中药枸骨叶中三萜皂苷和黄酮苷类成分研究

A new triterpene glycoside, pomolic acid 3-O-6″-methyl-β-D-glucuronopyranosyl-（1→3）-α-L-arabino- pyranoside, and a new flavonol glycoside, quercetin 3-O-β-D-glucopyranosyl-（1→2）-α-L-arabinopyranoside together with three known triterpene saponins and two flavonol glycosides, were isolated from the leaves of Ilex cornuta. Their structures were established on the basis of spectroscopic analysis.     

Optimization of Ultrasound-Assisted Extraction of Polyphenols from Ilex latifolia Using Response Surface Methodology and Evaluation of Their Antioxidant Activity

The polyphenolic extract of Ilex latifolia (PEIL) exhibits a variety of biological activities. An evaluation of the parameters influencing the ultrasonic extraction process and the assessment of PEIL antioxidant activity are presented herein. Response surface methodology (RSM) was used to optimize the experimental conditions for the polyphenols ultrasonic-assisted extraction (UAE) from the leaves of Ilex latifolia. We identified the following optimal conditions of PEIL: ethanol concentration of 53%, extraction temperature of 60 °C, extraction time of 26 min and liquid–solid ratio of 60 mL/g. Using these parameters, the UAE had a yield of 35.77 ± 0.26 mg GAE/g, similar to the value we predicted using RSM (35.864 mg GAE/g). The antioxidant activity of PEIL was assessed in vitro, using various assays, as well as in vivo. We tested the effects of various doses of PEIL on D-galactose induced aging. Vitamin C (Vc) was used as positive control. After 21 days of administration, we measured superoxide dismutase (SOD) and glutathione peroxidase (GSH-Px) activities, malondialdehyde (MDA) levels in mouse serum and liver tissue. The results demonstrated that the PEIL exhibits potent radical scavenging activity against 1,1-diphenyl-2-picrythydrazyl (DPPH∙), 2,2′-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid (ABTS⁺), and hydroxyl (∙OH) radicals. The serum concentrations of SOD and GSH-Px were higher, and MDA levels were lower, in the medium- and high-dose PEIL-treated groups than those in the aging group (p < 0.01), and the activity of MDA was lower than those of the model group (p < 0.01). The liver concentrations of SOD and GSH-Px were higher (p < 0.05), and MDA levels were lower, in the medium- and high-dose PEIL-treated groups than those in the aging control group (p < 0.01). These results suggest that optimizing the conditions of UAE using RSM could significantly increase the yield of PEIL extraction. PEIL possesses strong antioxidant activity and use as a medicine or functional food could be further investigated.     

Triterpene Glycosides of Fatsia japonica. IV. Structure of Glycosides D1 and D2 from Seeds

Seeds ofFatsia japonica(Araliaceae) afforded the known hederagenin 3-O--D-glucopyranosyl-(12)-O--L-arabinopyranoside and the new triterpene glycoside D ₂ , for which the structure hederagenin 3-O--D- galactopyranosyl-(12)-O--L-arabinopyranoside was proposed based on chemical methods and NMR spectroscopy     

Three New Cycloartane Triterpene Glycosides from Actaea asiatica

Three new cycloartane triterpene glycosides were isolated from the rhizomes of Actaea asiatica. Their structures were elucidated as 25-ethoxyl-cimigenol-3-O-β-D-xylopyranoside 1, 2'-O-acetyl soulieoside C 2, 2'-O-acetyl cimiracemoside M 3.     

Flavonoid Glycosides from the Leaves of Machilus philippinensis

Thirteen flavonoid glycosides ( 1‐7 , 11‐13 , 15 , 17 , and 18 ) were isolated from the EtOH extract of the leaves of Machilus philippinensis. Of these, kaempferol 3‐O‐(2‐O‐β‐D ‐apiofuranosyl)‐α‐L ‐rhamnopyranoside ( 1 ) and kaempferol 3‐O‐(2‐O‐β‐D ‐apiofuranosyl)‐a‐L ‐arabinofuranoside ( 2 ) are new natural products. By application of HPLC‐SPE‐NMR hyphenated technique, five additional flavonol glycosides were characterized ( 8‐10 , 14 , and 16 ). Their structures were elucidated based on spectroscopic analysis. Of these, quercetin 3‐O‐(6‐O‐α‐L ‐rhamnopyranosyl)‐β‐D ‐galactopyranoside ( 5 ) and kaempferol 3‐O‐α‐L ‐arabinopyranoside ( 15 ) showed moderate inhibitory activity against α‐glucosidase type IV from Bacillus stearothermophilus with the IC₅₀ values of 19.5 and 19.0 μM, respectively.     

Triterpenoids from the Leaves of Ilex hainanensis

Phytochemical investigation on the leaves of Ilex hainanensis Merr . led to the isolation of four new ursane‐ and oleanane‐based triterpenoids, ilexhainanins A–D ( 1 – 4 ), as well as two known compounds, 2α,3β,19α‐trihydroxyurs‐12‐ene‐23,28‐dioic acid and 2α,3β,19α‐trihydroxyolean‐12‐ene‐23,28‐dioic acid. Their structures were elucidated on the basis of chemical and spectroscopic evidence, and by comparison with literature data.     

Flavonol Glycosides from the Leaves of Embelia Keniensis

Five new flavonol glycosides characterized as syringetin 3‐O‐α‐rhamnoside‐7‐O‐β‐glucoside, syringetin 3‐O‐α‐rhamnoside‐7,4′‐di‐O‐β‐glucoside, quercetin‐7‐O‐β‐galactosyl (1→3)‐β‐galactoside, myricetin 3‐O‐α‐rhamnosyl (1→4)‐β‐galactoside and myricetin 3‐O‐β‐glucosyl (1→2)‐β‐glucoside‐7‐O‐β‐glucosyl‐(1→4)‐α‐rhamnoside have been isolated from a methanolic extract of Embelia keniensis leaves. Known flavonols isolated from the same extract included myricetin, quercetin, kaempferol, myricetin 3‐O‐α‐rhamnoside, myricetin 3‐O‐β‐glucoside, quercetin 3‐O‐α‐rhamnoside, quercetin 3‐O‐β‐glucoside, quercetin 3‐O‐β‐xyloside, isorhamnetin 3‐O‐α‐rhamnoside and myricetin 3‐O‐rutinoside. Their structures were established from extensive spectroscopic and chemical studies and by comparison with authentic samples.     

Triterpene Glycosides Analyzed by Two-Dimensional Thin-Layer Chromatography

Two-dimensional TLC with judiciously chosen solvent systems that differ in pH values is proposed for identification of triterpene glycosides in plant extracts (mono- and bisdesmosidic, acidic, sulfated, acylated)     

Triterpene Glycosides of Tetrapanax papyriferum. I. Isolation and Structure of Glycosides St-H2 and St-I2 from Stem Bark

Stem bark ofTetrapanax papyriferumC. Koch., Araliaceae, yielded new triterpene glycosides 28-O--L-rhamnopyranosyl-(14)-O-(6-O-acetyl--D-glucopyranosyl)-(16)-O--D-glucopyranosyl esters of the 3-O-[-D-glucopyranosyl-(13)-[-D-galactopyranosyl-(12)]-O--L-arabinopyranosides of oleanolic and echinocystic acids. The structures of these substances were established using chemical and physicochemical methods     

Triterpene Glycosides of Tetrapanax papyriferum. IV. Acidic Glycosides from Stem Bark of T. Papyriferum

Twelve acidic triterpene glycosides of oleanolic acid, two of which were new, were isolated from stem bark of Tetrapanax papyriferum C. Koch (Araliaceae). The structures of these compounds were established using chemical methods and NMR spectroscopy.     

Triterpene Glycosides from <Emphasis Type="Italic">Cussonia paniculata</Emphasis>. II. Acetylated Glycosides from Leaves

Structures of 13 new acetylated triterpene glycosides from leaves of Cussonia paniculata (Araliaceae) were established as 28-O-(2-O-acetyl- and 3-O-acetyl-α-L-rhamnopyranosyl)-(1→4)-O-β-D-glucopyranosyl-(1→6)-O-β -D-glucopyranosides of 23-hydroxybetulinic acid (1a and 1b) and hederagenin (2a and 2b), 3-O-α-L-arabinopyranosyl-28-O-(2-O-acetyl- and 3-O-acetyl-a-L-rhamnopyranosyl)-(1→ 4)-O-β-D-glucopyranosyl-(1→6)-O-β-D-glycopyranosides of oleanic (3a and 3b) and ursolic (3c and 3d) acids, 3-O-α-L-arabinopyranosyl-28-O-(4-O-acetyl-, 2-O-acetyl-, and 3-O-acetyl-α-L-rhamnopyranosyl)-(1→4)-O-β-D-glucopyranosyl-(1→ 6)-O-β-D-glucopyranosides of hederagenin (4, d5a and 5b), and 3-O-β-D-glucopyranosyl-(1→2)-O-α-L-arabinopyranosyl-28-O-(2-O-acetyl- and 3-O-acetyl-α-L-rhamnopyranosyl)-(1→4)-O-β-D-glucopyranosyl-(1→6)-O-β-D- glucopyranosides of oleanic acid (6a and 6b). The structures of the compounds were established using chemical methods and NMR spectroscopy. __________ Translated from Khimiya Prirodnykh Soedinenii, No. 4, pp. 351–356, July–August, 2005.     

Triterpene Saponins from the Leaves of Ilex pernyi

Eight new triterpene saponins, ilexpernosides C–J ( 1 – 8 , resp.), and eight known triterpene saponins were isolated from the 70% EtOH extract of the leaves of Ilex pernyi. The structures of the new compounds were elucidated by spectroscopic data and chemical degradation.     

New Triterpenoid and Ergostane Glycosides from the Leaves of Hydrocotyle umbellata L.

Two new triterpenoid glycosides, together with two new ergostane glycosides, umbellatosides A–D ( 1 – 4 , resp.), have been isolated from the leaves of Hydrocotyle umbellata L. Their structures were established by 2D‐NMR spectroscopic techniques (¹H,¹H‐COSY, TOCSY, NOESY, HSQC, and HMBC) and mass spectrometry as 3β,22β‐dihydroxy‐3‐O‐[α‐L ‐rhamnopyranosyl‐(1→2)‐β‐D ‐glucuronopyranosyl]olean‐12‐en‐28‐oic acid 28‐O‐β‐D ‐glucopyranosyl ester ( 1 ), 3‐O‐[α‐L ‐rhamnopyranosyl‐(1→2)‐β‐D ‐glucuronopyranosyl]oleanolic acid 28‐O‐β‐D ‐glucopyranosyl ester ( 2 ), (3β,11α,26)‐ergosta‐5,24(28)‐diene‐3,11,26‐triol 3‐O‐(β‐D ‐glucopyranosyl)‐11‐O‐(α‐L ‐rhamnopyranosyl)‐26‐O‐β‐D ‐glucopyranoside ( 3 ), and (3β,11α,21,26)‐ergosta‐5,24(28)‐diene‐3,11,21,26‐tetrol 3‐O‐(β‐D ‐glucopyranosyl)‐11‐O‐(α‐L ‐rhamnopyranosyl)‐26‐O‐β‐D ‐glucopyranoside ( 4 ).     

Triterpene Glycosides of Tetrapanax papyriferum. II. Isolation and Structure Determination of Glycosides St-E2, St-F2, St-J2, and St-K2 from Stem Bark

Stem bark ofTetrapanaxpapyriferum yielded the new triterpene glycosides 3-O-[-D-glucopyranosyl-(13)]--D-galactopyranosyl-(12)-O--L-arabinopyranosides of oleanolic and echinocystic acids and their 28-O--L-rhamnopyranosyl-(14)-O--D-glucopyranosyl-(16)-O--D-glucopyranosyl esters. Their structures were established using chemical and physicochemical methods     

Triterpene Glycosides of Fatsia japonica. VI. Structures of Glycosides D3a and D3b

Seeds of Fatsia japonica (Araliaceae) yielded the new glycosides of gypsogenin: 3-O--D-glucopyranosyl-(12)-O--D-glucopyranoside and 3-O--D-galactopyranosyl-(12)-O--D-glucopyranoside. The structures of these compounds were established by chemical methods and NMR spectroscopy.     

Two New Steroidal Glycosides from Fermented Leaves of Agave americana

Two new spirostanol glycosides named agamenoside A and B, ere isolated from the fermented leaves of Agave americana. Their structures were elucidated as (23S,25R)-5α-spirostan-3β,6α，23－triol 3-O-α-L-rhamnopyranosyl-(1→3)-β-D-glucopyranosyl-(1→2)-[β-D-xylopyranosyl-(1→3)]-β-D-glucopyranosyl-(1→4)-β-D-galactopyranoside(1) and (25R)-5α-spiro-stan-3β,6α-diol 3-O-β-D-glucopyranosyl-(1→2)-[β-D-xylopyranosyl-(1→3)]-β-D-glucopyra-nosyl-(1→4)-β-D-galactopyranoside(2) by a combination of chemical and spectral methods.     

Triterpene Glycosides of Scheffleropsis angkae. IV. Structure of Glycosides L-C2 and L-I2

Two new triterpene glycosides of the -amyrin series, L-C ₂ and L-I ₂ , 27-hydroxyursolic acid 3-O--L-arabinopyranoside and its 28-O--L-rhamnopyranosyl-(14)-O--D-glucopyranosyl-(16)-O--D-glucopyranosyl ester, are isolated from leaves ofScheffleropsis angkae(Araliaceae). The structures of the glycosides are established using chemical methods and NMR techniques ( ¹ H, ¹³ C, ¹³ C-APT, COSY, TOCSY, HSQC, HMBC, and ROESY).     

Triterpene Glycosides from Cussonia paniculata. I. Isolation and Structure Determination of Glycosides A, B1, B2, C, D, G2, H1, and H2 from Leaves of Cussonia paniculata

The 3-O-β-D-glucopyranoside of β-sitosterol (1) and the known triterpene glycosides 3-O-α-L-arabinopyranosides of oleanolic (2a) and ursolic (2b) acids and hederagenin (3), 3-O-β-D-glucopyranosyl-(1→2)-α-L-arabinopyranosideofoleanolic acid (4), 3-O-α-L-arabinopyranosyl-28-O-α-L-rhamnopyranosyl-(1→4)-O-β-D-glucopyranosyl-(1→6)-O-β-D-glucopyranosides of oleanolic (5a) and ursolic (5b) acids and the newglycoside 28-O-α-L-rhamnopyranosyl-(1→4)-O-β-D-glucopyranosyl-(1→6)-O-β-D-glucopyranoside of 23-hydroxyursolic acid (6) were isolated from leaves of Cussonia paniculata (Araliaceae). Their structures were established using chemical methods and NMR spectroscopy.__________Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 160–163, March–April, 2005.     

The Effect of Triterpene Glycosides on Electrical Activity Changes of Identified Mollusk Neurons

The effect of mono- and bisdesmoside triterpene glycosides on the background activity of the grape snail Helix pomatia identified neurons was studied. Monodesmoside glycosides at concentrations of 10^-3-10^-4 M elicit stable hyperpolarization of neurons by increasing the membrane permeability for K⁺ ions. At concentrations of 10^-5-10^-7 M, they briefly change the neuronal impulse activity. The type of monodesmoside triterpene glycoside activity on neurons depends on the structure of the hydrocarbon. The glycoside effect on neuron membranes is related to the hemolytic activity     

Three New E‐Secoursane Triterpenoid Saponins from the Leaves of Ilex dunniana

Three new triterpenoid saponins with an 18,19‐secours‐13(18)‐ene skeleton, dunnianaolactones A–C ( 1 – 3 , resp.), together with nine known compounds i.e., the ursane‐type triterpene saponin 4 , the two benzofuran lignans 5 and 6 , five flavonoid glycosides, and 4‐hydroxybenzoic acid, were isolated from the leaves of Ilex dunniana Levl . (Aquifoliaceae). Their structures were elucidated by means of spectroscopic and chemical methods. The configuration of dunnianaolactone A ( 1 ) was further confirmed by X‐ray crystal‐structure analysis.