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Plant mediated green synthetic route for silver and gold nanoparticles (AgNPs & AuNPs) from four plant families: Phyllanthaceae, Lamiaceae, Rutaceae and Euphorbiaceae and their therapeutic application of are summarized in the present review article. Silver and gold nanoparticles prepared from the mentioned plant families were visualized with various therapeutic applications viz., anti-microbial, ant-bacterial, anti-cancer and anti-oxidant activities etc. Owing to size and shapes, NPs green synthesized from various plants like Ricinus communis (Ag), Tectona grandis (Ag), Plectranthus amboinicus (Ag, Au), Phyllanthus emblica (Ag, Au), Ricinu communis (Ag), Leucas aspera (Ag, Au), Acalypha indica Linn. (Ag, Au) were envisioned with innumerable curative applications such as antimicrobial, anticancer, antibacterial, anti-oxidant, cytotoxicity, haemolytic and stimulating effect etc. In the current review, eco-friendly green synthetic itineraries for synthesis of AgNPs and AuNPs are mainly focused. Phyto-components present in plants such as anti-oxidant molecules, terpenes, alkaloids, coumarins like quercetin, d -allose, 1-valine, ocosenamide molecules etc. are the responsible reducing agents for the capping reaction (Ag+ to Ag0 and Au3+ to Au0) of nanoparticle from metal precursors like AgNO 3 and HAuCl 4. [Display omitted] • Bio-synthesis of AgNPs and AuNPs from four plant families: Phyllanthaceae, Lamiaceae, Rutaceae and Euphorbiaceae are summarized. • AgNPs and AuNPs green synthesized from plants belonging to Phyllanthaceae, Lamiaceae, Rutaceae and Euphorbiaceae families contain various medicinal applications like antimicrobial, anticancer, antibacterial, anti-oxidant, cytotoxicity etc. • Phyto-compounds present in plants are responsible for capping reaction of nano-particles. [ABSTRACT FROM AUTHOR]

• Sixteen compounds were isolated from the EtOAc extract of C. excavata fruits. • Nine compounds (1, 3, 5, 6, 8 – 10, 15 , and 16) were isolated from C. excavata for the first time. • The absolute configuration of the bioactive limonoids 15 and 16 were confirmed by the X-ray crystallography using Cu Kα radiation. • Compounds 7 (auraptene) and 14 (safrole) showed a moderate glucose uptake with ratios of 1.38-fold and 1.41-fold, respectively. • The cytotoxicity of auraptene 7, 8 , and 10 against lung cancer A549, RAW 264.7 cells, and colorectal cancer SW480 are reported for the first time in this study. Phytochemical investigation of the fruit extract of Clausena excavata Burm. f. resulted in the isolation and identification of 16 compounds, including seven coumarins (1 – 7), four phenylpropanoids (8 – 10 and 14), two benzaldehyde derivatives (11 and 12), one carbazole alkaloid (13), and two limonoids (15 and 16). Of these, nine compounds (1, 3, 5, 6, 8 – 10, 15 , and 16) were isolated from C. excavata for the first time. The absolute configuration of limonoids 15 and 16 was established by X-ray diffraction analysis using Cu Kα radiation. Some isolated compounds were evaluated for their in vitro cytotoxicity against three human cancer cell lines, namely lung cancer A549, colorectal cancer SW480, leukemic K562 cells as well as glucose uptake, glucose consumption, and antibacterial activity against Staphylococcus aureus (SA) and methicillin-resistant Staphylococcus aureus (MRSA). Compounds 7 (auraptene) and 14 (safrole) showed moderate glucose uptake with ratios of 1.38-fold and 1.41-fold compared to the positive control (metformin, 2.25-fold). Compound 7 (auraptene) also exhibited weak cytotoxicity against lung cancer A549, colorectal cancer SW480, and leukemic K562 cells with IC 50 values of 77.2, 157.3, and 105.3 µM, respectively, while compounds 8 ((E)-piperonylprop-2-enal) and 10 (ethyl p -coumarate) exhibited weak cytotoxicity against RAW 264.7 cells and colorectal cancer SW480 cells with IC 50 values of 234.9 and 219.5 μM, respectively. Compounds 1, 3, 7 , and 14 – 16 showed a MIC of >512 µg/mL revealing them to be inactive. : [Display omitted] [ABSTRACT FROM AUTHOR]

This study was designed to investigate the effects of five Rutaceae family ethanol extracts (FRFEE): Citrus medica Linn (CML), Citrus aurantium L. Cv. Daidai (CAD), Citrus medica Linn. var. sarcodactylis (Noot.) Swingle (CMS), Citrus sinensis L. Osbeck (CSO) and Zanthoxylum bungeanum Maxim (ZBM) on retarding the progression of H 2 O 2 and LPS-induced HaCaT cells. Cell inflammatory injury model was established by H 2 O 2 and LPS. The alleviative effects of FRFEE were evaluated by detecting the activity of superoxide dismutase (SOD), glutathione (GSH) and the generation of reactive oxygen species (ROS). The inflammatory signaling pathways of NF- κ B and JAK-STAT3 were detected by Western blotting, the mRNA expression levels of inflammatory factors and skin barrier factors were detected by RT-PCR. 50% ethanol extracts of five medicinal and food homologous herbs of Rutaceae family showed different levels of anti-oxidant and anti-inflammatory activities. The FRFEE effectively improved SOD and GSH content and decreased ROS levels. Meanwhile, FRFEE strongly suppressed two inflammatory signaling pathways NF- κ B and JAK-STAT3. The RT-PCR examination of inflammatory factors and skin barrier factor revealed significant anti-inflammatory effects of FRFEE. It was worth noting that among the five extracts, Zanthoxylum bungeanum Maxim extract had the best anti-inflammatory and anti-oxidation effects. In addition, it could strongly inhibit the expression of psoriasis factor CCL20. In summary, these results suggested that Zanthoxylum bungeanum Maxim extract could be used as an anti-psoriatic agent in the treatment of psoriasis among FRFEE. [ABSTRACT FROM AUTHOR]

The pericarps of Zanthoxylum schinifolium Sieb. et Zucc were called "green huajiao ", which were used as traditional folk medicine and popular seasoning in China. In this study, twenty-seven alkylamides, including a rare alkylamide containing two amide groups (1), an alkylamide with a furan ring (5), six new alkylamide analogues (2 – 4 , 6 – 8), together with nineteen known alkylamides (9 – 27) were isolated from green huajiao. Their structures were elucidated by extensive spectroscopic analysis, including 1D, 2D NMR, HRESIMS, and UV spectra. Furthermore, compounds 5 , 18 , 21 , and 22 exhibited weak protective activity for corticosterone-induced PC12 cells damage. [Display omitted] • Eight previously undescribed and nineteen known alkylamides were isolated from the green huajiao. • Compound 1 was the first example of alkylamide with two amide moieties and compound 5 was an alkylamide containing a rare furan ring. • Compounds 5 , 18 , 21 , and 22 exhibited potential neuroprotective effects against corticosterone-induced damage in PC12 cells. [ABSTRACT FROM AUTHOR]

• The high medical value of Zanthoxylum armatum has raised concern for its long-term sustainability. • The study reviews botany, uses, and threats, and offers suggestions for the sustainable utilization of the species. • Pharmaceutical potential of the species is well explored and reproductive constraints are well recognized. • Viable cultivation methods and sustainable harvesting techniques are urgently needed for its conservation. Zanthoxylum armatum has fascinated the botanical world due to its significance as the 'toothache relieving tree'. The high medical value of the species has raised concern for its long-term sustainability. The genus Zanthoxylum is represented by 225 species, distributed throughout the globe. Among others, Z. armatum is a high-value species, facing threats due to destructive harvesting and constraints in its reproduction. This study reviews botany, traditional uses, pharmacology, threats, and offers suggestions for the sustainable utilization of the species. Findings indicate that the pharmaceutical potential of the species is well explored and reproductive constraints are well recognized. Overharvesting is a major threat to its existing populations. Viable cultivation methods and sustainable harvesting techniques are urgently needed for its conservation and sustainable utilization. [ABSTRACT FROM AUTHOR]

Three new isoprenylated chromones, named harriforatins A−C (1 − 3), along with 13 known compounds (4 − 16) were isolated from the stems of Harrisonia perforata. Their planar structures were elucidated by spectroscopic measurements. The experimental and calculated ECD curves were used to determine their absolute configurations. Most isolated compounds were evaluated for inflammation inhibition against lipopolysaccharide (LPS)-induced nitric oxide (NO) production in RAW264.7 macrophages. Only compounds 5 and 6 showed inhibitory effects on NO production, with IC 50 values of 42.8 and 47.0 μM, respectively, that were stronger than that of the positive control, indomethacin (IC 50 = 68.6 μM). [Display omitted] • Three new isoprenylated chromones were isolated from Harrisonia perforata stems. • The structures with absolute configurations were established by extensive spectroscopic methods. • Two compounds showed a significant inhibitory effect on NO production. [ABSTRACT FROM AUTHOR]

Wampee (Clausena lansium) is a relative of cultivated citrus in the Rutaceae family. Its cracked fruit in orchard is not susceptible to Penicillium italicum infection, but the mechanism remains unknown. In this study, it was found that the volatiles from wampee leaf (WL) and wampee pericarp (WP) can repress the infection and development of P. italicum in vitro. Additionally, WL exhibited strong antifungal effects in in vivo experiments as well. Antifungal activity analysis of WL volatile organic compounds (VOCs) demonstrated that (E)-2-hexenal is the key antifungal compound against P. italicum by disrupting the integrity of cell membrane. Moreover, exogenous (E)-2-hexenal treatment significantly reduced the area covered by mycelia on citrus fruits and increased the expression of genes and accumulation of various metabolites related to disease resistance. These results indicate that WL can be used as a promising natural preservative in citrus postharvest handling mainly due to the antifungal activity of (E)-2-hexenal. • Volatiles from wampee leaves have antifungal activities. • (E)-2-hexenal is an important antifungal component in wampee leaves. • Exogenous (E)-2-hexenal treatment enhances the resistance of citrus fruit to blue mold. [ABSTRACT FROM AUTHOR]

Hesperetin is the aglycone of hesperidin and is widely found in the Rutaceae plants and herbal medicines. It exhibits antioxidant, detoxifying, anti-inflammatory, and antimicrobial properties, similar to hesperidin. It has also shown potential in the regulation of certain diseases. In order to detect hesperetin in complex matrix samples such as citrus and herbal, we developed an anti-hesperetin monoclonal antibody and established an indirect competitive enzyme-linked immunosorbent assay (icELISA). The half maximal inhibitory concentration (IC 50) was determined to be 2.03 ng/mL, the detection range was 0.39–12.73 ng/mL. In practical sample testing, the concentration of hesperidin measured by icELISA is consistent with the result of UPLC-MS/MS, and the correlation coefficient (R2) is 0.97. These results showed that the established method has good accuracy, reproducibility and broad application prospects, and can be used for the detection of hesperetin in complex matrix samples (such as citrus and herbal samples). Graphical Abstract (for review). [Display omitted] • A novel hapten of hesperetin was designed and synthesized. • A sensitive mAb (1D11) against hesperetin was prepareed with IC 50 of 2.03 ng/mL. • The developed icELISA can be used for the detection of hesperetin in complex matrix samples such as citrus and herbal. [ABSTRACT FROM AUTHOR]

Two additional oxyprenylated phenylpropanoids in Citrus paradisi Macfad. seeds extract • The isolation of novel O- prenylpropanoids from grapefruit is described. • Novel phytochemicals have been characterized by HPLC/DAD. • Novel phytochemicals have been isolated for the first time within the Rutaceae family. [ABSTRACT FROM AUTHOR]

Selenium nanoparticles (SeNPs), a potential cancer therapeutic agent, have attracted widespread attention owing to their high bioavailability and remarkable anticancer activity. Nevertheless, the poor water solubility and dispersibility of SeNPs seriously limit their applications. In the present study, we synthesized stable and individual spherical selenium nanoparticles (CL90-Tw-SeNP2) with an average diameter of approximately 79 nm using a polysaccharide extracted from Citrus limon (CL90) and Tween-80 as the decorator and stabilizers. The proportion of selenium in CL90-Tw-SeNP2 was 10.6%. CL90-Tw-SeNP2 possessed high stability and good dispersion in water for more than three months. The subsequent biological assay revealed that CL90-Tw-SeNP2 showed remarkable antitumor effects against HepG2 cells, with an IC 50 value of 49.13 μg/mL, by inducing cell apoptosis. Furthermore, an in vivo zebrafish assay to explore possible applications indicated that CL90-Tw-SeNP2 could inhibit the proliferation and migration of tumors and the zebrafish angiogenesis. These results indicated that CL90-Tw-SeNP2 could be a potential agent for cancer treatment, especially against human liver hepatoma cancer. [Display omitted] • High stability and selenium content of CL90-Tw-SeNP2 were synthesized successfully. • Citrus limon polysaccharides and Tween-80 acted as the stabilizers in the reaction. • CL90-Tw-SeNP2 exerted remarkable antitumor effects by inducing apoptosis. • CL90-Tw-SeNP2 inhibited the proliferation and migration of tumors. • CL90-Tw-SeNP2 can block the angiogenesis of zebrafish. [ABSTRACT FROM AUTHOR]

This study was designed to investigate the phytochemical and the antioxidant activities of the extracts of Citrus limon L Osbeck leaf using ethanol, acetone and distilled water as extraction solvents. The total alkaloids, saponin, phenolic acid and flavonoids were determined spectrophotometrically while antioxidant potentials were evaluated with 2,2'-diphenyl-1-picrylhydrazyl (DPPH), Ferric-reducing/antioxidant power (FRAP) and 2,2'-azino- bis (3ethylbenzothiazoline-6-sulfonic acid) (ABTS) protocols. The phytochemical evaluation of the leaf of C. limon, reveals high contents of alkaloids, (12.23%) and saponin (5.53%). In addition, the aqueous extract shows the highest phenolic acid content of 289.4 ± 5.73 mg/GAE/g followed by ethanol 209.72 ± 6.38 mg/GAE/g and the least was the acetone extracts 207.56 ± 7.03mg/GAE/g. Flavonoids content was also highest in the ethanol extract (1052.58 ± 39.44mg/QE/g) and the aqueous extract (447.41 ± 4.56mg/QE/g). All the extracts showed significant antioxidant activities with ABTS, FRAP and DPPH along a concentration gradient. The high phytochemical content and the antioxidant activity of C. limon leaf extracts observed in this study supports and justifies its use in folk medicine. [Display omitted] • The test plant is rich in bioactive components such as phenol, flavonoid, alkaloid, saponin. • Antioxidant capacity is also high in the test plant suggesting its biomedicinal value to human health. • Bioactivity observed could indicate the test plant as a potential biofungicid [ABSTRACT FROM AUTHOR]

Three new coumarins, integmarins A–C (1–3), and a new coumarin glycoside, integmaside A (4) were isolated from the leaves and stems of Micromelum integerrimum. Their structures were elucidated on the basis of 1D and 2D NMR and MS data, and their absolute configurations were assigned according to the ECD data of the in situ formed transition metal complexes and comparison of experimental and calculated ECD data. Compounds 1 and 2 are two rare coumarins with butyl and propyl moieties at the C-6 position; compound 3 is a novel coumarin with a highly oxidized prenyl group, and compound 4 is a rare bisdihydrofuranocoumarin glycoside. [Display omitted] [ABSTRACT FROM AUTHOR]

Ethyl acetate fraction of Toddalia asiatica was fractionated to yield fifteen previously undescribed prenylated coumarins, asiaticasics A-O (1 – 15) along with nine (16 – 24) known derivatives. The structures of these undescribed coumarins were established by spectroscopic analysis and reference data. Biological activity evaluation showed that compound 3 with the IC 50 value of 2.830 μM and compound 12 with the IC 50 value of 0.682 μM owned anti-inflammatory activity by detecting the rate of lactate dehydrogenase release in pyroptosis J774A.1 cells. The results showed that the expression of Caspase-1 and IL-1 β was decreased in a dose-dependent manner in the compound 12 treatment group, suggesting that compound 12 may reduce pyroptosis by inhibiting NLRP3 inflammasome. To further determine that compound 12 treatment can inhibit macrophage pyroptosis, morphological observation was performed and the results were consistent with the bioactivity evaluation. [Display omitted] • Twenty-four coumarins were isolated from the ethyl acetate fraction of Toddalia asiatica. • Fifteen coumarins that have not been described before. • Two undescribed compounds showed low IC 50 values and could exert effective anti-inflammatory effects. • Compound 12 inhibited pyroptosis in a dose-dependent manner. [ABSTRACT FROM AUTHOR]

In this research, five new indolequinazoline alkaloids (1 – 5), along with six known indolequinazoline alkaloids (6 – 11) were obtained from the fruits of Tetradium ruticarpum. Their structures were elucidated through comprehensive spectroscopic data of 1D and 2D NMR, HRESIMS and ECD spectra. Additionally, all isolates were assayed for their SIRT1 inhibitory activities in vitro and compounds 2 , 7 , 10 and 11 exhibited activities with IC 50 values ranged from 43.16 to 118.35 μM. Eleven indolequinazoline alkaloids, including five undescribed compounds, were isolated from the fruits of Tetradium ruticarpum and their SIRT1 inhibitory activities were assessed. [Display omitted] [ABSTRACT FROM AUTHOR]

From the 95% ethanol aqueous extract of the roots of Clausena lansium , six previously undescribed alkaloids (1 , 2a , 2b , 15 , 24a , 24b), a pair of prenylated phenylpropenols (26a , 26b), two coumarins (27 , 28), and two undescribed sesquiterpenes (37 , 38) were isolated and identified using spectroscopic and electron circular dichroism data, together with thirty-two known compounds. The absolute configurations of three alkaloids (3a , 3b , 4a) were determined for the first time. In vitro assay showed that alkaloids 7 , 10 , 12 , 19 , and furanocoumarins 34 , 35 displayed inhibitory effects on the production of nitric oxide in lipopolysaccharide (LPS)-induced BV-2 microglial cells, which were stronger than that of the minocycline (positive control). RT-PCR results indicated that indizoline (7) could inhibit the expression of pro-inflammatory factors (IL-1 β , TNF- α, and IL-6) in LPS-treated BV-2 cells. Study on natural inhibitors against overactivation of microglial cells from the roots of Clausena lansium. [Display omitted] • Twelve undescribed compounds were reported for the first time. • All compounds were evaluated for NO production inhibitory effects in vitro. • Indizoline could inhibit the expression of pro-inflammatory factors in BV-2 cells. [ABSTRACT FROM AUTHOR]

Monoamine oxidase inhibition is an important therapeutic approach for various neurodegenerative disorders. Reversible MAO inhibitors selectively targeting only one isoform possess substantial merit in terms of safety, efficacy, and side effect profile. This study aimed to isolate the secondary metabolites of Zanthoxylum flavum stems and evaluate their recombinant human MAO inhibition, antimicrobial, and antiprotozoal activities. As a result, fourteen compounds were isolated and identified (nine of them were reported from Z. flavum for the first time). Compound 3 (sesamin) exhibited potent selective MAO-B inhibition (IC 50 value of 1.45 ± 0.05 µM) which reported herein for the first time. Compound 2 showed selective MAO-A inhibition activity, compound 5 exhibited good trypanocidal activity, and compound 7 displayed moderate antibacterial activity. The promising MAO-B inhibitory activity of sesamin provoked us to further explore the kinetic properties, the binding mode, and the underlying mechanism of MAO-B inhibition by this lignan. This detailed investigation substantiated a reversible binding and mixed MAO-B catalytic function inhibition via sesamin (K i : 0.473 ± 0.076 μM). Selectivity and reversibility of sesamin on MAO-B provide exciting prerequisites for further in vivo investigation to confirm its therapeutic potentiality. [ABSTRACT FROM AUTHOR]

Murraya koenigii is a plant with exploited pharmacological potential and wide traditional use in Asian culture. This research investigated the chemical composition and seasonal variation of essential oil constituents of M. koenigii cultivated in the city of Goiânia, Goiás, region under climatic influence of the Cerrado domain. The larvicidal potential of these essential oils against Aedes aegypti was investigated. The constituents were evaluated by Gas Chromatography coupled to Mass Spectrometry (GC/MS). Climatological information and phenological conditions were also considered. Samples grouped into chemically similar sets were used in bioassays to investigate larvicidal activity. The results show the essential oil characterized by the majority presence of β-phellandrene, z-caryophyllene, α-pinene, sabinene and isodaucene. The phenological stage had more influence on the chemical composition of the essential oil than climatic factors. All essential oil samples were effective against Ae. aegypti , with no significant change in lethal concentrations. • Murraya koenigii essential oil has recognized insecticidal activity. • Plants cultivated in Goiânia, Brazil, showed chemical constitution similar to Indian chemotypes. • Murraya koenigii essential oil has shown promising larvicidal activity against Aedes aegypti. • Seasonal variation did not interfere with the larvicidal potential of the essential oil. • The evaluated samples did not show toxicity against sheep erythrocytes. [ABSTRACT FROM AUTHOR]

A pair of new enantiomeric indolopyridoquinazoline-type alkaloids, (+)-1,7 S ,8 R - and (−)-1,7 R ,8 S -trihydroxyrutaecarpine (3a and 3b), and a new limonoid-tyrosamine hybrid, austrosinin (8), along with six known alkaloids and limonoids, were isolated from the stems with leaves of Tetradium austrosinense. Their structures were elucidated on the basis of analysis of MS, NMR, ECD and time-dependent density functional theory-based electronic circular dichroism (TDDFT-ECD) calculations, as well as proposed biosynthetic pathway. An anti-inflammatory bioassay in vitro showed 8 had significant immunosuppressive effect against the production of pro-inflammatory cytokine TNF-α in lipopolysaccharide (LPS)-stimulated RAW264.7 cells. [Display omitted] • Six alkaloids and three limonoids were isolated from Tetradium austrosinense. • A pair of enantiomeric indolopyridoquinazoline-type alkaloids were isolated and resolved. • Austrosinin is the first example of limonoid-tyrosamine hybrid from the nature source. • Austrosinin displayed significant immunosuppressive effect. [ABSTRACT FROM AUTHOR]

• Sixty-six accessions of 'true citrus fruit trees' group were used in this study. • Conserved group I intron (PQRS) sequence motifs were detected in Citrus genus. • The secondary structure of the common P8 stem–loop region was predicted. • Our result shows that trn L UAA intron can be a good barcode for 'true citrus'group. Cytoplasmic chloroplast DNAs was explored to establish phylogenetic relationships among 'True citrus' group and elucidate its molecular evolution. Conserved group I intron (PQRS) sequence motifs were detected in Citrus genus and showed differences of nucleotide variation between elements and some species. The P8 stem-loop region was the only variable region in trn L intron of Citrus species. The deletion of 6 bp has been detected between sites (40–45) in the partial alignment of P8 stem-loop resulted in a change in conformation of the secondary structures in the ancestral species and other derived species and this could be explained by the evolution and speciation of this genus. The consistency index (CI=1) and the retention index (RI=1) values suggest that the changes are mostly apomorphic despite the absence of homoplasy (HI=0). The phylogenetic tree confirms and shows a branching of C. limon , C. sinensis , C. paradisi , C. tangelo and C. aurantium in a monophyletic clade. This result so far to C. reticulata ruled out the maternal contribution of mandarin gene pool in the elaboration of these secondary Citrus species. The Maximum Likelihood tree indicated that the genus Citrus is quite distant from the related genera Poncirus, Microcitrus, Eremocitrus and Fortunella except only Fortunella margarita species. Here new insight is given about mechanism involving in the evolution of the trn L intron in 'True Citrus'. From the study it appears that an explicit rejection of the null hypothesis and a scenario of a demography history and recent expansion of 'True Citrus' genotypes seem to be retained that may be an important factor influencing the power of genetic diversity in 'True Citrus'. [ABSTRACT FROM AUTHOR]

The evolution of phytochemical diversity and biosynthetic pathways in plants can be evaluated from a phylogenetic and environmental perspective. Pilocarpus Vahl (Rutaceae) , an economically important medicinal plant in the family Rutaceae, has a great diversity of imidazole alkaloids and coumarins. In this study, we used phylogenetic comparative methods to determine whether there is a phylogenetic signal for chemical traits across the genus Pilocarpus; this included ancestral reconstructions of continuous and discrete chemical traits. Bioclimatic variables found to be associated with the distribution of this genus were used to perform O LS regressions between chemical traits and bioclimatic variables. Next, these regression models were evaluated to test whether bioclimatic traits could significantly predict compound concentrations. Our study found that in terms of compound concentration, variation is most significantly associated with adaptive environmental convergence rather than phylogenetic relationships. The best predictive model of chemical traits was the OLS regression that modeled the relationship between coumarin and precipitation in the coldest quarter. However, we also found one chemical trait was dependent on phylogenetic history and bioclimatic factors. These findings emphasize that consideration of both environmental and phylogenetic factors is essential to tease out the intricate processes in the evolution of chemical diversity in plants. These methods can benefit fields such as conservation management, ecology, and evolutionary biology. Image 1 • There is an inverse relationship between coumarin and alkaloid diversity on the phylogeny. • Phylogenetic signal (discrete/continuous) was detected for compounds in Pilocarpus. • The impact of bioclimatic factors and shared phylogenetic history was compound specific. [ABSTRACT FROM AUTHOR]

Seven previously undescribed coumarin derivatives, panitins A‒G, an ethoxylated artifact, and 34 known analogues, were isolated from the roots of Murraya paniculata. Their structures were elucidated on the basis of comprehensive analysis of 1D and 2D NMR and HRMS spectroscopic data, and comparison with the data reported in literature. The absolute configurations of undescribed compounds were assigned via comparison of the specific rotation, Mosher's method, exciton chiral method, and comparison of calculated and experimental ECD data. Panitin D, trans -dehydroosthol, and exotimarin I showed potent inhibition against LPS-induced NO production in BV-2 microglial cells with IC 50 values of 19.6 ± 2.3, 12.4 ± 0.9, and 26.9 ± 0.8 μM, respectively. Seven previously undescribed coumarin derivatives, an ethoxylated artifact, and 34 known analogues were isolated from the roots of Murraya paniculata. Three compounds showed inhibition against LPS-induced NO production in BV-2 microglial cells. Image 1 • Seven previously undescribed coumarins were isolated from Murraya paniculata. • The absolute configurations were assigned via Mosher's method, ECD spectra, etc. • Three compounds showed potent inhibition on NO production. [ABSTRACT FROM AUTHOR]

Abstract Plant diseases are threat to global food security. The excessive use of agrochemicals is the leading cause of pesticides resistance and toxicity to beneficial life forms. The quest for innocuous and alternate antimicrobial agent is crucial in order to overcome the pathogen resistance and the birth of nanotech offers pledge to combat pathogenic organisms. In this study, a facile benign biogenic approach was adopted for the synthesis of biocompatible iron oxide nanoparticles (Fe 2 O 3− NPs) via Skimmia laureola leaf extract and the synthesized nanoparticles were evaluated for their antibacterial efficacy against bacterial wilt pathogen Ralstonia solanacearum in vitro and in planta. Physico-chemical characterization of the synthesized nanoparticles was performed through UV–Visible spectroscopy, Fourier Transform Infrared Spectroscopy, X-Ray Diffraction, Energy Dispersive X-ray Spectroscopy and Scanning Electron Microscopy. The results revealed polydisperse nanoparticles in the size range of 56 nm to 350 nm. The culture media containing 6 mg/mL of Fe 2 O 3− NPs dramatically inhibited the bacterial growth in vitro. Scanning electron microscopy revealed degenerative characteristics including degraded, shriveled and concentrated cell walls. Diseases severity was effectively reduced with 6% w/v of Fe 2 O 3− NPs treated root zone in planta. Plant shoots, root length and fresh biomass were enhanced with Fe 2 O 3− NPs treatments. The results indicated that the biosynthesized Fe 2 O 3− NPs have the potential to control agriculturally important phytopathogen Ralstonia solanacearum in vitro and in planta. Highlights • Iron oxide nanoparticles were synthesized by using Skimmia laureola leaf extract. • The synthesized Fe 2 O 3− NPs were cubic and polydisperse in the range of 56–350 nm. • The bacterial pathogen Ralstonia solanacearum was inhibited by 6 mg/mL of Fe 2 O 3− NPs. • The bacterial wilt severity was markedly reduced with 6% w/v of Fe 2 O 3− NPs in planta. [ABSTRACT FROM AUTHOR]

Graphical abstract Highlights • An optimized extraction and purification of Medicosma leratii is proposed. • Ultrasound assisted extraction gave the highest yields for skimmianine. • Two furoquinoline and two acridone alkaloids were isolated by HPCCC. • The crude extract and skimmianine were potent pro-apoptosis inducers HeLa cells. • Skimmianine augmented the pro-apoptotic properties of sorafenib. Abstract This study was aimed at improving the current knowledge about the new Caledonian plant species Medicosma leratii , by developing efficient methods of extraction and isolation of specialized metabolites. Ultrasound-assisted extraction (UAE) significantly gave higher yields of the furoquinoline alkaloid skimmianine (22.34 mg/100 g) than accelerated solvent extraction (ASE, 1.37–12.36 mg/100 g). High-performance countercurrent chromatographic (HPCCC) separation of the methanol leaf extract with n -hexane-ethyl acetate-methanol-water (6:5:6:5 v/v) afforded skimmianine (1 , 7.55 mg, HPLC-DAD purity 99.4%), normelicopidine (3 , 1.87 mg, 95.6%), normelicopicine (4 , 2.63 mg, 97.3%) and a new furoquinoline alkaloid named sarcodifurine C (2 , 1.20 mg, 95.8%). The effect of the crude extract and its main constituent, skimmianine, on apoptosis, autophagy, and necrosis induction in tumor cells has also been investigated. The crude extract and skimmianine were found to be effective apoptosis inducers in HeLa cervical cancer cell line, but not in colon cancer SW620 and HT-29 cells. Additionally, skimmianine effectively potentiated the pro-apoptotic properties of the antincancer agent sorafenib in cervical cancer cells. [ABSTRACT FROM AUTHOR]

Abstract Two new furoquinoline alkaloids, maculine B (1) and kokusaginine B (2) and one new dihydrooxazole alkaloid, veprisazole (3), along with four known compounds namely, N 13 -methyl-3-methoxyrutaecarpine (4), flindersiamine (5), skimmianine (6) and tilianin (7) were isolated from the methanol extract of the stem bark of Araliopsis soyauxii Engl. by various chromatographic methods. Their structures were determined using spectrometry and spectroscopic techniques including NMR and MS. The cytotoxicity of the new compounds compared to that of doxorubicin, the reference anticancer compound, was determined on a panel of nine cancer cell lines including sensitive and drug resistant phenotypes. The three previously undescribed alkaloids displayed selective activities. Maculine B (1), the most active one among the newly described compounds, exhibited IC 50 below 30 μM against CCRF-CEM leukemia and U87MG glioblastoma cells. Graphical abstract Unlabelled Image [ABSTRACT FROM AUTHOR]

Abstract Diaporhte species are plant pathogens rarely involved in human diseases, especially eye diseases. We report our findings in two undescribed Diaporhte species. Both were identified by their morphological characteristics and by DNA sequence analyses. In Case 1, an 81-year-old male farmer who had pterygium surgery 7 years earlier developed keratitis and the causal fungus was identified as a new species of Diaporthe , D. oculi. This species can be distinguished from the closely related D. limonicola on Citrus limon (Rutaceae) by the ITS, tef1 , and TUB (515/520 = 99.0% in ITS, 315/324 = 97.2% in tef1 , and 601/614 = 97.9% in TUB). The isolate from Case 2, a 68-year-old man with a rose thorn injury, was also identified as a new Diaporthe species, D. pseudooculi. Phylogenetically, D. pseudooculi is different from the closely related D. podocarpi-macrophylli by the ITS, tef1 , and TUB (525/531 = 98.9% in ITS, 314/333 = 94.3% in tef1 , and 436/442 = 98.6% in TUB). We report on the identification, drug sensitivity, and treatment outcomes for these two new species of Diaporthe , D. oculi and D. pseudooculi. [ABSTRACT FROM AUTHOR]

Graphical abstract Highlights • We recovered robust areas of endemism on different regions of the Brazilian Atlantic Forest, as well as in the Amazon. • Widespread species of Galipeinae explain overall distribution of the subtribe better than narrow ones. • We highlight new insights to the biogeography of Neotropical region. • Parsimony Analysis of Endemicity and Endemicity Analysis were both useful methods to identify the areas of endemism. Abstract The subtribe Galipeinae (Rutaceae) is a flowering plant group endemic to the Neotropical region, with its center of diversity in the Brazilian Atlantic Forest. Here, we aim to describe and analyze the distribution patterns of the group in Brazil, in search for possible areas of endemism. We then discuss our results to contribute to the debate on the Atlantic Forest history and endemism patterns. Our research relies on an updated database from herbarium collections and expert points, including taxonomic validation and georeferencing procedures. We performed both Parsimony and Endemicity analysis (PAE and NDM, respectively) and evaluated the contribution of narrowly distributed and widespread species to the overall pattern, testing if they are unevenly distributed at different latitudes of the Atlantic Forest. We recovered areas of endemism already found in other studies using other groups as study model. We identified five areas at different latitudes, according to PAE analysis: four in the Atlantic Forest, between Bahia and Rio de Janeiro states, and one in the Amazon. The latter area was not recovered by NDM analysis and we discuss that this is actually an artifact of PAE analysis due to collection bias. Although the widespread species have contributed more than the narrowly distributed ones for the overall pattern, the distribution of the group is more explained by species of medium-range distribution. We discuss our results considering current models based on historical events as Quaternary refugia forest and alternative hypothesis of vicariance. [ABSTRACT FROM AUTHOR]

Highlights • PTLC-DPPH method were used to locate active fraction. • Two new coumarin derivatives were isolated from M. minutum methanolic extract. • First report for sesamin and marmesin glycoside isolated from M. minutum. • Antioxidant capacities of the extract and selected compounds were investigated. • Extract, fractions and hydramicromelinin exhibited good antioxidant capacities. Abstract The application of preparative thin layer chromatography-2,2-diphenyl-1-picrylhydrazyl (PTLC-DPPH) bioautography technique successfully isolated a lignan sesamin (1), two prenylated coumarins (2 and 3) and a marmesin glycosides (4) from Micromelum minutum methanol bark extract. Compounds 2 and 3 were identified as new compounds whereas 1 and 4 were first isolated from Micromelum genus. Structural identification of all compounds were done by detailed spectroscopic analyses and comparison with literature data. Antioxidant capacities of extract, active fraction and compounds were measured based on DPPH free radical savenging activity, oxygen radical absorbance capacity (ORAC) and β-carotene bleaching. The DPPH activity of methanol extract and its fraction present the IC 50 values of 54.3 and 168.9 µg/mL meanwhile the β-carotene bleaching results were 55.19% and 5.75% respectively. The ORAC measurements of M. minutum extract, compounds 2 and 4 showed potent antioxidant activity with the values of 5123, 5539 and 4031 µmol TE/g respectively. [ABSTRACT FROM AUTHOR]

Abstract Ethnopharmacological relevance Citrus aurantium L. (Rutaceae) is used, either singly or as a part of a polyherbal preparation, in Nigerian traditional medicine for the management of cancer and inflammatory diseases. Currently, there is a dearth of knowledge demonstrating its anticancer potential. Aim of the study This study was carried out to determine the in vitro cytotoxicity of the crude extract of the stem bark of C. aurantium, identify and isolate the bioactive constituents and to establish the cytotoxicity of such constituents. Materials and methods The powdered bark of C. aurantium was extracted by MeOH at room temperature (25–34 °C) and the crude extract was partitioned successively, with n -hexane, dichloromethane and methanol. Amongst the fractions, the DCM fraction was the most active and compounds were isolated from this fraction using a combination of chromatographic techniques. The structures of the isolated compounds were elucidated by spectroscopic means (MS, 1D and 2D NMR). The cytotoxicity of the extract, and the isolated compounds were evaluated by the MTT assay against four human cancer cell lines: A549 (lung), HepG2 (liver), MCF7 (breast) and PC3 (prostate). The selectivity of the isolated compounds was assessed using the normal human prostate epithelium cells (PNT2). Results and discussion Of the three plant fractions, the DCM fraction showed significant cytotoxicity, with its highest activity against A549 cells (IC 50 = 3.88 µg/mL) and the least activity on HepG2 cells (IC 50 = 5.73 µg/mL). Six acridone alkaloids, citrusinine-I (1), citracridone-I (2), 5-hydroxynoracronycine (3), natsucitrine-I (4), glycofolinine (5) and citracridone-III (6), were isolated from the DCM fraction of C. aurantium. The isolated compounds demonstrated potent to moderate cytotoxicity (IC 50 = 12.65–50.74 µM) against the cancer cells under investigation. It is noteworthy that the compounds exerted cytotoxicity at least four times more selective towards the carcinoma cells than the PNT2 cells. Conclusion The results obtained from this study have provided some evidence for the ethnomedicinal use of C. aurantium against cancer and the acridone alkaloids present in its stem bark, have appeared to be responsible for the anticancer effects. Graphical abstract fx1 [ABSTRACT FROM AUTHOR]

Highlights • The expression of CsFUS 3 is positively related with the capacity of citrus callus for somatic embryogenesis (SE). • Overexpression of CsFUS 3 promotes SE and restores normal late embryogenesis in fus 3. • Overexpression of CsFUS 3 has effects on the expression of SE-related transcription factors and hormone pathways, especially the ABA and GA pathways. Abstract In citrus, genetic improvement via biotechnology is challenging due to insufficient understanding of molecular barriers that prevent regeneration by somatic embryogenesis (SE). Our previous study indicated that LEC genes were involved in SE in citrus, but their regulatory roles remain to be elucidated. Here, we cloned one of the LEC genes, CsFUS3 , and show that it is preferentially expressed during SE and in the embryogenic callus (EC) derived from citrus varieties with strong embryogenic competence. The overexpression of CsFUS3 in recalcitrant citrus callus restored embryogenic competence. Complementation of the loss-of-function Arabidopsis fus3 mutant with the CsFUS3 gene restored normal late embryogenesis, which is consistent with the CsFUS3 and AtFUS3 proteins contributing to the same regulatory network in Arabidopsis. Transcriptome profiling revealed that the expression of particular TFs that promote SE was up-regulated in the citrus overexpression (OE) line. The 104 differentially expressed genes associated with hormone biosynthesis, catabolism, and signaling are particularly noteworthy. The dynamic change in the ratio of ABA to GA during SE in wild-type callus mirrored the expression pattern of CsFUS3. In contrast, in the OE line, the ratio of ABA to GA was higher and the capacity for SE was greater when the OE line was separately treated with ABA and GA biosynthesis inhibitors. Taken together, our results demonstrate that the overexpression of CsFUS3 appears to establish a cellular environment favorable to SE, at least in part by promoting a high ABA to GA ratio and by regulating the expression of TFs that promote SE. [ABSTRACT FROM AUTHOR]

• Plumose hesperidin crystals occurred on the shoot apex and leaves of M. nigra. • Hesperidin crystals are excreted through the epidermis and remain on the cuticle. • Hesperidin crystals occurred in the epidermis, mesophyll and phloem cells. • Flavonoid autofluorescence was detected in cell walls and cytoplasm. • RER, tonoplast and vesicles are involved in material channeling toward the cell wall. Researches on the developmental and morphological features of organic crystals in plants are relatively scarce. Hesperidin is a flavanone glycoside found abundantly in Rutaceae, mainly in Citrus fruits. Due to the variety of biological activities, hesperidin is one of the most promising bioflavonoids. We investigated the distribution, micromorphology and intracellular localization of hesperidin crystals in the vegetative organs of Metrodorea nigra , a neotropical Rutaceae tree. Additionally, we analyzed the ultrastructural organization of crystal-bearing cells. Bright field, epifluorescence and polarized-light microscopy, scanning (SEM) and transmission electron microscopy (TEM) analysis were performed. Hesperidin crystals appeared as needle-shaped crystals forming plumose clusters under SEM, and as acicular solitary crystal or aggregate yellow/brown twisted filaments inside cells under light microscope. Hesperidin and calcium oxalate crystals often occurred together in the epidermis and mesophyll tissues. Hesperidin crystals were abundant inside the phloem, while calcium oxalate crystals were absent in the vascular tissues. Phenolic substances occurred in all tissues, but they were abundant within vascular tissues. Flavonoid autofluorescence in blue color was associated with crystals in the cell walls and cytoplasm. The crystal-bearing cells exhibited extensive rough endoplasmic reticulum (RER) and associated vesicles filled with electron-dense materials, proliferation of the tonoplast and abundance of multilamellar bodies containing electron-dense or crystalline materials close to irregular plasmalemma. Our ultrastructural observations allow us to speculate that the RER and tonoplast membranes and associated vesicles appeared to be involved in the packaging and channeling of the materials toward the cell walls. Crystals of hesperidin and calcium oxalate occurred on the surface of common epidermal cells and glandular trichomes. The mechanisms of condensation, crystallization and extrusion of hesperidin crystal through the cell walls remain to be investigate, and could be an interesting subject for future studies. [ABSTRACT FROM AUTHOR]

Fraxinifolines A-F (1 – 6), six new B- seco limonoids, together with four known A,D-di- seco ones, were isolated from the twigs with leaves of Tetradium fraxinifolium. Their structures with absolute configurations were elucidated on the basis of analysis of MS, NMR, single-crystal X-ray diffraction and biogenetic pathway. An anti-inflammatory bioassay in vitro showed limonoids 1 – 3 had significant immunosuppressive effect against the production of pro-inflammatory cytokines (IL-1 β and/or TNF-α) in lipopolysaccharide (LPS)-stimulated RAW264.7 cells. [Display omitted] • Ten limonoids were isolated from the twigs with leaves of Tetradium fraxinifolium. • Fraxinifolines A-F are the first examples of B- seco limonoids from Rutaceae plant. • Fraxinifolines A-D are unusal 7,8- seco -7,8-epoxide type limonoids. • Fraxinifolines A, B and C had significant immunosuppressive effect. [ABSTRACT FROM AUTHOR]

Two previously undescribed phloroglucinol derivatives [(±) evolephloroglucinols A and B], five unusual coumarins [evolecoumarins A and B and (±) evolecoumarins C–E], and one novel enantiomeric quinoline-type alkaloid [(±) evolealkaloid A], along with 20 known compounds, were isolated from the EtOH extract of the roots of Evodia lepta Merr. Their structures were elucidated by extensive spectroscopic analyses. The absolute configurations of the undescribed compounds were determined by X-ray diffraction or computational calculations. Their anti-neuroinflammatory effects were assayed. Among the identified compounds, compound 5a effectively reduced nitric oxide (NO) production with an EC 50 value of 22.08 ± 0.46 μM. Hence, it could indeed inhibit the lipopolysaccharide (LPS)-induced Nod-like receptor family, pyrin domain containing 3 (NLRP3) inflammasome. Eight previously undescribed compounds, including two phloroglucinol enantiomers, (±) evolephloroglucinols A and B, five coumarins, evolecoumarins A and B, (±) evolecoumarins C–E, and a quinoline-type alkaloid enantiomers, along with twenty known compounds were isolated from the roots of Evodia lepta Merr. Further study indicated that evolecoumarin C alleviated LPS-induced neuroinflammation via inhibiting the NLRP3 pathway. [Display omitted] • Eight previously undescribed compounds were isolated from the roots of Evodia lepta Merr. • Evolecoumarin C could induce a decrease of nitric oxide in LPS-treated BV-2 cells. • Evolecoumarin C could alleviate LPS-induced NLRP3-related neuroinflammation. [ABSTRACT FROM AUTHOR]

Abstract The investigation of the crude extract of leaves and bark of Pilocarpus pennatifolius Lemaire allowed isolated of a not yet described coumarin, together with three known coumarins (bergapten, xanthotoxin and dimethyl allyl xanthyletin), and a not yet described imidazole alkaloid. All structures were established by means of spectral analysis, including extensive 2D NMR studies. In addition, the alkaloid had its absolute stereochemistry determined by X-ray diffraction. Meanwhile, extracts and pure compounds were tested against various strains of bacteria and fungi, showing promising antimicrobial activities. We highlight the activities of crude bark methanol extract (CBME), of the leaf basic acetate fraction (LBAcF), and of compound 2 against the Gram negative bacteria Shigella flexneri (MICs = 7.8, 7.8 and 3.12 μg·mL−1, respectively), of compound 5 against the Gram positive Enterococcus fecalis (MIC = 1.56 μg·mL−1), and against two Gram negative bacteria Salmonella enteritidis (MIC = 1.56 μg·mL−1), and Pseudomonas aeruginosa (MIC = 6.25 μg·ml−1). On the other hand, CBME and compounds 3 – 5 showed excellent activity against the fungus Candida krusei with MICs of 15.6, 1.56, and 3.12 μg·mL−1 respectively, as actives or better than the antifungal standard fluconazole (MIC = 3.12 μg·mL−1). Graphical abstract Unlabelled Image Highlights • Coumarins from Pilocarpus pennatifolius • Absolute stereochemistry of pennatifoline A • Antimicrobial study of Pilocarpus pennatifolius [ABSTRACT FROM AUTHOR]

Citrous lemon (Rutaceae) an Indian folk medicine has been used for the treatment of various pathological diseases viz., diabetes, cardiovascular, inflammation, hepatobiliary dysfunction and neurodegenerative disorder. Can lemon oil altered the memory of unstressed and stressed mice, a basic question for which the present work was put on trial. The present investigation was intended to assess the impact of Lemon oil on memory of unstressed and Stressed Swiss young Albino mice. Lemon oil (50 and 100 mg/kg o.r.) and donepezil (10 mg/kg) were guided for three weeks to different groups of stressed and unstressed mice. The nootropic movement was assessed utilizing elevated plus maze and Hebbs Williams Maze. Cerebrum acetylcholinesterase (AChE), plasmacorticosterone, decreased glutathione, lipid per oxidation alongside superoxide dismutase and catalase was surveyed as marker for disease. Histopathology was performed for estimation of drug effects. Acute immobilized stress was induce, lemon oil (100 mg/kg) and donepezil together indicated memory enhancing movement both in stressed and unstressed mice. Lemon oil significantly (p < 0.001) altered and lowered brain AChE activity both in stressed and unstressed mice. Scopolamine induced amnesia was also significantly altered and reversed both in stressed and unstressed mice by lemon oil at a dose of 50 and 100 mg/kg. Lemon oil (50 and 100 mg/kg) was further able to control the corticosterone level in plasma for stressed mice. Lemon oil significantly (p < 0.001) elevated the level of catalase, superoxide dismutase and reduced glutathione levels both in stressed and unstressed animals with respect to controlled group along with TBARS both in stressed and unstressed compared with control group. Hence it can be concluded that memory enhancing activity might be related to reduction in AChE and TBARS activity and by elevated GSH, SOD and catalase through decrease in raised plasma corticosterone levels [ABSTRACT FROM AUTHOR]

Abstract Methanolic crude extracts obtained from leaves, stem bark and root bark of 57 accessions of Clausena excavata , C. harmandiana , of both varieties of C. wallichii, as well as of three unidentified Clausena samples, were analysed for the presence of coumarins and carbazoles. All accessions were collected from different locations all over Thailand. HPLC coupled with UV-DAD was applied for phytochemical profiling. Structures of known pyrano-coumarins 1 – 4 and of coumarins 5 – 8 bearing an O -geranyl moiety, as well as of carbazoles 9 – 12 were confirmed by NMR and MS spectroscopy, respectively. Observed chemical diversification in the studied samples is discussed in relation to geographic distribution and with respect to organ-specific accumulation. Chemotaxonomic significance is briefly addressed. Graphical abstract Image 1 Highlights • 57 Accessions of three Clausena species were studied phytochemically. • Eight coumarins and four carbazoles were isolated. • Organ specific accumulation of compounds 1 – 12 was studied in all accessions. • Chemical diversity in relation to geographic distribution patterns is discussed. [ABSTRACT FROM AUTHOR]

The genus Flindersia (Rutaceae) comprises 17 species of mostly Australian endemic trees. Although most species are restricted to rainforests, four have evolved to grow in semi-arid and arid environments. In this study, the leaf alkaloid diversity of rainforest and semi-arid/arid zone adapted Australian Flindersia were compared by LC/MS-MS and NMR spectroscopy. Contrary to expectations, Flindersia alkaloid diversity was strongly correlated with environmental aridity, where species predominating in drier regions produced more alkaloids than their wet rainforest congenerics. Rainforest species were also more chemically similar to each other than were the four semi-arid/arid zone species. There was a significant relationship between the presence of alkaloid structural classes and phylogenetic distance, suggesting that alkaloid profiles are influenced by both genetic and environmental factors. The results suggest that the radiation of Flindersia species out of the rainforest and into drier environments has promoted the evolution of unique alkaloid diversity. Plants growing in arid and semi-arid regions of Australia may represent an untapped source of undescribed specialised metabolites. [ABSTRACT FROM AUTHOR]

Three new alkamides, zanthoamides G-I ( 1-3 ), together with ten known compounds, araliopsine, skimmianine, N -methylplatydesminium cation, isoplatydesmine, myrtopsine, atanine, N -methylatanine, sesamin, hesperetin and hesperidin, were isolated from the fruits of Zanthoxylum zanthoxyloides . Their structures were elucidated by spectroscopic means. All isolated compounds were assessed for their cytotoxicity against A549, MCF7, PC3 and PNT2 cell lines. Among the alkamides, only zanthoamide G ( 1 ) showed low level of cytotoxicity against MCF7 cells. [ABSTRACT FROM AUTHOR]

Nine undescribed carbazole and quinoline alkaloids, named dunnines A–E, and 14 known analogues were isolated from the leaves and stems of Clausena dunniana. Their structures were elucidated on the basis of comprehensive analysis of NMR and HRMS spectroscopic data, and the absolute configurations were assigned via comparison of their specific rotations and calculated and experimental ECD data. (±)-Dunnines A–C and (±)-clausenawalline A are four pairs of biscarbazole atropisomers and (±)-dunnine D is a pair of dihydropyranocarbazole enantiomers. They were separated by chiral HPLC to obtain the optically pure compounds. Three compounds showed weak inhibitory effects on nitric oxide production stimulated by lipopolysaccharide in BV-2 microglial cells (IC 50  > 50 μM); five compounds could significantly promote insulin secretion in HIT-T15 cell line (1.9–3.1-fold of the control, p  < 0.01) at 40 μM, and nine compounds could inhibit the apoptosis of PC12 cell induced by 6-hydroxydopamine with IC 50 values in the range of 10.9–47.2 μM. [ABSTRACT FROM AUTHOR]

Fraxinellone, a degraded limonoid, has been mainly isolated from some renewable plants in Meliaceae and Rutaceae. In a continuous effort to discover new natural products-based pesticides, two series of fraxinellone derivatives containing N -phenylpyrazole moiety were designed, synthesized and evaluated for their pesticidal activities against Mythimna separata Walker and Plutella xylostella Linnaeus. Two structures of compounds 7g and 8k were unambiguously determined by X-ray diffraction further. The bioassay showed that over half of the target compounds exhibited better insecticidal activity against M. separata than the precursor fraxinellone. Among all the target compounds, the compounds 7g – i and 8g – j exhibited more potent insecticidal activity than toosendanin, a commercial botanical pesticide. Furthermore, the compound 8g displayed more promising larvicidal activity with the LC 50 value of 0.31 μmol mL −1 than the toosendanin against P. xylostella . The structure–activity relationship (SAR) revealed that introduction of polyhalogenated phenylpyrazole ring on furyl-ring of fraxinellone could lead more potent compounds both against M. separata and P. xylostella than that of monohalogenated phenylpyrazole ring or electron-donating groups substituted phenylpyrazole ring. [ABSTRACT FROM AUTHOR]

In this research, we investigated the profile and bioactivities of quinazoline alkaloids, a class of natural products boasting multiple bioactivities, from the unripe fruit of Evodia rutaecarpa (Juss.) Benth. Three new quinazoline alkaloids, evodiamide A ( 1 ), evodiamide B (2), and evodiamide C ( 3 ), as well as eight known quinazolines, were isolated from the MeOH extract of E. rutaecarpa . The new compounds are rare quinazolinedione derivatives with linked heterocyclic nuclei. Among these quinazolines, rhetsinine ( 8 ) showed potential as a pesticide and exhibited excellent inhibition against Xanthomonas oryzae pv. oryzae, Xanthomonas oryzae pv. oryzicola, and Xanthomonas campestris pv. campestris , with respective EC 50 values of 3.13, 14.32, and 32.72 nmol. [ABSTRACT FROM AUTHOR]

To explore antitumor agents with high efficiency and selectivity, two series of 16 H 2 S donating evodiamine derivatives 8–12 were synthesized and characterized by 1 H NMR, 13 C NMR and HRMS. Their antiproliferative activities were tested against five cancer cell lines (Bel-7402, MCF-7, SGC-7901, Caco-2 and HL-60) and human normal peripheral blood mononuclear cells. Among them, compound 12c showed the most potent inhibitory activities against human leukemia HL-60 and epithelial colorectal adenocarcinoma Caco-2 cells with IC 50 values of 0.58 and 2.02 μM, respectively. Additionally, high selectivity was also observed between human normal peripheral blood mononuclear cells and human leukemia HL-60 cells. Further mechanism studies confirmed that 12c could induce apoptosis, arrest cell cycle at the G 2 /M phase and lead to mitochondrial dysfunction in HL-60 cells. Furthermore, western blot assay demonstrated that 12c induced the intrinsic apoptotic mitochondrial pathway by upregulating protein expression of Bax, cytochrome c , caspase-3, -9 and p53, and downregulating the relative levels of Bcl-2. The levels of cell cycle related proteins cyclin B1 and cdc2 were also downregulated in which G 2 /M phase arrest was confirmed. Overall, 12c possessed immense potential for the discovery of antitumor candidates with high efficiency and selectivity. [ABSTRACT FROM AUTHOR]

From the stems of Paramignya trimera (Rutaceae), two new prenylated phenolic compounds, paratrimerins G ( 1 ) and H ( 2 ), together with 24 known compounds, as well as their α-glucosidase inhibitory activity was examined. Paratrimerins G ( 1 ) and H ( 2 ) showed moderate inhibitory effect, with the IC 50 values of 89.2 and 58.8 μM, respectively. The plausible biosynthetic pathways of two new compounds was proposed. [ABSTRACT FROM AUTHOR]

To assess the preservative effects of the active ingredients in the leaves of Liquidambar formosana Hance, the present study assessed the antioxidant activity of ellagic acid using various antioxidant assays; 2,2′-azino-bis-3-ethylbenzthiazoline-6-sulfonic acid, 1,1-diphenyl-2-picrylhydrazyl, superoxide anion radical scavenging activity and reducing power. The results of these assays were combined with principal component analysis to analyze the effect of ellagic acid treatment on the overall quality of kumquat. Whole kumquat fruit were immersed in different concentrations of ellagic acid (0, 100 and 300 mg L −1 ) for 5 min, naturally dried then stored at room temperature (14–16 °C) for 18 days. During storage, the percentage weight loss and decay, firmness, total soluble solids, titratable acid and contents of malondialdehyde, superoxide dismutase and vitamin C were measured every 3 days. The results showed that, by 1,1-diphenyl-2-picrylhydrazyl scavenging activity and reducing power, the antioxidant activity of ellagic acid was more effective than butylated hydroxyanisole or ascorbic acid. Compared with untreated kumquat fruit, ellagic acid treatments can delay the decline in fruit firmness, total soluble solids, titratable acid and vitamin C contents, inhibit increases in malondialdehyde and enhance superoxide dismutase activity. The comprehensive evaluation of the results using principal component analysis was consistent with the experimental results, namely that ellagic acid treatment can significantly reduce the rate of deterioration in the quality of kumquat fruit, with the 300 mg L −1 treatment being better than the 100 mg L −1 treatment. The results show that ellagic acid has good prospects as a preservative treatment for kumquat fruit. [ABSTRACT FROM AUTHOR]

The aim of this study is to determine the phytochemical profile, the total polyphenolic contents and the antioxidant activities of Haplophyllum tuberculatum leaves extracts. The most active extracts were analyzed by ultra-high performance liquid chromatography coupled to electrospray ionization mass spectrometry. Antioxidant activities were screened by the 3-[4,5-dimethylthiazol-2-yl]-2,5 diphenyl tetrazolium bromide (MTT) test and measured by the 2,2-diphenyl-1-picrylhydrazyl (DPPH), 2,2-azinobis 3-ethylbenzothiazoline-6-sulfonic acid (ABTS) and β-carotene bleaching inhibition assays. Phytochemical screening of the extracts revealed the presence of various secondary metabolites. The ethyl acetate extract was the richest extract in phenolics and flavonoids with 262 mg gallic acid equivalents/g and 99.1 mg quercetin equivalent/g of dry weight, respectively. The same extract showed an important scavenging effect on DPPH, ABTS and β-carotene/linoleic acid with IC 50 of 0.020 mg/mL, 0.029 mg/mL and 0.022 mg/mL, respectively. The correlations between the antioxidant capacities and the polyphenolic content were ranging between 0.889 and 0.256 and occasionally found to be significant. The UPLC–ESI–MS analysis showed the presence of polyphenolic and alkaloid compounds. Arabelline, majidine, dictamine and a qudsine derivative are found for the first time in H. tuberculatum . The results indicate that polyphenolic and alkaloid compounds may be major contributors to the antioxidant activity of these extracts. [ABSTRACT FROM AUTHOR]

A biotechnological process that combines the treatment of Citrus processing waste to extract a high-valuable biomolecule, neohesperidin (NEO), and its further modification by biocatalysis to enhance the lipophilicity of its flavonoic moiety is presented. NEO was extracted from immature fruits of Citrus aurantium and hydrolyzed by a commercial alpha-rhamnosidase to obtain hesperetin 7-glucoside (HG). NEO and HG were mono-acylated with vinyl laurate by using Novozym 435 in their primary OH-groups, but the esterification reaction was substantially faster for HG than NEO. Furthermore, the activation energy of the reaction lowers as solvents’ log-P decreases linearly. Under best conditions, HGL was obtained at gram scale with a simple downstream process. The solubility in n-octanol increased with each biocatalytic step (NEO

Research of detailed chemical constituents from the pericarps of Zanthoxylum bungeanum Maxim resulted in the isolation of twenty-two compounds (1–22), including eight alkaloids (1–8), three alkylamines (9 – 11), five monoterpenoids (12–16), one benzophenone (17), two coumarins (18 and 19) and three lignanoids (20–22). Among them, compounds 2 and 8 were firstly found in the genus Zanthoxylum, while compounds 13 – 15 and 20 were firstly reported in the Rutaceae family. This work enriches the secondary metabolites of Z. bungeanum and provides valuable information for chemotaxonomic studies on the genus Zanthoxylum. [Display omitted] • A phytochemical investigation of the pericarps from Zanthoxylum bungeanum has been carried out. • Two Compounds (2 and 8) were first found in the genus Zanthoxylum. • Four Compounds (13 – 15 and 20) were first reported in the Rutaceae family. • Compound 4 and 20 exhibited antibacteritic activity against Staphylococcus aureus. • The study revealed the chemotaxonomic significance in Zanthoxylum bungeanum. [ABSTRACT FROM AUTHOR]

Chemical investigation on the fruits of Zanthoxylum motuoense have led to the isolation of a new flavonolignan (1), together with three known flavonoids (2 - 4), as well as five alkylamides (5 – 9). Their structures were determined by NMR, IR, UV, CD spectra and HRESIMS data. The chemotaxonomic significance of these compounds was discussed. The neuroprotective activity of the isolated compounds were evaluated. Compound 6 showed a significant protective effect against corticosterone-induced neuronal damage at 20 μmol/L. [Display omitted] • Nine compounds were isolated from the fruits of Zanthoxylum Motuoense. • Compounds 1 was identified as a new flavonolignan. • All the compounds were isolated from Z. motuoense for the first time. • Alkylamides could be recognized as a typical biomarker for Zanthoxylum genus and Rutaceae family. [ABSTRACT FROM AUTHOR]

Rutaceae is a family expressed by approximately 2100 species distributed in 154 genera widespread in tropical and temperate regions of Australasia, America, and South Africa. Substantial species of this family are employed as folk medicines. The literature describes the Rutaceae family as a great source of natural and bioactive compounds like terpenoids, flavonoids, and, especially, coumarins. To data, 655 coumarins were isolated and identified from Rutaceae in the past twelve years and, most of them, showed different biological and pharmacological activities. There are studies with coumarins from Rutaceae indicating that these compounds showed activity against cancer, inflammation, infectious diseases, and in the treatment of endocrinal and gastrointestinal conditions. Although coumarins are considered versatile bioactive molecules, until the present, there is no compiled information about coumarins from the Rutaceae family demonstrating the potency of these compounds in all dimensions and chemical similarities among the genera. The present review covers the relevant studies dealing with isolation of Rutaceae coumarins from 2010 until 2022 and outlines the current data on pharmacological activities these coumpounds. Additionally, the chemical disposition and similarity among Rutaceae genera are also statistically discussed employing PCA and HCA methods. [Display omitted] [ABSTRACT FROM AUTHOR]

Zanthoxylum armatum DC. is an important medicinal plant, and its pericarps are commonly used as a natural spice in Asian countries. In this study, fifteen alkylamides were isolated and elucidated from the pericarps of Z. armatum , including five undescribed alkylamides (1–5) and ten known compounds (6–15). The molecular structures of all compounds were elucidated by 1D and 2D NMR spectroscopic analysis and mass spectrometry, among which the absolute configuration of compound 15 was determined by the Mo 2 (OAc) 4 -induced circular dichroism method. Moreover, all compounds were screened for their neuroprotective activity against H 2 O 2 -induced oxidative stress in human neuroblastoma SH-SY5Y cells for the evaluation of their neuroprotective activity. Especially, compounds 2 – 4 expressed potential neuroprotective activity, and further research showed that the cell viability was significantly enhanced in a concentration dependent manner when the cells were treated for 6 h. Moreover, compounds 2 – 4 could decrease reactive oxygen species accumulation. This paper enriched structure types of alkylamides in Zanthoxylum armatum. [Display omitted] • Five undescribed alkylamides and ten known compounds were reported. • The absolute configuration of compound with vicinal diol was determined by the ICD. • Compounds 2–4 expressed potential neuroprotective activity. [ABSTRACT FROM AUTHOR]

• Ensemble modeling predicted suitable habitats for citrus medica in northeast India, northern Myanmar, eastern Bangladesh, bordering areas of southern Bhutan and northeast India, Nepal, southern Yunnan region in China, Laos, Vietnam, and Taiwan. • Precipitation of warmest quarter, elevation, mean temperature of wettest quarter, and temperature seasonality were the most importnat environmental variables. • The predicted suitable habitat would expand by 8%, 20%, 12%, and 1% in 2050 and 11%, 20%,19%, and 14% in 2070, under the RCP2.6, RCP4.5, RCP6.0, and RCP8.5, respectively. • Northeast India and northern Myanmar remain moderately or highly suitable for citron under future climate change scenarios. Citron (Citrus medica) is one of the major citrus fruits of commerce. It is cultivated mostly in the warm temperate Mediterranean coastal region, and in the tropical and subtropical regions of South and Southeast Asia. It also grows naturally in northeast India, Myanmar, and Yunnan (China). Citron populations are declining in their natural habitats due to forest degradation and change in land use patterns. To predict the habitat suitability for citron, we evaluated four widely used species distribution models (SDMs), namely Generalized Linear Models (GLM), Support Vector Machine (SVM), Random Forest (RF), and Maximum Entropy (MaxEnt) in 'sdm' package. Based on Area under ROC Curve (AUC; >0.97) and True Skill Statistics (TSS; >0.9) of all four models, an ensemble modeling was carried out using 111 geo-referenced datasets and 19 bioclimatic and three topographic variables under three climate change scenarios (current, 2050 and 2070). Precipitation of warmest quarter (bio18, 69.6%), elevation (11.1%), mean temperature of wettest quarter (bio8, 10.6%), and temperature seasonality (bio4, 10.1%) were the most important environmental variables for determining the distribution of citron in the study area. Potentially suitable habitat for citron was predicted to occur from 12 – 29 °N to 79 – 108 °E. The total suitable habitat covers about 875,868 km2, including 195,846 km2, 274,386 km2, and 405,636 km2, representing high, moderate, and least suitable areas, respectively. Increase in habitat suitability was predicted for 2050 and 2070 under four representative concentration pathways (RCPs), i. e., RCP2.6, RCP4.5, RCP6.0, and RCP8.5. This study predicted that northeast India and northern Myanmar would remain moderately or highly suitable for citron. [ABSTRACT FROM AUTHOR]