhibition of proliferation of both cancerous cells because of the presence of bioactive compounds including xanthomicrol, 5,4'-dihydroxy-6,7,8,3'-tetramethoxyflavone, and ursolic acid which were clearly revealed by nuclear magnetic resonance spectroscopy (1H-NMR, 13C-NMR, Heteronuclear Multiple Bond Coherence, and Heteronuclear Single Quantum Coherence Spectroscopy) analyses. According to the radical scavenging capacity, the 5,4'-dihydroxy-6,7,8,3'-tetramethoxyflavone compound (AB2) exhibited the highest anticancer activity on both NCI-H460 and HepG2 with IC50 values of 4.57 ± 0.32 and 5.67 ± 0.09 µg/mL respectively, followed by the ursolic acid with the lower percent inhibition at 13.05 ± 0.55 and 10.00 ± 0.16 µg/mL, respectively (p < 0.05). Remarkably, the AB2 compound induced to significant increase in the production of reactive oxygen species accompanied by attenuation of mitochondrial membrane potential, thus inducing the activation of caspase-3 activity in both human lung and liver cancer cells. These results suggest that A. bracteosum is a promising source of useful natural products and AB2 offers opportunities to develop the novel anticancer drugs.

Essential oil from leaves of Conobea scoparioides (Cham. & Schltdl.) Benth. (Plantaginaceae) causes cell death in HepG2 cells and inhibits tumor development in a xenograft model.

Conobea scoparioides (Cham. & Schltdl.) Benth. (syn. Sphaerotheca scoparioides Cham. & Schldtl.) (Plantaginaceae), popularly known as "pataqueira", "vassourinha-do-brejo" and/or "hierba-de-sapo", is a popular medicinal plant used to treat leishmaniasis, pain and beriberi. In addition, inhibition of cell adhesion, antioxidant, cytotoxic and leishmanicidal activities of compounds or fractions of C. scoparioides have been reported. In the present work, chemical constituents and in vitro and in vivo anti-liver cancer potential of essential oil (EO) from leaves of C. scoparioides were investigated using human hepatocellular carcinoma HepG2 cells as a cell model. EO was obtained by hydrodistillation using a Clevenger-type apparatus and characterized by GC-MS and GC-FID. The in vitro cytotoxic effect was evaluated on three human cancer cell lines (MCF-7, HepG2 and HCT116) and one human non-cancerous cell line (MRC-5) using the Alamar blue assay. Phosphatidylserine externalization and cell cycle distribution were quantified in HepG2 cells by flow cytometry after 48 h incubation. The effectiveness of EO in anti-liver cancer model was studied with HepG2 cells grafted on C.B. 17 SCID mice. The main constituents of EO were thymol methyl ether (62 %), thymol (16 %) and α-phellandrene (14 %). EO displayed an in vitro cytotoxic effect against all human cancer cell lines and caused externalization of phosphatidylserine and DNA fragmentation in HepG2 cells, suggesting induction of apoptotic-like cell death. In vivo tumor mass inhibition of 36.7 and 55.8 % was observed for treatment with EO at doses of 40 and 80 mg/kg, respectively. These results indicate in vitro and in vivo anti-liver cancer potential of EO from leaves of C. scoparioides.