Chemical constituents from Bupleurum chinese and their chemotaxonomic significance

A phytochemical investigation of the roots of Bupleurum chinese DC. led to the isolation of eighteen compounds, including three chromones (1–3), seven flavonoids (4–10), one dihydrochalcone (11), two phenylpropanoid glycosides (12–13), one lignan (14), three sterols (15–17) and one stilbenoid (18). Their structures were elucidated on the basis of NMR spectroscopic analysis and comparison with literature data. Compounds 6–7, 11–14 and 18 were firstly reported from the genus Bupleurum and the family Apiaceae. Moreover, the chemotaxonomic value of the isolates was also discussed.     

New saikosaponins from the roots of Bupleurum chinense

Seven new saikosaponins (1 − 7), together with four known ones (8 − 11), were isolated from the roots of Bupleurum chinense. Their structures were elucidated by comprehensive spectroscopic analysis and chemical methods. All obtained saikosaponins were oleanane-type, except for compound 11, which was the first lupane–type saikosaponin isolated from the genus Bupleurum. Compound 1 represented the first example of saikosaponins bearing a hydroxyl group at C-15, while compound 4 was a saikosaponin containing acetoxy group at C-23 rarely found in genus Bupleurum. Compounds 6 and 7, bearing an n-butoxy moiety at C-11, were confirmed to be artifacts by LC–MS experiment. All the isolates were evaluated for their inhibitory effects towards nitric oxide production induced by lipopolysaccharide in BV-2 microglial cells, and saikosaponins A (9) and D (10) exhibited the most potent activity, which were comparable to the positive control dexamethasone.     

Chemical constituents from the pericarps of Zanthoxylum bungeanum and their chemotaxonomic significance

The phytochemical study of the pericarps of Zanthoxylum bungeanum Maxim under the guidance of bioactivity led to the isolation of 18 compounds, including a new isobutylhydroxyamide (1) and 17 known compounds, i.e. six alkylamides (2–7), five coumarins (8–12), one benzene derivative (13), three flavonoids (14–16), and two sterols (17–18). Their structures were elucidated based on extensive spectroscopic methods (HRESIMS, 1D and 2D NMR experiments) and by comparison with literature data. New compound (1) and known compound (2) are cis-trans isomeric isobutylhydroxyamides. Among them, compounds 9, 10, and 12 were isolated for the first time from Z. bungeanum, compound 11 was firstly recovered from the genus Zanthoxylum, and compound 14 was reported for the first time from the Rutaceae family. The chemotaxonomic significance of isolated compounds from Z. bungeanum is discussed.     

Phytochemical and chemotaxonomic study on Piper pleiocarpum Chang ex Tseng

The phytochemical study of Piper pleiocarpum Chang ex Tseng led to the isolation of eighteen compounds (1–18), including ten lignanoids, galbelgin (1), (+) sesamin (2), denudatin A (3), hancinone (4), (7S,8S, 3′R)-Δ^8'-3,3′,4-trimethoxy-3′,6′-dihydro-6′-oxo-7.0.4′,8.3′-lignan[(2S,3S,3aR)-2-(3,4-dimethoxyphenyl)-3,3a-dihydro-3a-methoxy-3-methyl-5-(2-propenyl)-6(2H))-benzofuranone] (5), (−)-(7R,8R)-machilin D (6), (1R,2R)-2-[2-methoxy-4-((E)-prop-1-enyl)phenoxy]-1-(3,4-dimethoxyphenyl)propyl acetate (7), piperbonin A (8), machilin D (9), 4-methoxymachilin D (10), one amide alkaloid, Δ^α,β-dihydropiperine (11), six polyoxygenated cyclohexenes, ent-curcuminol F (12), uvaribonol E (13), ellipeiopsol A (14), 1S,2R,3R,4S-1-ethoxy-2-[(benzoyloxy)methyl]cyclohex-5-ene-2,3,4-triol, 3-acetate (15), (+)-crotepoxide (16), (+)-senediol (17), and one benzoate derivative, 2-acetoxybenzyl benzoate (18). Their structures were established by spectroscopic data and by comparison with the literature. All the compounds were firstly isolated from P. pleiocarpum, while ten compounds 6–7, 9–10, 12–15, 17–18 were isolated from the genus Piper and the family Piperaceae for the first time. The chemotaxonomic significance of these compounds was also discussed. The isolation of compounds 6–7, 9–10 may be used as chemotaxonomic markers for the genus of Piper.     

Sesquiterpenoids and flavonoids from Pteris multifida Poir.

Phytochemical research of Pteris multifida Poir. led to the isolation of fifteen compounds, including six flavonoids (1–6) and nine sesquiterpenoids (7–15). Their structures were characterized by NMR, MS, ORD and CD data. Compounds kaempferol 3-O-α-L-rhamnoside-7-O-β-D-glucoside (1), myricetin 3-O-β-D-glucoside (2), kaempferol 3-O-β-D-glucoside (4), luteolin-7-O-β-D-rutinoside (5), quercetin-3-O-α-L-rhamnopyranoside (6), (2S,3S)-12-hydroxypterosin Q (7), (2S,3S)-pterosin Q (8), 2-hydroxypterosin C (9) and (2S)-12-hydroxypterosin A (10) were first isolated from P. multifida, and compounds 1–2 and 10 were first isolated from the family Pteridaceae. Furthermore, the chemotaxonomic significance of the isolates was discussed.     

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.     

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.     

Diarylpentanoids from Diplomorpha canescens and Diplomorpha ganpi

Two new α-hydroxy ketone type diarylpentanoids, diplomorphanone A, 2(S)-hydroxy-1-(4-hydroxyphenyl)-5-phenyl-1-pentanone (1) and diplomorphanone B, 2(R)-hydroxy-1,5-diphenyl-1-pentanone (2) were isolated from aerial parts of Diplomorpha canescens (Meisn.) C.A. Meyer and roots of Diplomorpha ganpi (Sieb. et Zucc.) Nakai, respectively. Nine known compounds including diarylpentanoids (3–6), phenylpropanoid derivatives (7–9), (+)-afzelechin (10) and apiosylskimmin (11) were also isolated for the first time from D. ganpi. Structures of these compounds were elucidated on the basis of spectroscopic data.     

Phytochemistry and antiglycation activity of Aloe sinkatana Reynolds

A new anthraquinone along with 10 known compounds were isolated from the leaves of Aloe sinkatana Reynolds (Aloaceae), and their structures were elucidated as the new compound 2,8-dihydroxy-6-(hydroxymethyl)-1-methoxyanthracene-9,10-dione (1) and the known compounds Aloe-emodin (2), feralolide (3), 1-hydroxy-5-methoxy-3-methyl-9,10 dihydroanthracene 9,10-dione (4), β-sitosterol (5), β-sitosterol with glycosidic bond (6), microdontin (7), homoaloins A (8) and B (9) and aloins A (10) and B (11). Characterization of compounds 1–9 was based on spectral analyses and comparison with reported data, particularly the new compound 1 was identified by 1D- and 2D NMR, mass spectroscopic and X-ray crystallography analyses. Antiglycation activity of the extracts and isolated compounds were carried out using the hemoglobin-δ-gluconolactone and glucose–bovine serum albumin assays. The results obtained showed that MeOH and EtOAc extracts as well as compound 1 showed an inhibitory effect on early stage protein glycation. Compound 1 also showed significant inhibitory effects against glucose-induced advanced glycation end-products.     

Chemical constituents from Valeriana officinalis L. var. Iatifolia Miq. and their chemotaxonomic significance

Twenty-one compounds, including four monoterpenoids (1–4) (two new natural products, 1 and 2), four sesquiterpenes (5–8), two iridoids (9 and 10), four steroids (11–14), five phenolic compounds (15–19), and two alkaloids (20 and 21), were isolated from the roots of Valeriana officinalis L. var. Iatifolia Miq. Their chemical structures were established by spectroscopic methods and further confirmed by comparison with published data in the literature. Among them, eight compounds (1, 2, 6–8, 13, 18, and 21) are being reported from the family Valerianaceae for the first time, and compounds 9–12 were obtained from V. officinalis for the first time. The chemotaxonomic significance of the isolated compounds is discussed.     

Phytochemical and chemotaxonomic studies on Pteris wallichiana J. Agardh

A systematic phytochemical investigation of Pteris wallichiana J. Agardh resulted in the isolation of twenty compounds, including five sesquiterpenes (1–5), six flavonoids (6–11), seven phenolic acids (12–18) and two fatty acids (19 and 20). Their structures were deduced from MS, NMR and ORD data. This is the first report of compounds dehydropterosin B (2), (2R,3S)-pterosin C (4), (2R,3R)-pterosin L (5), apigenin (6), luteolin (7), luteolin-7-O-glucoside (10), caffeic acid (13), vanillin (14), 3,4-dihydroxybenzaldehyde (15), chlorogenic acid (17), 3,5-dicaffeoylquinic acid (18), suberic acid (19) and azelaic acid (20) from P. wallichiana and of compounds 15, 19 and 20 from the family Pteridaceae. Furthermore, a chemotaxonomic study of the isolates was performed.     

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 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.     

Pentacyclic triterpenoids and other constituents isolated from the leaves of Gambeya lacourtiana and their antibacterial activity

The phytochemical study was done on the leaves of Gambeya lacourtiana. This plant has been used in traditional medicine to treat of different ailments such as uterine heamorrhage, metritis and other vaginal infections. Chromatographic fractionation and purification on the leaves crude extract afforded lupeol acetate (1), lupenone (2), lupeol (3), taraxerol (4) stigmasterol (5), erythrodiol (6), chamaedrydiol (7), methyl pheophorbide-a (8), corosolic acid (9), tormentic acid (10), epicatechin (11) and 22-dihydrospinasterol 3-O-β-D-glucopyranoside (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. Compounds 4, 7–10 and 12 were isolated for the first time from Gambeya genus. Crude extract, fractions and compounds 6–12 were evaluated for their antibacterial activity. Methyl pheophorbide-a (8) demonstrated moderate activity against Salmonella typhi CPC with MIC values of 62.5 μg/mL. The chemophenetic significance of these compounds is also discussed.     

Chemical constituents from the fruits of Vitex trifolia L. (Verbenaceae) and their chemotaxonomic significance

One new labdane-type diterpenoid (1) named viterotulin D, along with twenty-three known compounds, including fourteen diterpenoids (2–15), one monoterpenoid (16), three steroids (17–19), one flavonoid (20), and four phenols (21–24) were isolated from the fruits of Vitex trifolia L. The structures of these compounds were identified based on spectroscopic data interpretation and comparison with previously reported values in the literature. This is the first report on the isolation of compounds (1, 6, 14, 15, 17, and 22) and (2, 9, and 10) from the family Verbenaceae and Vitex trifolia, respectively. The chemotaxonomic significant of the isolates was also discussed.     

Phytochemical and network-based chemotaxonomic study of Lonicera japonica Thunb

Phytochemical research on the flower buds of Lonicera japonica Thunb. led to the isolation of 15 compounds, including nine terpenoids (1–9), three phenylpropanoid glycosides (10–12), two alkyl glycosides (13–14) and an alkaloid (15). The structures of these compounds were determined by NMR spectroscopy and comparison with data from previous literatures. Among them, eleven compounds (2–5, 8, 10 and 11–15) were reported from the genus Lonicera for the first time and compounds 3, 4, 5, 10 and 11–15 were firstly reported from the family Caprifoliaceae. Network analysis was carried out to explore the chemotaxonomic significance of these compounds for L. japonica in this study.     

Chemical constituents from Artemisia argyi and their chemotaxonomic significance

Twelve compounds, including one monoterpene (1), two sesquiterpene lactones (2–3), six flavonoids (4–9), one phenolic glycoside (10), one chromone (11) and one phenolic acid (12), were isolated and identified from the leaves of Artemisia argyi. Compounds 1–2, 4 and 6–7 have not been recorded before in this plant. Compounds 3, 9 and 11 were isolated from the genus Artemisia for the first time. This paper is the first report on the presence of compound 10 in species of Asteraceae. In addition, the chemotaxonomic significance of these compounds was summarized.     

A new bicyclic sesquiterpenoid from Merremia yunnanensis

A new sesquiterpenoid, 1α,4β,8β,9β-eudesmane-tetrol-1-O-β-D-glucopyranoside (1), together with nine known compounds (2–10), were isolated from Merremia yunnanensis. The structures of these compounds were elucidated by spectroscopic methods and compared to data in the literature. All these compounds (1–10) were firstly isolated from this plant, and compounds 3, 5, 7, and 10 were reported from the Merremia genus for the first time. The significance of the chemotaxonomy for these compounds is described herein.     

Chemical constituents from Ficus natalensis hochst (Moraceae) and their chemophenetic significance

Phytochemical investigation of the stem bark of Ficus natalensis afforded eleven compounds including one ceramide (1), two anthraquinones (2, 3), four triterpenes (4–7), two polyols (8, 9) and two steroids (10, 11). The structures of the compounds were determined by spectroscopic analyses including IR, UV, MS, 1D- and 2D- NMR (¹H, ¹³C, ¹H–¹H COSY, HMQC, HMBC and NOESY), as well as by comparison with literature data. The antibacterial activity and the cytotoxicity of the extract, fractions and some isolated compounds (3, 5, 8 and 9) were evaluated. Some fractions and sub-fractions from various column chromatography displayed moderate antibacterial activity with diameter zone of inhibition (DZI) ranging from 7 to 10 mm. None of the compounds tested had activity. In the present study, all the compounds are isolated for the first time from the species F. natalensis. Compounds 2, 4–7, 10 and 11 were previously reported from the genus Ficus. The chemophenetic significance of the isolated compounds is discussed.     

Polyphenols from the bark of Rhus verniciflua and their biological evaluation on antitumor and anti-inflammatory activities

Bioassay-guided fractionation and chemical investigation of the extract of Rhus verniciflua bark resulted in the identification of six polyphenols, rhusopolyphenols A–F (1–6), together with four known compounds including (2R,3S,10S)-7,8,9,13-tetrahydroxy-2-(3,4-dihydroxyphenyl)-2,3-trans-3,4-cis-2,3,10-trihydrobenzopyrano[3,4-c]-2-benzopyran-1-one (7), peapolyphenol C (8), cilicione-b (9) and (αR)-α,3,4,2′,4′-pentahydroxydihydrochalcone (10). The structures of these polyphenols were elucidated by spectroscopic analysis, including 1D and 2D NMR, and HR-ESIMS, and their absolute configurations were further confirmed by a combination of chemical methods and CD data analysis. All isolates were evaluated for their antiproliferative activities against four human tumor cell lines (A549, SK-OV-3, SK-MEL-2, and HCT-15), and compounds 4–6, 9 and 10 showed antiproliferative activity against the tested cells, with IC₅₀ values of 3.31–18.51 μM. On the basis of the expanded understanding that inflammation is a crucial cause of tumor progression, the anti-inflammatory activities of these compounds were determined by measuring nitric oxide (NO) levels in the medium of murine microglia BV-2 cells. Compounds 5 and 10 significantly inhibited NO production in lipopolysaccharide (LPS)-stimulated murine microglia BV-2 cells with IC₅₀ values of 28.90 and 12.70 μM, respectively.