Four new glycosides from the seeds of Cassia obtusifolia

Four new glycosides, including one anthraquinone glycoside (1), one naphthalene glycoside (2), and two naphthopyrone glycosides (3–4), with 10 known compounds (5–14) were isolated from the seeds of Cassia obtusifolia L. The new structures were determined by spectroscopic analysis and chemical transformations.     

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.     

Cytotoxic cardiac glycosides and coumarins from Antiaris toxicaria

Eight new cardiac glycosides/aglycones (antiaritoxiosides A–G, 1–7, and antiarotoxinin B, 8), two new coumarins (anticarins A–B, 41–42), and two new flavanones (antiarones L–K, 43–44) were isolated from trunk bark of Antiaris toxicaria together with 53 known compounds. The new structures were established by extensive analysis of spectroscopic data. Compound 1 (10-carboxy and 3α-hydroxy) and compounds 3–6 (10-hydroxy) contain unique substituents that are rarely found in cardiac glycosides. The cytotoxic effects of isolated compounds against ten human cancer cell lines, KB, KB-VIN, A549, MCF-7, U-87-MG, PC-3, 1A9, CAKI-1, HCT-9 and S-KMEL-2, were tested using the sulforhodamine B assay. Five compounds (12, 16, 20, 22, and 31) showed significant cytotoxicity against all ten cancer cell lines, with notable potency at the ng/mL level against some cell lines, which merits further development as clinical trial candidates.     

Four new phenylpropanoid glycosides from Clausena dunniana var. robustaand their antiinflammatory activities

Four new phenylpropanoid glycosides, clausenaglycosides A–D (1–4), along with fourteen known compounds (5–18) were isolated from the leaves and twigs of Clausena dunniana var. robusta. The structures of the isolated compounds were determined by a combination of 1D and 2D NMR, MS, and CD spectroscopic data. The NF-κB inhibitory activity was evaluated in HeLa cells. Compound 17 displayed a moderate inhibition against NF-κB activation.     

New phenolic glycosides isolated from Penthorum chinense Pursh

A phytochemical investigation from 80% ethanol extract of Penthorum chinense Pursh (Saxifragaceae) resulted in the isolation of three new phenolic glycosides (1–3), together with three known phenolic glycosides (4–6). The structures of the new compounds were deduced from their comprehensive spectroscopic analysis including IR, HR-EI-MS, ¹H NMR, ¹³C NMR, DEPT, COSY, HMBC and HMQC. And the structures of known compounds 4–6 were identified by comparison of their spectral data with those reported in the literature.     

Chemical constituents from Orobanche cernua Loefling

Phytochemical study of Orobanche cernua Loefling afforded 17 compounds, including eleven phenylpropanoid glycosides (1–11), two flavonoids (12, 13), one lignan (14), and three phenolic acids (15–17) were isolated from the fresh whole plant of O. cernua. Their structures were identified by spectroscopic analyses and by comparison of their spectral data with those reported in the literature. This is the first report of isolation of compounds (6, 8, 9, 11, 14–16) from O. cernua and compounds (14, 15) from the family Orobanchaceae, respectively. Compound 14 was obtained from natural source for the first time, the chemotaxonomic significance of these compounds was summarized.     

New phenanthrene glycosides from Dendrobium denneanum and their cytotoxic activity

Five new phenanthrene glycosides, denneanosides A–E (1–5), and one new 9,10-dihydrophenanthrene glycoside, denneanoside F (6) were isolated from the stem of Dendrobium denneanum. The chemical structures of the new compounds were established on the basis of extensive spectroscopic data. The isolated compounds were evaluated for their in vitro cytotoxic activity against SNU387 hepatocellular carcinoma cell line. Compounds 1–3 showed moderate cytotoxic activities while compounds 4–6 showed weak activities.     

New lignan glycosides from the root barks of Litsea glutinosa

An investigation on the chemical constituents in the root barks of Litsea glutinosa was performed for the first time. Three new lignan glycosides named Litseasins A–C (1–3), together with a known one (4), were obtained. The structures of the new compounds were established through extensive spectroscopic analyses including HR-ESI–MS, NMR, and circluar dichroism (CD). The new compounds were evaluated for their anti-inflammatory activities on lipopolysaccharide (LPS)-induce nitric oxide (NO) production in RAW264.7 murine macrophage cells. However, these compounds showed no inhibition on LPS-induced NO productions.     

Brevistylumsides A and B,diterpene glycosides from Illicium brevistylum

A phytochemical investigation of 80% ethanol extract of Illicium brevistylum (Illiciaceae) resulted in the isolation of two new diterpene glycosides (1 and 2), together with three known diterpenes (3–5). The structures of the new compounds were deduced on the basis of comprehensive spectroscopic analysis including IR, HR-ESI–MS, ¹H NMR, ¹³C NMR, DEPT, COSY, HMBC and HSQC. The structures of known compounds 3–5 were identified by comparison of their spectral data with those reported in the literature.     

Three new phenolic glycosides from the whole plant of Aconitum tanguticum (Maxim.) Stapf

Three new phenolic glycosides 2-(3-O-β-d-glucopyranosyl-4-hydroxyphenyl) ethanol 1-O-β-d-glucopyranoside (1), 2-(4-O-β-d-fructopyranosylphenyl) ethanol 1-O-β-d-galactopyranoside (2) and 3-methoxy-4-O-β-d-allopyranosyl acetophenone (3), along with nine known compounds (4–12), were isolated from the ethanol extract of the whole plant of Aconitum tanguticum (Maxim.) Stapf. Their structures were elucidated by analysis of spectroscopic data including 1D-, 2D-NMR and HRESIMS, and the reported literature data comparison. All the compounds were evaluated for their potential anti-inflammatory effects by the inhibition of TNF-α production on LPS-stimulated RAW264.7 macrophages. Compounds 1, 3, 5 and 7–9 showed certain inhibition activity and their IC₅₀ values were 38.18, 27.64, 3.25, 84.45, 12.76 and 18.44 μg/mL, respectively.     

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.     

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.     

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.     

Chrysoeriol derivatives and other constituents from Glandularia selloi

Glandularia selloi (Verbenaceae) presents phenylethanoids, iridoids and flavone glycosides as the main constituents. Two novel chrysoeriol derivatives, selloiside A (1) and selloiside B (2) were isolated from the methanolic extract of the aerial parts. Both flavones are acylated disaccharides. Two known compounds, verbascoside (3) and 6β-hydroxy-ipolamiide (4), were isolated from the methanolic extract of the roots. The structures were elucidated using 1D, 2D NMR and MS. Acylflavones have taxonomic significance since they occur mainly is species from the order Lamiales, specifically from the family Lamiaceae, closely related to Verbenaceae. The compounds 1 – 4 and the methanolic extract were investigated for antichemotactic activity.     

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 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.     

Monoterpenoid glycoside derivatives from Melaleuca alternifolia

The phytochemical investigation of leaves of Melaleuca alternifolia (Maiden & Betche) Cheel led to the isolation of a new monoterpenoid glycoside derivative melaleuoside (1), together with four known monoterpenoid glycoside derivatives (2–5). Structure elucidation of these compounds was performed based on NMR spectral data and MS. Compounds 2–5 were isolated from the genus of Melaleuca for the first time. Furthermore, we also discussed the chemotaxonomic significance of the isolates in this thesis.     

New iridoid glycosides from the fruits of Forsythia suspensa and their hepatoprotective activities

A novel iridoid glycoside trimer named forsydoitriside A (1) and five new iridoid glycosides (2–6) were isolated from the fruits of Forsythia suspensa together with two known compounds (7, 8). These new structures were elucidated by comprehensive spectroscopic data and the comparison of experimental and calculated electronic circular dichroism spectra. Compounds 1–8 were all assayed on acetaminophen-induced HepG2 cell damage. The results exhibited that compounds 2, 3, 5 and 6 possessed strong hepatoprotective activities against the damage in HepG2 cell.     

Bibenzyl and phenolic glycosides from Pterospermum heterophyllum

A new bibenzyl, heterophyllic acid (1), and three new phenolic glycosides, heterophylloside A–C (2–4), along with two known phenolic glycosides oldhamioside (5) and 6′-O-vanilloylisotachioside (6) were isolated from Pterospermum heterophyllum. The structures of these compounds were elucidated on the basis of 1D, 2D NMR, MS spectroscopic analysis, and chemical methods. Their cytotoxic activities against KB and MCF-7 cancer cell lines were evaluated. Compound 2 showed significant cytotoxic activities.     

Three new phthalide glycosides from the rhizomes of Ligusticum chuanxiong

Three new phthalide glycosides, named chuanxiongoside A (1), chuanxiongoside B (2) and ligusticoside B (3) together with two known glycosides, celephthalide A (4) and icariside F₂ (5), were isolated from the rhizomes of Ligusticum chuanxiong. This is the first report of compounds 4⿿5 from the title plant. The structures of compounds 1⿿3 were identified using various spectroscopic methods.