Chemical constituents from Lagopsis supina (Steph.) Ik.-Gal. ex Knorr

Phytochemical investigation of the whole plants of Lagopsis supina (Steph.) Ik.-Gal. ex Knorr. led to the isolation of 18 compounds (1–18), including ten phenylethanoid glycosides (1–10), one phenylmethanoid glycoside (11), four megastigmane glycosides (12–15), and three monoterpenoid glycosides (16–18). Lagopsides A (1) and B (2) were identified as new phenylethanoid glycosides. This is the first report of compounds 7, 11, 12, 15, and 16 from the Labiatae family, while compounds 4–6, 8–10, 13–14, and 17–18 were isolated from the genus Lagopsis for the first time. The chemotaxonomic significance of these isolated compounds was summarized.     

Chemical constituents from the leaves of Ilex urceolatus

Eighteen compounds, including four hemiterpene glycosides (1–4), three triterpenoid saponins (5–7), four triterpenes (8–11), five sterols (12-16) and two monoterpene glucosides (17 and 18), were isolated from the leaves of Ilex urceolatus C. B. Shang, K. S. Tang et D. Q. Du, which was identified as a new species belonging to the genus Ilex. Among them, compounds 14–18 were firstly isolated from the genus Ilex, others were obtained from I. urceolatus for the first time. This work represented the initially phytochemical study on this plant. The isolated compounds have significant chemotaxonomic characteristics with the other species from this genus.     

A new phenylpropanoid glycoside from the bark of Streblus ilicifolius (Vidal) Corner

A new compound, pheglycoside A (1), along with four known aromatic glycosides (2-5) and three known lignan glycosides (6–8) were isolated from Streblus ilicifolius (Vidal) Corner. The structure of compound 1 was determined by spectral analyses, including HRESIMS, 1D, and 2D NMR (COSY, HSQC, and HMBC) experiments. The absolute configuration of compound 1 was determined using the CD spectrum and experiment data. From the present investigation, all these compounds were isolated for the first time from S. ilicifolius. It is interesting that phenylpropanoid glycoside and aromatic glycosides are reported for the first time in the genus Streblus. The chemotaxonomic significance of these compounds was summarized.     

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.     

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 the root bark of Dictamnus dasycarpus Turcz. (Rutaceae) and their chemotaxonomic significance

This work described the isolation and characterization of seven compounds from Dictamnus dasycarpus Turcz., including one new ester, (2R)-4-(2,2-dimethyl-5-oxotetrahydrofuran-3-yl)-2-hydroxypent-3-anoic acid ethyl ester (1); and six known glycosides (2–7). The structure of compound 1 was elucidated on the basis of extensive spectral analyses, including IR, HR-ESIMS, 1D and 2D NMR (NOESY, HMBC and HSQC). All these compounds were described here for the first time from the genus Dictamnus. Moreover, the results provide further information about the diversity of compounds in the genus Dictamnus.     

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.     

Chemical constituents from the stems of Dendrotrophe frutescens

Phytochemical investigation of Dendrotrophe frutescens (Benth.) Danser led to the isolation of eight compounds (1–8), including a furan-2-carbonyl C-glycoside together with a series of polyphenols and their glycosides. The structures were elucidated on the basis of spectroscopic analysis, including 1D and 2D-NMR experiments and by comparison with data in the literature. This is the first report of the isolation of compounds 1–6 from the family Santalaceae, while compound 7 was isolated from the genus Dendrotrophe for the first time.     

Chemical constituents isolated from the roots of Sanguisorba officinalis L. and their chemotaxonomic significance

Phytochemical investigation of the roots of Sanguisorba officinalis L. led to the isolation of thirty-eight compounds, including seventeen triterpenoids (1–17), six monoterpenoid glycosides (18–23), six flavonoids (24–29), six phenols (30–35), two glycosides (36–37), and one lignan (38). The chemical structures of these compounds were elucidated on the basis of spectral data and by comparisons of spectroscopic data with reported values in the literature. Compounds 18, 29, and 36–37 were the first to be reported in the family Rosaceae, compounds 10, 12, 15, 27–28, and 38 were firstly identified from the genus Sanguisorba, and compound 11 was obtained from S. officinalis for the first time. The chemotaxonomic significance of these isolated compounds has also been discussed.     

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.     

Phenylethaniod glycosides from Orobanche pycnostachya Hance and their chemotaxonomic significance

In this current study, we investigated the chemical ingredients of the whole plants of Orobanche pycnostachya Hance. Eighteen compounds, including fifteen phenylethaniod glycosides (2–16), two lignans (17, 18), and one flavonoid (1) were obtained from this plant and they were elucidated utilizing spectroscopic methods. This is the first study to describe the isolation of compounds 1-5, 7–11, 13, and 15–18 from O. pycnostachya and compound 2, 4, 7, and 9 from the genus Orobanche L.     

Chemical constituent and chemotaxonomic study on the root of Anemone vitifolia Buch.-Ham

Thirty-four reported compounds were obtained from Anemone vitifolia Buch.-Ham., and were identified as triterpenoid saponins (1–28), flavonoid glycosides (29–32) and steroidal saponins (33–34). The structure of these compounds was determined by physicochemical constants and spectral analyses (NMR, MS, IR). Twelve compounds (7, 8, 10, 14, 20, 21, 23, 26–28, 30 and 32) were firstly identified in genus Anemone. Compounds 2, 4 and 14 can be considered as characteristic components of A. vitifolia. Finally, the chemotaxonomic significance of these compounds is discussed.     

Chemical constituents from starfish Culcita novaeguineae

Seven polyhydroxylated steroidal glycosides (1–7) and two polyhydroxylated sterols (8, 9) were isolated and identified from the 75% ethanol extract of starfish Culcita novaeguineae which was collected in Xisha Islands of South China Sea. The structures of the isolated compounds were elucidated on the basis of spectroscopic data, physical and chemical evidence, MS spectrum and assisted by comparison with the reported data. To the best of our knowledge, this is the first time to report compounds 1–6, 8 and 9 from genus Culcita. Moreover, compounds 1, 4–6, 8 and 9 were isolated from family Oreasteridae for the first time. And the chemotaxonomic significance of the isolated compounds was discussed.     

Iridoids from the flowers of Gardenia jasminoides Ellis and their chemotaxonomic significance

Phytochemical investigation of the flowers of Gardenia jasminoides Ellis (Rubiaceae Gardenia) resulted in the isolation and identification of four iridoid aglycones (1–4) and eleven iridoid glycosides (5–15). This is the first report of the occurrence of these compounds in the genus Gardenia: garjasmine (1), dunnisin (2), α-gardiol (3), β-gardiol (4), diffusoside A (6), diffusoside B (7), genameside C (13), and deacetylasperulosidic acid (14). The chemotaxonomic significance and biosynthetic pathways of these iridoid aglycones (1–4) and iridoid glycosides (5–15) are summarized. Iridoid aglycones and iridoid glycosides are considered as important chemotaxonomic markers in Rubiaceae and this work indicates that the iridoid aglycones (1–4) have a limited distribution in the Rubiaceae.     

Secondary metabolites from Sterculia lychnophora Hance (Pangdahai)

From the ethanolic extracts of dried seeds of Sterculia lychnophora Hance Pierre (Malvaceae), a total of twenty-two (22) compounds were isolated. These included one lignan (1), three phenylpropanoids (5–6, 21), two flavonoid glycosides (8–9), two sesquiterpenoids (3, 17), two nucleosides (10, 12), three nitrogenous bases (4, 7, 14), three phenolic acids (2, 13, 20), two heterocyclic aromatic acids (11, 16) and two phytosteroids (18–19). For eighteen out of the 22 compounds, there is no report of their presence in S. lychnophora. There is no report of sixteen of them being present in the Sterculia genus, hence the first report. The isolated compounds showed a significant taxonomic relationship between S. lychnophora and other species of genus Sterculia. Compounds 13 and 20 might serve as important taxonomic markers for the Sterculia genus.     

Two new glycosides from the whole plant of Anemone rivularis var. flore-minore

Phytochemical investigation on the whole plant of Anemone rivularis var. flore-minore led to the isolation of a new labdane-type diterpene glycoside (1) and a new trihydroxyfuranoid lignanoid glycoside (2), together with three known triterpene and triterpenoid glycosides (3–5). The structures of the two new compounds were elucidated as β-d-glucopyranosyl (13S)-13-hydroxy-7-oxo-labda-8,14-diene-18-oate (1) and (7S,7′R,8R,8′S)-7′-butoxy-7,9′-epoxy-4,4′,9-trihydroxy-3,3′-dimethoxylignane 9-O-β-d-glucopyranoside (2), on the basis of extensive spectral analysis and chemical evidence. Compound 1 is characterized by a glucose (Glc) esterified C-18 carboxyl group, which is a rarely encountered labdane-type diterpene glycoside in nature. The two new compounds (1 and 2) reported here are the first examples of diterpene glycoside and lignanoid glycoside found in the genus Anemone, and the known triterpene and triterpenoid glycosides (3–5) are identified for the first time from the title plant.     

Three new glycosides from the whole plant of Clematis lasiandra Maxim and their cytotoxicity

Phytochemical investigation on the whole plant of Clematis lasiandra Maxim led to the isolation of two new phenolic glycosides (1 and 2), one new lignanoid glycoside (3), together with three known lignanoid glycosides (4–6). The structures of the new compounds were elucidated as 4-O-β-d-galactopyranosyl-ethyl-E-caffeate (1), 4-O-β-d-galactopyranosyl-3-hydroxyl-phenylethene (2) and (8R)-3,3′-dimethoxy-4,4′,9,9′-tetrahydroxy-5′,8-lignan 3′-O-β-d-glucopyranoside (3), on the basis of extensive spectral analysis and chemical evidence. The characteristic of the polymerized C-5′–C-8 type lignanoid aglycone in glycoside 3 was found from genus Clematis for the first time. Compounds 1–6 were evaluated for their cytotoxicity against human tumor cell lines HL-60, Hep-G2 and SGC-7901, the new glycosides 1 and 2 showed significant cytotoxicity against those three tumor cell lines with IC₅₀ in the range from 9.73 to 22.31 μM, while lignanoid glycosides 3–6 showed weak cytotoxicity to those test cell lines with IC₅₀ value more than 52.71 μM.     

Flavonoid glycosides from Barringtonia acutangula

Using various chromatographic separation techniques, ten flavonoid glycosides, including six new compounds namely barringosides A?F (1–6), were isolated from a methanol extract of the Barringtonia acutangula leaves. The structure elucidation was confirmed by spectroscopic analyses, including 1D and 2D NMR, and HR ESI MS. Their inhibitory effects on LPS-induced NO production in RAW264.7 cells were also evaluated. Among the isolated compounds, quercetin 3-O-β-d-(6-p-hydroxybenzoyl)galactopyranoside (9) showed significant effect with an IC₅₀ of 20.00 ± 1.68 µM. This is the first report of these flavonoid glycosides from Barringtonia genus and their inhibition on LPS-induced NO production in RAW264.7 cells was reported here for the first time.     

Chemical constituents from the rhizome of Anemone hupehensis

A phytochemical investigation on the rhizome of Anemone hupehensis resulted in the isolation of thirteen compounds, including six neolignan glycosides (1-6), two phenylpropanoid glycosides (7, 8), a phenolic glycoside (9) and four triterpenoid saponins (10-13). The structures of the isolated compounds were elucidated on the basis of spectroscopic data. This is the first report of neolignan glycoside, phenylpropanoid glycoside, and phenolic glycoside from genus Anemone. This is also the first study to report compounds 1-5 and 7-9 from family Ranunculaceae. All the compounds, except 10 were isolated from A. hupehensis for the first time. The chemotaxonomic significance of the isolated compounds was discussed.     

Sesquiterpenoids from Saussurea laniceps and their chemotaxonomic significance

Twenty-five sesquiterpenoids including seventeen guaiane-type sesquiterpenoids and glucose glycosides (1–17), six eudesmane-type sesquiterpenoids (18–23), and two germacrane-type sesquiterpenoids (24 and 25) were isolated from the aerial parts of Saussurea laniceps Hand.-Mazz. Their structures were elucidated by spectroscopic methods and comparison with previously reported spectral data. Among them, compounds (6 and 8) are new, and seven compounds (2, 9, 12, 18–19, 22–23) are reported for the first time from the genus Saussurea. This paper deals with the isolation, structural elucidation and chemotaxonomic significance of these sesquiterpenoids from S. laniceps.