Records of Natural Products Articles
Articles In Press
Records of Natural Products
Articles In Press
1) Secondary Metabolites with Tyrosinase and Acetylcholinesterase Inhibitory Activities from Leonuri Fructus
Fourteen secondary metabolites, including one cinnamate derivative (1), three spirocyclic nortriterpenoids (2–4), three phenylethanoid glycosides (5–7), four lignans (8–11) and three phenolic compounds (12–14) were isolated from the EtOH extract of Leonuri Fructus. Their structures were elucidated on the basis of 1D NMR, 2D NMR and HR-ESI-MS data analysis. All isolates were tested for their antioxidant, tyrosinase and acetylcholinesterase inhibitory activities. Most of them showed moderate antioxidant activities. Compounds 2–4 exhibited obvious inhibitory activities against mushroom tyrosinase at 25 μM, with %inhibition values of 49.36 ±2.69%, 43.43 ± 3.35%, 51.69 ± 2.81%, respectively, with arbutin used as the positive control (51.90 ± 2.57%). Compounds 3, 5–6 and 9–10 exhibited significant inhibitory activities against acetylcholinesterase, similar to the positive control, galantamineDOI http://doi.org/10.25135/rnp.297.2110.2223 Keywords Leonuri Fructus Leonurus japonicus nortriterpenoid phenylethanoid glycoside tyrosinase acetylcholinesterase Available online: November 25, 2021 DETAILS DOWNLOAD PDF © ACG Publications. All rights reserved.
2) Cytotoxic Drimane-type Sesquiterpenoids from the Fungus Aspergillus flavipes 297
Chemical investigation of the marine-derived fungus Aspergillus flavipes 297 led to the isolation and identification of three drimane-type sesquiterpenoids, asperflavinoid A (1) and (6-strobilactone-B) esters of (E,E)-6,7-dihydroxy-2,4-octadienoic acids (2 and 3). Asperflavinoid A (1) was characterized as unseparated diastereomers and its chemical structure was determined by spectroscopic analysis of NMR and MS data. In the cytotoxic assay, compound 1 showed promising inhibitory effects on HepG2 and MKN-45 cell lines.DOI http://doi.org/10.25135/rnp.294.2109.2194 Keywords Aspergillus flavipes natural products drimane sesquiterpenoids cytotoxicity Available online: November 15, 2021 DETAILS DOWNLOAD PDF © ACG Publications. All rights reserved.
3) A New Iridoid Glucoside from the Stems of Myoporum bontioides (Sieb.et Zucc.) A. Gray
A phytochemical investigation of the stems of Myoporum bontioides (Sieb. et Zucc.) A. Gray, a semi-mangrove plant distributed along coastlines of north-eastern Vietnam and some Asian countries led to the isolation of a new iridoid glucoside (1), named myobontioside E, together with fourteen known compounds (2-15). Their structures were elucidated by means of HR ESI-MS, 1D and 2D NMR spectroscopy as well as comparison with the data reported in the literature. The cytotoxic effects on 8505C, MKN7, HT29, and T24 cell lines were assessed using SRB assay. Only iridoid 2 exhibited weak cytotoxicity against all tested cell lines with IC50 values ranging from 60.19 to 69.14 µM.DOI http://doi.org/10.25135/rnp.296.2108.2191 Keywords Myoporum bontioides Myoporaceae iridoid glucoside dammarane saponin cytotoxicity Available online: November 15, 2021 DETAILS DOWNLOAD PDF © ACG Publications. All rights reserved.
4) Sesquiterpenoids and Diterpenoids from the Flowers of Nicotiana tabacum L. and Their Antifungal Activity
Two new guaiane-type sesquiterpenoids, nicotiasesquiterpenes A (1) and B (2), and seven known cembrane-type diterpenoids (3−9), were isolated from glandular trichome secretions of fresh flowers of Nicotiana tabacum L. These new chemical structures were established by extensive analyses of HRESIMS and 1D and 2D NMR data, while the other structures were elucidated by comparison of 1D NMR data with those reported in the literature. All of the isolated compounds were tested for their antiphytopathogenic fungal activity against Valsa mali var. mali, Alternaria porri, and Botrytis cinerea at a concentration of 10 µg/mL. Compounds 3, 4, and 5 exhibited medium antifungal effects against Valsa mali var. mali, with inhibitory rates of 45.3±16.1, 53.4± 4.6, and 40.1±4.5%, respectively, while the other compounds showed only insignificant activities.DOI http://doi.org/10.25135/rnp.293.2109.2211 Keywords Nicotiana tabacum Valsa mali var. mali Alternaria porri Botrytis cinerea antifungal activity Available online: November 15, 2021 DETAILS DOWNLOAD PDF © ACG Publications. All rights reserved.
5) A New Short Chain Acetamide from the Biosphere and Bioactive Glycerolipids Extracted from the Marine Bibalve Codakia orbicularis (Lucinidae).
The marine bivalve Codakia orbicularis, harbors endosymbiotic bacteria located in its gill filaments. Bioassay-guided fractionation of an ethyl acetate extract of the gill tissues led to antibacterial fractions (against Gram positive and negative bacteria). The fraction eluted in AcOEt/ MeOH 90:10 displayed the greatest bioactivity. This fraction was analyzed using usual chromatographic and spectrometric methods and revealed three compounds. The first one (compound 1) was an acetamide isolated for the first time from the biosphere. The other two were mono-glycerolipids (compound 2) and (compound 3) with at the position sn-2 of their glycerol monounsaturated fatty acid chains (respectively C18:1Δ9 and C16:1Δ9). Compounds 2 and 3 showed bacteriostatic activity against two pathogenic Gram-negative bacteria using a disc diffusion assay method. These molecules have been isolated for the first time from a bivalve. Further investigations are currently in progress, so as to understand the role of these bioactive compounds into the regulation of C. orbicularis’ endosymbionts and/or to free-living pathogens.DOI http://doi.org/10.25135/rnp.295.2108.2194 Keywords Antibacterial activity monoacylglycol ceramide Available online: November 15, 2021 DETAILS DOWNLOAD PDF © ACG Publications. All rights reserved.
6) A New Isoflavan Glucoside from the Roots of Astragalus membranaceus var. mongholicus
A new isoflavan glucoside, namely astramemside A (1), together with six known compounds (2-7) were obtained from the roots of a traditional Chinese medicine, Astragalus membranaceus var. mongholicus. Their structures were elucidated by spectroscopic analyses (HRESIMS, UV, IR, 1D and 2D NMR), and the absolute configuration of 1 was determined by combination of chemical transformation and single-crystal X-ray diffraction. Compound 1 showed moderate inhibition on nitric oxide (NO) production induced by lipopolysaccharide in RAW264.7 cells with an IC50 value of 38.98 ± 5.28 uM.DOI http://doi.org/10.25135/rnp.292.2109.2203 Keywords Astragalus membranaceus var. mongholicus Leguminosae isoflavan glucoside Available online: November 08, 2021 DETAILS DOWNLOAD PDF © ACG Publications. All rights reserved.
7) Two New Bibenzyls from Dendrobium hercoglossum
Two new bibenzyl compounds 3-hydroxy-4, 5, 3′-trimethoxybibenzyl (1) and (R)-4-hydroxy-3, 5, 3′, α-tetramethoxybibenzyl (2), along with twelve known compounds (3−14), were isolated from the stems of Dendrobium hercoglossum Reichb. f. The structures of the new compounds were elucidated on the basis of detailed spectroscopic analysis. The cytotoxic effects of the isolated compounds on two human tumors cell lines (MDA-MB-231 and Hela) were evaluated by the MTT assay.DOI http://doi.org/10.25135/rnp.291.2109.2198 Keywords Orchidaceae Dendrobium hercoglossum bibenzyl cytotoxicity Available online: November 02, 2021 DETAILS DOWNLOAD PDF © ACG Publications. All rights reserved.
8) Insecticidal and Repellent Activities of Volatile Constituents from Litsea dilleniifolia P. Y. Pai et P. H. Huang Against Stored-Product Insects
The volatile oil from leaves of Litsea dilleniifolia P. Y. Pai et P. H. Huang was obtained by hydrodistillation. The qualitative and quantitative analysis of volatile constituents were performed by GC/MS and GC/FID. The volatile oil along with two major components was evaluated for their fumigant, contact toxicity and repellency against stored-product insects, namely Tribolium castaneum and Liposcelis bostrychophila. The volatile oil mainly contained decanal (48.4%), eremanthin (10.4%), zerumbone (10.1%) and estragole (9.2%). In bioassays, L. dilleniifolia volatile oil showed toxicity and repellent activities against T. castaneum and L. bostrychophila. The volatile oil, decanal and estragole at 78.63 nL/cm2 could cause 82-92% repellency against T. castaneum at 4h post-exposure. Among them, decanal (LC50 = 3.90 mg/L air) and estragole (LC50 = 5.33 mg/L air) had significant fumigant toxicity against T. castaneum, and estragole was strongly toxic to L. bostrychophila (LC50 = 0.61 mg/L air). The two components displayed a similar level of toxicity against T. castaneum in contact assays (LD50 = 21.91 and 20.41 µg/adult, respectively). This work indicates that L. dilleniifolia is promising to be developed as botanical insecticides and repellents to control pest damage in warehouses and storage rooms.DOI http://doi.org/10.25135/rnp.290.2108.2157 Keywords Botanical insecticides Liposcelis bostrychophila repellency Tribolium castaneum the volatile oil toxicity Available online: November 02, 2021 DETAILS DOWNLOAD PDF © ACG Publications. All rights reserved.
9) Monoester-Type C19-Diterpenoid Alkaloids from Aconitum carmichaelii and Their Cardiotoxicity
A new (1) and six known (2-7) monoester-type C19-diterpenoid alkaloids were isolated from the lateral roots of Aconitum carmichaelii Debx. Their structures were determined by spectroscopic techniques and calculations of NMR chemical shifts. Compound 1 (1-epi-hokbusine A) was an aconitine-type diterpenoid alkaloid possessing an unusual 1β-methoxy group. According to the main toxicity of the lateral roots of A. carmichaelii, the cardiotoxic effects of the isolates were evaluated using H9c2 rat myocardial cells and zebrafish embryos. The results showed that all the monoester-type C19-diterpenoid alkaloids exhibited cardiotoxicity, and compound 6 was found to be the most toxic compound.DOI http://doi.org/10.25135/rnp.287.2107.2127 Keywords Aconitum carmichaelii monoester-type C19-diterpenoid alkaloids H9c2 cells zebrafish embryos cardiotoxicity Available online: October 25, 2021 DETAILS DOWNLOAD PDF © ACG Publications. All rights reserved.
10) Two New Seco-Abietanoids with Xanthine Oxidase Inhibitory Activity from Cryptomeria japonica D. Don
Two new seco-abietanoids, 12-hydroxy-6-nor-5,6-secoabieta-8,11,13-trien-7-oic acid (1) and 7-hydroxy-7,8-secoabieta-8,12-diene-6,11,14-trione (3), together with one known seco-abietanoid, 12-hydroxy-6-nor-5-oxo-5,6-secoabieta-8,11,13-trien-7-al (2), were isolated from the methanol extract of the bark of Cryptomeria japonica. Their structures were elucidated by mean of spectroscopic analysis, as well as on comparison of NMR data with those of known analogues. At a concentration of 50 μM, compounds 1–3 showed inhibitory activity toward xanthine oxidase by 38.2%, 55.9%, and 23.0%, respectively.DOI http://doi.org/10.25135/rnp.289.2106.2121 Keywords Cupressaceae Cryptomeria japonica bark diterpenoid Available online: October 25, 2021 DETAILS DOWNLOAD PDF © ACG Publications. All rights reserved.
11) A New Iridoid Glycoside Isolated from Valeriana officinalis L.
A new iridoid glycoside, (5S,7S,8S,9R)-7- hydroxy-∆4,11-dihyronepeta-1,3-diol-8-O-β-D-glucopyranosyl (1), along with 5 known compounds, dioscoridin A (2), jatamanin J (3), longiflorone (4), apigenin-8-O-β-D-glucopyranoside (5), isosakuranetin-5-O-rutinoside (6), were isolated from the Valeriana officinalis L. Their structures were determined by extensive analysis using various spectroscopic techniques. Moreover, the cytotoxic activity assay toward three human tumor cell (A549, HCT116 and SW620) lines were evaluated by the MTT method in vitro for compounds 1-2, using cisplatin as positive control. Experimental results showed that these compounds displayed weak cytotoxicity in the human cancer cell lines. Notably, compounds 2, 3 and 6 were firstly isolated from this plant, compound 4 was isolated from the genus Valeriana for the first time, compound 5 was isolated for the first time from Valerianaceae family.DOI http://doi.org/10.25135/rnp.283.2107-2145 Keywords Iridoids Valeriana officinalis L. Valerianaceae cytotoxicity Available online: October 25, 2021 DETAILS DOWNLOAD PDF © ACG Publications. All rights reserved.
12) Honeybee Propolis Phenol, Caffeic Acid Phenethyl Ester, Attenuates Cisplatin-Induced Kidney Damage – a Multitarget Approach
Cisplatin utilization is known to be limited due to numerous side effects, especially to the ones related to kidney tissue injury. The application of antioxidants, as potential supportive drugs, to prevent oxidative cisplatin tissue damage appears intuitive. In this work, we explored the usage of caffeic acid phenethyl ester (CAPE) in this respect through the analysis of standard serum biochemical parameters and the ones related to oxidative tissue damage, the changes in arginine metabolism, and apoptosis occurrence that follow cisplatin application in rat kidneys. Additionally, pathohistological analysis and a specific TUNEL staining for the detection of apoptosis was studied. Cisplatin produced marked changes in serum parameters that reflect kidney tissue function, while at the same time produced extensive tissue oxidative damage, increased arginase activity, and depleted reduced glutathione. Moreover, both biochemical and micromorphological analyses indicated significant tubular cell apoptosis. The application of CAPE together with cisplatin prevented the disturbance in serum biochemical and tissue oxidative stress parameters, without affecting arginase activity. Interestingly, CAPE inhibited different enzymes involved in the glutathione metabolism and the apoptotic process. The results of the present study indicate that CAPE could be used as supportive therapy for oncological patients receiving cisplatin since it attenuates the nephrotoxicity of this chemotherapeutic.DOI http://doi.org/10.25135/rnp.284.2107.2146 Keywords Caffeic acid phenethyl ester kidney cisplatin oxidative damage arginase apoptosis Available online: October 14, 2021 DETAILS DOWNLOAD PDF © ACG Publications. All rights reserved.
13) Current Techniques For The Search For Natural Products In Actinobacteria
The actinobacteria, also referred to as actinomycetes, have been the most widely used bacteria to produce industrial interest compounds due to their great biosynthetic capacity to generate structural diversity molecules. The actinobacteria with the most significant biosynthetic potential are the genus Streptomyces, Saccharopolyspora, and Micromonospora containing groups of biosynthetic genes such as polyketide synthase systems, non-ribosomal peptide synthase systems, terpenoid systems, ribosomally synthesized and post-translationally modified peptide systems, among others. This review focuses on genomic mining techniques and current helpful software to search for new natural products in actinobacteria. Currently, molecular techniques have been developed to improve the isolation of natural products, and bioinformatics programs, many are free to access, have been designed to analyze genes and microbial genomes that predict new molecule production. Thanks to these techniques, new natural products of industrial interest have been found in rare actinobacteria such as Nocardia and Rhodococcus.DOI http://doi.org/10.25135/rnp.286.2107-2132 Keywords Actinobacteria Bioinformatics Genomic mining Natural products Available online: October 14, 2021 DETAILS DOWNLOAD PDF © ACG Publications. All rights reserved.
14) Essential Oil Composition and Antioxidant Activity of Endemic Achillea lingulata Waldst. & Kit. Compared to Common A. millefolium L.
In this study, the chemical composition and antioxidant activity of the hydrodistilled essential oil of Achillea lingulata, an endemic species of the Euro-Mediterranean region, originating from Bosnia and Herzegovina, was investigated for the first time. For comparison, an analysis of the essential oil of the widely distributed Achillea millefolium, which grows together in the same habitat, was made. Ninety-six components were identified in A. lingulata and A. millefolium oils comprising 97.8% and 85.8%, of the total oil, respectively. The oil of A. lingulata was characterized by a high content of oxygenated monoterpenes (76.8%). The main compounds were borneol (30.1%), trans-verbenol (15.5%), 2-tridecanone (12.2%), fragranol (8.3%), and myrtenol (7.9%). In contrast, essential oil of A. millefolium had oxygenated sesquiterpenes (60.8%) as the most abundant compounds, with elemol (32.9%) as the main constituent. In addition, γ-eudesmol (12.9%), caryophyllene oxide (7.7%), trans-caryophyllene (5.7%) and γ-muurolene (4.7%) were present in a significant percentage in A. millefolium oil. Antioxidant activity was tested by three methods, ABTS, DPPH and FRAP, and the obtained results showed low activity of both investigated oils.
DOI http://doi.org/10.25135/rnp.285.2107.2143 Keywords Achillea lingulata Achillea millefolium GC-MS essential oil terpenes antioxidant activity Available online: October 09, 2021 DETAILS DOWNLOAD PDF © ACG Publications. All rights reserved.
15) Annonaceae Essential Oils: Antimicrobial and Compositions of the Leaves of Uvaria hamiltonii Hook. f. & Thoms. and Fissistigma kwangsiensis Tsiang & P. T. Li
In this study, essential oils hydrodistilled from the leaves of Uvaria hamiltonii Hook. f. & Thoms. and Fissistigma kwangsiensis Tsiang & P. T. Li (Annonaceae) collected in Vietnam were analyzed by gas chromatographic techniques, and screened for the antimicrobial activities. The composition of both essential oils was dominated by sesquiterpenoids (70.0% and 78.7%, respectively). The main constituents of U. hamiltonii were germacrene D (22.9%), β-caryophyllene (21.1%), bicyclogermacrene (11.2%) and caryophyllene oxide (8.6%). The essential oil of F. kwangsiensis also showed abundant sesquiterpenes β-caryophyllene (24.5%), d-cadinene (13.4%) and α-copaene (5.6%), but also included (Z)-β-ocimene (6.7%). The leaf oil of U. hamiltonii demonstrated notable antimicrobial activity against Enterococcus faecalis ATCC299212 with minimum inhibitory concentration (MIC) value of 7.99 µg/mL and Bacillus cereus ATCC14579 (MIC 5.67 µg/mL) while F. kwangsiensis showed the most potent activity towards Pseudomonas aeruginosa ATCC27853 and Candida albicans ATCC10231, with MIC values of 3.45 µg/mL and 16.45 µg/mL, respectively. Both essential oils should be considered for further investigation as renewable “green” antimicrobial agents.DOI http://doi.org/10.25135/rnp.281.2108-2161 Keywords Antimicrobial activity essential oil composition sesquiterpenes Available online: October 09, 2021 DETAILS DOWNLOAD PDF © ACG Publications. All rights reserved.
16) Chemical Constituents and Biological Activity of the Stems of Adinandra hainanensis Hayata
Phytochemical study of Adinandra hainanensis stems led to the isolation of a new triterpene lupan-3β,20-dihydroxy-28-carbaldehyde (1) and eleven known compounds 2-12. The stems of A. hainanensis was rich in lupane-type triterpenes, especially betulinic acid (9) was abundant (around 0.45% w/w). The isolated triterpenes, including new compound 1 showed strong α-glucosidase inhibitory activity with IC50 values ranging of 2.27 ± 0.05 μg/mL to 12.25 ± 0.36 μg/mL. In the cytotoxic evaluation, betulinic acid, the major component, showed good cytotoxic activity against all tested cancer cell lines while new compound 1 was weakly active.DOI http://doi.org/10.25135/rnp.282.2108.2158 Keywords Adinandra hainanensis lupane triterpene betulinic acid α-glucosidase cytotoxicity Available online: October 09, 2021 DETAILS DOWNLOAD PDF © ACG Publications. All rights reserved.
17) Quantitative Analysis and In Silico Molecular Docking Screening for Acetylcholinesterase Inhibitor and ADME Prediction of Coumarins and Carbazole Alkaloids from Clausena harmandiana
Coumarins and carbazole alkaloids are natural compounds, often with neurological properties, especially as acetylcholinesterase inhibitors. In order to screen the candidate anti-acetylcholinesterase agents, in-silico molecular docking was performed aiming to predict the binding mechanism and the results were used to identify pharmacophores of coumarins and carbazole alkaloids from Clausena harmandiana as AChE inhibitory activity. All isolated compounds are xanthoxyletin (1), dentatin (2), nordentatin (3), clausarin (4), 7-methoxymukonal (5), 7-methoxyheptaphylline (6) and heptaphylline (7) displayed the stable binding interactions with Torpedo californica acetylcholinesterase (TcAChE) enzyme via π-π interactions, hydrogen bonds and hydrophobic interactions. All compounds exhibited the interaction with the peripheral anionic site of TcAChE same manner of standard anti-alzheimer drugs. ADME prediction revealed that all compounds met the requirement of drug likeness of Lipinski’s rule of five and had high CNS absorption, excepted 4 should be structure modification to improve CNS penetration. Besides 4, 6 and 7 displayed the highest acetylcholinesterase inhibitor activity among the other compounds. Interestingly, 6 had a high yield (58.01 mg/g extract) from C. harmandiana. It should be a candidate as an anti-acetylcholinesterase inhibitor agent.DOI http://doi.org/10.25135/rnp.288.2106-2112 Keywords Clausena harmandiana molecular docking coumarins carbazole alkaloids Alzheimer’s disease ADME Available online: October 05, 2021 DETAILS DOWNLOAD PDF © ACG Publications. All rights reserved.
18) Fissistigmol A: A New Polyacetylene alcohol from Fissistigma Minuticalyx
Abstract: A new polyacetylene alcohol, Fissistigmol A (1), along with four known polyacetylene alcohol compounds (2-5) were isolated from the aerial part of Fissistigma minuticalyx (McGr. et W. W. Sm.). Their structures were elucidated based on the spectroscopic evidence, mainly including NMR and induced ECD, and HRESIMS data. In addition, bioactivity assay showed that 1-5 showed notable nitric oxide (NO) inhibitory effects (IC50 < 10 μM) on the model of the lipopolysaccharide (LPS)-activated RAW 264.7 macrophages.DOI http://doi.org/10.25135/rnp.280.2108.2156 Keywords Polyacetylene alcohol Annonaceae Fissistigma minuticalyx nitric oxide (NO) inhibitory activity Available online: October 05, 2021 DETAILS DOWNLOAD PDF © ACG Publications. All rights reserved.
19) Essential Oil from Hedyotis chrysotricha: Chemical Composition, Cytotoxic, Antibacterial Properties and Synergistic Effects with Streptomycin
Hedyotis chrysotricha (Palib.) Merr. is a traditional Chinese herb that has been used to treat multiple ailments. In this study, we extracted and characterized the essential oil of H. chrysotricha for the first time and assessed its in vitro cytotoxic, antibacterial activities and the synergistic interaction with Streptomycin. Chemical constituents were determined using GC-FID/MS, which showed 37 components constituted 94.7% of the total oil; borneol (32.7%), linalool (7.5%), isobornyl formate (5.4%) and α-terpineol (4.8%) were the dominant components. The essential oil of H. chrysotricha inhibited strongly the growth of Gram-positive bacteria and possessed a significant cytotoxic activity towards LO2, HepG2 and MCF-7 cells. Besides, the checkerboard assay revealed that the H. chrysotricha essential oil exhibited synergistic potential with Streptomycin. Based on these findings, it can be concluded that the H. chrysotricha essential oil exhibits interesting bioactivities, and could be used as a source of natural antibacterial and anti-tumor compounds.DOI http://doi.org/10.25135/rnp.279.2108.2168 Keywords Hedyotis chrysotricha (Palib.) Merr essential oil antibacterial activity cytotoxic activity synergistic effects Available online: October 05, 2021 DETAILS DOWNLOAD PDF © ACG Publications. All rights reserved.
20) A New Diterpenoid with Antitumor Cytotoxicity from Millipede
A new diterpenoid, namely millipedine A (10), along with nine known compounds (1–9), were isolated from the methanol extract of Millipede. Their structures were established on the basis of spectroscopic analysis including one and two-dimensional NMR spectroscopy and comparison with previously reported data. New compound showed moderate cytotoxicity against A549, HCT-116, and SW1990 cell lines in MTT assay.DOI http://doi.org/10.25135/rnp.278.21.07.2135 Keywords Millipede diterpenoid antitumor activities Available online: September 05, 2021 DETAILS DOWNLOAD PDF © ACG Publications. All rights reserved.
21) The Limonoids and Other Constituents from the Fruits of Melia azedarach and Their Biological Activity
Eleven chemical constituents, including one new limonoid trichilinin G (1), were identified from the fruit extracts of M. azedarach. The structure of 1 was established by various spectroscopic and mass spectrometric analyses. Among the eleven isolated compounds, trichilinin G (1) and meliatoxin B1 (2) were examined for their antifungal activity against Fusarium oxysporum, Magnaporthe grisea, Phytophthora spp. (PS), and P. capsici (PC). Limonoid 2 showed the best antifungal activity against PS (IC50 = 103.8 µg/mL) and PC (IC50 < 62.5 µg/mL) in a dose-dependent manner. While limonoid 1 exhibited a weak to moderate activity against these Phytophthora species, F. oxysporum and M. grisea were less sensitive to the two compounds tested. The inhibitory effects of trichilinin G on superoxide anion generation and elastase release by human neutrophils were also assessed in cellular model and did not show significant activity.DOI http://doi.org/10.25135/rnp.277.21.06.2097 Keywords Triterpenoid limonoid trichilinin antifungal anti-inflammatory Available online: September 05, 2021 DETAILS DOWNLOAD PDF © ACG Publications. All rights reserved.
22) A New Organic Acid Derivative from the Fruits of Rosa roxburghii
Phytochemical investigation of the fruits of Rosa roxburghii resulted in the isolation of four organic acid derivatives and three phenylpropanoids, including a new organic acid derivative, Roxbuacidester A (1) and six known compounds (2-7). The structures of all isolates were established by 1D and 2D NMR spectra referring to the literatures, together with HR-MS spectrometric analysis. In addition, compounds 1 and 2 were evaluated for their inhibitory activities on nitric oxide (NO) production stimulated by lipopolysaccharide (LPS) in a RAW 264.7 cell line. Compounds 1 and 2 showed moderate inhibition of NO production with IC50 values of 46.8 ± 2.3 and 62.5 ± 3.7 μM, respectively.DOI http://doi.org/10.25135/rnp.276.21.07.2138 Keywords Rosaceae Rosa roxburghii organic acid derivative Available online: August 24, 2021 DETAILS DOWNLOAD PDF © ACG Publications. All rights reserved.
23) Anti-Obesity and Antihyperlipidemic Effects of Musa cavendishii
Obesity is a major risk factor in many health problems. This study explored the anti-obesity and antihyperlipidemic effects of Musa cavendishii Lamb. leaves. Doses of 1200 mg/kg of M. cavendishii methanol extract, or 300 mg/kg of fractions, were given to C57BL/6J mice fed with a high-fat diet (HFD) for 7 weeks. The reduction in fat volume was determined using CT scan and histopathological examination of mice livers. The results showed that the n-hexane and the EtOAc fractions reduced the body fat volume to 2.0% and 2.2% respectively, compared to 20.1% in the HFD group. Also, treated groups showed almost normal liver architecture with no fat vacuoles compared to the HFD group. Moreover, the treated groups showed a reduction in the levels of some obesity-related biochemical parameters, including plasma glucose, cholesterol, and triglycerides levels. Chromatographic fractionation of the bioactive n-hexane extract afforded four known compounds viz., palmitic acid (1), 5-methyl-5-(4,8,12-trimethyl-tridecyl)-dihydro-furan-2-one (2), cycloeucalenol (3), and stigmasterol (4). These compounds were in vitro and in silico studied for their pancreatic lipase (PL) inhibition. Compound 2 showed remarkable PL inhibition (89.8%) compared to orlistat (85.0%) at 200 µM, which was in full agreement with the docking scores (-7.19 and -4.05, respectively).DOI http://doi.org/10.25135/rnp.275.2103.2001 Keywords musa cavendishii anti-obesity antihyperlipidemic banana leaf anti-adipogenesis pancreatic lipase Available online: August 18, 2021 DETAILS DOWNLOAD PDF © ACG Publications. All rights reserved.
24) Constituents of the Flower of Maxillaria tenuifolia and Their Anti-Diabetic Activity
The EtOAc extract of the flower of Maxillaria tenuifolia, which had shown potent α-glucosidase inhibitory, was subjected to activity-guided isolation to yield four compounds, 3,4-dihydroxy benzoic acid methyl ester (1), flavanthridin (2), vanillic acid (3) and mangiferin (4). Their structures were ascertained by comparison of their physical and spectroscopic properties with those reported in the literature. Among them, flavanthridin (2), vanillic acid (3) and mangiferin (4) showed significant α-glucosidase inhibitory activity compared to acarbose at the concentration 1.0 mg/mL. Besides, 3,4-dihydroxy benzoic acid methyl ester (1) and mangiferin (4) also showed more effective in against the peroxidation of linoleic acid in an aqueous system than trolox. These results indicated that the EtOAc extract of M. tenuifolia and the related constituents might have anti-diabetic effect by suppressing carbohydrate disintegration and could prevent damage to organisms by oxidative stress.DOI http://doi.org/10.25135/rnp.274.2106.2093 Keywords α-glucosidase diabetes maxillaria tenuifolia antioxidative Available online: August 18, 2021 DETAILS DOWNLOAD PDF © ACG Publications. All rights reserved.
25) Phenolic Acid Analogues from Balanophora laxiflora Inhibit Proliferation of In Vitro Acute Myeloid Leukemia Cells
Four phenolic analogues isolated from Balanophora laxiflora; methylgallate (1, MG), 4-hydroxy-3-methoxycinnamaldehyde (2), 3-methoxycinnamic acid (3), and methyl caffeate (4, MC) were shown to have antiproliferative activity on acute myeloid leukemia (OCI-AML3) cells due to impaired cell cycle progression. Three of these compounds (1, 3, and 4) caused increased apoptosis and decreased proliferationin cells. Interestingly, MC (compound 4) significantly decreased the percentage of cells in S phase and G2/M phase, and significantly increased apoptosis in cells at low concentrations. Treatment with these compounds increased Fas ligand production and caspase-8/3, but not caspase-9-dependent, apoptosis. These results suggest that dosing with these compounds decreases proliferation and increases apoptosis in cell lines derived from hematological cancers.DOI http://doi.org/10.25135/rnp.273.2106.2117 Keywords Balanophora laxiflora hemsl. ex forbes & hemsl phenolic acid analogues antiproliferative activity caspase-8 acute myeloid leukemia cell (OCI-AML) human cancer cell lines Available online: August 18, 2021 DETAILS DOWNLOAD PDF © ACG Publications. All rights reserved.
26) Scopariaine A: A New Alkaloid from Scoparia dulcis with Protective effect on Cardiomyocytes Injury in Vitro
A new alkaloid, named scopariaine A (1), was obtained from the whole plant of Scoparia dulcis L. The new structure was established by various spectroscopic tmethods including 1D (1H-, 13C-NMR), 2D-NMR (HMBC, HSQC) and high resolution electrospray ionization mass spectrometry (HR-ESI-MS). Scopariaine A (1) was tested for its protective effect on attenuating palmitate-induced viability at 5, 10 and 25 μM. The results showed that the cell viability was increased in palmitic acid combined with scopariaine A (1) treated H9C2 cells.DOI http://doi.org/10.25135/rnp.268.2105.2073 Keywords Scoparia dulcis L. scopariaine A alkaloid H9C2 cells Available online: July 23, 2021 DETAILS DOWNLOAD PDF © ACG Publications. All rights reserved.
27) Chemical Composition of Flower Volatiles and Seeds Fatty Acids of Rosa iliensis Chrshan, an Endemic Species from Kazakhstan
In the present work, the flower volatiles and seed fatty acids compositions of three populations (P-I, P-II, P-III) of Rosa iliensis were investigated for the first time. R. iliensis is a rare, endangered, narrow-endemic species growing in floodplains of the Ili and Sharyn rivers of Almaty region. The flower volatiles have been investigated with the tandem of MSD-SPME and GC-MS/FID techniques. The seed lipids were extracted from the ripe fruits with the microextraction technique. The flower volatiles of R. iliensis three populations were characterized by the abundance of oxygenated monoterpenes with benzaldehyde (13.3-38.7 %) and citronellol (2.6-8.8 %) as the major constituents. There were detected significant differences in floral scents between the populations. The flowers of P-I (from Sharyn River) contain sesquiterpene g-elemene (8.8%), the flowers of P-II (upper reaches of the Ili River) were rich in a-gurjunene (12.8%), while flowers of P-III (lower reaches of the Ili River) contained any sesquiterpenes. Seven fatty acids were determined in the seeds and unsaturated acids were found to be dominant for studied populations. Linoleic (43.0-51.0%), a-linolenic (26.5-28.1%) and oleic (12.0-16.1%) acids were detected as the major constituents. The present study shows that R. iliensis species is rich source of valuable volatiles and fatty acids.
DOI http://doi.org/10.25135/rnp.271.2105.2083 Keywords Rosa iliensis population volatiles fatty acids MSD-SPME GC-MS/FID Available online: July 23, 2021 DETAILS DOWNLOAD PDF © ACG Publications. All rights reserved.
28) Two New 13-oxomilbemycins from a NTG-Induced Mutation Strain of Streptomyces avermitilis AVE-H39
Two new 13-oxomilbemycins, 13-oxomilbemycin β3 (1) and 25-ethyl-13-oxomilbemycin β3 (2), were isolated from the broth of a NTG-induced mutation strain of Streptomyces avermitilis AVE-H39. The structures of 1 and 2 were determined based on MS and extensive NMR analysis. Compounds 1 and 2 possessed moderate nematocidal activity.DOI http://doi.org/10.25135/rnp.269.2105.2075 Keywords Streptomyces avermitilis AVE-H39 NTG-induced mutation 13-oxomilbemycins nematocidal activity Available online: July 23, 2021 DETAILS DOWNLOAD PDF © ACG Publications. All rights reserved.
29) Anti-Inflammatory Components from the Fruits of Amomum aromaticum
In the course of searching for bioactive components from a Vietnamese spice, the fruits of Amomum aromaticum, a new bicyclic nonane (1) and seven known compounds including 4 monoterpenes (2, 3, 5, 6), one fatty acid (4), and two steroids (7-8) were isolated. Their structures were determined on the basis of spectroscopic analysis. This is the first report of compounds tsaokoin (2), 1β,2α-dihydroxy-p-menth-5-ene (3), oleic acid (4), β-sitosterol (7), and daucosterol (8) in A. aromaticum. To evaluate the anti-inflammatory activities of the isolates, we measured their inhibitory activity against lipopolysaccharide-induced nitric oxide production in a RAW264.7 murine macrophage model. The new compound rel-(1S,5R,6S)-5-methoxybicyclo[4.3.0]non-2-ene-2-carbaldehyde (1) and tsaokoin (2) showed substantial anti-inflammatory effects, with IC50 values of 17.78 and 6.31 µM, respectively. Thus, A. aromaticum fruits could be a rich source for the discovery of anti-inflammatory agents.DOI http://doi.org/10.25135/rnp.270.2105.2068 Keywords Amomum aromaticum bicyclic nonane tsaokoin anti-inflammation Available online: July 23, 2021 DETAILS DOWNLOAD PDF © ACG Publications. All rights reserved.
30) Investigation of Pesticidal Activities of Essential Oils Obtained from Vitex Species
Essential oils from renewable plant sources are important considerations for environmentally benign botanical pesticides. In this work, the leaf essential oils of four species of Vitex (Lamiaceae) have been collected from north-central Vietnam, analyzed by gas chromatographic techniques, and screened for mosquito larvicidal activity and molluscicidal activity. Vitex ajugifolia and V. pinnata essential oils were dominated by sesquiterpenoids (97.8% and 95.8%, respectively). In contrast, however, the essential oils of V. trifolia subsp. litoralis showed monoterpenoids to be dominant. The essential oils of V. trifolia subsp. trifolia also showed abundant monoterpenoids (38.4% and 68.0%), but also included (E)-β-caryophyllene (15.8 and 14.5%). Vitex pinnata essential oil showed excellent larvicidal activity against Aedes aegypti and Culex quinquefasciatus. Both V. trifolia litoralis and V. trifolia trifolia demonstrated notable molluscicidal activities against Gyraulus convexiusculus and Pomacea canaliculata. The research results suggest that essential oils of Vitex species might have potential to be used as natural pesticides.DOI http://doi.org/10.25135/rnp.266.21.06.2108 Keywords mosquito larvicidal molluscicidal chemical composition botanical pesticide Available online: July 23, 2021 DETAILS DOWNLOAD PDF © ACG Publications. All rights reserved.