Chemical constituents isolated from the roots and rhizomes of Smilacina japonica

Phytochemical investigation of the roots and rhizomes of Smilacina japonica A. Gray led to the isolation of 16 compounds, including six steroidal saponins (1-6), one amide (7), one fatty alcohol (8), one steroidal sapogenin (9), two flavones (10-11), one glycoside (12), one phenol (13), one aliphatic acid (14), and two sterols (15-16). All of these compounds were isolated for the first time from the roots and rhizomes of S. japonica while compounds 1-13 were identified for the first time from the genus Smilacina, of which compounds 9, 11, and 13 were isolated from the Liliaceae family for the first time. Furthermore, the isolation of compound 9 was reported for the first time in plants. Their structures were identified by spectroscopic methods and compared previously published data. The chemotaxonomic significance of these isolated compounds has also been discussed.     

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 the roots of Fallopia multiflora var. Ciliinerve

Phytochemical investigations on the roots of Fallopia multiflora var. Ciliinerve led to the isolation of eighteen compounds, including six chromones [2-methyl-5- carboxymethyl-7-hydroxychromone (1), 2-methyl-5-methylcarboxymethyl-7- hydroxychromone (2), 2,5-dimethyl-7-hydroxychromone (3), 2-methyl-5-hydroxymeth-yl-7-hydroxychromone (4), 2-methyl-5-carboxylicacid-7-hydroxy-chromone (5), and 2,5-dimethyl-7-hydroxychromone-7-O-β-D-glucopyranoside (6)], three lignans [Isolariciresinol (8), 5-[4-(3,4-dimethoxyphenyl)-2,3-dimethylbutyl]-1,3-benzodioxole (9), and isolariciresinol-9-O-β-D-xylopyranoside (10)], four anthraquinones [physcion-8-O-β-D-glucopyranoside (11), emodin-8-O-β-D-glucopyranoside (12), Rhein (13), and Chrysophanol (14)], three isobenzofurans [5,7-dihydroxy-isobenzofuran (15), 5-methoxy-7-hydroxy-isobenzofuran (16), and 5-methoxy-isobenzofuran-7-O-β-D-glucoside (17)], one phenolic acid [2,5-diacethylhy-droquinone (7)], and one pyran [Zanthopyranone (18)]. Among them, compounds 1, 3, 6, 13 and 14 were reported from F. multiflora var. Ciliinerve for the first time, compounds 2, 8, 10 and 15–17 were isolated from the genus Fallopia for the first time, and compounds 4, 9 and 18 were isolated for the first time from Polygonaceae family. Furthermore, the isolation of compounds 5 and 7 were reported for the first time in plants. Their structures were identified by spectroscopic methods and compared with those previously published. The chemotaxonomic significance of these isolated compounds has also been discussed.     

Phytochemical investigation of Eremostachys moluccelloides Bunge (Lamiaceae)

Phytochemical investigation of the aerial parts of Eremostachys moluccelloides Bunge led to the identification of a new diterpene, 2β,14-dihydroxy −11-formyl- 12-carboxy-13-des-isopropyl-13-hydroxymethyl-abieta-8,11,13- triene- 16(17)- lactone (1), along with the known compounds 12, 18-dicarboxy-14-hydroxy-13-des -isopropyl-13-hydroxymethyl- abieta-8,11,13-triene-16(17)-lactone (2), 5-hydroxy-3′,4′,7-trimethoxyflavone (3), 5-hydroxy-4’,7-dimethoxyflavone (4), luteolin-7-O-β-glucoside (5), verbascoside (6), luteolin 7-O-(6″-O-β-D-apiofuranosyl) -β-D-glucopyranoside (7), chlorogenic acid (8), echinacoside (9), apigenin-7-O-β-D-glucoside (10), p-coumaric acid (11), vanillic acid (12), apigenin-7-O-(6″-E-p-coumaroyl)-β-D-glucopyranoside (13), apigenin-7-O-(3″,6″-E-p-dicoumaroyl)-β-glucoside (14), lamalbide (15), 6β-hydroxy-7-epi-loganin (16), phloyoside II (17) The structures were elucidated on the basis of 1D and 2D NMR spectroscopy, UV, MS and by comparison with compounds previously reported in the literature. Compounds 1–4, 8, 9, 11, 12, 14 have not been reported previously from any species within the genus Eremostachys. Compounds 1–14, 17 were obtained from this species for the first time. The chemotaxonomic significance of the isolated compounds is discussed.     

Chemical constituents from Hovenia dulcis Thunb. And their chemotaxonomic significance

Phytochemical investigations on the fruit stalks and seeds of the plant Hovenia dulcis Thunb. led to the isolation of twenty-one compounds, including three triterpenes (1–3), two sterols (4–5), five flavonoids (6–10), two sesquiterpenes (11–12), one lignan (13), two phenylpropanoids (14–15), four benzoic acid derivatives (16–19), one acid amide (20) and one cerebroside (21). The structures of these compounds were elucidated on the basis of spectroscopic analysis and comparison with previous literatures. Among them, ten compounds (4, 11–12, 14–20) were isolated from familiy Rhamnaceae, two (13, 21) from the genus Hovenia, and three (5, 8, 10) from the species Hovenia dulcis Thunb. for the first time, respectively. The chemotaxonomic significance of these isolates was also discussed.     

Chemical constituents from the roots of Peucedanum praeruptorum Dunn and their chemotaxonomic significance

Chemical investigation on the roots of Peucedanum praeruptorum Dunn afforded 15 compounds, including five linear furocoumarins (1–5), six angular pyranocoumarins (6–11), two simple coumarins (12 and 13), a benzaldehyde derivative (14), and a phenylpropanoid glycoside (15). The structures of these compounds were established via spectroscopic analysis and comparison of their NMR data with the literature. Compound 1 was a new linear furocoumarin glycoside, while compounds 10–12, 14 and 15 were isolated from P. praeruptorum for the first time. The chemotaxonomic significance of these isolated compounds was summarized herein.     

Flavonoids and other constituents from Alpinia sichuanensis Z.Y. Zhu

Seven flavonoids (2, 4, 6, 10, 14–16), five phenolic acids (3, 5, 7–9), one monoterpene (11), two sterols (1 and 12) and an esters compound (13) were isolated from the whole plant of Alpinia Sichuanensis for the first time. Among them, compounds 7, 8 and 16, are reported from the family Zingiberaceae for the first time. The chemotaxonomic significance of these compounds was summarized.     

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.     

Chemical constituents from Picrasma quassioides (D.Don) Benn. and their network analysis of chemotaxonomic significance

A phytochemical investigation of Picrasma quassioides (D.Don) Benn led to the isolation of seventeen compounds including five coumarins (1–5), six lignans (6–11), two alkaloids (12–13), two phenolic compounds (14–15), one megastigman glycoside (16) and one phenylpropanoid (17). The structures of those compounds were determined by spectroscopy data of NMR spectra. All of the compounds were isolated from P. quassioides for the first time. In this study, in order to discuss the chemotaxonomic significance of those compounds from P. quassioides, network analysis was carried out to determine the chemotaxonomic relationships among the Simaroubaceae family and the other families. The result showed that the Simaroubaceae family and the Rutaceae family, together with the Asteraceae family have some chemotaxonomic relationships.     

Chemical constituents from Laggera pterodonta

A phytochemical investigation on the aerial parts of Laggera pterodonta resulted in the isolation and identification of fourteen compounds, including six sesquiterpenoids (1–6), five flavonoids (7–11), one lignan (12), and two pyrrole alkaloids (13, 14). Among them, compounds 1–3, 7–9, and 11 are the characteristic class of secondary metabolites of L. pterodonta. Compounds 4 and 5 were firstly isolated from L. pterodonta and this is the first report of the presence of compounds 6, 10, and 12 from the genus Laggera. Pyrrole alkaloids 13 and 14 may serve as potential chemotaxonomic markers for L. pterodonta and could be used to distinguish among species of Compositae.     

Chemical constituents of Uncaria rhynchophylloides How and their chemotaxonomic significance

One undescribed 1,4-diazaindan-type alkaloid, namely howlumine (1), along with seventeen known compounds, including a known analogue, agrocybenine (2), three iridoid glycosides (3–5), four megastigmane glycosides (6–9), two benzoic acid derivatives (10–11), two phenylpropanoids (12–13), and five flavonoids (14–18), were isolated from the 95% EtOH extract of the aerial parts of Uncaria rhynchophylloides How. The structures of these compounds were elucidated by spectroscopic analyses. All compounds were isolated from this plant for the first time. Howlumine and agrocybenine represent the first report of 1,4-diazaindan-type alkaloids from the genus Uncaria. Furthermore, the chemotaxonomic significance of the isolates was also discussed.     

Chemical constituents from the fruits of Rhus typhina L. and their chemotaxonomic significance

This work describes the isolation and characterization of twenty-nine compounds from the fruits of Rhus typhina L., including eleven flavonoids (1–11), eleven phenols (12–22), two pentacyclic triterpenes (23–24), two organic acids (25–26), one lumichrome (27), one courmarin (28) and one pyrimidine (29) on the basis of their spectroscopic data. Compounds apigenin (1), daidzein (4), orobol (5), 3′, 5, 5′, 7-tetrahydroxyflavanone (6), naringenin (7), butein (8), (-)-catechin (9), quercetin-3-O-α-L-(3″-O-galloyl)-rhamnoside (11), 2-hydroxybenzoic acid (13), 4-hydroxybenzaldehyde (14), vanillin (15), methyl 3,4-dihydroxybenzoate (16), 3,5-dihydroxybenzamide (18), tyrosol (19), caffeic acid (20), 3-(2,4,6-trihydroxyphenyl)-1-(4-hydroxyphenyl)-propan-1-one (21), phlorizin (22), friedelin (23), oleanolic acid (24), 4,4-dimethyl-heptanedioic acid (25), anthranilic acid (26), lumichrome (27), scoparone (28) and uracil (29) have not been recorded before in this plant. This is the first report on the occurrence of compounds 4–7, 9, 11, 13–14, 16, 18–21, 25–29 from the genus Rhus. Moreover, the chemotaxonomic significance of these isolated compounds was also summarized.     

Triterpenoids from the seedpods of Holarrhena curtisii King and Gamble

Two new hydroperoxy pentacyclic triterpenoids, 3β-hydroxy-11α-hydroperoxyolean-12-en-28-oic acid (1) and 3β-hydroxy-11α-hydroperoxyursan-12-en-28-oic acid (2), together with nine known triterpenoids, squalene (3), β-amyrin acetate (4), α-amyrin acetate (5), lupeol acetate (6), lupeol (7), lanosta-7,24-dien-3β-ol (8), cycloeucalenol (9), oleanolic acid (11) and ursolic acid (12), a known phytosterol, 24-methylenepollinastanol (10), and two known flavanols, (–)-catechin (13) and (–)-gallocatechin (14), were isolated from the methanolic extract of the fresh seedpods of Holarrhena curtisii. Their structures were determined by spectroscopic analysis (one and two dimensional nuclear magnetic resonance, high resolution electrospray ionization mass spectrometry and attenuated total reflectance-Fourier transform infrared spectroscopy). All compounds (except squalene) were evaluated for their in vitro α-glucosidase inhibitory activity. Compounds 1, 2, 11 and 12, which had a pentacyclic triterpenoid acid skeleton, showed a strong in vitro α-glucosidase inhibitory activity compared to that of the standard control, acarbose.     

Phytochemical and chemotaxonomic studies on Phyllodium pulchellum (Leguminosae)

A phytochemical investigation on the aerial part of Phyllodium pulchellum led to the isolation of 16 compounds including five flavonoids (1–5), three lignans (6–8), four indole alkaloids (9–12), and four other-type compounds (13–16). Their structures were elucidated by their spectroscopic data analysis. Among them, 12 compounds (1, 2, 4–9, and 11–14) are reported from the genus Phyllodium for the first time, while compound 14 was isolated from the Leguminosae family for the first time and compound 11 was firstly reported in the plant kingdom. The chemotaxonomic significance of these compounds was also summarized.     

Alkenylresorcinols and cytotoxic activity of the constituents isolated from Labisia pumila

Phytochemical investigation on the leaves of Labisia pumila (Myrsinaceae), an important medicinal herb in Malaysia, has led to the isolation of 1-O-methyl-6-acetoxy-5-(pentadec-10Z-enyl)resorcinol (1), labisiaquinone A (2) and labisiaquinone B (3). Along with these, 16 known compounds including 1-O-methyl-6-acetoxy-5-pentadecylresorcinol (4), 5-(pentadec-10Z-enyl)resorcinol (5), 5-(pentadecyl)resorcinol (6), (−)-loliolide (7), stigmasterol (8), 4-hydroxyphenylethylamine (9), 3,4,5-trihydroxybenzoic acid (10), 3,4-dihydroxybenzoic acid (11), (+)-catechin (12), (−)-epicatechin (13), kaempferol-3-O-α-rhamnopyranosyl-7-O-β-glycopyranoside (14), kaempferol-4′-O-β-glycopyranoside (15), quercetin-3-O-α-rhamnopyranoside (16), kaempferol-3-O-α-rhamnopyranoside (17), (9Z,12Z)-octadeca-9,12-dienoic acid (18) and stigmasterol-3-O-β-glycopyranoside (19) were also isolated. The structures of these compounds were established on the basis of 1D and 2D NMR spectroscopy techniques (¹H, ¹³C, COSY, HSQC, NOESY and HMBC experiments), mass spectrometry and chemical derivatization. Among the constituents tested 1 and 4 exhibited strongest cytotoxic activity against the PC3, HCT116 and MCF-7 cell lines (IC₅₀ values ⩽10 μM), and they showed selectivity towards the first two-cell lines relative to the last one.     

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 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.     

Alkaloids from the stem bark of Strychnos icaja

A comprehensive phytochemical study of the stem bark of Strychnos icaja was done for the first time and led to the isolation of two new monoindole alkaloids 15-hydroxyvomicine (1) and 12-methoxyicajine (2) along with 13 known alkaloids: the monoindoles N-methyl-sec-iso-pseudostrychnine (3), vomicine (4), icajine (5), 19,20-α-epoxy-12-methoxyicajine (6), 19,20-α-epoxy-12,15-dihydroxy-11-methoxyicajine (7), 19,20-α-epoxy-15-hydroxynovacine (8), 15-hydroxyicajine (9), 12-hydroxystrychnine (10), strychnine (11) and the tertiary bisindoles sungucine (12), isosungucine (13), strychnogucine C (14) and bisnordihydrotoxiferine (15). Apart from 10 and 11, the other alkaloids were isolated for the first time from the stem bark of this plant. The hemisynthetic derivative, N_b-chloromethosungucine (16) and the previously reported synthetic compound 3 were isolated from a natural source for the first time. Fractions and some isolated compounds were tested against the chloroquine-sensitive 3D7 strain of Plasmodium falciparum. The bisindole alkaloids were most active with IC₅₀ ranging from 0.72 to 3.41 μg/ml whilst the monomers 1 and 3 were slightly active (IC₅₀ 39.92 and 40.27 μg/ml respectively) and 6 inactive. The structures of the compounds were determined based on the analysis of their spectral data. The full ¹H and ¹³C NMR data of compounds 3, 6 and 7 are also reported in the present work for the first time.     

Chemical constituents from the aerial parts of Ajania fruticulosa

The isolation and identification of sixteen compounds extracted from the aerial parts of A. fruticulosa have been reported in the present study, including eight flavonoids (1, 2, 3, 4, 5, 6, 7 and 8), three terpenoids (9, 10 and 11), two sterols (12 and 13), one lignan (14), one fatty acid (15) and one fatty acid ethyl ester (16), wherein six compounds (2, 3, 4, 5, 10 and 14) have been isolated from A. fruticulosa for the first time. Furthermore, among the identified compounds, three compounds (6, 7 and 11) have also been reported for the first time in the genus Ajanin and three compounds (8, 15 and 16) have not been isolated and reported from other plants of the family Asteraceae. In addition, the chemotaxonomic significance of these compounds was discussed.     

Chemical constituents from the aerial sections of Ajania potaninii

Nineteen compounds were isolated from Ajania potaninii, including one sulfur paraffin (1), one monoterpene (6), one lactone (3), one aliphatic acid (15), two sterols (8 and 10), one triterpenes (13), one alkaloid (18), eleven flavonoids (2, 4, 5, 7, 9, 11, 12, 14, 16 and 17) and one cyclic amide (19). All of these compounds were obtained from A. potaninii for the first time. This is the first report of N-nonanemercaptan (1), 3-hydroxy-5-decanolide (3), cirsiliol (5), 1,2,4-trihydroxy-p-mentane (6), 6-methoxytricin (7), eriodictyol (11), pectolinarigenin (12), 3,3′-di-O-methylquercetin (14), tetradecanoic acid (15), lappaconitine (18) and 1,1′,1″,1‴,1‴'-tricontane lactam (19) from the genus Ajania. The occurrence of compounds 18 and 19 in A. potaninii warrants further study.