Chemical study of Anthospermum emirnense (Rubiaceae)

Chemical study of the aerial parts of Anthospermum emirnense led to the isolation of one original iridoid glycoside (1) along with six known iridoids (2–7), three lignans (8–10), two flavonoids (11–12), one coumarin (13), two anthraquinones (14–15), two benzoic acids (16–17) and three triterpenoids (18–20). These results are the first chemical data on non-volatile constituents of this genus. The chemotaxonomic significance of these compounds is discussed.     

Chemical constituents from Pteris ensiformis Burm. (Pteridaceae)

Phytochemical study of Pteris ensiformis Burm. resulted in the isolation of eleven compounds, including three sesquiterpenoids (1–3), one alkaloid (5), one amino acid (6), one flavonoid (7), four phenolic acids (4, 8, 9 and 10), and one coumarin (11). Structures of these compounds were deduced from the ESI-MS and NMR data. This is the first report on the isolation of compounds 1, 2, 7 and 11 from P. ensiformis, compounds 6 and 9 from the genus Pteris, and compound 5 from the family Pteridaceae. In addition, a detailed discussion of the chemotaxonomic significance of these compounds was presented.     

Phytochemical and chemotaxonomic study on Berchemiella wilsonii (Schneid.) Nakai

Phytochemical investigation of the aerial parts of Berchemiella wilsonii (Schneid.) Nakai (Rhamnaceae) led to the isolation of four flavonoids (1–4), three phenolic acids (5–7), two megastigmane derivatives (8–9) and one triterpene (10). The structures of these compounds were elucidated as taxifolin (1), (−)-epicatechin (2), quercetin 3-O-a-l-arabinopyranoside (3), vitexin (4), methyl p-hydroxycinnamat (5), 3,4-dihydroxybenzoic acid (6), 2-hydroxy-4-methoxy-3,6-dimethyl benzoic acid (7), (3S,5R,6R,7E,9S)-3,5,6,9-tetrahydroxy-7-en-megastigmane (8), (6S,9R)-roseoside (9) and lupeol (10) on the basis of NMR spectral data and comparison with literature values. These results are the first chemical constituent data of the genus Berchemiella, and the chemotaxonomic significance of these compounds is discussed.     

Phytochemical and chemotaxonomic studies on Dioscorea collettii

A chemical investigation of Dioscorea collettii led to the isolation of twenty-nine compounds, including six steroid saponins (1–6), thirteen monocyclic phenols (7–19), two flavonoids (20–21), three sterols (22–24), and five cyclodipeptides (25–29). The chemical structures of these compounds were elucidated using spectroscopic methods and by comparing their data to that reported in the literature. This study is the first report of compounds 2–4, 7, 14–17, 21, and 23–24 in D. collettii, while compounds 8–13, 18–20, and 25–29 were first isolated from the genus Dioscorea and the family Dioscoreaceae. The chemotaxonomic significance of the isolated compounds is discussed.     

Antibacterial and antioxidant activities of compounds isolated from the leaves of Symphonia globulifera (Clusiaceae) and their chemophenetic significance

The phytochemical study was done on the methanol extract from of the leaves of Symphonia globulifera. This plant has been used in traditional medicine to treat of different ailments such as malaria, diseases of the skin, diabetes, cough, intestinal worms, pre-hepatic jaundice and fever. Chromatographic fractionation and purification of this extract led to the isolation and characterization of twelve compounds (1–12) including pristriol (1), robustaflavone (2), polycarpol (3), 7''-O-methylrobustaflavone (4), amentoflavone (5), stigmasterol glucoside (6), epicatechin (7), apigenin (8), luteolin (9), 1,5-dihydroxyxanthone (10), β-sitosterol 3-β-D-glucopyranoside (11) and a mixture of stigmasterol and β-sitosterol (12). The structures of compounds 1–12 were elucidated on the basis of 1D and 2D NMR, mass spectrometric and the spectroscopic data as well as comparison with the literature. All these compounds were isolated for the first time from Symphonia genus. The NMR spectra and structure elucidation of compound 1 were reported for the first in the literature. The antibacterial and antioxidant activities of three of these compounds were evaluated. The chemophenetic significance of these compounds is also discussed.     

Chemical constituents from the stem bark of Clausena excavata Burm. f

Phytochemical study on the stem bark of Clausena excavata Burm. f. led to the isolation and identification of 11 compounds, including four prenylated coumarins (1–4), three carbazole alkaloids (5–7), a limonoid (8), a sterol (9), a depside (10) and a xanthone (11). The chemical structures of the compounds were elucidated based on NMR and mass spectroscopic data, and further supported by comparison with previously literature values. This is the first report on the isolation of compounds 10 and 11 from the genus Clausena. The chemotaxonomic significance of the isolated compounds is discussed.     

Phytochemical study of Joannesia princeps Vell. (Euphorbiaceae) leaves

A phytochemical study of chloroform-methanol and methanol extracts of Joannesia princeps Vell. Leaves led to the isolation of twenty eight compounds, including two α-ionones (2, 5), three glycosylated monoterpenes (1, 3, 4), eight phenolic compounds (6, 8, 9, 12, 14, 17, 18, 24), two gallotannins (10, 11), twelve flavonoids (7, 15, 16, 19, 20–23, 25–28), and one lignan (13). The structural characterization of the isolated compounds was performed by spectroscopic data and comparison with the literature. All compounds were isolated from this species and from the genus Joannesia for the first time. The chemotaxonomic importance of these metabolites is therefore summarized.     

Natural products from the medicinal plant Duguetia staudtii (Annonaceae)

The phytochemical investigation of the ethyl acetate soluble fraction of Duguetia staudtii stem bark led to the isolation of eight compounds consisting into a new bisnorlignan named pachypolignan (1), a known bisnorlignan (2), four flavonoids (3–6), one alkaloid (7), and one triterpenoid (8). The structures of all the compounds were established with help of spectral data including IR, UV, MS, 1D- and 2D-NMR spectroscopic data, as well as by comparison with previously-reported data in literature. The anti-inflammatory and urease inhibitory activities of the isolated compounds were assessed. Furthermore, the chemotaxonomic significance of these compounds was discussed.     

Flavonoids,stilbenoids, and phenolic derivatives from the stems of Gnetum macrostachyum (Gnetaceae)

Gnetum species have been traditionally consumed as food and used as folk medicine to treat various pathological conditions. Ten compounds including three simple phenolic compounds (1–3), five stilbenoids (4, 5, 8–10), and two C-glycosyl flavanones (6 and 7), were isolated from the stems of Gnetum macrostachyum Hook. f. The structures of these compounds were elucidated by the analysis of spectroscopy data and their comparison with the reported values. This is the first report of the isolation of compounds 1–4 and 6–9 from G. macrostachyum. Compounds 1–3, 6, and 7 have not been previously reported from the genus Gnetum. The C-glycosyl flavanones in G. macrostachyum can be used as chemotaxonomic markers.     

Chemical constituents of Odontites serotina (Lam.) Dumort. (Orobanchaceae)

The study of the whole plants of Odontites serotina (Lam.) Dumort. has led to the isolation of one nucleoside compound (2), three iridoids (1, 3, and 4), two phenylethanolic glycosides (6 and 8), four phenolic acids (5, 10, 12, and 15), and nine flavonoids (7, 9, 11, 13, 14, and 16–19). The structures of the compounds were identified by nuclear magnetic resonance (NMR) and high-resolution mass spectrometer. To the best of our knowledge, this is the first study to describe the isolation and identification of compounds 2–3, 6–8, 10, 12, 14–16, and 19 in O. serotina. The chemotaxonomic significance of these compounds was discussed.     

Chemical constituents from the roots of Caragana grandiflora (M. B.) DC. and their chemotaxonomic importance

A comprehensive phytochemical research on roots of Caragana grandiflora, a native plant to Iran, resulted in isolation of ten compounds including four phenolic compounds (2, 4, 5, 8), two fatty alcohols (1, 6), one fatty acid (9), one triterpene (3), one glyceride derivatives (7) and one fatty acid methyl ester (10), from which eight compounds (1, 2, 4–6 and 8–10) were isolated from the genus Caragana and two compounds (5 and 10) from the family Fabaceae, for the first time. All compounds (1–10) were described from Caragana grandiflora for the first time. Chemical structures of the purified compounds were identified through FT-IR, NMR and MSS, and spectral data comparison with literature reported evidences.Our findings provide valuable information in reporting the rare existence of natural fatty acid methyl ester (10) in the Fabaceae family. Moreover, the chemotaxonomic significance of these compounds was discussed.     

Chemical constituents from Anemone vitifolia Buch.-Ham. (Ranunculaceae)

A phytochemical investigation of Anemone vitifolia (Buch.-Ham.) led to the isolation of twelve compounds, including six lignans (1–6), four benzoic acid esters (7–10), one norsesquiterpenoid (11) and one lactone (12). The structures of these metabolites were established on the basis of detailed spectroscopic analysis, as well as comparisons with the data available in the literature. Among them, compounds 10 (dimethyl 2-(benzoyloxy)succinate) and 12 (4-hydroxy-5-methyl-γ-butyrolactone) were isolated for the first time as natural products. Compounds 1 and 11, compounds 2, 3, 5–7 and 9, and compounds 4 and 8 were isolated for the first time in family Ranunculaceae, genus Anemone and A. vitifolia respectively. The chemotaxonomic significance of the isolated compounds was discussed.     

Chemical constituents from Psychotria arborea Hiern (Rubiaceae)

The chemical study of the stems extract of Psychotria arborea Hiern led to the isolation of thirteen compounds, including four anthraquinones: 2-methylanthracene-9,10-dione (1), 2-methoxyanthracene-9,10-dione (2), 2-hydroxy-3-methylanthracene-9,10-dione (3) and 3-hydroxy-1-methoxy-2-methylanthracene-9,10-dione (4); two diterpenes: ent-kaur-16-en-19-oic acid (5) and 15-acetoxy-ent-kaur-16-en-19-oic acid (6); two triterpenes, β-amyrin (8) and oleanolic acid (9), one flavonoid: Quercetin (7), three sterols: A mixture of stigmasterol (10) and β-sitosterol (11) and β-sitosterol-3-O-β-D-glucopyranoside (12) and one fatty acid (13). The structures of these compounds were elucidated based on NMR and HR-ESIMS analysis, further supported by comparison with previously reported spectral data. Compounds 1–4 and compounds 10–12 were tested for their antibacterial activity against three bacteria strains Escherichia coli, Staphylococcus aureus and Salmonella enterica. All these tested compounds were found to be inactive. Furthermore, the chemotaxonomic significance of the obtained compounds was discussed in detail.     

Phenylpropanoids and some nitrogen-containing constituents from the roots of Isatis indigotica Fort. (Cruciferae)

The present phytochemical investigations of Isatis indigotica Fort. resulted in the isolation of seven lignans (1–7), three aromatic glycosides (8–10), three nucleosides (11–13) and two bis-indole alkaloids (14–15). Among them, compounds 5, 6 and 9 were obtained from this genus for the first time. The chemotaxonomic importance of these compounds was also summarized.     

Phytochemical and chemotaxonomic study on Dictamnus angustifolius G. Don ex Sweet (Rutaceae)

A phytochemical investigation of Dictamnus angustifolius led to the isolation of 14 compounds, including six furoquinoline alkaloids (1–6), two sesquiterpenoids (7, 8) and six flavonoids (9–14). The structures of these compounds were identified by spectroscopic methods and a comparison of their data with those reported in the literature. This is the first report of three furoquinoline alkaloids 1–3 and six flavonoids 9–14 from the genus Dictamnus and the first isolation of compounds 4–8 from D. angustifolius. The chemotaxonomic significance of furoquinoline alkaloids and sesquiterpenoids has also been summarized.     

Phytochemical investigation on the fruits of Camptotheca acuminata and their chemotaxonomic significance

A phytochemical investigation on the fruits of Camptotheca acuminata led to the isolation of 13 compounds, including five coumarins (1–5), two alkaloids (6 and 7), two triterpenoids (8 and 9), three lactones (10–12) and a sesquiterpene (13). The structures of these compounds were elucidated by extensive spectroscopic methods and comparion with literature data. All compounds were isolated from the Nyssaceae family for the first time. Additionally, it should be noted that this is the first report of coumarins in the C. acuminata. The chemotaxonomic significance of the isolated compounds was summarised.     

Chemical constituents from the roots of Cichorium glandulosum Boiss. et Huet (Asteraceae)

A phytochemical investigation of the roots extract of Cichorium glandulosum led to the isolation and characterization of fourteen compounds, including five sesquiterpene lactones (1–5), five flavonoids (6–10), and four lignans (11–14). Their structures were determined by spectroscopic data analysis and comparison with the literatures. This is the first report of the crystal data of lactucopicrin (1). This is the first time to report the isolation of 6,8,11-epi-desacetylmatricarin (2), desacetylmatricarin (3), ixerisoslde C (4), magnodelavin (5), 2ʹ,4-dihydroxy-4ʹ-methoxy-6ʹ-O-β-glucopyranoside dihydrochalcone (6), (−)-evofolin B (7), isoquercitrin (8), myricetin 7-methyl-ether-3-O-glucoside (9), (+)-medioresinol (12), 4-O-methylcedrusin [2-(3ʹ,4ʹ-dimethoxyphenyl)-3-hydroxymethyl-2,3-dihydro-7-hydroxybenzofuran-5-propan-1-ol] (13), and (2R,3S)-samwirin A (14) from C. glandulosum. Among them, compounds 5, 9, 13, and 14 were obtained from Asteraceae family for the first time. The chemotaxonomic significance of all the isolates 1–14 was discussed.     

Chemical constituents from Lespedeza cuneata G. Don (Leguminosae)

Phytochemical investigation of Lespedeza cuneata led to the isolation of seventeen compounds including three steroids (β-sitosterol 1, β-sitosterol-6′-linolenoyl-3-O-β-d-glucopyranoside 3, and β-sitosterol glucoside 13), nine flavonoids (quercetin 4, kaempferol 5, isovitexin 8, hirsutrin 9, nicotiflorin 10, vitexin 11, astragalin 12, trifolin 14, and isorhamnetin 17), two phenolics (benzyl-β-d-glucopyranoside 7 and homovanillyl alcohol 16), one carotenoid (loroxanthin 2), one lignin (7R,8S–dihydrodehydrodiconiferyl alcohol 15), and one hexose (pinitol 6) on the basis of their spectroscopic data. Among these compounds, 2, 3, 7, 15 and 16 were reported for the first time from the genus Lespedeza. The taxonomic significance of these isolated compounds was also summarized.     

Chemical constituents from Cistanche sinensis (Orobanchaceae)

Phytochemical investigation of 70% aqueous EtOH extract of Cistanche sinensis led to the isolation of fifteen compounds (1–15), including nine phenylethanoid glycosides (PhGs, 1–9), five iridoid glycosides (10–14), and one lignan glycoside (15). Their structures were determined on the basis of 1D- and 2D-NMR experiments and by comparison with physical data of known compounds. Among the isolated compounds, 1 was identified as a new compound, three compounds (9, 14, and 15) were firstly reported from the genus Cistanche, and seven compounds (2–6, 11, and 12) were isolated from C. sinensis for the first time. PhGs with a 6′-O-rhamnosyl moiety such as cistansinenside B (1), poliumoside (7), and 2′-O-acetylpoliumoside (9) could serve as chemotaxonomic markers to differentiate C. sinensis from other species of Cistanche.     

Phenolic constituents from the roots of Rosa laevigata (Rosaceae)

Chemical investigation of the root of Rosa laevigata led to the isolation of sixteen phenolic compounds, including seven flavonoids (1–7), five condensed tannins (8–12), two stilbenes (13 and 14) and two benzoic acid derivatives (15 and 16). Their structures were identified as (+)-catechin (1), (+)-gallocatechin (2), (2R, 3S, 4S)-cis- leucocyanidin (3), (2R, 3S, 4S)-cis-leucofisetinidin (4), (2S, 3R, 4R)-cis- leucofisetinidin (5), dehydrodicatechin A (6), phloridzin (7), procyanidin B3 (8), fisetinidol-(4α, 8)-catechin (9), guibourtinidol- (4α, 8)-catechin (10), ent- isetinidol -(4α, 6)-catechin (11), fisetinidol-(4β, 8)-catechin (12), (Z)-3-methoxy-5-hydroxy- stilbene (13), (Z)-piceid (14), gallic acid (15) and 4-hydroxybenzoic acid- 4-O-β-D-glucopyranoside (16). Among them, compounds 3–7, 9–14, and 16 were isolated from R. laevigata for the first time, and compounds 3–7, 9, 10, 12–14 and 16 were reported for the first time from the genus Rosa. The chemotaxonomic significance of these compounds was summarized.