Two new limonoids from the roots of Trichilia connaroides with inhibitory activity against nitric oxide production in lipopolysaccharide-stimulated RAW 264.7 cells

Two new rearranged limonoids, trichiliton I (1) and 12-deacetoxyltrijugin A (2) along with four previously reported compounds (3–6) were isolated from the roots of Trichilia connaroides. Their structures were established on the basis of extensive spectroscopic analysis including HR-ESI–MS and 1D and 2D NMR. The new compounds 1 and 2 exhibited weak inhibitory effects on lipopolysaccharide-stimulated nitric oxide production in RAW 264.7 cells in a dose-dependent manner.     

Phytochemicals with NO inhibitory effects and interactions with iNOS protein from Trigonostemon howii

A phytochemical investigation to obtain new NO inhibitors led to the isolation of nine compounds including one new guaiane-type sesquiterpenoid (1) and two new cleistanthane diterpenoids (2 and 3) from the stems of Trigonostemon howii. Their structures were elucidated on the basis of extensive 1D and 2D NMR spectroscopic data analysis, and the absolute configurations of new compounds 1–3 were established via comparison of experimental and calculated electronic circular dichroism (ECD) spectra. Compounds 2 and 3 possess a rare 3,4-seco-cleistanthane diterpenoid skeleton. All of the compounds showed inhibitory effects on lipopolysaccharide-induced NO production in murine microglial BV-2 cells. The further molecular docking studies indicated the strong interactions between some bioactive compounds with the iNOS protein, which revealed the possible and potential mechanism of NO inhibition of bioactive compounds.     

Evolvosides C–E,flavonol-4-O-triglycosides from Evolvulus alsinoides and their anti-stress activity

Phytochemical investigation of the n-butanol fraction of Evolvulus alsinoides (Linn.) led to the isolation of three new phenolic glycosides, evolvosides C, D and E (1–3) along with six known compounds (4–9). The structures of the compounds were elucidated on the basis of spectroscopic analysis, viz. 1D and 2D NMR experiments, chemical study, and comparison with literature data. Evolvoside C (1) was characterized as kaempferol 4′-O-β-d-glucopyranosyl-(1→2)-α-l-rhamnopyranosyl-(1→6)-β-d-glucopyranoside, whereas evolvosides D and E (2–3) were found to be mono and di-O-methyl derivatives of 1. The new compounds (1–3) represent rare triglycoside derivatives of flavonol at C-4′. The isolated compounds (1–6) were screened for acute stress-induced biochemical changes in male Sprague–Dawley rats at a dose of 40 mg/kg body weight. Compounds 1 and 2 displayed anti-stress effects by normalizing hyperglycemia, plasma corticosterone, plasma creatine kinase, and adrenal hypertrophy. Compounds 3 and 6 were also found to be effective in normalizing most of these stress parameters, whereas compounds 4 and 5 were ineffective in normalizing most of these effects.     

New cis-ent-clerodanes from Linaria japonica

Five new cis-ent-clerodanes, linarenones A–E (1–5) and two known compounds (6 and 7) were isolated from whole plant of Linaria japonica. The structures of these compounds were determined by various spectroscopic analyses (UV, IR, HR–ESI–MS, 1D and 2D NMR). The absolute configuration of five new diterpenoids was confirmed by circular dichroism (CD) analysis and chemical conversion. Cytotoxicity of the isolated compounds against A549 cell lines and Leishmania major were evaluated. The new cis-ent-clerodane 3 was found to be moderately active against A549 cell lines, and new cis-ent-clerodanes 1, 6 and desacetyl-linarienone (7) were active against L. major.     

New antiproliferative and immunosuppressive withanolides from the seeds of Datura metel

Two new withanolides baimantuoluoside H (1) and baimantuoluoline K (2), and one known withanolide glycoside (3) were isolated and identified from the ethyl acetate-soluble fraction of ethanol extract of Datura metel seeds. The structures of the new compounds were determined using 1D and 2D NMR spectroscopy, and mass spectrometry. All isolated compounds were evaluated for their antiproliferative activity against human gastric adenocarcinoma (SGC-7901), human hepatoma (Hepg2), and human breast cancer (MCF-7) cells, as well as their immunosuppressive properties. It was determined that compounds 1–3 exhibited medium antiproliferative and potential immunosuppressive effects.     

Chemical constituents from Alnus mandshurica (Callier) Hand.-Mazz. and their chemotaxonomic significance

A new phenol compound, (9S)-9-hydroxy-9-[(2-hydroxyphenyl)methoxy]-nonanoic acid methyl ester (1) was isolated from the stem bark of Alnus mandshurica (Callier) Hand.-Mazz., along with eight known compounds (2–9). The structure of compound 1 was determined by spectral analyses, including HR-ESI-MS, 1D and 2D NMR (COSY, HMQC and HMBC) experiments. All the isolated compounds were reported for first time from A. mandshurica. Furthermore, compounds 3–9 were found in the family Betulaceae for the first time.     

Cytotoxic cycloartanes from the fruits of Caloncoba glauca

Two new cycloartane-type triterpenoids, glaucartanoic acids A (1) and B (2), together with five known compounds were isolated from the fruits of Caloncoba glauca. Their structures were elucidated by spectroscopic methods including extensive 1D and 2D NMR techniques, by chemical evidence and by comparison with literature data. The new compounds were evaluated for their in vitro cytotoxicity against five human cancer cell lines.     

Biotransformation of 20(R)-panaxatriol by Aspergillus niger AS 3.739

Microbial transformation of 20(R)-panaxatriol (PT) was performed by using the fungus Aspergillus niger AS 3.739. Six metabolites (1–6) including five new compounds were obtained. The chemical structures of these transformed products were elucidated based on various spectroscopic analyses, including 1D and 2D NMR and HRESI-MS. Metabolites 2–6 are new compounds. Furthermore, metabolites 2, 3, 5, and 6 exhibited significant anti-hepatic fibrosis activity, while 4 showed cytotoxicity against HSC-T6 cells.     

Ecdysteroids from the flowers of Aerva javanica

Four new ecdysteroids (1–4), along with three known steroids, β-ecdysone (5), 5-β-2-deoxyintegristerone A (6) and 24-epi-makisterone A (7) (Fig. 1), were isolated from the methanolic extract of the flowers of Aerva javanica by using normal and reverse phase chromatography. The structures of the new compounds (1–4) were determined due to 1D (¹H and ¹³C), 2D NMR (HSQC, HMBC, COSY, NOESY) techniques and high resolution mass spectrometry (HREIMS). The known compounds (5–7) were characterized based on the 1D NMR spectroscopy and mass spectrometry and by comparison with the literature values. All isolates were evaluated for their inhibitory activities against enzymes acetylcholinesterase (AChE), butyrylcholinesterase (BChE) and lipoxygenase (LOX).     

Chemical constituents from the stems of Alyxia schlechteri

The extraction of the stems of Alyxia schlechteri and then using chromatographic separation and recrystallization afforded 2 new compounds, a benzyl coumarin derivative named alyterinin (1) and a germacrane sesquiterpene named alyterinone (2). In addition, 20 known compounds were discovered from the stems of this plant. Mosher's method was used to identify the absolute configuration of 2. Ficusequilignan A (12) showed strong antifungal activity against Pythium insidiosum. Structural determination of all compounds was accomplished by 1D and 2D NMR, IR and MS spectrometry.     

Norlignan glycosides from the leaves of Molineria latifolia

Two new norlignan glycosides, molinerioside D (5) and molinerioside E (9), were isolated from the methanol extract of fresh leaves of Molineria latifolia. Their structures were determined using spectroscopic evidence, such as 1D and 2D NMR and HR-ESI-MS studies. The structure of molinerioside D (5) was determined to be a norlignan glycoside with a C6-C5-C6 skeleton, while the structure of molinerioside E (9) was determined to be a glucosyl-fused norlignan derivative. In addition to the new compounds, twenty known compounds were found in the extract of M. latifolia fresh leaves.     

A new secoiridoid and a new xanthone glycoside from the whole plants of Lomatogonium rotatum

A new secoiridoid (1) and a new xanthone glycoside (2), together with fourteen known compounds (3−16) were isolated from the dried whole plants of Lomatogonium rotatum (L.) Fries ex Nym. The chemical structures were elucidated based on extensive spectroscopic experiments, including 1D and 2D NMR as well as HR-ESI-MS, and comparison with those reported in the literature. All the compounds were evaluated for anti-complementary activity against the alternative pathways. Compounds 12 and 16 exhibited anti-complementary activity.     

Two new compounds from Trigonostemon heterophyllus

Phytochemical investigation on the stems of Trigonostemon heterophyllus led to the isolation of a new diterpene, trigonoheterene (1), and a new naphthoquinone, trigonoheterone (2), together with two known compounds, 3,4-seco-sonderianol, (3) and trigonochinene E, (4). Their structures were determined by spectroscopic techniques (UV, IR, MS, 1D and 2D NMR). All compounds were evaluated for cytotoxic activities and antibacterial activities.     

Two new germacranolides from Elephantopus tomentosus

The bioassay-guided chemical investigation of the whole plant of Elephantopus tomentosus led to the isolation of two new germacranolides, tomenphantopin C (1) and tomenphantopin D (2), together with four known compounds (3–6). Their structures were determined by spectroscopic techniques (UV, IR, MS, 1D and 2D NMR). All compounds were evaluated for cytotoxic and antibacterial activities.     

New sesterterpenoids and other constituents from Salvia dominica growing wild in Jordan

A new nor-oleanane triterpene 24-nor-4(23)-12-oleanadien-2α,3α,28-triol (1) and two new sesterterpenes salvidominicolide A (2), salvidominicolide B (3) together with fifteen known compounds were isolated from Salvia dominica L. growing wild in Jordan. The known compounds comprised six flavones, three triterpenes, one diterpene, one sesterterpene, two oxygenated monoterpenes, one sterol glucoside and one flavone glucoside. The isolated compounds were elucidated by extensive spectroscopic methods including NMR (1D and 2D), UV, IR and MS (HRMS).     

Two new butanolides from the roots of Litsea acuminata

Two new butanolides, licunolides A (1) and B (2), were isolated from the roots of Litsea acuminata, together with three known compounds: isolancifolide (3), longifolin (4), and sesquirose furan (5). The structures of compounds 1 and 2 were determined by spectroscopic studies (IR, MS, 1D and 2D NMR) and chemical evidence. This is the first report of 4-hydroxy-5-methylbutanolides with a C₁₀-side chain from a natural source. Longifolin (4) and sesquirose furan (5) showed a significant cytotoxicity against HeLa cell lines in vitro.     

Bioactive terpenoids from Silybum marianum and their suppression on NO release in LPS-induced BV-2 cells and interaction with iNOS

Three new (1–3) and one known (4) bioactive terpenoids were isolated from the seeds of Silybum marianum based on the investigation to get new NO inhibitors. Their structures were determined by extensive NMR (1D and 2D NMR) and MS spectroscopic data, and the absolute configurations were identified by experimental and calculated ECD spectra. The NO inhibitory activities in murine microglial BV-2 cells and interactions with iNOS protein by molecular docking were evaluated for all compounds. The results showed that these compounds had potent NO inhibitory effects.     

Novel cassane diterpenes from the seeds of Caesalpinia minax

Three new cassane diterpenes, sucutiniranes G (1), H (2) and I (3) were isolated from the seeds of Caesalpinia minax Hance. Their structures were elucidated by various spectroscopic techniques (UV, IR, MS, CD, 1D and 2D NMR). All compounds were evaluated for cytotoxic activities against MCF-7 and HepG-2 human cancer cell lines.     

Chemical constituents of the roots of Eupatorium chinense and their anti-inflammatory activities

In this study, three new compounds (1-3), together with fifteen known ones (4-18) were isolated from a petroleum ether extract of the roots of Eupatorium chinense. The structures of new compounds were elucidated by 1D, 2D nuclear magnetic resonance (NMR), circular dichroism spectrum (CD), mass spectrum (MS) along with other spectroscopy methods. In addition, twelve compounds were evaluated in vitro for their anti-inflammatory activities, while compounds 3 and 5 exhibited moderate activities with inhibition rates of 23.08 % and 25.19 %, respectively.     

Eremophilane sesquiterpenes from the endophyte Microdiplodia sp. KS 75-1 and revision of the stereochemistries of phomadecalins C and D

Two new eremophilane sesquiterpenes, compounds 1 and 2, were isolated from the endophytic fungus Microdiplodia sp. KS 75-1, together with the known compounds phomadecalins C (3) and D (4). Their structures were determined by extensive 1D– and 2D–NMR and MS spectral analyses. The previously reported stereochemistry at C-8 of 3 and 4 were revised on the basis of NOEs experiments. Compounds 1 and 2 showed antimicrobial activity against Pseudomonas aeruginosa.