Monoterpene glycosides from Paeonia veitchii

The EtOH extract of the roots of Paeonia veitchii afforded two new monoterpene glycosides paeonidanin I (1) and paeonidanin J (2), and a new dimeric monoterpene glycoside paeonidanin K (3). Their structures were elucidated on the basis of spectroscopic means and hydrolysis products.     

New lignan glycosides from Justicia procumbens

Four new lignan glycosides (1–4), named procumbenosides I, K, L, and M, together with cleistanthin B (5) reported for the first time in the genus Justicia, and 5 other known arylnaphthalene lignan glycosides (6–10) were isolated from the whole plant of Justicia procumbens. The structures of the new compounds were elucidated by extensive one-dimensional (1D) and two-dimensional (2D) NMR experiments and mass spectrometry. Procumbenoside M (4) was a rare sesquilignan glycoside never previously reported in the species of Justicia. The paper also provided insight into the conformational equilibria existing in the lignan glycosides of the plant.     

Three new monoterpene glycosides from the roots of Paeonia lactiflora

Three new monoterpene glycosides, 2′-O-benzoylpaeoniflorin, albiflorin R₂, and albiflorin R₃ (1–3) were isolated from the roots of Paeonia lactiflora. Their structures were elucidated on the basis of spectroscopic means including one- and two-dimensional NMR experiments.     

Acetylated anthraquinone glycosides from Cassia obtusifolia

Three new acetylated anthraquinone glycosides (1–3) were isolated from the seed of Cassia obtusifolia, together with one parent anthraquinone glycoside (1a). Their structures were determined on the basis of spectroscopic methods and physicochemical properties as obtusifoline-2-O-β-d-2, 6-di-O-acetylglucopyranoside (1), obtusifoline-2-O-β-d-glucopyranoside (1a), obtusifoline-2-O-β-d-3, 6-di-O-acetylglucopyranoside (2), and obtusifoline-2-O-β-d-4, 6-di-O-acetylglucopyranoside (3).     

A new eudesmane sesquiterpene glycosides from Liriope muscari

A new eudesmane sesquiterpene glycoside, ophiopogonoside B (1), along with five known compounds, ophiopogonoside A (2), ruscogenin-1-O-[β-d-glucopyranosyl (1 → 2)]-[β-d-xylopyranosyl (1 → 3)]-β-d-fucopyranoside (3), palmitic acid (4), palmitic acid glyceride (5), and β-sitosterol-d-glucopyranoside (6),was isolated from the tuberous roots of Liriope muscari (Decn.) Bailey (Liliaceae). Their structures were confirmed by 1D and 2D NMR spectroscopy. Among them, compounds 1, 2, 4, and 5 were the first reported from the genus Liriope. Ophiopogonoside B (1) showed moderate inhibitory activity to glycogen phosphorylase a.     

Three new lignan glycosides from the fruits of Forsythia suspense

Two new lignan glycosides forsythiayanoside A (1) and forsythiayanoside B (2), one new stereoisomer of lignan glycoside (+)-8-hydroxyepipinoresinol-4-O-β-d-glucopyranoside (3), together with seven known compounds (4–10), were isolated from the fruits of Forsythia suspense (Thunb.) Vahl. Compounds 4 and 10 were isolated from this species for the first time. The structures of 1–3 were elucidated on the basis of chemical and spectral analyses, including 1D and 2D NMR data and HR-ESI-MS. The absolute configurations were determined by the circular dichroism method. All isolates were tested for their cytotoxicities against five human cancer cell lines (A549, Colo-205, Hep-3B, HL60, and KB). In particular, compound 3 showed significant cytotoxicity with IC₅₀ values of 9.48, 7.75, 0.59, 4.06, and 38.38 μM, respectively.     

Phenyl and phenylethyl glycosides from Picrorhiza scrophulariiflora

A new phenyl glycoside, scrophenoside D (1) and a new phenylethyl glycoside, scroside F (2), together with three known phenylethyl glycosides, scroside A (3), plantainoside D (4), and plantamajoside (5), were isolated from the stems of Picrorhiza scrophulariiflora. Their structures were elucidated by spectroscopic and chemical methods.     

Further flavonol and iridoid glycosides from Ajuga remota aerial parts

Five new iridoid glycosides characterised as 6-keto-8-acetylharpagide (1), 6,7-dehydro-8-acetylharpagide (2), 7,8-dehydroharpagide (3), 8-acetylharpagide-6-O-β-glucoside (4), harpagide-6-O-β-glucoside (5) together with three flavonol glycosides, myricetin 3-O-rutinoside-4′-O-rutinoside (6), myricetin 3-O-rutinoside-3′-O-rutinoside (7) and isorhamnetin 3-O-rutinoside-7-O-rutinoside-4′-O-β-glucoside (8) have been isolated from the aerial parts of Ajuga remota. Also isolated were two known compounds ajugarin IV and ajugarin V. Their structures were established using spectroscopic methods including UV, IR, FAB-MS, HR-MS, 1D and 2D NMR techniques.     

Two new compounds from Acanthopanax senticosus Harms

From the dried aerial part of Acanthopanax senticosus, a new coumarin glycoside, eleutheroside B₂ (1), and a new sesquiterpenoid, oplopanone B (2), were isolated. Their structures were elucidated on the basis of chemical and spectroscopic methods.     

Ionone glycosides from the roots of Rehmannia glutinosa

Four new ionone and ionone glycosides (1–4), and a new monoterpene (5), together with 10 known analogues (6–15), were isolated from the air-dried roots of Rehmannia glutinosa. The structures of these compounds were elucidated on the basis of spectroscopic data analysis. Furthermore, in in vitro assays, compound 3 (10 μM) exhibited moderate hepatoprotective activities against d-galactosamine-induced HL-7702 cell damage.     

Two new glycosides from Dryopteris fragrans with anti-inflammatory activities

Phytochemical investigation on the aqueous extract from Dryopteris fragrans led to the isolation of one new chromone glycoside, frachromone C (1), and one new coumarin glycoside, dryofracoulin A (2), together with one known undulatoside A (3). Their structures were elucidated by a combination of 1D and 2D NMR, HRMS, and chemical analysis. Compounds 1–3 exhibited inhibition on nitric oxide production in lipopolysaccharide induced RAW 264.7 macrophages with their IC₅₀ values of 45.8, 65.8, and 49.8 μM, respectively.     

Chemical constituents of Euonymus fortunei

A new flavonol glycoside, kaempferol-3-O-β-d-(2-O-E-p-coumaroyl)-glucopyranosyl-7-O-α-l-rhamnopyranoside (1), along with eleven known compounds including five flavonol glycosides (2–6), one phenolic glycoside (7), two megastigmane glycosides (8 and 9), two triterpenoids (10 and 11) and one alditol (12), was isolated from the aerial parts of Euonymus fortunei. Their structures were determined on the basis of spectroscopic analysis and chemical evidence. Compounds 2–4, 7, 8, and 10–12 were evaluated their antimicrobial activities against Ureaplasma urealyticumin vitro, but all tested compounds have no useful activities against Ureaplasma urealyticum.     

Phenolic glycosides from Rhodohypoxis baurii

Three new phenolic glycosides (1–3), together with a known glycoside (4), were isolated from the bulbs of Rhodohypoxis baurii (Hypoxidaceae). The structures of the new glycosides (1–3) were determined on the basis of extensive spectroscopic analyses, including two-dimensional (2D) NMR data, and of hydrolytic cleavage followed by chromatographic or spectroscopic analyses.     

Phenolic glycosides from Glycosmis pentaphylla

Three new phenolic glycosides, named as glycopentosides A–C (1–3), along with nine known compounds were isolated from the n-BuOH extract of stems of Glycosmis pentaphylla. Their structures were determined by using spectroscopic and chemical methods. Bioassay showed that compound 10 (tachioside) could inhibit nitric oxide production in lipopolysaccharides-stimulated RAW 264.7 cells with IC₅₀ value of 12.14 μM.     

Two new lignan glycosides from the fruits of Pyrus ussuriensis

Two new lignan glycosides, ussuriensislignan A (1) and ussuriensislignan B (2), together with seventeen known compounds (3–19), were isolated from the fruits of Pyrus ussuriensis. Their structures were determined by various spectroscopic methods. This is the first report of the isolation of lignans (compounds 1–3) from the genus Pyrus, and compounds 3–6, 12–16 were reported from Pyrus for the first time.     

Two new glycosides from the fruits of Forsythia suspense

Two new glycosides suspensaside C (1) and 2,3,5,6-tetrahydro-jacaranone-4-O-β-d-glucopyranoside (2), together with four known compounds suspensaside A (3), rengynic acid-1′-O-β-d-glucopyranoside (4), forsythoside A (5), and rengynic acid (6), were isolated from the fruits of Forsythia suspense (Thunb.) Vahl. The structures of 1 and 2 were elucidated on the basis of chemical and spectral analysis, including 1D, 2D NMR analyses and HR-ESI-MS. All isolates were tested for their cytotoxicities against five human cancer cell lines (A549, Colo-205, Hep-3B, HL60, and KB). Compound 3 exhibited cytotoxicity against HL-60, Hep-3B, and A549 cancer cell lines.     

Two new sesquiterpene glycosides from Pogostemon cablin

Two new rearranged patchoulane sesquiterpene glycosides, 3α-hydroxypatchoulol 3-O-β-d-glucopyranoside (1) and 15-hydroxypatchoulol 15-O-β-d-glucopyranoside (2) together with rubusoside, a known diterpene glycoside, were isolated from the ethanol extract of the whole plant of Pogostemon cablin (Blanco) Benth. The structures of 1 and 2 were elucidated by spectroscopic analysis.     

Phenolic glycosides from Lavandual angustifolia

Abstract

Four new phenolic glycosides (1–4), together with 12 known ones (5–16), were isolated from the essential oil extraction waste of Lavandula angustifolia. Their structures were unequivocally determined by extensive spectroscopic analysis (1D and 2D NMR, HR-ESI-MS, UV, and optical rotation), chemical method, and comparison with data reported in the literature. The antioxidant activities of all compounds and new compounds’ influence on melanin content in B16 melanoma cells were examined, which indicated that compounds 1, 8, 13 had a certain degree of DPPH free radical scavenging activities, while only compound 2 could increase the melanin content with a dose-dependent manner.     

Jacaranone glycosides from Senecio scandens

Bioassay-guided fractionation of the ethanol extract of Senecio scandens led to the isolation of four new compounds 1–4. These compounds were obtained as tautomeric mixture of α/β epimers, but their structures were confirmed unambiguously by 1D and 2D NMR spectra and LC NMR technology. ¹H NMR spectra of pure 1α and 1β were furnished by HPLC NMR technology. Compounds 1–4 exhibited moderate cytotoxicities against five tumor cell lines.     

New flavonol glycosides and new xanthone from Polygala japonica

Three new flavonol glycosides and a new xanthone were isolated from Polygala japonica HOUTT. with eight known compounds. Their structures were identified as 1,7-dihydroxy-3,4-dimethoxy-xanthone (1), kaempferol-7,4′-dimethyl ether (2), physcion (3), guazijinxanthone (4), rhamnetin (5), polygalin A (6), 3,5,7-trihydroxy-4′-methoxy-flavone-3-O-β-d-galactopyranoside (7), 3,5,3′-trihydoxy-7,4′-dimethoxy-flavone-3-O-β-d-galactopyranoside (8), 3,5,3′,4′-tetrahydroxy-7-methoxy-flavone-3-O-β-d-galactopyranoside (9), 3,5,3′,4′-tetrahydroxy-7-methoxy-flavone-3-O-β-d-glucopyranoside (10), polygalin B (11), polygalin C (12). Among them, compound 4 is a new xanthone, and 6, 11 and 12 are new flavonol glycosides. Compounds 1, 4, 7 and 8 were tested for cytotoxic activity with MTT assays on five human tumor cell lines, K562, A549, PC-3M, HCT-8 and SHG-44. Compound 4 showed cytotoxic activity against all the five cell lines.