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The phytochemical study of the 70% ethanol extract of the aerial parts of Diplotaxis erucoides afforded one new flavonoid glycoside, namely kaempferol-3-O-[α-L-rhamnopyranosyl-(1→2)-β-D-xylopyranoside]-7-O-α-L-rhamnopyranoside (1), named diploerucoside A and seven known compounds including one flavonoid (2), one phenolic glycoside (3), one monoterpene (4), one triterpene (5), one sitosterol (6) and two monoglycerolipids (7, 8). Their structures were established by extensive spectroscopic analysis including 1 D- and 2 D-NMR (1H, 13C, 1H-1H COSY, HSQC and HMBC), mass spectrometry (HR-ESI-MS) and by comparison with the data reported in the literature. [ABSTRACT FROM AUTHOR]

A new alkaloid pyrroloquinolone A (1), along with fifteen known compounds 2–16 were isolated from the petroleum ether, EtOAc and n-BuOH extracts of the whole plant Atractylis cancellata L. Their structures were elucidated on the basis of extensive spectroscopic analysis including 1D- and 2D-NMR and HR-ESI-MS techniques. This is the first report of alkaloids in the genus Atractylis. Some of the isolated compounds and extracts were evaluated for their antioxidant potential (scavenging activity of DPPH and ABTS radicals, and reducing Fe+3 and Cu+2 power assays) and acetylcholinesterase and butyrylcholinesterase inhibitory activities. Compounds 8 and 11 showed good antioxidant capacity compared to ascorbic acid, BHA, and BHT used as standards, whereas compounds 1 and 2 exhibited good anticholinesterase activities compared to galantamine used as standard. [ABSTRACT FROM AUTHOR]

A new C-glycosylflavone, identified as 6"'-O-acetylisospinosin (1), was isolated from the aerial parts of Cladanthus mixtus together with 30 known compounds. The structures of these compounds were established by interpretation of their spectral data, mainly UV, 1D and 2D NMR spectroscopic methods including (1H and 13C NMR, COSY, ROESY, HSQC and HMBC experiments), ESI-MS, and by comparison with the literature data. [ABSTRACT FROM AUTHOR]

• Thirty-two glycosides including flavonoids, phenolic acids and coronillins were identified. • 13C NMR-based dereplication was used to identify major compounds of the extracts. • A bioactivity-guided fractionation lead to the isolation of three new triglycosylated flavonoids. • The structures of compounds were determined by 1D and 2D NMR spectra and MS spectra. • Three quercetin glycosides exhibited a significant radical-scavenging activity. This study presents the bio-guided chemical investigation of a 80% methanol extract of Hippocrepis emerus flowers, a perennial non-climbing shrub. Liquid-liquid partitioning in solvents of increasing polarity combined to biological screening enabled to determine the EtOAc and n -BuOH soluble fractions as the most active parts of the extract. These fractions were chemically profiled by using a 13C NMR-based dereplication method, resulting in the identification of twenty-six compounds. The dereplication process was completed by purification of some unknown or minor compounds of the n -BuOH fraction. Three new glycosylated flavonoids, namely kaempferol-3- O -β- d -glucopyranosyl-7- O -β- d -glucopyranosyl-(1→3)-α- l -rhamnopyranoside (1), isorhamnetin-3- O -β- d -glucopyranosyl-7- O -β- d -glucopyranosyl-(1→3)-α- l -rhamnopyranoside (2) and quercetin-3- O -β- d -glucopyranosyl-7,4′- O -α- l -dirhamnopyranoside (3), together with twelve known compounds (4 – 15) were isolated. Their structures were elucidated by spectroscopic methods including NMR, HR-ESI-MS and UV. The antioxidant activity of fractions and isolated compounds were evaluated using DPPH and hydroxyl radical scavenging and CUPRAC assays. In parallel, their inhibitory properties against mushroom tyrosinase and human neutrophil elastase enzymes were assessed. Three quercetin glycosides exhibited a significant radical-scavenging activity and two flavonoids showed a moderate elastase inhibitory activity. [ABSTRACT FROM AUTHOR]

A previously undescribed triterpenoid saponin, 3-O-[α-l-rhamnopyranosyl-(1→2)-{β-d-glucopyranosyl-(1→6)-}β-d-galactopyranosyl-(1→2)-β-d-glucuronopyranosyl]-sophoradiol (1), in addition to twenty-nine known constituents (2–30) were isolated from the aerial parts of Genista numidica Spach. Structures elucidation was performed by comprehensive 1D- and 2D-NMR analyses and HRESIMS. The extracts, fractions and isolated compounds were evaluated for their antibacterial, antioxidant and tyrosinase inhibitory activities. The experimental findings indicated that genistin (16), isosalipurpol (27), and koaburaside (29) have moderate to low antibacterial activity against E. faecalis, S. aureus, S. epidermidis and P. aeruginosa bacteria with MICs ranging from 31.2 to 125 μg/mL. Compounds 19 and 27 exhibited a good antiradical activity potential (IC50 11.8 and 11.1 μg/mL, respectively). Only compounds 23, 27 and 28 exhibited low inhibitory effect against mushroom tyrosinase (IC50 from 90.2 to 225.6 μg/mL). [ABSTRACT FROM AUTHOR]

From the aerial parts of Salvia barrelieri Etl. (Lamiaceae), 12 compounds including a new triterpene, 3β-acetoxy-olean-18-ene-2α-ol, were isolated. Their structures were established by the combination analyses of spectroscopy including 1D-, 2D-NMR and HRESIMS and in comparison with the reported data in the literature. The antibacterial activity of these compounds was evaluated by bioautography on Staphylococcus aureus followed by the determination of MIC values by serial dilution technique against five bacteria. Three compounds were active against Enterococcus faecalis, S. aureus, Staphylococcus epidermidis, Escherichia coli and Pseudomonas aeruginosa (MIC 15.1 to 125 μg/mL). Two compounds showed moderate DPPH radical scavenging activity (IC50 79.1 and 21.2 μg/mL). These compounds did not show significant tyrosinase inhibitory activities (IC50> 1.5 mg/mL). Their cytotoxic activity was evaluated against promyelocytic leukaemia (HL60), human erythromyeloblastoid leukaemia (K562) and fibrosarcoma (HT1080) cell lines and four compounds exhibited a moderate cytotoxic activity (IC50 28.75 to 85.0 μM). [ABSTRACT FROM AUTHOR]

This is the first study on the phytochemistry and antioxidant activity of Ferula longipes Coss. ex Bonnier and Maury (Apiaceae). A new flavonoid quercetin-3-O-α-L-rhamnopyranoside-7-O-ß-D-[2-O-caffeoyl]-glucopyranoside (1), along with 10 known compounds kaempferol-3-O-α-L-rhamnopyranoside (2), quercetin-3-O-α-L-rhamnopyranoside (3), kaempferol-3-O-ß-D-glucopyranoside-7-O-α-L-rhamnopyranoside (4), isorhamnetin-3-O-α-L-rhamnopyranoside-7-O-ß-D-glucopyranoside (5), quercetin-3-O-α-L-rhamnopyranoside-7-O-ß-D-glucopyranoside (6), isorhamnetin-3,7-di-O-β-D-glucopyranoside (7), apigenin (8), apigenin-7-O-ß-D-glucopyranoside (9), 3,5-dicaffeoylquinic acid (10), deltoin (11) were isolated from the aerial parts of Ferula longipes Coss. Structures elucidation was performed by comprehensive 1D and 2D NMR analyses, mass spectrometry and by comparison with literature data. The compounds 1, 3, 4, 6, 7 and 10 were evaluated for their antioxidant activity, compound 1 exhibited the best antiradical activity potential and showed IC50 and A0.5 values 5.70, 7.25, 5.00, and 2.63 μg/mL towards DPPH free radical-scavenging, ABTS, CUPRAC, and reducing power assays, respectively compared with BHA, BHT and ascorbic acid which were used as positive controls. [ABSTRACT FROM AUTHOR]

A new 2-alkylhydroquinone glucoside, 1-O-β-d-glucopyranosyl-1,4-dihydroxy-2-((E) 2-oxo-3-butenyl)benzene (1), in addition to nine known compounds were isolated from the aerial parts of Phagnalon saxatile (L.) Cass. (Asteraceae). Their structures were identified based on spectroscopic methods including 1D and 2D NMR, mass spectrometry (HR-ESI-MS), UV spectral analyses and by comparison with literature data. The cytotoxic activity of three isolated compounds (1-3) was evaluated against fibrosarcoma (HT1080), human lung cancer (A549) and breast cancer (MCF7) cell lines. [ABSTRACT FROM AUTHOR]

This study presents the chemical profile investigation of a 70% ethanol extract obtained from Scabiosa stellata , a medicinal herbaceous traditionally used to treat heel cracks. A 13 C NMR-based dereplication methodology was firstly applied on centrifugal partition chromatography-generated fractions in order to quickly identify the major compounds of the extract. The dereplication process was then completed by semi-preparative high-performance liquid chromatography in order to identify unknown or minor compounds. Two new bis-iridoids, namely 7- O -caffeoyl-sylvestroside I ( 1 ) and 7- O -( p -coumaroyl)-sylvestroside I ( 2 ), together with ten known compounds ( 3 − 12 ) were isolated. Their structures were elucidated by spectroscopic methods including NMR and HR-ESI-MS. The antibacterial, anti-tyrosinase and DPPH radical scavenging activities of the crude extract, fractions, and isolated compounds were evaluated. A significant antibacterial activity was observed for nine isolated compounds, particularly 1 and 2 which yielded MIC values of 31.2 μg/mL against Enterococcus faecalis and 62.5 μg/mL against Staphylococcus epidermidis . The cytotoxic activity of these new bis-iridoids was evaluated on a fibrosarcoma cell line (HT1080) and only compound 1 exhibited a moderate cytotoxic activity (IC 50 35.9 μg/mL). [ABSTRACT FROM AUTHOR]

A previously undescribed phenolic sulphate ester, potassium 34-dihydroxy-3-methoxybenzoic acid methyl ester-5-sulphate (1), along with nine known flavonoids, kaempferol-3-O-potassium sulphate-4′,7-dimethyl ether (2), kaempferol-4′,7-dimethyl ether (3), rhamnocitrin-3-O-potassium sulphate (4), rhamnocitrin (5), kaempferol (6), quercetin (7), afzelin (8), quercetin-3-O-α-l-rhamnopyranoside (9) and luteolin-3′-O-potassium sulphate (10) were isolated from the aerial parts of Tamarix balansae. Structures elucidation was performed by comprehensive 1D and 2D NMR analyses, mass spectrometry and by comparison with literature data. The antibacterial assay against Enterococcus faecalis, Staphylococcus aureus, Staphylococcus epidermidis, Escherichia coli and Pseudomonas aeruginosa bacteria showed a good activity for 2, 3, 7 and 9, with MICs ranging from 62.5 to 250 μg/mL. The abilities of these compounds to scavenge the DPPH were evaluated. Compounds 1, 7, 9 and 10 exhibited a good antiradical activity potential with IC50 values ranging from 3.0 to 115.5 μg/mL, compared with ascorbic acid (IC50 7.4 μg/mL) which was used as positive control. [ABSTRACT FROM AUTHOR]

Context:Phytochemical study and biological potential ofEvax pygmaea(L.) Brot. (Asteraceae) are reported for the first time. Objective:To identify the secondary metabolites ofEvax pygmaeaand to determine its antioxidant, antibacterial and cytotoxic activities. Materials and methods:Dried aerial parts (1 kg) were macerated in 70% MeOH (5 L) during 72 h. The concentrated hydromethanolic extract was subjected to extractions with chloroform (3 × 300 mL), ethyl acetate (3 × 300 mL) andn-butanol (3 × 300 mL), successively. VLC of combined ethyl acetate (EAEP) andn-butanol (BEP) fractions was followed by column purifications. Antioxidant activity was investigated using DPPH, CUPRAC, and metal chelating, β-carotene/linoleic acid and ABTS assays. Agar method was used in the antibacterial study. Cytotoxic activity was determined by Brine shrimp lethality test in DMSO and ethanol, at varying concentrations (2, 1 and 0.2%) and (1, 0.2 and 0.1%) successively. Results:Quercetin (1), isorhamnetin 3-O-β-d-xyloside (2), isorhamnetin 3-O-β-d-glucoside (3), quercetin 3-O-β-d-glucoside (4), quercetin 7-O-β-D-glucoside (5), patuletin 3-O-β-d-glucoside (6) were isolated from for the first time fromEvaxgenus. The EAEP was the most active in ABTS (IC50: <3.125 μg/mL) assay whereas the BEEP exhibited the highest activity in the β-carotene/linoleic acid assay (IC50: <3.125 μg/mL). The EAEP and BEP exhibited good antibacterial activity (MIC: 40–80 µg/mL). The plant did not show any toxicity (LD50>80 µg/mL). Discussion and conclusions:Six flavonoids were isolated for the first time fromEvax pygmaeawhich exhibited good antioxidant and antibacterial activities. [ABSTRACT FROM PUBLISHER]

A new phorbol-type diterpene ester, 4,20-dideoxy-4α-phorbol-12β-acetate-13α-isobutyrate, in addition to 11 known compounds were isolated from the latex and roots of Euphorbia clementei Boiss. Structure elucidation was performed by comprehensive 1D and 2D NMR analyses (¹H and 13C NMR, COSY, ROESY, HSQC and HMBC experiments), mass spectrometry (HR-ESI-MS) and by comparison with literature data. The inhibitory activity of all isolated compounds was evaluated against promyelocytic leukemia HL60 and human erythromyeloblastoid leukemia K562 cell lines and seven of these compounds exhibited a weak cytotoxicity with IC50 values ranging from 40 to 97 µM. [ABSTRACT FROM AUTHOR]

A new sulfonyl flavonol glucoside, 5,7,4′,5′-tetrahydoxyflavonol 2′-[propanoic acid-(2″′-acetoxy-1″′-sulfonyl)]-5′-O-β-d-glucopyranoside (1) was isolated from the aerial parts ofCotula anthemoidesL. in addition to 15 known compounds (2–16). The structure elucidation of these compounds was based on analyses of spectroscopic data including 1D-, 2D-NMR and HR-ESI-MS techniques and by comparing their NMR data with those reported in the literature. These compounds were evaluated for their DPPH radical scavenging and tyrosinase inhibitory activity. Compound6showed a high DPPH radical scavenging with EC50value of 9.1 ± 0.4 μM. Compound11,9and1exhibited a mild tyrosinase inhibitory activity with IC50values of 85 ± 0.8, 95 ± 1.5 and 100 ± 0.5 μM, respectively. [ABSTRACT FROM PUBLISHER]

Context:The phytochemical study and biological activities ofAstragalus armatusWilld. subsp.numidicus(Fabaceae) pods, an endemic shrub of Maghreb, are reported. Objective:This study isolates the secondary metabolites and determines the bioactivities ofAstragalus armatuspods. Materials and methods:The chloroform, ethyl acetate andn-butanol extracts of hydro-ethanolic extracts were studied. Antioxidant activity was investigated using DPPH and ABTS radical scavenging, CUPRAC and ferrous chelating assays at concentrations ranging from 3 to 200 μg/mL. Anticholinesterase activity was determined against acetylcholinesterase and butyrylcholinesterase enzymes at 50, 100 and 200 μg/mL. Antibacterial activity was performed according to minimum inhibitory concentration (MIC) method. Carbon clearance method in albino mice was used for the phagocytic activity at concentrations 50, 70 and 100 mg/kg body weight. Spectroscopic techniques were used to elucidate the compounds. Results:Ethyl acetate extract afforded a flavonoid (1) while then-butanol extract gave four flavonoids (2–5), a cyclitol (6) and a cycloartane-type saponin (7). The ethyl acetate extract exhibited highest antioxidant activity in DPPH (IC50: 67.90 ± 0.57 μg/mL), ABTS (IC50: 11.30 ± 0.09 μg/mL) and CUPRAC (A0.50: 50.60 ± 0.9 μg/mL) assays. The chloroform extract exhibited the best antibacterial activity againstStaphylococcus aureus,Escherichia coliandPseudomonas aeruginosa,each with 80 μg/mL MIC values. Then-butanol extract enhanced phagocytic activity. Discussion and conclusion:Isorhamnetin (1), isorhamnetin-3-O-α-l-rhamnopyranosyl-(1 → 6)-β-d-galactopyranoside (2), isorhamnetin-3-O-β-d-apiofuranosyl-(1 → 2)-[α-l-rhamnopyranosyl-(1 → 6)]-β-d-galactopyranoside (3), kaempferol-3-O-(2,6-di-O-α-l-rhamnopyranosyl)-β-d-galactopyranoside (4), kaempferol-3-O-(2,6-di-O-α-l-rhamnopyranosyl)-β-d-glucopyranoside (5), pinitol (6) and cyclomacroside D (7) were isolated whereas1, 2, 6and7are reported for the first time fromA. armatus. [ABSTRACT FROM AUTHOR]

A new pentacyclic triterpenoid glucoside, together with fourteen known compounds, was isolated from the roots of Combretum racemosum . Combretaceae). The structure of the new compound was established as 28- O - β - d -glucopyranosyl-2 α ,3 β ,21 β ,23-tetrahydroxyolean-18-en-28-oate ( 1 ) on the basis of detailed spectroscopic data including MS, 1D, and 2D NMR. The inhibitory activity of compounds 1 – 15 against promyelocytic leukemia HL-60 and human erythromyeloblastoid leukemia K562 cell lines was evaluated. Compounds 11 (3- O - β -acetyl-ursolic acid), 14 (betulinic acid), and 15 (quadranoside II) exhibited significant cytotoxicity, with IC 50 values of 13 to 50 μM. Among the isolated triterpenes, compounds 1 , 3 (arjungenin), 5 (terminolic acid), and 11 exhibited moderate antibacterial activity against Staphylococcus aureus , Escherichia coli and Enterococcus faecalis (MICs within a range of 64 and 256 μg/mL). [ABSTRACT FROM AUTHOR]

Ten phenylalkyl-substituted iminosugars ( 1 – 10 ) and a cinnamic acid derived glucoside ( 11 ) were isolated from the roots of Glyphaea brevis (Malvaceae). Their structures were elucidated by 1D and 2D NMR analysis, as well as by HR-ESIMS. Compounds 1 – 10 retain an unprecedented structure composed of an iminosugar-like core identified as 1-deoxyfuconojirimycin in glyphaeaside A 1 –A 4 ( 1 , 2 , 5 , 6 ), 1-deoxygalactonojirimycin in glyphaeaside B 1 –B 5 ( 3 , 4 , 7 – 9 ) or 1-deoxynojirimycin in glyphaeaside C ( 10 ), substituted by a β - d -glucopyranose in compounds 2 , 4 , 6 and 9 . These compounds feature a di-, tri- or tetra-hydroxylated nine-carbon chain at the pseudo-anomeric position, substituted by a terminal phenyl group. All alkyl C -iminosugars displayed potent and selective inhibition towards β -glucosidase with IC 50 values ranging from 0.15 to 68 μM. Compound 10 with an 1-deoxynojirimycin backbone was the most active and was found to act as a competitive inhibitor with K i = 31 nM, therefore emerging as one of the most potent inhibitor of β -glucosidase reported to date. Inhibition of β -mannosidase was observed with compounds 1 , 3 , 7 and 10 , but only weak inhibition could be detected with the alkyl- C -iminosugars on the other tested glycosidases ( α -glucosidase, α -fucosidase, α - and β -galactosidase). [ABSTRACT FROM AUTHOR]

Alfalfa (Medicago sativa) has been used to cure a wide variety of ailments. However, only a few studies have reported its anticancer effects. In this study, extracts were obtained from alfalfa leaves and their cytotoxic effects were assessed on several sensitive and multidrug-resistant tumor cells lines. Using the mouse leukaemia P388 cell line and its doxorubicin-resistant counterpart (P388/DOX), we showed that the inhibition of cell growth induced by alfalfa leaf extracts was mediated through the induction of apoptosis, as evidenced by DNA fragmentation analysis. The execution of programmed cell death was achieved via the activation of caspase-3, leading to PARP cleavage. Fractionation of toluene extract (To-1), the most active extract obtained from crude extract, led to the identification of 3 terpene derivatives and 5 flavonoids. Among them, (-)-medicarpin, (-)-melilotocarpan E, millepurpan, tricin, and chrysoeriol showed cytotoxic effects in P388 as well as P388/DOX cells. These results demonstrate that alfalfa leaf extract may have interesting potential in cancer chemoprevention and therapy. [ABSTRACT FROM PUBLISHER]

Sialidases, also called neuraminidases, are involved in several human pathologies such as neurodegenerative disorders, cancers, as well as infectious and cardiovascular diseases. Several studies have shown that neuraminidases, such as neuraminidase 1 (NEU-1), may be promising pharmacological targets. Therefore, the discovery of new selective inhibitors of NEU-1 are necessary to better understand the biological functions of this sialidase. In the present study, we describe the isolation and characterization of nine known compounds from Olyra latifolia L. leaves. This plant, known to have several therapeutic properties, belongs to the family of Poaceae and is found in the neotropics and in tropical Africa and Madagascar. Among the purified compounds, feddeiketone B, 2,3-dihydroxy-1-(4-hydroxy-3,5-diméthoxyphényl)-l-propanone, and syringylglycerol were shown to present structural analogy with DANA, and their effects on membrane NEU-1 sialidase activity were evaluated. Our results show that they possess inhibitory effects against NEU-1-mediated sialidase activity at the plasma membrane. In conclusion, we identified new natural bioactive molecules extracted from Olyra latifolia as inhibitors of human NEU-1 of strong interest to elucidate the biological functions of this sialidase and to target this protein involved in several pathophysiological contexts. [ABSTRACT FROM AUTHOR]

Five undescribed ursane-type triterpenes, identified as 1 β ,3 β ,15 α -trihydroxy-urs-9(11)-12-diene (1), 1 β ,3 β ,15 α ,28-tetrahydroxy-urs-9(11),12-diene (2), 1 β ,3 β -dihydroxy-urs-9(11),12-dien-28-al (3), 1 β ,3 β ,7 β ,15 α ,28-pentahydroxy-urs-12-ene (4), and 1 β ,3 β ,15 α -trihydroxy-urs-11-en-28-al (5), together with five known compounds (6 – 10), were isolated from the acetone extract of the dried aerial parts of Salvia argentea L. var. aurasiaca (Pomel) Batt. et Trab. (Lamiaceae). Structures were elucidated on the basis of extensive spectroscopic analysis including HR-ESI-MS, 1D- and 2D-NMR techniques and comparison with literature data. The antibacterial evaluation of compounds 1 – 10 of the acetone extract of the dried aerial parts, in addition to nine compounds (11 – 19) previously isolated from the extract of the fresh aerial parts, by bioautography on Staphylococcus aureus followed by the determination of MIC values of active compounds by serial dilution technique against five bacteria, revealed that two compounds have an antibacterial effect comparable to antibiotics. The cytotoxic activity evaluation of compounds 1 – 19 showed that Six compounds exhibited an antiproliferative activity against K562 and HT1080 cells with IC 50 values ranging from 30.25 to 70.32 μM. Unlabelled Image [ABSTRACT FROM AUTHOR]

Chemical investigation of the aerial parts of Pentzia monodiana Maire led to the isolation and identification of one sesquiterpene lactone glucoside of the guaianolide type (dihydropseudoivalin-4- O - β -d-glucopyranoside), along with nine known compounds including one diterpenoid, two sesquiterpenoids, three lignanes and three flavonoids. Their structures were established on the basis of spectroscopic analysis. All these compounds were evaluated for their DPPH radical scavenging and tyrosinase inhibitory activities. Only lignanes and flavonoids showed good to moderate DPPH radical scavenging activity with EC 50 ranging from 10.6 to 47.5 μM. The new sesquiterpene lactone glucoside showed low tyrosinase inhibitory activity whereas the isolated lignanes and flavonoids exhibited a moderate activity with IC 50 ranging from 45.4 to 97.2 μM).

A new alkaloid pyrroloquinolone A ( 1 ), along with fifteen known compounds 2-16 were isolated from the petroleum ether, EtOAc and n -BuOH extracts of the whole plant Atractylis cancellata L. Their structures were elucidated on the basis of extensive spectroscopic analysis including 1D- and 2D-NMR and HR-ESI-MS techniques. This is the first report of alkaloids in the genus Atractylis . Some of the isolated compounds and extracts were evaluated for their antioxidant potential (scavenging activity of DPPH and ABTS radicals, and reducing Fe +3 and Cu +2 power assays) and acetylcholinesterase and butyrylcholinesterase inhibitory activities. Compounds 8 and 11 showed good antioxidant capacity compared to ascorbic acid, BHA, and BHT used as standards, whereas compounds 1 and 2 exhibited good anticholinesterase activities compared to galantamine used as standard.

A new 2-alkylhydroquinone glucoside, 1-O-β-d-glucopyranosyl-1,4-dihydroxy-2-((E) 2-oxo-3-butenyl)benzene (1), in addition to nine known compounds were isolated from the aerial parts of Phagnalon saxatile (L.) Cass. (Asteraceae). Their structures were identified based on spectroscopic methods including 1D and 2D NMR, mass spectrometry (HR-ESI-MS), UV spectral analyses and by comparison with literature data. The cytotoxic activity of three isolated compounds (1-3) was evaluated against fibrosarcoma (HT1080), human lung cancer (A549) and breast cancer (MCF7) cell lines.

Fourteen new triterpenoid saponins (1-14) were isolated from the methanol extract of the fruits of Caryocar villosum along with 10 known saponins. Their structures were established on the basis of extensive NMR (1H, 13C, COSY, TOCSY, ROESY, HSQC, and HMBC) and ESIMS studies. The toxicity of the methanolic extracts of the peel and the pulp of fruits and the crude saponin fraction of the peel was assessed using the Artemia salina test. The antimicrobial activities of caryocarosides IV-21 (14), II-1 (16), III-1 (17), and IV-9 (20) and of saponin 23 were also studied in vitro on Escherichia coli, Staphylococcus aureus, Pseudomonas aeruginosa, Mycobacterium smegmatis, and Enterococcus faecalis bacteria.

Twenty-one new triterpenoid saponins, named caryocarosides (1-21), glycosides of 2beta-hydroxyoleanolic acid, hederagenin, bayogenin, and gypsogenic acid, have been isolated from the fruits of Caryocar glabrum along with nine known triterpenoid saponins (22-30) that are described for the first time from a plant in the Caryocaraceae. Their structures were established by 1D and 2D NMR techniques ((13)C, COSY, TOCSY, HSQC, HMBC, and ROESY experiments), ESIMS, and acid hydrolysis. The isolated compounds could be classified into two series: glucosides (1-8, 22, 27, and 30) derived from the 3-O-monoglucoside and glucuronides (9-21, 23-26, 28, and 29) derived from the 3-O-monoglucuronide. In 22 of the saponins (1-8, 12-22, and 24-26), a galactose moiety was linked to C-3 of a glucuronic acid or a glucose moiety. The galactose was substituted in position 3 by a second galactose unit (6, 7, 20, and 21) or by a xylose unit (8). Seven saponins (4, 5, 16-19, and 26) were found to be bidesmosides with one glucose unit linked to C-28 of the aglycon. The hemolytic activity of the major saponins (2, 3, 5, 12-15, 17, 24, and 28) was measured on sheep erythrocytes in order to establish structure-activity relationships based on the type of sugar attached to the aglycon and on the structure of this aglycon.