Three new isoflavone glycosides from Tongmai granules

Three new isoflavone glycosides, 3′-methoxydaidzein-7,4′-di-O-β-d-glucopyranoside (1), biochanin A-8-C-β-d-apiofuranosyl-(1 → 6)-O-β-d-glucopyranoside (2), daidzein-7-O-β-d-glucopyranosyl-(1 → 4)-O-β-d-glucopyranoside (3), and a new natural isoflavone glycoside, daidzein-7-O-α-d-glucopyranosyl-(1 → 4)-O-β-d-glucopyranoside (4) were isolated along with 18 known isoflavones from the EtOAc and n-BuOH fractions of the aqueous extraction of Tongmai granules. All the isoflavones were obtained and determined for the first time from Tongmai granules. The structures of these compounds were elucidated by spectral methods. It was confirmed that the compounds 1–4 were originally from Puerariae Lobatae Radix based on HPLC-DAD analysis of the crude drug extract. The isoflavones isolated were tested for their antioxidative activities by measuring the capacities of scavenging the 2,2′-diphenyl-1-picrylhydrazyl radical.     

Alkaloids from Clematis manshurica Rupr.

Three new alkaloids together with two known compounds have been isolated from the roots of Clematis manshurica. On the basis of their spectroscopic and chemical evidence, the new compounds were elucidated as methyl 7-ethoxy-3-indolecarbonate (2), methyl 7-O-α-l-rhamnopyranosyl-(1 → 6)-β-d-glucopyranosyl 3-indolecarbonate (3) and α-l-rhamnopyranosyl-(1 → 6)-β-d-glucopyranosyl 3-indolecarbonate (4).     

Flavonoids from the leaves of Pleioblastus argenteastriatus

A new flavonoid, 5,7,3′-trihydroxy-6-C-β-d-digitoxopyranosyl-4′-O-β-d-glucopyranosyl flavonoside (1), along with four known flavonoids 5,7,4′-trihydroxy-3′,5′-dimethoxy flavone (2), 5,3′,4′-trihydroxy-7-O-β-d-glucopyranosyl flavonoside (3), 5,4′-dihydroxy-3′,5′-dimethoxy-7-O-β-d-glucopyranosyl flavonoside (4), 5,3′,4′-trihydroxy-6-C-[β-d-glucopyranosyl-(1 → 6)]-β-d-glucopyranosyl flavonoside (5) were isolated from 95% EtOH extract of the leaves of Pleioblastus argenteastriatus. Their structures were determined on the basis of spectroscopic techniques and chemical methods.     

Two new flavone glycosides from the seeds of Impatiens balsamina L.

Two new flavone glycosides were isolated from the seeds of Impatiens balsamina L. and their structures were determined as quercetin-3-O-[α-l-rhamnose-(1 → 2)-β-d-glucopyranosyl]-5-O-β-d-glucopyranoside (1), and quercetin-3-O-[(6?-O-caffeoyl)-α-l-rhamnose-(1 → 2)-β-d-glucopyranosyl]-5-O-β-d-glucopyranoside (2) on the basis of various spectral and chemical studies.     

Two new flavonoid glycosides from the whole herbs of Hyssopus officinalis

Two new flavonoid glycosides, quercetin 7-O-β-d-apiofuranosyl-(1 → 2)-β-d-xylopyranoside (1) and quercetin 7-O-β-d-apiofuranosyl-(1 → 2)-β-d-xylopyranoside 3′-O-β-d-glucopyranoside (2), together with nine known flavonoids were isolated from the whole herbs of Hyssopus officinalis L. cultivated in Xinjiang Uygur Autonomous Region of China. All structures were characterized by the spectroscopic methods including UV, IR, ESI-MS, 1D, and 2D NMR. Their potent free radical scavenging activity against the stable 2,2-diphenyl-1-picrylhydrazyl (DPPH) free radical was evaluated.     

Steroidal alkaloids from the bulbs of Fritillaria unibracteata

Two new steroidal alkaloids peimisine-3-O-β-d-glucopyranoside (1) and puqiedinone-3-O-β-d-glucopyranoside (3), together with three known compounds peimisine (2), puqiedinone (4), and puqiedine (5), were isolated and characterized from the bulbs of Fritillaria unibracteata. Their structures were fully elucidated by spectroscopic and chemical methods. Compound 1 showed moderate protection effect on neurotoxicity of PC12 cell lines induced by rotenone.     

Two new anthraquinone glycosides from the roots of Rheum palmatum

Two new anthraquinone glycosides, named 1-methyl-8-hydroxyl-9,10-anthraquinone-3-O-β-d-(6′-O-cinnamoyl)glucopyranoside (1) and rhein-8-O-β-d-[6′-O-(3″-methoxyl malonyl)]glucopyranoside (2), have been isolated from the roots of Rheum palmatum, together with seven known compounds, rhein-8-O-β-d-glucopyranoside (3), physcion-8-O-β-d-glucopyranoside (4), chrysophanol-8-O-β-d-glucopyranoside (5), aleo-emodin-8-O-β-d-glucopyranoside (6), emodin-8-O-β-d-glucopyranoside (7), aleo-emodin-ω-O-β-d-glucopyranoside (8), and emodin-1-O-β-d-glucopyranoside (9). Their structures were elucidated on the basis of chemical and spectral analysis.     

Two new phenolic glycosides from Inula cappa

Two new phenolic glycosides, syringic acid-4-O-α-L-rhamnoside (1) and ( ? )-hydnocarpin-7-O-β-D-glucoside (2), were isolated from the traditional Chinese medicinal herb Inula cappa. The structures of the new compounds were elucidated by means of spectroscopic methods such as 1D, 2D NMR, and HR-ESI-MS.     

Two new C21 steroidal glycosides from Cynanchum wallichii Wight

Two new C₂₁ steroidal glycosides, characterized with caudatin as the aglycone moiety and 2,6-dideoxy-pyranoses as component sugars, have been isolated from the roots of Cynanchum wallichii Wight. Their structures were elucidated as caudatin-3-O-β-d-cymaropyranosyl-(1 → 4)-β-d-digitoxopyranoside (1) and caudatin-3-O-β-d-oleandropyranosyl-(1 → 4)-β-d-cymaropyranoside (2) by spectroscopic evidence.     

Two new compounds from the leaves of Indocalamus latifolius

Two new compounds, erythro-syringylglycerol-9-O-trans-4-hydroxycinnamate 7-O-β-d-glucopyranoside (1) and indocalatin A (2), together with three known ones, 5,7,3′-trihydroxy-6-C-β-d-digitoxopyranosyl-4′-O-β-d-glucopyranosyl flavonoid (3), 5,4′-dihydroxy-3′,5′-dimethoxy-7-O-[β-d-apiose-(1→2)]-β-d-glucopyranosyl flavonoid (4), and tricin-6-C-β-boivinopyranosyl-8-C-β-glucopyranoside (5), were isolated from the 95% EtOH extract of Indocalamus latifolius leaves. Their molecular structures were determined by UV, IR, HRESIMS, CD, and 1D and 2D NMR data analyses.     

Two new compounds from Urena lobata L.

Two new compounds 1 and 2 have been isolated from the aerial parts of Urena lobata L. The structures of the two new compounds were established as ceplignan-4-O-β-d-glucoside (1) and 2,5-dihydroxy benzoic acid-7-(2,6-dimethyl-6-hydroxy-2,7-octadienoic acid) anhydride-5-O-β-d-apiofuranosyl(1 → 2)-β-d-glucoside (urenoside A) (2), on the basis of chemical and spectral evidence, including 1D and 2D NMR spectroscopic data as well as mass spectrometry (HR-ESI-MS).     

The synthesis of pennogenin 3-O-β-d-glucopyranosyl-(1 → 3)-[α-l-rhamnopyranosyl-(1 → 2)]-β-d-glucopyranoside

Pennogenin 3-O-β-d-glucopyranosyl-(1 → 3)-[α-l-rhamnopyranosyl-(1 → 2)]-β-d-glucopyranoside, a monodesmosidic saponin isolated from Paris polyphylla Smith var. yunnanensis with promised antitumor activities, was firstly synthesized from glucoside thiol via nine steps and with 27% overall yield.     

Two new terpenoid glucosides from Aster flaccidus

Two new terpenoid glucosides, namely 2-O-β-d-glucopyranoside-vicodiol (1) and 10-O-β-d-glucopyranoside-oplopanone (2), along with seven known compounds, were isolated from the aerial part of Aster flaccidus (composite), a traditional Chinese herb medicine. The structures of 1 and 2 were established by spectroscopic methods, especially 2D NMR experiments.     

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.     

Bioactivity-guided isolation and identification of anti-adipogenic compounds from Sanguisorba officinalis

Context: Sanguisorba officinalis Linne (Rosaceae) is a medicinal plant used traditionally for the treatment of inflammatory and metabolic diseases in Korea, China, and Japan. In our previous study, a 50% ethanol extract inhibited fat accumulation in 3T3-L1 adipocytes.

Objective: This study investigates bioassay-guided fractionation, isolation, and identification of anti-adipogenic bioactive compounds in S. officinalis.

Materials and methods: The bioassay-guided fractionation was conducted using effective differentiation of 3T3-L1 cells into adipocytes (with 50?μg/mL test material for 8 days) to isolate the inhibitory compounds from ethyl acetate fraction of S. officinalis 50% ethanol extract. The cytotoxicity of each fraction and isolated compound was tested using MTT assay (with 25–300?μg/mL test material). Structures of the isolated active compounds were elucidated using ¹H NMR, ^13?C NMR, HSQC, HMBC, FT-IR, and MS.

Results: An active ethyl acetate fraction obtained with solvent partition of the extract inhibited lipid accumulation (44.84%) on 3T3-L1 cells without cytotoxicity (102.3%) at the concentration of 50?μg/mL. The ethyl acetate fraction was determined to be mainly composed by isorhamnetin-3-O-d-glucuronide (1) and ellagic acid (2). Pure isorhamnetin-3-O-d-glucuronide (IC₃₀ is 18.43?μM) and ellagic acid (IC₃₀ is 19.32?μM) showed lipid accumulation inhibition on 3T3-L1 cells without cytotoxicity (117.5% and 104.3%) at the concentration of 20?μM, respectively.

Discussion and conclusions: These results suggested that S. officinalis is a potential natural ingredient for the prevention of obesity, which may due to bioactive compounds such as isorhamnetin-3-O-d-glucuronide and ellagic acid.     

A new flavonoid glucoside from Rhododendron seniavinii

The leaves of Rhododendron seniavinii Maxim with little phytochemical information are used as folk remedies for the treatment of acute and chronic bronchitis in China. In our pursuing for the biologically active chemical constituents in the leaves, a new flavonoid glycoside 5,7,3′-trimethoxy-quercetin-3-O-β-d-glucopyranoside (1) was isolated from the water extract of its leaves, together with two known compounds 5,7,3′-trimethoxy-quercetin (2) and ovafolinin B-9′-O-β-d-glucopyranoside (3). The structures of the new flavonoid glucoside as well as two known compounds were elucidated by spectroscopic and chemical methods.     

Isolation,structural elucidation of flavonoid constituents from Leptadenia pyrotechnica and evaluation of their toxicity and antitumor activity

An investigation of Leptadenia pyrotechnica (Forsk.) Decne (Asclepiadaceace) chemical constituents led to the isolation of six flavonoids, kaempferol-3-O-α-l-rhamnopyranosyl (1′″→6″)-O-β-d-glucopyranoside (E-I.1), kaempferol-3-O-β-d-rhamnopyranosyl (1′″→6″)-O-β-d-glucopyranoside (E-I.2), texasin-7-O-β-d-glucopyranoside E-II.2, kaempferol-3-O-β-d-glucopyranoside (E-III.1), kaempferol (E-IV.1) and kaempferide-3-O-α-l-rhamnopyranosyl (1′″→6″)-O-β-d-glucopyranoside (E-I.1a). The isolation of these compounds was carried out using Sephadex LH-20 low pressure liquid chromatography (LPLC), preparative paper chromatography (PC), and high performance liquid chromatography (HPLC). The chemical structures of the isolated compounds were established by mass spectrometry (FAB- and EI- techniques), nuclear magnetic resonance NMR (¹H-, ¹³C- and COSY) spectral data and ultraviolet (UV) spectroscopic techniques. The acute toxicity of total alcoholic and total flavonoid extracts were examined by brine shrimp. The LC₅₀ values were 11.89 and 84.14 ppm for the total alcoholic and total flavonoid extracts, respectively. The mortality rates of the isolated flavonoid fractions of E-I, E-I.1, E-I.2 represent the higher percentages of mortality compared with the rest of the flavonoid fractions. The plant exhibited activity as an antitumor agent in the initial potato disc screen.     

Two new triterpenoid saponins from Ilex cornuta

Two new triterpenoid saponins (1 and 2) were isolated from the stems of Ilex cornuta, along with two known triterpenoids (3 and 4). The structures of compounds 1 and 2 were determined as ursane-12,19-diene-28-oic acid 3β-O-β-d-glucuronopyranoside-6-O-methyl ester (1), 3α,23α-dihydroxy-olean-9(11),12-diene-28-oic acid 28-O-β-d-glucopyranosyl ester (2), on the basis of hydrolysis and spectral evidence, including 1D and 2D NMR and high resolution electrospray ionization mass spectrometry (HR-ESI-MS) analyses. Protective effects of compounds 1–4 were tested against H₂O₂-induced H9c2 cardiomyocyte injury, and the data showed that all these compounds had no cell-protective effect.     

Chemical constituents from Mahkota dewa

A new phenolic glycoside (1), mahkoside A, together with six known compounds including mangiferin (2), kaempferol-3-O-β-d-glucoside (3), dodecanoic acid (4), palmitic acid (5) ethyl stearate (6) and sucrose (7), were isolated from the pit of Mahkota dewa. Their structures were identified on the basis of spectroscopic analysis. All the compounds were isolated from the title plant for the first time.     

Chemical constituents of Osyris alba and their antiparasitic activities

Phytochemical investigation of Osyris alba L. (Santalaceae) of Jordanian origin resulted in the isolation and identification of one new pyrrolizidine alkaloid, osyrisine (1), together with 16 other known compounds. The structures of all compounds were established on the basis of spectroscopic analysis. Osyrisine, catechin, and catechin-3-O-α-l-rhamnopyranoside exhibited a significant level of antiparasitic activity against two parasites, Entamoeba histolytica and Giardia intestinalis.