Alkaloids from aerial parts of Houttuynia cordata and their anti-inflammatory activity

New alkaloids, houttuynamide B and C (1, 2) and houttuycorine (14), were isolated from the aerial parts of Houttuynia cordata Thunb. in addition to eighteen known alkaloids. Their structures were elucidated through extensive spectroscopic analysis. All the isolates were tested for their inhibitory activity against NO production in RAW 264.7 cells stimulated by LPS. Of the tested compounds, compound 15 showed the most potent anti-inflammatory activity with an IC₅₀ value of 8.7 μM.     

盐分对滨海湿地植物番杏生长和光合特征的影响

筛选耐盐又具有重要经济价值的植物品种是滨海地区生态修复工程的关键.本研究通过砂培方式对番杏(Tetragonia tetragonoides)幼苗进行不同盐度(0、100、200、300、400、600 mmol·L-1)处理,7周后测定其生长指标、生物量、光合和荧光参数,探讨番杏的耐盐能力.结果表明:番杏生长的适宜盐度范围为0～400 mmol·L-1,受抑制盐度为600mmol·L-1,说明番杏是一种耐盐性较高的盐生植物;番杏叶片净光合速率、气孔导度和蒸腾速率均随盐度的增加而降低,气孔限制值则相反;高盐通过影响番杏光合系统Ⅱ反应中心的关闭程度、光化学反应吸收光的比例和电子传递速率来抑制叶片光合速率,从而降低其生长速率;番杏是一种耐盐性高、具有食用价值的盐生植物,值得在滨海湿地生态修复工程重点推广.     

New labdane diterpenoids from Leonurus japonicus and their anti-inflammatory activity

Two new, 16-oxo-leoheteronone A (1) and 15-methoxyleoheteronin B (2), and four known, 8,9-secohispanolone (3), galeopsin (4), hispanone (5), and leoheteronin B (6), labdane diterpenoids were isolated from the aerial parts of Leonurus japonicus. Compound 3 was isolated for the first time as a naturally occurring compound. Structures of the two compounds were determined on the basis of extensive spectroscopic techniques, including 1D, 2D NMR, and HREIMS. In addition, compounds 1–3, 5 and 6 were examined for inhibition of superoxide anion generation and elastase release, and the results suggested that compound 5 possesses anti-inflammatory activity.     

Sesquiterpenes from the aerial parts of Artemisia tournefortiana

Sixteen eudesmane-type sesquiterpenes, including six unknown ones (1−6), were isolated from the aerial part of A. tournefortiana. NMR, HERIS-MS, IR spectra and ECD calculation assigned their relative and absolute configurations. Six (6, 7, 9, 13, 15, and 16) were tested for cytotoxic and anti-inflammatory activities, and seven (6, 7, 8, 12, 13, 15, and 16) were tested for antimicrobial activity. Among them, compound 15 showed significant cytotoxicity with IC₅₀ values in the range of 1.49–5.30 μM and moderate antimicrobial activity.     

Rearranged limonoids and chromones from Harrisonia perforata and their anti-inflammatory activity

Two new rearranged limonoids, harperforatin (1) and harperfolide (2), and a new chromone, harperamone (3), were isolated from fruits and roots of Harrisonia perforata, together with eight known compounds. Their structures were elucidated on the basis of spectroscopic data. Harperfolide (2) exhibited potent anti-inflammatory activity by suppressing nitric oxide (NO) production from activated macrophages with IC₅₀ value of 6.51 μM. Furthermore, its effect is mediated by reduction of iNOS protein expression, attributable to the inhibitory action of LPS-induced NO production.     

Further sesquiterpenoids from the rhizomes of Homalomena occulta and their anti-inflammatory activity

The rhizomes of Homalomena occulta are called Qian-nian-jian in Traditional Chinese Medicine (TCM), which is widely consumed in China owing to its health benefits for the treatment of rheumatoid arthritis and for strengthening tendons and bones. A phytochemical investigation on this famous TCM yielded 19 sesquiterpenoids (1–19) with various carbocyclic skeletons including isodaucane (2, 8, and 9), guaiane (3), eudesmane (4 and 10–15), oppositane (5, 16, and 17), and aromadendrane (18 and 19) types. The structures of new compounds, Homalomenins A-E (1–5), were determined by diverse spectroscopic data. Compound 1 possessed a rare sesquiterpenoid skeleton and compound 5 represented the first example of 1,4-oxa-oppositane sesquiterpenoid. These isolates were evaluated for their inhibitory effects on COX-2 mRNA, COX-2 protein expression, and prostaglandin E2 (PGE2) production in Raw264.7 cells, which demonstrated that compounds 5, 18, 19 showed potent anti-inflammatory activity by suppressing LPS-induced COX-2 expression and PGE2 production in a dose-dependent manner.     

Terpenoids isolated from Chinese liverworts Lepidozia reptans and their anti-inflammatory activity

Five new terpenoids (1–5) including two dollabellane-type, one ent-kaurane-type diterpenoids and two sesquiterpenoids were isolated from the Chinese liverwort Lepidozia reptans (L.) Dumort., together with nine known terpenoids (6–14). Their structures were determined on the basis of analysis of MS and NMR spectroscopic data, single-crystal X-ray diffraction and electronic circular dichroism calculations. The selected compounds 1, 2, 6, 7, 9 and 14 were screened for anti-inflammatory activities by the model of LPS-induced nitric oxide (NO) production with macrophage cells, and the mechanism of the active compounds 1 and 2 were further explored.     

Thiophenes,polyacetylenes and terpenes from the aerial parts of Eclipata prostrata

One new bithiophenes, 5-(but-3-yne-1,2-diol)-5′-hydroxy-methyl-2,2′-bithiophene (2), two new polyacetylenic glucosides, 3-O-β-d-glucopyranosyloxy-1-hydroxy-4E,6E-tetradecene-8,10,12-triyne (8), (5E)-trideca-1,5-dien-7,9,11-triyne-3,4-diol-4-O-β-d-glucopyranoside (9), six new terpenoid glycosides, rel-(1S,2S,3S,4R,6R)-1,6-epoxy-menthane-2,3-diol-3-O-β-d-glucopyranoside (10), rel-(1S,2S,3S,4R,6R)-3-O-(6-O-caffeoyl-β-d-glucopyranosyl)-1,6-epoxy menthane-2,3-diol (11), (2E,6E)-2,6,10-trimethyl-2,6,11-dodecatriene-1,10-diol-1-O-β-d-glucopyranoside (12), 3β,16β,29-trihydroxy oleanane-12-ene-3-O-β-d-glucopyranoside (13), 3,28-di-O-β-d-glucopyranosyl-3β,16β-dihydroxy oleanane-12-ene-28-oleanlic acid (14), 3-O-β-d-glucopyranosyl-(1→2)-β-d-glucopyranosyl oleanlic-18-ene acid-28-O-β-d-glucopyranoside (15), along with fifteen known compounds (1, 3–7, and 16–24), were isolated from the aerial parts of Eclipta prostrata. Their structures were established by analysis of the spectroscopic data. The isolated compounds 1–9 were tested for activities against dipeptidyl peptidase IV (DPP-IV), compound 7 showed significant antihyperglycemic activities by inhibitory effects on DPP-IV in human plasma in vitro, with IC₅₀ value of 0.51 μM. Compounds 10–24 were tested in vitro against NF-κB-luc 293 cell line induced by LPS. Compounds 12, 15, 16, 19, 21, and 23 exhibited moderate anti-inflammatory activities.     

Phytochemicals from the aerial parts of Ligularia thomsonii and their radical scavenging activity

Phytochemical investigation of the aerial parts of Ligularia thomsonii has led to the isolation of three new phenylpropanoid glucosides ligularoside I (1), ligularoside II (2) and ligularoside III (3) along with nine known compounds; cinnamic acid (4), 3-phenylpropanoic acid (5), 3,4,5-trihydroxybenzoic acid (6), 4-hydroxybenzoic acid (7), p-coumaric acid (8), caffeic acid (9), 3,4-dihydroxybenzoic acid (10), kaempferol 3-O-β-d-glucopyranoside (11) and 3,5-di-O-caffeoylquinic acid (12), hitherto unreported from L. thomsonii. Their chemical structures were elucidated by spectroscopic analysis and chemical transformation. All these compounds were tested for antioxidant activity using the 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging assay. Among them, compounds 9, 10 and 12 showed significant antioxidant activity against DPPH radicals with IC₅₀ of 19.6, 23.3 and 8.9 μm, respectively.     

Pentacyclic triterpenoids from the aerial parts of Lantana camara and their nematicidal activity

Two new olean-12-ene triterpenoids, camarolic acid (1) and lantrigloylic acid (2), have been isolated from the aerial parts of Lantana camara, along with ten known triterpenes, namely, camaric acid, lantanolic acid, lantanilic acid, pomolic acid, camarinic acid, lantoic acid, camarin, lantacin, camarinin, and ursolic acid. The new compounds have been characterized as 3,25-epoxy-3alpha-hydroxy-22beta-{[(S)-3-hydroxy-2-methylidenebutanoyl]oxy}olean-12-en-28-oic acid (1) and 3,25-epoxy-3alpha-hydroxy-22beta-[(3-methylbut-2-enoyl)oxy]olea-9(11),12-dien-28-oic acid (2) through spectroscopic studies and a chemical transformation. Seven of the constituents, namely pomolic acid, lantanolic acid, lantoic acid, camarin, lantacin, camarinin, and ursolic acid, were tested for nematicidal activity against root-knot nematode Meloidogyne incognita. Pomolic acid, lantanolic acid, and lantoic acid showed 100% mortality at 1 mg/ml concentration after 24 h, while camarin, lantacin, camarinin, and ursolic acid exhibited 100% mortality at this concentration after 48 h. These results are comparable to those obtained with the conventional nematicide furadan (100% mortality at 1 mg/ml concentration after 24 h).     

Alkaloids of Aconitum laeve and their anti-inflammatory antioxidant and tyrosinase inhibition activities

A lycoctonine-type norditerpenoid alkaloid, swatinine (1), along with four known norditerpenoid alkaloids, delphatine (3), lappaconitine (4), puberanine (5), and N-acetylsepaconitine (6), and were isolated from the aerial parts of Aconitum laeve Royle. Compound 2 has been isolated for the first time from a natural source. The structure of compound 1 was deduced on the basis of spectral data. The anti-inflammatory, antioxidant and tyrosinase inhibition studies on all six compounds have also been carried out.     

Three new compounds isolated from the bulbs of Fritillaria pallidiflora Schrenk and their anti-inflammatory activity

Three new compounds, 17β-cevanin-6-oxo-5α,20β-diol yibeinine (1), 2-(tetrahydro-5-(2-hydroxyphenyl)-2H-pyran-3-yl) phenol (2), 1,3-O-diferuloyl-2-methoxypropane diol (3), as well as four known compounds (4–7), have been isolated from the ethanol extract of dried bulbs of Fritillaria pallidiflora Schrenk. All structures were determined based on their spectroscopic data (1D and 2D NMR (including ¹H NMR, ¹³C NMR, ¹H-¹H COSY, HMBC, HSQC, HSQC-TOCSY, and NOESY experiments), and MS). Biological evaluation showed that compounds 1–4 inhibited the production of nitric oxide (NO) in LPS-stimulated RAW 264.7 cells with IC₅₀ values of 18.0, 38.7, 29.5, and 47.1 μM, respectively. These results indicated that compound 1 has potential anti-inflammatory activity.     

Two new metabolites from Portulaca oleracea and their anti-inflammatory activities

Two new metabolites, identified as 6-phenylbenzofuran-4-ol, named olerabenzofuran (1), and 2-(furan-2-yl)− 6-hydroxy-1 H-inden-1-one, named oleraindenone (2), together with eight furan compounds obtained for the first time, (+)-pinoresinol (3), (-)-syringaresinol (4), (+)-diasyringaresinol (5), (+)-episyringaresinol (6), (2 S)− 1-[2-(furan-2-yl)− 2-oxoethyl]− 5-oxopyrrolidine-2-carboxylic acid (7), methyl (2 S)− 1[2-(furan-2-yl)− 2-oxoethyl]− 5-oxopyrrolidine-2-carboxylate (8), drynaran (9), and 2-furoic acid (10), were isolated from Portulaca oleracea L., and spectroscopic methods, including 1D and ²D NMR and UHPLC-ESI-QTOF/MS spectrometry techniques, were employed to determine their structures. It was suggested that both olerabenzofuran (1) and oleraindenone (2) could significantly inhibit inflammatory factor interleukin-1β (IL-1β) in RAW 264.7 cells induced by LPS.     

Pharmacological insight into the anti-inflammatory activity of sesquiterpene lactones from Neurolaena lobata (L.) R.Br. ex Cass

PurposeNeurolaena lobata is a Caribbean medicinal plant used for the treatment of several conditions including inflammation. Recent data regarding potent anti-inflammatory activity of the plant and isolated sesquiterpene lactones raised our interest in further pharmacological studies. The present work aimed at providing a mechanistic insight into the anti-inflammatory activity of N. lobata and eight isolated sesquiterpene lactones, as well as a structure–activity relationship and in vivo anti-inflammatory data.MethodsThe effect of the extract and its compounds on the generation of pro-inflammatory proteins was assessed in vitro in endothelial and monocytic cells by enzyme-linked immunosorbent assay. Their potential to modulate the expression of inflammatory genes was further studied at the mRNA level. In vivo anti-inflammatory activity of the chemically characterized extract was evaluated using carrageenan-induced paw edema model in rats.ResultsThe compounds and extract inhibited LPS- and TNF-α-induced upregulation of the pro-inflammatory molecules E-selectin and interleukin-8 in HUVECtert and THP-1 cells. LPS-induced elevation of mRNA encoding for E-selectin and interleukin-8 was also suppressed. Furthermore, the extract inhibited the development of acute inflammation in rats.ConclusionsSesquiterpene lactones from N. lobata interfered with the induction of inflammatory cell adhesion molecules and chemokines in cells stimulated with bacterial products and cytokines. Structure–activity analysis revealed the importance of the double bond at C-4–C-5 and C-2–C-3 and the acetyl group at C-9 for the anti-inflammatory activity. The effect was confirmed in vivo, which raises further interest in the therapeutic potential of the compounds for the treatment of inflammatory diseases.     

6-Methoxyflavonols from disjunct populations of Brickellia cylindracea (compositae)

Eight identical 6-methylated flavonols including aglycones and glycosides were isolated from two geographically disjunction population of Brickellia cylindracea from Mount Livermore and Austin, Texas, suggesting that they are best treated as a single taxon. Among the flavonol aglycones identified were patuletin, centaureidin, quercetagetin 3,6,3′,4′-tetramethyl ether and artemetin. The flavonol glycosides were patuletin and its 3-galactoside, 3-galactogalactoside, 3-rhamnogalactoside and a 3-rhamnogalactoside derivative.     

Synthesis of novel of 2, 5-disubstituted 1, 3, 4- oxadiazole derivatives and their in vitro anti-inflammatory,anti-oxidant evaluation,and molecular docking study

A series of novel 2, 5-disubstituted 1, 3, 4-Oxadiazole derivatives as a potential anti-inflammatory, and anti-oxidant agent were synthesized via cyclisation. Hydrazide molecule treated with substituted acids in the presence of phosphorus oxychloride (POCl₃) as an efficient reagent as well as solvent by conventional method with shorter reaction time and excellent yield. The newly synthesized 1, 3, 4- oxadiazole derivatives exhibited excellent to good anti-inflammatory and anti-oxidant activities compaired to the standard drugs. Molecular docking study on the crucial anti-inflammatory target–cyclooxygenase-2 (COX-2) revealed the ability of the scaffold to correctly recognize the active site and achieve significant bonded and non-bonded interactions with key residues therein. This study could identify potential compounds which can be pertinent starting points for structure-based drug design to obtain newer anti-inflammatory agents.     

Phenylpropanoids and triterpenoids from Tripterygium regelii and their anti-inflammatory activities

Two new compounds named cleroserroside C (1), schisphenlignan O (2), as well as twenty-one known compounds (3–23) were isolated from the roots of Tripterygium regelii. The structures of the new compounds were determined by 1D and ²D NMR spectra and HR-ESI-MS data. The known compounds were determined by comparing the ¹D NMR data in the literature. All compounds were evaluated for anti-inflammatory activity using the LPS-induced RAW264.7 inflammatory cell model, and the results showed that compounds 1, 8-11, 15-16, and 20-21 had good anti-inflammatory activity (IC₅₀ < 20 μM). The cytotoxicity of all compounds was tested by CCK-8 assay, using RAW264.7 cells. The results showed that all compounds had no cytotoxicity to RAW264.7 in the range of 0 ~ 200 μM.     

Pancreatic lipase inhibitory and antioxidative constituents from the aerial parts of Paeonia lactiflora Pall. (Ranunculaceae)

To date, there have been reports mostly about research results of the peony root in comparison to the aerial parts. According to our study, the aerial parts of P.lactiflora showed superior anti-oxidative and pancreatic lipase inhibitory activities than its root. Especially, the water extract and the ethyl acetate fraction of the ethanol extract exhibited potent pancreatic lipase inhibitory activity by 53.11 ± 1.22% and 46.16 ± 1.55% at the same dose of orlistat (62.5 ± 1.27%). The ethanol extract exhibited the best anti-oxidative activity with IC₅₀ of 17.08 ± 0.9 μg/mL, and the ethyl acetate fraction 19.75 ± 0.02 μg/mL, respectively, comparing to the positive control rutin (IC₅₀, 22.66 ± 0.29 μg/mL). From the anti-oxidative and pancreatic lipase inhibitory active fractions three new compounds, monplacphloroside (1), monplachydroxyquinoside (2) and herbacetin-7-O-β-d-sophoroside (3) were isolated along with 19 (4-22) known ones.Compounds, PGG (14), 1-O-methyl-2,3,4,6-tetra-O-galloyl-β-d-glucopyranose (17) and ethylgallate (9) were found to be the strongest antioxidants and pancreatic lipase inhibitors. Monoterpenes, albiflorin R₂ (19) and albiflorin (20) were determined for the first time as strong pancreatic lipase inhibitors. The presence of the esterified galloyl moiety, with its increasing numbers or the β-lactone cycle within the molecular structure plays an essential role for the enhancement of the pancreatic lipase enzyme inhibitory activity.     

Compounds from the fruits of Nicandra physaloides and their potential anti-inflammatory activities

Twenty-one compounds were isolated and identified from the ethanol extract of the fruits of Nicandra physaloides, including four new (1–4) and 17 known compounds (5–21). All the compounds were isolated from the genus Physalis for the first time. In this study, NMR spectroscopy was used to study the compound structures by comparing their data with those reported in the literature. Moreover, the potential anti-inflammatory activity of RAW264.7 cells induced by lipopolysaccharide (LPS) was evaluated. Among the monoterpenoids, compounds (5–7, 9) exhibited weak anti-inflammatory activities, with IC₅₀ values ranging from 29.10 to 68.30 μM.     

Hexahydrobenzophenanthridine alkaloids from Corydalis bungeana Turcz. and their anti-inflammatory activity

As part of a bioprospecting program aimed at the discovery of anti-inflammatory agents from the Corydalis bungeana Turcz. (C. bungeana), five new hexahydrobenzophenanthridine alkaloids, corycaline A-E (1–5), along with four known alkaloids, were isolated from the whole plant of C. bungeana. Their structures including absolute configurations were elucidated on the basis of extensive spectroscopic analyses and electronic circular dichroism (ECD) calculations. The inhibitory activities of the nine compounds on lipopolysaccharide (LPS)-induced nitric oxide (NO) production in RAW 264.7 mouse macrophage cells were determined; all tested compounds except 2 and 7 exhibited significant inhibitory effects with IC₅₀ values in the range of 1.00–2.79?μM.