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.     

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.     

New phenolic glycosides with cyclooxygenase inhibition from the roots of Tecoma mollis

Three new phenolic glycosides (1–3) together with nine known ones were isolated from the roots of Tecoma mollis using DPPH radical scavenging bioassay-guided chromatographic separation. The structures of the new compounds were established using extensive spectroscopic data and HR-MS. The antioxidant, COX-2 inhibition, and cytotoxic activities were evaluated for the isolated compounds. Compound 4 displayed the strongest radical scavenging activity relative to ascorbic acid with IC₅₀ 8.7 μM. Compounds 5, 6, and 10 showed promising COX-2 inhibitory action, IC₅₀ values of 11.3 μM, 9.4 μM, and 13.4 μM, respectively. All compounds exhibited weak cytotoxic activity against Hela and A549 cancer cell lines.     

New antioxidant phenolic glycosides from Walsura yunnanensis

Four new polyphenolic glycosides (1-4) were isolated from the BuOH extract of the bark of Walsura yunnanenis C. Y. Wu. These compounds comprise two lignans, i.e., the 9-O-alpha-L-arabinopyranosides 1 and 2 of (-)-isolariciresinol and of (+)-5-methoxyisolariciresinol, respectively, and the two phenolic glycosides 3,4,5-trimethoxyphenyl 2-O-(alpha-L-fucopyranosyl)-beta-D-glucopyranoside (3) and 3,5-dihydroxyphenyl 6-O-(4-hydroxy-3,5-dimethoxybenzoyl)-beta-D-glucopyranoside (walsuraside; 4). In addition, three known compounds, 3,4,5-trimethoxyphenyl beta-D-glucopyranoside, asperglaucide, and butyl alpha-D-fructofuranoside were identified. Their structures were elucidated spectroscopically and by chemical transformation (hydrolysis). The new compounds 1, 2, and 4 displayed significant antioxidant activities, with IC(50) values in the range of ca. 42 to 49 microg/ml.     

Anti-inflammatory iridoid glycosides from fruits of Cornus officinalis

Three undescribed iridoid glycosides, cyc(7β-O-6′)-morroniside (1), 6′-methyl succinate-7β-O-methylmorroniside (2), and 7β-O-methyl phenyllactate morroniside (3) were isolated from 50% ethanol extract of Cornus officinalis fruits. The structures of the isolated compounds were determined by HRESIMS, ¹D NMR, ²D NMR, UV and IR spectroscopic methods. Compounds 1-3 exhibited moderate anti-inflammatory activities in vivo in a CuSO₄-induced zebrafish inflammation model (when evaluated at 50 μM).     

Three new chlorinated phenolic glycosides from Przewalskia tangutica

Three new chlorinated phenolic glycosides, namely przewatangosides A-C (1-3), along with one known compound, globosumoside A (4), were isolated from the whole plants of Przewalskia tangutica. Their structures were unequivocally determined by extensive spectroscopic analysis and chemical method. The cytotoxic activities of the isolated phenolic glycosides (1-4) were evaluated against the five human cancer cell lines A549, MCF-7, SMMC-7721, HepG2 and HL-60. Przewatangoside A (1) exhibited weak cytotoxicity against SMMC-7721 with the IC₅₀ value of 38.1 μM. All the tested compounds were inactive (IC₅₀ > 50 μM) to the normal human hepatocyte cell line (L02).     

Acylated phenolic glycosides from Solenostemma argel

From the aerial parts of Solenostemma argel, four new acylated phenolic glycosides sinapyl alcohol 9-O-feruloyl-4-O-alpha-rhamnopyranosyl-(1-->2)-beta-glucopyranoside, solargin I (1), sinapyl alcohol 9-O-caffeoyl-4-O-alpha-rhamnopyranosyl-(1-->2)-beta-glucopyranoside, solargin II (2), sinapyl alcohol 9-O-feruloyl-4-O-alpha-rhamnopyranosyl-(1-->2)-alpha-rhamnopyranosyl-(1-->2)-beta-glucopyranoside, solargin III (3) and sinapyl alcohol 9-O-caffeoyl-4-O-alpha-rhamnopyranosyl-(1-->2)-alpha-rhamnopyranosyl-(1-->2)-beta-glucopyranoside, solargin IV (4) have been isolated. The structures of the isolated compounds were verified by means of MS and NMR spectral analyses.     

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.     

Acylated kaempferol glycosides from Aconitum (ranunculaceae)

Four new acylated kaempferol glycosides were isolated and identified from the leaves of Aconitum noveboracense and A. columbianum.     

Four new phenolic diglycosides from the roots of Illicium oligandrum

Four new phenolic diglycosides (1–4), named illoliganoside A–D, and three known glycosides (5–7), were isolated from the roots of Illiciumoligandrum. The structures of the new diglycosides were determined on the basis of HRMS, NMR spectroscopic, and chemical methods. The anti-inflammatory and cytotoxic activities for 1–7 were evaluated.     

Anticomplement cycloartane triterpene glycosides from Beesia calthaefolia (Maxim.)

Investigation of the n-BuOH extract of the whole plant of Beesia calthaefolia led to the isolation of three new cycloartane triterpenoids (1–3) and two known compounds (4, 5). Their structures were elucidated by 1D and 2D NMR, HRESIMS and optical rotation spectral data. All of the isolates were investigated for their inhibitory effects on the classical pathway of the complement system. Among them, compound 3 showed stronger inhibitory activity (IC₅₀ 148.0 μM) than the positive control (rosmarinic acid, IC₅₀ 181.8 μM), while other compounds (1, 2, 4 and 5) showed moderate activity. The chemical compound studied in this article was rosmarinic acid (PubChem CID: 5281792).     

Isolation and characterization of two new phenolic acids from cultured cells of Saussurea involucrata

Two new phenolic acids, 1, 5-O-dicaffeoyl-3-O-(4-maloyl)-quinic acid (1) and 3, 5-di-O-caffeoyl-1-O-(2-O-caffeoyl-4-maloyl)-quinic acid (2), were isolated from cultured cells of Saussurea involucrata. Their structures were elucidated using 2D NMR spectroscopy and MS. Further in vitro bioactive investigations demonstrated that 3, 5-di-O-caffeoyl-1-O-(2-O-caffeoyl-4-maloyl)-quinic acid (2) had significant scavenging activities against radicals 1, 1-diphenyl-2-picryl-hydrazyl (DPPH) and 2, 2′-azino-bis-3-ethylbenzothiazoline-6-sulphonic acid (ABTS).     

Three new phenolic acid derivatives from Oenothera biennis

Three new phenolic acid derivatives, 1-methyl glyceric acid-2-vanillic acid ether (1), methyl 2-hydroxy-6-(3-methoxy-3-oxoprop-1-en-2-yloxy) benzoate (2), methyl 2-hydroxy-6-(1-Carboxyvinyloxy) benzoate (3) and five known compounds namely 4-hydroxymellein (4), mellein methyl ether (5), 2-methyl-5,7-dihydroxychromone (6), latifolicinin C (7) and oresbiusin A (8) were isolated from Oenothera biennis L. The structures of these secondary metabolites were elucidated using different spectroscopic techniques, including ¹H, ¹³C NMR, HR-ESI-MS, ECD and comparison with published data.     

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.     

Three new flavonoid glycosides from the aerial parts of Graptophyllum grandulosum Turril (Acanthaceae)

Grandulosides A-C, three new flavonoid glycosides, were isolated from the aerial parts of Graptophyllum grandulosum Turill and identified as chrysoeriol-7-O-β-d-apiofuranosyl-(1 → 2)-β-d-xylopyranoside (1), chrysoeriol-7-O-[4′′′-O-acetyl-β-d-apiofuranosyl-(1 → 2)]-β-d-xylopyranoside (2) and 7-O-α-l-rhamnopyranosyl-(1 → 6)-β-d-(4′′-Sodium hydrogeno sulfate) glucopyranoside (3). Four known compounds, chrysoeriol-7-O-β-d-xyloside (4), isorhamnetin-3-O-α-l-rhamnopyranosyl-(1 → 6)-β-d-glucopyranoside (5), luteolin-7-O-β-d-apiofuranosyl-(1 → 2)-β-d-xylopyranoside (6) and sucrose (7) were also obtained. The structures of these compounds were established by interpretation of their spectral data, mainly HR-TOFESIMS, 1D-NMR (¹H, ¹³C) and 2D-NMR (COSY, NOESY, HSQC and HMBC) and by comparison with the literature data.     

Antibacterially active phenolic lipid derivatives from Comarum salesovianum (Steph.) Aschers. et Gr.

The antibacterial activity-guided purification of the dichloromethane fraction of the aerial parts of Comarum salesovianum (Steph.) Aschers.et Gr. led to the isolation and elucidation of three phenolic lipid derivatives: 6-(non-8-enyl) salicylic acid (1), 6-nonyl salicylic acid (2) and 3-(non-8-enyl) phenol (3), which were found for the first time in the natural source. The equal mixture of compounds 1 and 2 exhibited potent inhibitory activity against all tested Gram-positive bacterial strains (Enterococcus faecalis, Micrococcus luteus, Staphylococcus epidermidis and Staphylococcus aureus) with inhibitory zones of 12.2–22.1 mm, whereas each single compound showed weaker activity than the mixture of 1 and 2. However, compound 3 strongly inhibited (29.9 ± 1.8) the growth of M. luteus. The presence of salicylic acid with the unsaturated aliphatic side chain is essential for the antibacterial activity strength of phenolic lipid molecules.     

Two new hemiterpene glycosides and one new phenolic glycoside from the roots of Securidaca inappendiculata Hassk

Two new hemiterpene glycosides, named as securiterpenoside B (1), and securiterpenoside C (2), and one new phenolic glycoside, named as securiphenoside A (3) were isolated from the roots of Securidaca inappendiculata Hassk. Their structures were elucidated on the basis of 1D and 2D NMR data and HRESIMS and comparisons with published data. Moreover, compounds 1–3 were evaluated for cytotoxicities against A549 (Lewis lung cancer), Hela (human cervical cancer) and MCF-7 (human breast cancer) cell lines.     

Biochemical ecology of the forest tent caterpillar: responses to dietary protein and phenolic glycosides

Summary Interactions between quaking aspen (Populus tremuloides) and the forest tent caterpillar (Malacosoma disstria) are likely to be influenced by leaf protein and phenolic glycoside levels, and insect detoxication activity. We investigated the direct and interactive effects of dietary protein and phenolic glycosides on larval performance and midgut enzyme activity of forest tent caterpillars. We conducted bioassays with six artificial diets, using both first and fourth stadium larvae. Four of the diets comprised a 2×2 factorial design-two levels of protein, each with and without phenolic glycosides. Additionally, we assayed high protein diets containing S,S,S-tributylphosphorotrithioate (DEF, an esterase inhibitor) and DEF plus phenolic glycosides. Enzyme solutions were prepared from midguts of sixth instars and assayed for -glucosidase, esterase and glutathione transferase activities. First instar mortality and development times were higher for larvae on diets low in protein or containing phenolic glycosides. Effects of phenolic glycosides were especially pronounced at low protein levels and when administered with DEF. Fourth instar development times were prolonged, and growth rates reduced, in response to consumption of low protein diets. Effects of phenolic glycosides on growth were less pronounced, although the effect for larvae on the low protein diet was nearly significant. Activity of each of the enzyme systems was reduced in larvae reared on low protein diets, and esterase activity was induced in larvae fed phenolic glycosides. Our results suggest that larval performance may be strongly affected by levels of protein and phenolic glycosides commonly occurring in aspen foliage, and that these factors may play a role in differential defoliation of aspen by forest tent caterpillars.     

红树白骨壤果实中酚苷类化学成分研究

采用柱色谱、凝胶层析和高效液相色谱分离技术,从白骨壤果实中分离获得6个酚苷类单体化合物。运用波谱分析和文献对照方法,分别鉴定为Rhyncoside A(1)、松柏苷(2)、对羟基苯甲酰葡萄糖(3)、顺式香豆酸-4-O-β-D-吡喃葡萄糖苷(4)、香草酸4-O-β-D-吡喃葡萄糖苷(5)、苯基-β-D-葡萄糖苷(6)。化合物1-6均是首次从该种海洋植物中分离得到。     

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.