Ursane-type triterpenoid saponins from Elsholtzia bodinieri

Investigation of the n-BuOH extract of the aerial parts of Elsholtzia bodinieri led to the isolation of two new ursane-type triterpenoid saponins, bodiniosides O (1) and P (2), along with five known saponins, rotungenoside (3), 3,28-O-bis-β-d-glucopyranosides of 19α-hydroxyarjunolic acid (4), oblonganosides I (5), rotungenic acid 28-O-α-L-rhamnopyranosyl-(1→2)-β-d-glucopyranoside (6), and bodinioside M (7) isolated from the species. The structures of compounds 1 and 2 were characterized by spectroscopic data as well as acid hydrolysis and GC analysis as 3-O-β-d-xylopyranosyl-23-acetoxy-urs-12(13)-en-28-oic acid 28-O-β-d-xylopyranosyl-(1→6)-[β-d-glucopyranosyl-(1→4)-α-L-rhamnopyranosyl-(1→2)]-β-d-glucopyranoside and 3-O-β-d-xylopyranosyl-23-hydroxy-urs-12(13)-en-28-oic acid 28-O-β-d-glucopyranosyl-(1→6)-β-d-glucopyranoside. Compounds 1 and 2 exhibited potent anti-HCV activities in vitro with a selective index of 30.63 and 9.08, respectively.     

A new flavonol glycoside and other flavonoids from the aerial parts of Taverniera aegyptiaca

Isolation of flavonoids from the aerial parts of Taverniera aegyptiaca Bioss. (Fabaceae) led to identification of one new flavonol glycoside, isorhamnetin-3-O-α-l-rhamnopyranosyl-(1→2)-α-l-arabinopyranoside (1), along with eleven compounds, which previously have not been isolated from this plant quercetin-3-O-α-l-rhamnopyranosyl-(1→2)-[α-l-rhamnopyranosyl-(1→6)-β-d-galactopyranoside] (2), isorhamnetin-3-O-α-l-arabinopyranoside (3), quercetin-3-O-α-l-rhamnopyranosyl-(1→6)-β-d-glucopyranoside (4), isorhamnetin-3-O-α-l-rhamnopyranosyl-(1→6)-β-d-glucopyranoside (7), isorhamnetin 3-O-α-l-rhamnopyranosyl-(1→2)-[α-l-rhamnopyranosyl-(1→6)-β-d-galactopyranoside] (8), isorhamnetin 3-O-α-l-rhamnopyranosyl-(1→2)-[α-l-rhamnopyranosyl-(1→6)-β-d-glucopyranoside] (9), kaempferol 3-O-α-l-rhamnopyranosyl-(1→2)-[α-l-rhamnopyranosyl-(1→6)-β-d-galactopyranoside] (10), isorhamnetin (11), 4,4′-dihydroxy-2′-methoxychalcone (12), formononetin (13) and calycosin (15)] and some compounds already known from this plant [quercetin-3-O-robinobioside (5), isorhamnetin-3-O-robinobioside (6), afrormosin (14) and odoratin (16)].     

Structural determination of two new acacic acid-type saponins from the stem barks of Albizia zygia (DC.) J. F. Macbr

As a continuation of our interest in the study of triterpenoid saponins from Albizia zygia, phytochemical investigation of its stem barks led to the isolation of two new oleanane-type saponins, named zygiaosides C–D (1–2). Their structures were established on the basis of extensive analysis of 1D and 2D NMR (1H-, 13C NMR, DEPT, COSY, TOCSY, ROESY, HSQC and HMBC) experiments, HRESIMS studies, and by chemical evidence as, 3-O-[ β-d-glucopyranosyl-(1→2)-[α-l-arabinopyranosyl-(1→6)]-β-d-glucopyranosyl]-21-O-[(2E,6S)-2,6-dimethyl-6-O-(β-d-quinovopyranosyl) octa-2,7-dienoyl]acacic acid 28-O-α-l-arabinofuranosyl-(1→4)-[β-d-glucopyranosyl-(1→3)]-α-l-rhamnopyranosyl-(1→2)-β-d-glucopyranosyl ester (1) and 3- O-[β-d-glucopyranosyl-(1→2) -[ β-d-fucopyranosyl-(1→6)]-β-d-glucopyranosyl]-21-O-[(2E,6S)-2,6-dimethyl-6-O-(β-D-quinovopyranosyl) octa-2,7-dienoyl]acacic acid 28-O-α-l-arabinofuranosyl-(1→4)-[β-d-glucopyranosyl-(1→3)]-α-l-rhamnopyranosyl-(1→2)-β-d-glucopyranosyl ester (2).     

Lebbeckoside C,a new triterpenoid saponin from the stem barks of Albizia lebbeck inhibits the growth of human glioblastoma cells

One new acacic acid-type saponin, named lebbeckoside C (1), was isolated from the stem barks of Albizia lebbeck. Its structure was established on the basis of extensive analysis of 1D and 2D NMR (¹H, ¹³C NMR, DEPT, COSY, TOCSY, ROESY, HSQC and HMBC) experiments, HRESIMS studies, and by chemical evidence as 3-O-[β-d-xylopyranosyl-(l→2)-β-d-fucopyranosyl-(1→6)-[β-d-glucopyranosyl(1→2)]-β-d-glucopyranosyl]-21-O-{(2E,6S)-6-O-{4-O-[(2E,6S)-2,6-dimethyl-6-O-(β-d-quinovopyranosyl)octa-2,7-dienoyl]-4-O-[(2E,6S)-2,6-dimethyl-6-O-(β-d-quinovopyranosyl)octa-2,7-dienoyl]-β-d-quinovopyranosyl}-2,6-dimethylocta-2,7-dienoyl}acacic acid 28 O-[β-d-quinovopyranosyl-(l→3)-[α-l-arabinofuranosyl-(l→4)]-α-l-rhamnopyranosyl-(l→2)-β-d-glucopyranosyl] ester. The isolated saponin (1) displayed significant cytotoxic activity against the human glioblastoma cell line U-87 MG and TG1 stem-like glioma cells isolated from a patient tumor with IC₅₀ values of 1.69 and 1.44 μM, respectively.     

Insecticidal and α-glucosidase inhibitory activities of chemical constituents from Viburnum fordiae Hance

The ethanolic extract of the stems of Viburnum fordiae Hance showed insecticidal and α-glucosidase inhibitory activities and then was fractionated by bioactivity-guided fractionation to obtain a rare C₁₃-norisoprenoid (1), together with a new phenolic glycoside (2), and seven known compounds, alangionoside C (3), pisumionoside (4), koaburaside (5), 3,5-dimethoxy-benzyl alcohol 4-O-β-d-glucopyranoside (6), 3,4,5-trimethoxybenzyl-β-d-glucopyranoside (7), arbutin (8), and salidroside (9). The previously undescribed compounds were elucidated as (3R,9R)-3-hydroxy-7,8-didehydro-β-ionyl 9-O-α-d-arabinopyranosyl-(1→6)-β-d-glucopyranoside (1) and 2-(4-O-β-d-glucopyranosyl)syringylpropane-1,3-diol (2) by spectroscopic data (¹H and ¹³C NMR, HSQC, HMBC, ¹H-¹H COSY, HSQC-TOCSY, HRESIMS, IR and ORD) and chemical methods. Compound 1 showed potent insecticidal effect against Mythimna separata with LD₅₀ value of 140 μg g^?1. Compounds 2, 5, 6, 8 and 9 showed varying α-glucosidase inhibitory activity with IC₅₀ values ranging from 148.2 to 230.9 μM.     

Heptyl vicianoside and methyl caramboside from sour star fruit

Two new alkyl glycosides, heptyl vicianoside (1) and methyl 2-O-β-d-fucopyranosyl-α-l-arabinofuranoside (methyl caramboside, 4), were isolated from the sour fruit of Averrhoa carambola L. (Oxalidaceae), along with octyl vicianoside (2), cis-3-hexenyl rutinoside (3), and methyl α-d-fructofuranoside (5). Their structures were determined by spectroscopic and chemical methods. Compounds 2, 3, and 5 were obtained from the genus Averrhoa for the first time. All the compounds were evaluated for in vitro α-glucosidase, pancreatic lipase, and acetylcholinesterase inhibitory activities, but none of them were potent.     

Two new compounds from the fruit of Ailanthus altissima

A new phenolic derivative, 4-hydroxyphenol-1-O-[6-O-(E)-feruloyl-β-d-glucopyranosyl]-(1→6)-β-d-glucopyranoside (1), and a new terpenylated coumarin, named altissimacoumarin H (2) were identified from the fruit of Ailanthus altissima (Mill.) Swingle (Simaroubaceae), together with ten known compounds (3–12), including two coumarins and eight phenylpropanoids. Their structures were determined on the basis of chemical method and spectroscopic data. Antiviral effect against Tobacco mosaic virus (TMV) of all the compounds obtained were evaluated using leaf-disc method.     

Two new triterpenoids from Nauclea officinalis

Two new triterpenoids and three 27-nor-triterpenoids were isolated from the stems (with bark) of Nauclea officinalis. Their structures were identified to be 2β,3β,19α,23-tetrahydroxy-urs-12-en-28-oic acid (1), 2β,3β,19α,23-tetrahydroxy-urs-12-en-28-O-[β-d-glucopyranosyl (1-2)-β-d-glucopyranosyl] ester (2), pyrocincholic acid 3β-O-α-l-rhamnopyranoside (3), pyrocincholic acid 3β-O-α-l-rhamnopyranosy1-28-O-β-d-glucopyranosyl ester (4), pyrocincholic acid 3β-O-α-l-rhamnopyranosy1-28-O-β-d-glucopyranosyl-(1-6)-β-d-glucopyranosyl ester (5) by spectroscopic methods including 1D, 2D NMR and HR-MS analyses. The cytotoxic activity of 1–5 against lung cancer A-549 cells was also investigated.     

A new furostanol saponin from Dendrobium chrysanthum Lindl. with cytotoxic activity

A new furostanol saponin, (25R)-26-O-(α-d-glucopyranosyl)-(1→2)-α-l-rhamnopyranosyl-furost-5-ene-3β, 22α, 26-triol-3-O-α-d-glucopyranoside (1), together with four known compounds 2–5 were isolated from the ethanolic extract of the stems of Dendrobium chrysanthum Lindl. The structures of these new compounds were identified by extensive spectroscopic analysis including 1D and 2D NMR and HR-ESI-MS, as well as chemical methods. Compounds 1–3 were isolated from D. chrysanthum for the first time. Furthermore, the inhibitory effects of the compounds on tumor cells were evaluated, and compounds 1–2 exhibited significant cytotoxic activities potentially against SPC-A1, MCF-7 and HeLa human cancer cell lines. Compounds 3–5 showed inhibitory activity against the SPC-A1 and MCF-7.     

Chemical constituents of Genista numidica Spach aerial parts and their antimicrobial,antioxidant and antityrosinase activities

A previously undescribed triterpenoid saponin, 3-O-[α-l-rhamnopyranosyl-(1→2)-{β-d-glucopyranosyl-(1→6)-}β-d-galactopyranosyl-(1→2)-β-d-glucuronopyranosyl]-sophoradiol (1), in addition to twenty-nine known constituents (2–30) were isolated from the aerial parts of Genista numidica Spach. Structures elucidation was performed by comprehensive 1D- and 2D-NMR analyses and HRESIMS. The extracts, fractions and isolated compounds were evaluated for their antibacterial, antioxidant and tyrosinase inhibitory activities. The experimental findings indicated that genistin (16), isosalipurpol (27), and koaburaside (29) have moderate to low antibacterial activity against E. faecalis, S. aureus, S. epidermidis and P. aeruginosa bacteria with MICs ranging from 31.2 to 125 μg/mL. Compounds 19 and 27 exhibited a good antiradical activity potential (IC₅₀ 11.8 and 11.1 μg/mL, respectively). Only compounds 23, 27 and 28 exhibited low inhibitory effect against mushroom tyrosinase (IC₅₀ from 90.2 to 225.6 μg/mL).     

A new alkylbenzoquinone from Embelia rowlandii Gilg. (Myrsinaceae)

A new alkylbenzoquinone named embeliquinone (1) together with five known compounds, lupeol (2), 3-O-[6′-O-palmitoyl-β-d-glucosyl]-spinasta-7,22(23)-diene (3), quercetin (4), (2S,3S,4R,8E)-2-[(2′R)-2′-hydroxy-heneicosanoylamino]-heneicosane-1,3,4-triol-8-ene (5), and β-sitosterol-3-O-β-d-glucopyranoside (6) were isolated from the MeOH leaf extract of Embelia rowlandii by using repeated open column chromatography techniques. The structure of the new compound was characterized by analyses of 1D- and 2D-NMR, and MS data. Embeliquinone (1) had moderate anti-cell proliferation activity against A549 cell line with the IC₅₀ value of 21.8 μM. In addition, 1 exhibited weak antibacterial activities against Klebsiella pneumoniae and Staphylococcus aureus with an MIC value of 206.0 μM in both cases.     

Two new quercetin glycoside derivatives from the fruits of Gardenia jasminoides var. radicans

Two new quercetin glycoside derivatives named quercetin-3-O-[2-O-trans-caffeoyl-α-l-rhamnopyranosyl-(1 → 6)-β-d-glucopyranoside] (1) and quercetin-3-O-[2-O-trans-caffeoyl-β-l-rhamnopyranosyl-(1 → 6)-β-d-glucopyranoside] (2) along with three known flavonoids, 5-hydroxy-6,7,3′,4′,5′-pentamethoxyflavone (3), 5,7-dihydroxy-8-methoxyflavone (4) and kaempferol 3-O-β-d-glucopyranoside (5), were isolated from the fruits of Gardenia jasminoides var. radicans. The structures of the new compounds were determined by means of extensive spectroscopic analysis (1D, 2D NMR and HR-ESI-MS), glycoside hydrolysis and sugar HPLC analysis after derivatisation. This is the first report on the isolation of a pair of compounds with α or β-l-rhamnopyranosyl configuration from plant and the first detail assignment of their NMR data.     

Mimics of the Structural Elements of Type III Group B Streptococcus Capsular Polysaccharide. Part I: Synthesis of a Carboxylate-Containing Pentasaccharide

Abstract

A carboxylate-containing pentasaccharide, methyl O-(β-d-galactopyranosyl)-(1→4)-O-(β-d-glucopyranosyl)-(1→6)-O-{3-O-[(S)-1-carboxyethyl]-β-d-galactopyranosyl-(1→4)-O}-(2-acetamido-2-deoxy-β-d-glucopyranosyl)-(1→3)-β-d-galactopyranoside (27) was synthesized by block condensation of suitably protected donors and acceptors. Phenyl 3-O-benzyl-4,6-di-O-chloroacetyl-2-deoxy-2-phthalimido-1-thio-β-d-glucopyranoside (17) was condensed with methyl 2,4,6-tri-O-benzyl-β-d-galactopyranoside (4) to afford a disaccharide, methyl O-(3-O-benzyl-4,6-di-O-chloroacetyl-2-deoxy-2-phthalimido-β-d-glucopyranosyl)-(1→3)-2,4,6-tri-O-benzyl-β-d-galactopyranoside (18). Removal of chloroacetyl groups gave 4,6-diol, methyl 0-(3-O-benzyl-2-deoxy-2-phthalimido-β-d-glucopyranosyl)-(1→3)-2,4,6-tri-O-benzyl-β-d-galactopyranoside (19), in which the primary hydroxy group (6-OH) was then selectively chloroacetylated to give methyl O-(3-O-benzyl-6-O-chloroacetyl-2-deoxy-2-phthalimido-β-d-glucopyranosyl)-(1→3)-2,4,6-tri-O-benzyl-β-d-galactopyranoside (20). This acceptor was then coupled with 2,4,6-tri-O-acetyl-3-O-[(S)-1-(methoxycarbonyl)ethyl]-α-d-galactopyranosyl trichloroacetimidate (14) to afford a trisaccharide, methyl O-{2,4,6-tri-O-acetyl-3-O-[(S)-l-(methoxycarbonyl)ethyl]-β-d-galactopyranosyl}-(1→4)-O-(3-O-benzyl-6-O-chloroacetyl-2-deoxy-2-phthalimido-β-d-glucopyranosyl)-(1→3)-2,4,6-tri-O-benzyl-β-d-galactopyranoside (21). Removal of the 6-O-chloroacetyl group in 21 gave 22, which was coupled with 4-O-(2,3,4,6-tetra-O-acetyl-β-d-galactopyranosyl)-2,3,6-tri-O-acetyl-α-d-glucopyranosyl trichloroacetimidate (23) to yield protected pentasaccharide 24. Standard procedures were used to remove acetyl groups and the phthalimido group, followed by N-acetylation, and debenzylation to yield pentasaccharide 27 and a hydrazide by-product (28) in a 5:1 ratio, respectively. Compound 27 contains a complete repeating unit of the capsular polysaccharide of type III group B Streptococcus in which terminal sialic acid is replaced by an (S)-1-carboxyethyl group.     

Enzymatic synthesis of novel quercetin sialyllactoside derivatives

Quercetin and its derivatives are important flavonols that show diverse biological activity, such as antioxidant, anticarcinogenic, anti-inflammatory, and antiviral activities. Adding different substituents to quercetin may change the biochemical activity and bioavailability of molecules, when compared to the aglycone. Here, we have synthesised two novel derivatives of quercetin, quercetin-3-O-β-d-glucopyranosyl, 4′′-O-d-galactopyranosyl 3′′′-O-α-N-acetyl neuraminic acid i.e. 3′-sialyllactosyl quercetin (3′SL-Q) and quercetin-3-O-β-d-glucopyranosyl, 4′′-O-β-d-galactopyranosyl 6′′′-O-α-N-acetyl neuraminic acid i.e. 6′-sialyllactosyl quercetin (6′SL-Q) with the use of glycosyltransferases and sialyltransferases enzymes. These derivatives of quercetin were characterised by high-resolution quadrupole-time-of-flight electrospray ionisation mass spectrometry (HR-QTOF-ESI/MS) and ¹H and ¹³C nuclear magnetic resonance (NMR) analyses.     

Stereoselective Glycosidic Coupling Reactions of Fully Benzylated 1,2-Anhydro Sugars with N-Tosyl- or N-Benzyloxycarbonyl-l-serine Methyl Ester

Abstract

The glycosidic coupling reaction of 1,2-anhydro-3,4,6-tri-O-benzyl-β-d-mannopyranose (7), 1,2-anhydro-3,4,6-tri-O-benzyl-α-d-galactopyranose (21), and 1,2-anhydro-3,4-di-O-benzyl-α-d-xylopyranose (18) with N-tosyl- (10) or N-benzyloxycarbonyl- (11) L-serine methyl ester provides a new stereocontrolled synthesis of 1,2-trans linked glycopeptides. The 1,2-anhydro sugars are shown to react smoothyl with 10 or 11 in the presence of Lewis acid (ZnCl₂ or AgOTf) as well as powdered 4A molecular sieves in CH₂Cl₂ at room temperature to afford glycosyl serine derivatives with high stereoselectivity and high yield in less than 30 min. An improved method using 2-O-acetyl-3,4,6-tri-O-benzyl-α-d-mannopyranosyl chloride (6) as the key intermediate for ring closure was applied for the synthesis of 1,2-anhydro-3,4,6-tri-O-benzyl-β-d-mannopyranose.     

Synthesis of 4-Octuloses from a Derivative of d-Fructose

Abstract

Reaction of 2,3:4,5-di-O-isopropylidene-β-d-arabino--hexos-2-ulo-2,6-pyranose (1) with (methoxycarbonylmethylene)triphenylphosphorane in either dichloromethane or methanol gave methyl (E)-2,3-dideoxy-4,5:6,7-di-O-isopropylidene-β-d-arabino-oct-2-ene-4-ulo-4,8-pyranosonate (2) or a 1:2.3 mixture of 2 and its Z-isomer (3), respectively. Bishydroxylation of 2 with osmium tetraoxide gave a mixture of methyl 4,5:6,7-di-O-isopropylidene-β-d-glycero-d-galacto- (4) and -d-glycero-d-ido-oct-4-ulo-4,8-pyranosonate (5) which were carefully resolved by column chromatography. Compound 4 was transformed into its 2,3-di-O-methyl derivative (6) which was deacetonated to 7 and subsequently degraded to dimethyl 2,3-di-O-methyl-(+)-L-tartrate (8). On the other hand, acetonation of a mixture of 4 and 5 gave the corresponding tri-O-isopropylidene derivatives (9) and (10). Compounds 4 and 5 were reduced with LiAlH₄ to the related 4,5:6,7-di-O-isopropylidene-β-d-glycero-d-galacto- (11) and β-d-glycero-d-ido-oct-4-ulo-4,8-pyranose (12). Treatment of 11 and 12 with acetone/PTSA/CuSO₄ only produced the acetonation at the C-2,3 positions. Finally, compounds 11 and 12 were deacetonated to the corresponding D-glycero-d-galacto- (15) and D-glycero-d-ido-oct.-4-ulose (16).     

SYNTHESIS OF SIALYL-α-(2→3)-NEOLACTOTETRAOSE DERIVATIVES MODIFIED AT C-2 OF THE N-ACETYLGLUCOSAMINE RESIDUE: PROBES FOR INVESTIGATION OF ACCEPTOR SPECIFICITY OF HUMAN α-1,3-FUCOSYLTRANSFERASES,FUC-TVII,AND FUC-TVI *

A variety of sialyl-α-(2→3)-neolactotetraose (IV³NeuAcnLcOse₄ or IV³NeuGcnLcOse₄) derivatives (23, 31–37, 58–60) modified at C-2 of the GlcNAc residue have been synthesized. The phthalimido group at C-2 of GlcNAc in 2-(trimethylsilyl)ethyl (3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-d-glucopyranosyl)-(1→3)-(2,4,6-tri-O-benzyl-β-d-galactopyranosyl)-(1→4)-2,3,6-tri-O-benzyl-β-d-glucopyranoside (5) was systematically converted to a series of acylamino groups, to give the per-O-benzylated trisaccharide acceptors (6–11). On the other hand, modification of the hydroxyl group at C-2 of the terminal Glc residue in 2-(trimethylsilyl)ethyl (4,6-O-benzylidene-β-d-glucopyranosyl)-(1→3)-(2,4,6-tri-O-benzyl-β-d-galactopyranosyl)-(1→4)-2,3,6-tri-O-benzyl-β-d-glucopyranoside (42) gave three different kinds of trisaccharide acceptors containing D-glucose (49), N-acetyl-d-mannosamine (50), and D-mannose (51) instead of the GlcNAc residue. Totally ten trisaccharide acceptors (5–11 and 49–51) were each coupled with sialyl-α-(2→3)-galactose donor 12 to afford the corresponding pentasaccharides (14–21 and 52–54) in good yields, respectively, which were then transformed into the target compounds. Acceptor specificity of the synthetic sialyl-α-(2→3)-neolactotetraose probes for the human α-(1→3)-fucosyltransferases, Fuc-TVII and Fuc-TVI, was examined.     

A Convenient Synthesis of Pyranosyl-1-carbaldoximes

Abstract

A simple high-yielding procedure is described for the preparation of tri-O-acetyl-β-l-fucopyranosylformaldoxime (1) involving stannate(II)-mediated reduction of the readily accessible tri-O-acetyl-β-l-fucopyranosylnitromethane (3). The d-mannosyl, d-glucosyl, d-galactosyl, and d-xylosyl analogues 7–12 were prepared similarly. The structure of tetra-O-acetyl-β-d-mannopyranosylformaldoxime (7) was determined by X-ray crystallography.     

A new triterpenoid saponin from Clinopodium chinense (Benth.) O. Kuntze

A new triterpene saponin, 3β,16β,23α,28β,30β-pentahydroxyl-olean-11,13(18)-dien-3β-yl-[β-d-glucopyranosyl-(1→2)]-[β-d-glucopyranosyl-(1→3)]-β-d-fucopyranoside, was named Clinoposaponin D (1), together with six known triterpene saponins, buddlejasaponin IVb (2), buddlejasaponin IVa (3), buddlejasaponin IV (4), clinopodisides D (5), 11α,16β,23,28-Tetrahydroxyolean-12-en-3β-yl-[β-d-glucopyranosyl-(1→2)]-[β-d-glucopyranosyl-(1→3)]-β-d-fucopyranoside (6) and prosaikogenin A (7), and two known triterpenes, saikogenin A (8) and saikogenin F (9) were isolated from Clinopodium chinense (Benth.) O. Kuntze. Their structures were elucidated on the basis of 1D, 2D NMR and MS analysis. Meanwhile, the effects of all compounds on rabbit platelet aggregation and thrombin time (TT) were investigated in vitro. Compounds 4 and 7 had significant promoting effects on platelet aggregation with EC₅₀ value at 53.4 and 12.2 μM, respectively. In addition, the highest concentration (200 μM) of compounds 2 and 9 shortened TT by 20.6 and 25.1%, respectively.     

A new diarylheptanoid and a new diarylheptanoid glycoside isolated from the roots of Juglans mandshurica and their anti-inflammatory activities

A new diarylheptanoid, (2S,3S,5S)-2,3,5-trihydroxy-1,7-bis(4-hydroxy- 3-methoxyphenyl)heptane (1), and a new diarylheptanoid glycoside, (2S,3S,5S)-2,3-dihydroxy-5-O-β-d-xylopyranosyl-7-(4-hydroxy-3-methoxyphenyl)-1-(4-hydroxyphenyl)heptane (2), together with three known compounds, rhoiptelol C (3), rhoiptelol B (4) and 3′,4″-epoxy-2-O-β-d-glucopyanosyl-1-(4-hydroxyphenyl)- 7-(3-methoxyphenyl)heptan-3-one (5) were isolated from the roots of Juglans mandshurica (Juglandaceae). The structures of compounds 1 and 2 were identified based on HR-ESI-MS, 1D and 2D NMR spectroscopic methods. Compounds 1–5 were assayed for their inhibitory effects on the production of NO, TNF-α and IL-6 in LPS-stimulated RAW264.7 cells.