Four New C19-Diterpenoid Alkaloids from Aconitum nagarum Stapf

Four new aconitine-type C₁₉-diterpenoid alkaloids, were isolated from the roots of Aconitum nagarum Stapf which were named as nagarutines A–D ( 1–4 ), together with eleven known compounds ( 5–15 ). The structures of the compounds were identified by IR, HR-ESI-MS, 1D and 2D NMR spectra. All compounds were tested for the inhibitory effect on LPS induced NO production in RAW 264.7 macrophages, compound 7 showed moderate anti-inflammatory activity effect and Inhibition rate is about 44.50%.     

Tricalycoside,a New Cerebroside from Tricalysia coriacea (Rubiaceae)

A new cerebroside, named as tricalycoside ( 1 ), was isolated from the CH₂Cl₂/MeOH (1:1) extract of twigs and leaves of Tricalysia coriacea using repeated silica gel open column chromatography followed by preparative TLC and Sephadex LH‐20, together with six known compounds ( 2 – 7 ). The structure of the new compound was determined by analysis of 1D‐ and 2D‐NMR, MS data, chemical conversion, and by comparison of these data with those from the literature. Tricalycoside ( 1 ) possessed a weak antibacterial activity against Klebsiella pneumoniae (MIC = 75 μg/mL).     

Three New Steriodal Saponins from the Rhizomes of Tupistra chinensis Baker

The phytochemical constituent investigation on the 70 % ethanol extract of the rhizomes of Tupistra chinensis Baker resulted in the isolation of three new steroidal saponins which were named tuchinosides A–C ( 1 – 3 ). Their structures were determined by extensive spectrum analysis and chemical evidence, especially 2D NMR and HR-ESI-MS techniques. In addition, the cytotoxicity of compounds 1–3 against several human cancer cell lines was evaluated.     

Three New Constituents with Anti-Inflammatory and Antimicrobial Activities in Vitro from the Roots of Capsicum annuum L.

Three new compounds, including two new sesquiterpenes ( 1–2 ), named Annuumine E−F, and one new natural product, 3-hydroxy-2,6-dimethylbenzenemethanol ( 3 ), together with seventeen known compounds ( 4–20 ) were isolated from the ethanol extract of the roots of Capsicum annuum L. Among them, five compounds ( 4 , 5 , 9 , 10 and 20 ) were isolated from this plant for the first time. The structures of new compounds ( 1–3 ) were determined via detailed analysis of the IR, HR-ESI-MS and 1D and 2D NMR spectra. The anti-inflammatory activities of the isolated compounds were evaluated by their ability to reduce NO release by LPS-induced RAW 264.7 cells. Notably, compound 11 exhibited moderate anti-inflammatory activity (IC₅₀=21.11 μM). Moreover, the antibacterial activities of the isolated compounds were also evaluated.     

A New Alkaloid from the Aerial Parts of Bupleurum chinense DC.

A new isoalloxazine alkaloid, named bupleurine A ( 1 ), along with five known compounds ( 2 – 6 ), were isolated from the aerial parts of Bupleurum chinense DC. The structure elucidation of the new alkaloid ( 1 ) was employed by combining NMR and HR‐MS data with comparison of reference in the literature. Five known compounds ( 2 – 6 ) were isolated from Bupleurum genus for the first time. Additionally, their antiproliferative activities on HeLa cells were evaluated by MTT assay and IC₅₀ of compounds 1 and 4 – 6 were below 10 μm after treatment for 24 h.     

Two new benzofuran derivatives from the fungus Stereum sp. YMF1.1684

A basidiomycete fungus, Stereum sp. YMF1.1684, was studied for its ability to produce new compounds on nutrient-enriched cultivation media. One new benzofuran, 2-hydroxy-1-((S)-2-(prop-1-en-2-yl)-2,3-dihydrobenzofuran-5-yl)propan-1-one, named as phenostereum A (1) and one novel dimer benzofuran, named as phenostereum B (2) were isolated from EtOAc extract of the culture broth of the fungus Stereum sp. YMF1.1684. The structures were elucidated using spectroscopic data from 1D, 2D NMR and HRESIMS experiments.     

Four New Diterpenoid Alkaloids from The Roots of Aconitum coreanum

Four new hetisine‐type C₂₀‐diterpenoid alkaloids, named as coreanines A–D ( 1 – 4 ), were isolated from the roots of Aconitum coreanum, together with thirteen known alkaloids ( 5 – 17 ). Their structures were elucidated by extensive spectroscopic methods including IR, HR‐ESI‐MS and NMR techniques. All the isolated compounds were screened for the acetylcholinesterase (AChE) inhibitory effects, and none of them showed considerable inhibitory activity.     

A New Prenylated Flavanonol from Seseli annuum Roots Showing Protective Effect on Human Lymphocytes DNA

A new prenylated flavanonol named seselinonol ( 1 ) was isolated from the roots of Seseli annuum, together with the well‐known biologically active polyacetylenes falcarinol ( 2 ) and falcarindiol ( 3 ), and the prenylated furanocoumarin phellopterin ( 4 ). Its structure was elucidated by extensive spectroscopic analysis, including HR‐ESI‐MS, 1D‐ and 2D‐NMR. Seselinonol and phellopterin were tested for in vitro protective effect on chromosome aberrations in peripheral human lymphocytes using cytochalasin‐B blocked micronucleus (CBMN) assay. The new compound exerted a beneficial effect by decreasing DNA damage of human lymphocytes.     

New Guaiane-Type Sesquiterpene and Norsesquiterpene from Alisma plantago-aquatica and Their Xanthine Oxidase Inhibitory Activity

A new sesquiterpene ( 1 ) and a new norsesquiterpene ( 2 ) belonging guaiane-type skeleton together with six known compounds ( 3 – 8 ) were isolated from the rhizomes of Alisma plantago-aquatica. Their structures were determined by HR-ESI-MS, 1D and 2D NMR spectroscopic methods. Absolute configurations of new compounds were established by experimental and TD-DFT computational ECD spectra. Compounds 1 – 8 exhibited xanthine oxidase inhibitory activity with their IC₅₀ values in range of 9.4–66.7 μM. The sesquiterpenoids 1 – 5 displayed the inhibitory activity and hence they could be potential xanthine oxidase inhibitors from A. plantago-aquatica.     

Bergamotane Sesquiterpenes with Alpha‐Glucosidase Inhibitory Activity from the Plant Pathogenic Fungus Penicillium expansum

Two new bergamotane sesquiterpene lactones, named expansolides C and D ( 1 and 2 ), together with two known compounds expansolides A and B ( 3 and 4 ), were isolated from the plant pathogenic fungus Penicillium expansum ACCC37275. The structures of the new compounds were established by detailed analyses of the spectroscopic data, especially 1D‐, 2D‐NMR, and HR‐ESI‐MS. In an in vitro bioassay, the epimeric mixture of expansolides C and D ( 1 and 2 ) (in a ratio of 2:1 at the temprature of the bioassay) exhibited more potent α‐glucosidase inhibitory activity (IC₅₀ =0.50 ± 0.02 mm ) as compared with the positive control acarbose (IC₅₀ = 1.90 ± 0.05 mm ). To the best of our knowledge, it was the first report on the α‐glucosidase inhibitory activity of bergamotane sesquiterpenes.     

Elsholblanosides A−D,Four New Oleuropeic Acid Derivatives Isolated from Elsholtzia blanda and Their Inhibition of NO Production in LPS-activated RAW264.7 Cells

Phytochemical investigation on the aerial parts of Elsholtzia blanda Benth. afforded four new oleuropeic acid derivatives ( 1 – 4 ), named as elsholblanosides A−D, respectively, together with 11 known compounds ( 5 – 15 ). Their structures were determined based on extensive analyses of HR-ESI-MS, 1D and 2D NMR, and ECD spectra. Compounds 1 – 4 and 14 showed moderate NO production inhibition in LPS-activated RAW264.7 cells with their IC₅₀ values ranging from 23.2 to 86.33 μM, compared to that of the positive control compound, dexamethasone, IC₅₀ value of 16.9 μM.     

Two New Sesquiterpene Derivatives from the Tunisian Endemic Ferula tunetana Pom.

A new sesquiterpene ester, tunetanin A ( 1 ), a new sesquiterpene coumarin, tunetacoumarin A ( 2 ), together with eight known compounds, i.e., coladin ( 3 ), coladonin ( 4 ), isosmarcandin ( 5 ), 13‐hydroxyfeselol ( 6 ), umbelliprenin ( 7 ) propiophenone ( 8 ), β‐sitosterol ( 9 ), and stigmasterol ( 10 ), were isolated from the roots of Ferula tunetana. Their structures were elucidated on the basis of extensive spectroscopic methods, including 1D‐ and 2D‐NMR experiments and MS analysis, as well as by comparison with published data. The cytotoxicity of compounds 1 – 7 towards two human colon cancer cell lines, HT‐29 and HCT 116, was evaluated. Compounds 3, 4 , and 6 showed weak cytotoxic activities.     

Bacillinaphthin A: A New Naphthohydroquinone from the Endophyte Bacillus subtilis NPROOT3

The present study explores the endophyte associated with the halophyte Salicornia brachiata for uncovering new biologically important compounds. Thus, HPLC-PDA guided chemical investigation of the ethyl acetate extract of the Bacillus subtilis NPROOT3 led to the isolation of a new compound named bacillinaphthin A ( 1 ) along with previously known rubinaphthin A ( 2 ). The structure of 2 was determined by a comparison of HR-ESI-MS, ¹H and ¹³C nuclear magnetic resonances (NMR) with those of reported data, whereas the structure of new compound 1 was elucidated by interpretation of 1D- and 2D-NMR and MS data. Bacillinaphthin ( 1 ) and rubinaphthin ( 2 ) feature 1,4-dihydroxy-2-naphthoic acid derivatives which have been isolated herein for the first time from the genus Bacillus. Bacillinaphthin ( 1 ) is a new congener of 2 with an additional succinic acid side chain attached to the sugar moiety. Production of succinoglycan compounds was reported to regulate symbiosis, hence the isolation of 1 exhibits an example of chemical ecology between the halophyte and its endophyte. In silico tools were used to assess the bioactive potential of both isolated molecules.     

A New Iridoid Dimer and Other Constituents from the Traditional Kurdish Plant Pterocephalus nestorianus Nábělek

Accompanied by other rare compounds, a new iridoid dimer, named kurdnestorianoside ( 1 ), showing an unprecedented secologanol configuration, has been isolated for the first time from the Kurdish medicinal plant Pterocephalus nestorianus, which is used in Kurdistan for treating oral diseases and inflammation. The structure of 1 was established from 1D‐ and 2D‐NMR spectroscopic data. Kaempferol 3‐O‐[3,6‐di‐O‐(E)‐p‐coumaroyl]‐β‐d ‐glucopyranoside ( 7 ) showed a remarkable antiproliferative activity against several human tumor cell lines.     

Antitumor Cembrane Diterpenoids from the South China Sea Soft Coral Lobophytum sp.

Two new highly functionalized cembrane diterpenoids named ximaolobophytolides A ( 1 ) and B ( 2 ) as minor components, together with seven related known compounds ( 3 – 9 ), have been isolated and identified from the Ximao soft coral Lobophytum sp. They were characterized by the presence of an α-methylene-γ-lactone moiety. Based on the comprehensive analyses of 1D and 2D NMR spectroscopic data, the absolute configurations of these two new compounds were elucidated by the combination of quantum mechanical (QM)-NMR and time-dependent density functional theory/electronic circular dichroism (TDDFT-ECD) calculation approaches. In the anti-tumor bioassays, compounds 3 – 9 showed moderate to significant inhibitory effects (IC₅₀ values ranging from 29.66 to 0.39 μM) against the proliferations of five tumor cells HEL, A549, H1975, MDA-MB-231, and H1299. It might be worthy to point out that compounds 4 , 7 , and 8 exhibited better anti-tumor activities than that of the positive control Doxorubicin.     

Three New Flavone Glycosides from Drymaria diandra B1.

In order to find new structural and biologically active compounds, the constituents from the whole plant of Drymaria diandra B1. （Caryophyllaceae） were investigated and three new flavone glycosides, named drymariatins B （1）, C （2）, and D （3）, were isolated by solvent partition, Si gel, sephadex LH-20, and Rp- 18 column chromatography. Using spectroscopic methods, including two-dimensional nuclear magnetic resonance analysis, the structures of these compounds were elucidated as 6-C-（2-deoxy-β-D-fucopyranosyl）- 5,7,4＇-trihydroxyl-flavone, 6-C-（2-deoxy-β-D-fucopyranosyl）-7-O-（β-D-glucopyranosyl）-5,4＇-dibydroxyl- flavone, and 6-C-（3-keto-β-digitoxopyranosyl）-7-O-（β-D-glucopyranosyl）-5,4＇-dihydroxyl-flavone.     

Koninginin W,a New Polyketide from the Endophytic Fungus Trichoderma koningiopsis YIM PH30002

A new compound named koninginin W ( 1 ) and four known polyketides ( 2 – 5 ) were isolated from endophytic fungus Trichoderma koningiopsis YIM PH30002 of Panax notoginseng. The structures of 1 - 5 , including absolute configuration of 1 , were elucidated on the detailed analysis of the HR-ESI-MS, 1D and 2D NMR, and X-ray crystallographic data. Koninginin W ( 1 ) presented weak antibacterial activity against Escherichia coli, Bacillus subtilis and Salmonella typhimurium.     

New Isocoumarins from a Cold‐Adapted Fungal Strain Mucor sp. and Their Developmental Toxicity to Zebrafish Embryos

Three new isocoumarin derivatives, mucorisocoumarins A–C ( 1 – 3 , resp.), together with seven known compounds, 4 – 10 , were isolated from the cold‐adapted fungal strain Mucor sp. (No. XJ07027‐5). The structures of the new compounds were identified by detailed IR, MS, and 1D‐ and 2D‐NMR analyses. It was noteworthy that compounds 1, 2, 4 , and 5 were successfully resolved by chiral HPLC, indicating that 1 – 7 should exist as enantiomers. In an embryonic developmental toxicity assay using a zebrafish model, compound 3 produced developmental abnormalities in the zebrafish embryos. This is the first report of isocoumarins with developmental toxicity to zebrafish embryos.     

Caryophyllene Sesquiterpenes from Pulicaria vulgaris Gaertn.: Isolation,Structure Determination,Bioactivity and Structure−Activity Relationship

A new caryophyllene, named pulicaryenne A ( 1 ), along with four other known caryophyllene derivatives ( 2 , 3 , 4 and 5 ) were isolated from the ethyl acetate extract of aerial parts of Pulicaria vulgaris Gaertn . (Asteraceae). All compounds were isolated for the first time from this species. Compound 2 was identified as a new epimer of a known caryophyllene derivative isolated previously from P. dysenterica. Their structures were established by spectroscopic means including NMR analysis (1D‐ and 2D‐NMR) and ESI‐TOF‐MS. All compounds were evaluated for their anticholinesterase, antityrosinase and cytotoxic activities against two human cell lines (A549 and HeLa). Results showed that compound 5 exhibited the highest cytotoxic effect against A549 and anticholinesterase activity with IC₅₀ values of 8.50±0.75 and 6.45±0.09 μg/mL, respectively. Furthermore, compound 5 showed also an interesting antityrosinase activity with percent inhibition value of 79.0±2.5 % at 50 μg/mL. The bioactivity and drug likeness scores of the isolated compounds 1–5 were calculated using Molinspiration software and discussed. These results may suggest that the five caryophyllene derivatives endowed with good biological properties, which could be used as bioactive alternatives in pharmaceutical preparations.     

New Spirostane from a Fungus Neohelicomyces hyalosporus and Its Bioactivity

A new spirostane, namely neohelicomyine B ( 1 ), together with six known steroids ( 2 – 7 ) were isolated from the fermentation of fungus Neohelicomyces hyalosporus. The structures of these compounds were elucidated by extensive analyses of spectroscopic methods including 1D and 2D NMR and HR-ESI-MS. The absolute configuration of 1 was confirmed by single-crystal X-ray diffraction. The bioactivities of compounds 1 – 7 were evaluated using cellular assays. Compound 1 displayed moderate cytotoxicity against HepG2 cells (hepatoma cells) with IC₅₀ value of 8.4±2.1 μM. Compound 7 also exhibited cytotoxic activity against HepG2 cells with the IC₅₀ value of 3.0±0.2 μM.