Chemical constituents from the roots of <Emphasis Type="Italic">Senecio scandens</Emphasis>

The chemical constituents of the roots of Senecio scandens Buch.-Ham. grown in the Funiu mountains in China have been investigated. Four compounds were isolated and identified as β−sitosterol (1), pentacosanoic acid (2), 19α-H lupeone (3), and sucrose (4). The structures of these compounds were elucidated on the basis of chemical and spectroscopic evidence. 19α-H Lupeone (3) was isolated as a single compound and its structure established unambiguously by the spectral method for the first time, and ¹H and ¹³C NMR data were assigned wholly by 1D and 2D NMR.     

New chalcanonol glycoside from the seeds of saw palmetto: antiproliferative and antioxidant effects

A new chalcanonol glycoside dimer, bis-O-[(I-4′) → (II-6′)]-α-hydroxyphloretin-2′-O-β-glucoside (1), in addition to six known compounds, namely ( ? )-epicatechin (2) and ( ? )-epiafzelechin (3), 4-hydroxybenzoic acid (4), protocatechuic acid (5), methylgallate (6), β-sitosterol (7) and β-sitosterol-3-O-glucoside (8), was isolated from the seeds of saw palmetto. The structures of the isolated compounds were established from the analysis of their MS and 1D and 2D NMR spectroscopic data. The antiproliferative activities of the isolated compounds towards PC3, the human prostate cancer cells were investigated. Amongst the isolated compounds, the new compound and the sterolic derivatives showed antiproliferative effects. Screening of the antioxidant effects of the isolated compounds by 2,2′-azino-bis-(3-ethylbenzthiazoline-6-sulfonic acid radical assay revealed that the isolated phenolics were active free radical scavengers.     

A new flavane acid from the fruits of Illicium verum

A new compound, illiciumflavane acid (1), along with 13 known compounds (2–14), were isolated from the fruits of Illicium verum Hook. F. Their structures were elucidated through various spectroscopic methods, including 1D NMR (¹H NMR, ¹³C NMR), 2D NMR (HMQC, HMBC and NOESY) and HRMS. The stereochemistry at the chiral centres was determined using CD spectrum as well as analyses of coupling constants and optical rotation data. Cytotoxicity evaluation of four compounds showed that illiciumflavane acid and (E)-1,2-bis(4-methoxyphenyl)ethene exhibited potential against A549 activities with IC₅₀ values of 4.63 μM and 9.17 μM, respectively.     

Two new polyacetylene glycosides from the roots of Codonopsis tangshen Oliv.

Two new polyacetylene glycosides, tangshenyne A (1) and tangshenyne B (2), along with six known polyacetylenes were isolated from an 85% MeOH extract of the roots of Codonopsis tangshen Oliv. The chemical structures of the new compounds were determined on the basis of extensive spectroscopic analyses, including UV, IR, 1D and 2D NMR (¹H–¹H COSY, HSQC and HMBC) and HR-ESI-MS.     

A new chromene from the fruiting bodies of Chroogomphus rutilus

A new chromene, acetic acid 2R-(4,8-dimethylnona-3,7-dienyl)-8-hydroxy-2-methyl-2H-chromen-6-yl ester (1), was isolated from the fruiting bodies of Chroogomphus rutilus, together with six known compounds (2–7). The structures of these compounds were identified based on 1D and 2D NMR, including ¹H–¹H COSY, HMQC and HMBC spectroscopic methods. Of these seven compounds, 2 and 3 showed cytotoxicity against HSC-T6, SK-Hep1 and A549 cell lines.     

Two new ionone glycosides from the roots of Rehmannia glutinosa Libosch.

Two new ionone glycosides, named frehmaglutoside G (1) and frehmaglutoside H (2), together with six known compounds, rehmapicroside (3), sec-hydroxyaeginetic acid (4), dihydroxy-β-ionone (5), trihydroxy-β-ionone (6), rehmaionoside A (7) and rehmaionoside C (8), were isolated from the 95% EtOH extract of the dried roots of Rehmannia glutinosa Libosch. Their structures were determined on the basis of extensive spectroscopic analyses, including HR-ESI-MS, UV, IR, 1D and 2D NMR (¹H–¹H COSY, HSQC, HMBC and NOESY) methods. The absolute configurations were confirmed via the circular dichroism spectra.     

Three New Pentacyclic Triterpenoids from Lantana camara

Three new pentacyclic triterpenes ursoxy acid ( 1 ), methyl ursoxylate ( 2 ), and ursangilic acid ( 3 ), along with three known compounds dotriacontanoic acid, oleanolic acid acetate, and tetracosanoic acid, were isolated from the aerial parts of Lantana camara Linn . Structures of the new compounds were elucidated by chemical transformation and spectral studies including 1D (¹H‐ and ¹³C‐NMR) and 2D (COSY‐45, NOESY, J‐resolved, HMQC, and HMBC) NMR spectroscopy.     

Studies of C-Glycosides. XIX. Selective Acetolysis of Primary Benzyl Ethers of C-Glucosides

Abstract

Selective acetolysis of primary benzyl ethers of O-benzyl C-glucosides has been investigated. β-anomers were shown to give fully acetylated compounds, while the α-anomers remained unchanged under the same conditions. The products were assigned by IR, ¹H NMR, ¹³C NMR, and EI-MS.     

Chemical Constituents of Brown Rice Grain (<Emphasis Type="Italic">Oryza sativa</Emphasis>)

One new compound 3,7,11,15,19-pentamethyl-9α,10α,11α,17α,18α-pentahydroxy-n-tetracosan-1-oxy-p-hydroxycaffeoate (oryzaterpenyl caffeoate) (1), together with three known fatty acids linoleic acid, stearic acid and myristic acid were isolated and identified from the rice grain of Oryza sativa. The structure of the new compound was elucidated by 1D and 2D NMR spectroscopic techniques (¹H-¹HCOSY, ¹H-¹³C HETCOR) aided by EI-MS, and IR spectra. __________ Published in Khimiya Prirodnykh Soedinenii, No. 6, pp. 535–537, November–December, 2005.     

Amberinone,a new guaianolide from Amberboa ramosa

The Amberboa is a medicinally important genus present in the family Asteraceae; members of this genus are mainly distributed in Pakistan and India. It has been used in different systems of traditional medicines for different diseases. Amberinone (1), a new sesquiterpene lactone, has been isolated from the ethyl acetate (EtOAc) soluble fraction of Amberboa ramosa together with chrysin (2), quercitine (3), eriodictyol (4) and keamferol (5). This is the first report of these compounds from this species. The structures of the isolated compounds have been elucidated by 1D and 2D ¹H ¹³C NMR spectroscopy.     

Secondary metabolites from Triclisia gilletii (De Wild) Staner (Menispermaceae) with antimycobacterial activity against Mycobacterium tuberculosis

Triclisinone (2), a new ochnaflavone derivative, was isolated from the aerial parts of Triclisia gilletii, along with known drypemolundein B (1) and eight other known compounds. The chemical shifts of drypemolundein B (1) have been partially revised based on reinterpretation of NMR spectroscopic data. The eight other secondary metabolites are composed of: (+)-nonacosan-10-ol (3); stigmasterol (4), 3-O-β-D-glucopyranosylsitosterol (5), 3-O-β-D-glucopyranosylstigmasterol (6); oleanic acid (7); myricetin (8), quercetin (9) and 3-methoxyquercetin (10). Their structures were elucidated using IR, MS, NMR 1D and 2D, ¹H and ¹³C and comparison with literature data. Furthermore, compounds 1, 2, 5, 6, 8, 9 and the crude extract were tested against Mycobacterium tuberculosis. Compounds 1, 2, 8 and 9 displayed moderate to very good activity against resistant strain (codified AC 45) of M. tuberculosis with minimum inhibitory concentrations MICs ranging from 3.90 to 62.5 μg/mL.     

Separation of xanthones and a biphenyl fromKielmeyera coriacea by centrifugal partition chromatography

Summary Eight xanthones and a biphenyl have been isolated from the dichloromethane extract ofKielmeyera coriacea (Guttiferae) stem bark by a combination of centrifugal partition chromatography and gel filtration on Sephadex LH-20, with HPLC-UV monitoring of fractions. The structures of the isolated compounds (Figure 1) were established by spectroscopic methods (UV, EI-MS, D/CI-MS,¹H NMR,¹³C NMR).     

A new lactam alkaloid from Portulaca oleracea L. and its cytotoxity

A new lactam alkaloid named oleraciamide D (1), indentified as (5R)-4-(3-methoxy-4-hydroxyphenyl)-5-(4-hydroxyphenyl)-5,6-dihydropyridin-2(1H)-one, together with five known compounds, indole-3-aldehyde (2), portulacatone (3), N-trans-feruloyloctopamine (4), N-trans-feruloyl-3′-O-methyldopamine (5) and N-trans-feruloyltyramine (6) were isolated from Potulaca oleracea L. Among them, indole-3-aldehyde (2) was isolated from the medicine for the first time. The structure of the new alkaloid was elucidated via UHPLC-ESI-Q-TOF/MS, 1D NMR and 2D NMR. The five known compounds were established by comparing the ¹H-NMR and ¹³C NMR with the reported literature. Oleraciamide D (1) showed cytotoxicity against SH-SY5Y cells when concentration at 50 uM by CCK-8 method.     

Chemical constituents from Gueldenstaedtia verna and their anti-inflammatory activity

A new triterpenoid glycoside (1) and 15 known compounds (2–16) were isolated from the whole plants of Gueldenstaedtia verna. The new compound (1) was identified as complogenin 22-O-β-d-glucopyranoside by extensive spectroscopic techniques including 1D (¹H and ¹³C) and 2D NMR experiments (HSQC, HMBC and NOESY), HR-DART-MS and chemical methods. Most of the isolates were evaluated for their inhibitory activities on LPS-induced NO production in RAW 264.7 cells. The inhibitory effects of the active compounds, sulphuretin (8) and (22E,24S)-5α,8α-epidioxy-24-methyl-cholesta-6,9(11),22-trien-3β-ol (13), on the production of pro-inflammatory mediators (including IL-6, IL1β and PGE₂) were further estimated in vitro by ELISA in RAW 264.7 macrophages.     

Qualitative and quantitative analysis of chemical constituents of Ptychopetalum olacoides Benth

Ptychopetalum olacoides is a folk medicinal plant for health care in market, especially in Brazil. Fourteen known compounds were isolated from P. olacoides and their chemical structures were elucidated by extensive spectroscopic data, including 1D NMR, 2D NMR, UV, IR and HR-ESI-MS. The 14 known compounds were identified as N-trans-feruloyl-3,5-dihydroxyindolin-2-one (1), magnoflorine (2), menisperine (3), 4-coumaroylserotonin (4), moschamine (5), luteolin (6), 4′-methoxyluteolin (7), 3-methoxyluteolin (8), 3, 7-dimethoxyluteolin (9), caffeic acid (10), ferulic acid (11), vanillic acid (12), syringic acid (13) and ginsenoside Re (14). To our knowledge, compounds (1–6, 13–14) were isolated from the plant for the first time. Additionally, quantitative analysis results indicated that calibration equations of compounds (1–3, 6, 9, 11–13) exhibited good linear regressions within the test ranges (R² ≥ 0.9990) and magnoflorine and menisperine were the major constituents in the barks of P. olacoides. The contents of magnoflorine and menisperine accounted for 75.96% of all analytes. However, the content of phenolic components was smaller and the highest content was no more than 1.04 mg/g. Collectively, these results suggested that alkaloids are the dominant substances in P. olacoides, which can make a difference for the quality control and further use of P. olacoides.     

Nepetadiol,a new triterpenediol from <Emphasis Type="Italic">Nepeta suavis</Emphasis>

Nepetadiol, a new tetracyclic triterpene diol (1), was isolated from the chloroform-soluble portion of the whole plant of Nepeta suavis. In addition, lawsonin (2) and lawsonic acid (3) have been isolated for the first time from this species. The structures of the isolated compounds were based on ¹H and ¹³C NMR spectra, including two-dimensional NMR techniques like COSY, HMQC, and HMBC, and comparison with the literature data.     

A new benzofuran from Artemisia halodendron Turcz. ex Bess.

A new benzofuran, methyl (2S,2″S,3′E)-[2-(1″-acetoxypropan-2-yl)-2,3-dihydrobenzofuran-5-yl]acrylate (1), and 13 known compounds (2–14) were isolated from an ethanol extract of Artemisia halodendron Turcz. ex Bess. The chemical structures of these compounds were determined by 1D and 2D NMR (¹H-¹H COSY, HMBC, HMQC and NOESY) and HR-ESI-MS spectra, and results were compared with data from the literature. The effects of compounds 1–14 were measured on NF-κB activation, with compounds 2 and 3 exhibiting inhibitory activities against TNF-α-induced NF-κB reporter gene expression in HeLa cells from 10 to 100 μM.     

New ent-kaurane diterpenoid dimer from Pulicaria inuloides

A new naturally occurring ent-kaurane diterpenoid dimer, 15β, 15′β-oxybis (ent-kaur-16-en-19-oic acid) (1) along with six known compounds, 15β-hydroxy-ent-kaur-16-en-19-oic acid (2), 15β-hydroxy-ent-kaur-16-en-19-oate-β-d-glucopyranoside (3), 6-hydroxykaempferol-3, 7-dimethyl ether (4), quercetagetin 3, 7, 3′-trimethyl ether (5), β-sitosterol (6) and β-sitosterol glucoside (daucosterol) (7) were isolated from the aerial parts of Pulicaria inuloides DC. Compounds 2–5 were isolated for the first time from genus Pulicaria. The structures of compounds 1–7 were established on the basis of extensive 1D and 2D NMR spectroscopic techniques in combination with ESI-MS. The antimicrobial activity of the isolated compounds was evaluated against Staphylococcus aureus, Escherichia coli and Candida albicans. Sulphorhodamine B cytotoxic assay against HepG2 (liver cancer) cell line and ABTS antioxidant assay were carried out.     

New glycosidic and other constituents from hulls of <Emphasis Type="Italic">Oryza sativa</Emphasis>

Three new compounds, 4-hydroxymethylene-7-(9,9,13-trimethylcyclohexyl)-heptanyl-3′,7′,7′-trimethylcyclohexa-2′,4′-dien-1′-oate (1), 1-(n-hexadec-7-enoxy)-6-(n-octadecanoxy)-β-D-glucopyranoside (2), and (Z)-12-hydroxy-9-octadecenoic acid-12-β-D-glucopyranoside (3), along with the known compound hexacosanoic acid (4), were isolated and identified from the rice hulls of Oryza sativa. Their structures were elucidated by 1D and 2D NMR spectroscopic techniques (¹H-¹H COSY, ¹H-¹³C HETCOR, DEPT) aided by EIMS, FABMS, HRFABMS, and IR spectra. Published in Khimiya Prirodnykh Soedinenii, No. 4, pp. 344–347, July–August, 2007.     

New cyclic tetrapeptide from the coral-derived endophytic bacteria Brevibacterium sp. L-4 collected from the South China Sea

One new cyclic tetrapeptide cyclic-(Tyr-Ala-Leu-Ser) (1) along with four natural compounds firstly obtained 3H-imidazole-4-carboxylic acid (2), 2-methyl-3H-imidazole-4-carboxylic acid (3), 3-ethylidene-6-isopropyl-piperazine-2,5-dione (4), and 3-isobutylidene-6-methyl piperazine-2,5-dione (5) have been isolated from the coral derived endophytic bacteria Brevibacterium sp. L-4 collected from the South China Sea. Their structures were elucidated through spectroscopic techniques including NMR (1D and 2D), MS, and EA, and their relative configurations were also assigned by NMR analysis.