Diarylheptanoid Glycosides Research Articles

Diarylheptanoid glycosides from Dioscorea nipponica rhizomes

A group of previously undescribed diarylheptanoids with mono/di-glucose substitution, diodiarylheptosides A–F (1–6), together with six known diarylheptanoids (7–12) were isolated from the rhizomes of Dioscorea nipponica. Their structures were established by comprehensive UV, IR, HR-ESI-MS and NMR analyses, and their absolute configurations were determined by a comparison of calculated and experimental ECD, some with optical rotations, after acid-hydrolysis. Moreover, bioassay results showed that compounds 3 and 11 exhibited stronger NO inhibitions on lipopolysaccharides-induced RAW 264.7 cells, with the IC50 values of 14.91 ± 0.62 and 12.78 ± 1.12 μM.

Diarylheptanoid glycosides from Zingiber officinale peel and their anti-apoptotic activity

Four new diarylheptanoid glycosides (1–4), (1S,3R,5S)-2-(4-hydroxy-3- methoxyphenyl)-6-[2-(4-hydroxyphenyl)ethyl]-tetrahydropyran-4-ol-4’-O-β-D-glucopyranoside (1), (1S,3R,5S)-2-(4,5-dihydroxy-3-methoxyphenyl)-6-[2-(4-hydroxyphenyl) ethyl]-tetrahydropyran-4-ol-4’-O-β-D-glucopyranoside (2), (1S,3R,5S)-2-(4-hydroxy- 3,5-dimethoxyphenyl)-6-[2-(4-hydroxy-3-methoxyphenyl)ethyl]-tetrahydropyran-4-ol-4’-O-β-D-glucopyranoside (3), and (1R,3R,5R)-2-(4-hydroxy-3,5-dimethoxyphenyl)- 6-[2-(4-hydroxy-3-methoxyphenyl)ethyl]-tetrahydropyran-4-ol-3-O-β-D-glucopyranoside (4) were isolated from the 50% ethanol extract of Zingiber officinale peel. The structures of the isolated compounds were determined by HR-ESI-MS and extensive spectroscopic techniques (UV, IR, 1D-NMR, and 2D-NMR). Compounds 1–4 significantly increased the survival rate of human normal lung bronchial epithelial cells (BEAS-2B) induced by lipopolysaccharide (LPS) at the concentration of 10 μM.

A New Diarylheptanoid from the Twigs of Quercus Acutissima and their Neuroprotective Activity

A new diarylheptanoid glycoside, acutissioside A (4), along with five known diarylheptanoids (1–3, 5, 6) was isolated from the twigs of Quercus acutissima Carruth. The structure of the new compound was determined via spectral analysis, including NMR spectra (1H and 13C NMR, 1H–1H COSY, HSQC, HMBC) and HR-ESI-MS, acid hydrolysis, and specific optical rotation data. The neuroprotective effect of all the diarylheptanoid compounds (1–6) was evaluated. Compound 1 exhibited NGF secretion to 154.60 ± 2.87%, which was stronger than that of the positive control 6-shogaol (140.45 ± 2.18%).

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.

ChemInform Abstract: Diarylheptanoid Glycosides from Tacca plantaginea and Their Effects on NF‐ϰB Activation and PPAR Transcriptional Activity.

Abstractisolation, structure determination and biological activity of two new diarylheptanoid glycosides, plantagineosides A (I) and B (II), an unusual cyclic diarylheptanoid glycoside, plantagineoside C (II), and three known compounds

Diarylheptanoid glycosides from Tacca plantaginea and their effects on NF-κB activation and PPAR transcriptional activity

In the screening search for NF-κB inhibitory and PPAR transactivational agents from medicinal plants, a methanol extract of the whole plant of Tacca plantaginea and its aqueous fraction showed the significant activities. Bioassay-guided fractionation combined with repeated chromatographic separation of the aqueous fraction of the methanol extract of T. plantaginea resulted in the isolation of two new diarylheptanoid glycosides, plantagineosides A (1) and B (2), an unusual new cyclic diarylheptanoid glycoside, plantagineoside C (3), and three known compounds (4–6). Their structures were determined by extensive spectroscopic and chemical methods. Compounds 3–6 significantly inhibited TNFα-induced NF-κB transcriptional activity in HepG2 cells in a dose-dependent manner, with IC50 values ranging from 0.9 to 9.4μM. Compounds 1–6 significantly activated the transcriptional activity of PPARs in a dose-dependent manner, with EC50 values ranging from 0.30 to 10.4μM. In addition, the transactivational effects of compounds 1–6 were evaluated on three individual PPAR subtypes, including PPARα, γ, and β(δ). Compounds 1–6 significantly enhanced the transcriptional activity of PPARβ(δ), with EC50 values in a range of 11.0–30.1μM. These data provide the rationale for using T. plantaginea and its components for the prevention and treatment of inflammatory and metabolic diseases.

Melanogenesis‐Inhibitory and Cytotoxic Activities of Diarylheptanoids from Acer nikoense Bark and Their Derivatives

Nine cyclic diarylheptanoids, 1-9, including two new compounds, i.e., 9-oxoacerogenin A (8) and 9-O-β-D-glucopyranosylacerogenin K (9), along with three acyclic diarylheptanoids, 10-12, and four phenolic compounds, 13-16, were isolated from a MeOH extract of the bark of Acer nikoense (Aceraceae). Acid hydrolysis of 9 yielded acerogenin K (17) and D-glucose. Two of the cyclic diarylheptanoids, acerogenin A (1) and (R)-acerogenin B (5), were converted to their ether and ester derivatives, 18-24 and 27-33, respectively, and to the dehydrated derivatives, 25, 26, 34, and 35. Upon evaluation of compounds 1-16 and 18-35 for their inhibitory activities against melanogenesis in B16 melanoma cells, induced with α-melanocyte-stimulating hormone (α-MSH), eight natural glycosides, i.e., six diarylheptanoid glycosides, 2-4, 6, 9, and 12, and two phenolic glycosides, 15 and 16, exhibited inhibitory activities with 24-61% reduction of melanin content at 100 μM concentration with no or almost no toxicity to the cells (88-106% of cell viability at 100 μM). In addition, when compounds 1-16 and 18-35 were evaluated for cytotoxic activity against human cancer cell lines, two natural acyclic diarylheptanoids, 10 and 11, ten ether and ester derivatives, 18-22 and 27-31, and two dehydrated derivatives, 34 and 35, exhibited potent cytotoxicities against HL60 human leukemia cell line (IC(50) 8.1-19.3 μM), and five compounds, 10, 11, 20, 29, and 30, against CRL1579 human melanoma cell line (IC(50) 10.1-18.4 μM).

ChemInform Abstract: A New Diarylheptanoid Glycoside from the Stem Bark of Alnus hirsuta and Protective Effects of Diarylheptanoid Derivatives in Human HepG2 Cells.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

A New Diarylheptanoid Glycoside from the Stem Bark of Alnus hirsuta and Protective Effects of Diarylheptanoid Derivatives in Human HepG2 Cells

To search for secondary metabolites of Alnus hirsuta (Betulaceae), various chromatographic separations of the ethyl acetate soluble fraction of the stem bark of A. hirsuta led to the isolation of a new diarylheptanoid glycoside, (3R)-1,7-bis-(4-dihydroxyphenyl)-3-heptanol 3-O-beta-D-glucopyranosyl(1-->3)-beta-D-xylopyranoside (13) and twelve diarylheptanoid derivatives, namely, oregonin (1), rubranoside A (2), hirsutanonol 5-O-beta-D-glucopyranoside (3), rubranoside B (4), rubranoside C (5), hirsutanonol (6), hirsutenone (7), (5S)-O-methylhirsutanonol (8), platyphylloside (9), platyphyllonol 5-O-beta-D-xylopyranoside (10), aceroside VII (11) and platyphyllenone (12). Isolates were assessed for their hepatoprotective effects against tert-butylhydroperoxide (t-BHP)-induced toxicity in HepG2 cells. Of these isolates, compounds 1-8 showed significant hepatoprotective effects on t-BHP-induced damage to HepG2 cells, with 8 exhibiting the greatest protective effect (50.7 + or - 3.7% at a concentration of 10 microM).

Anticancer diarylheptanoid glycosides from the inner bark of Betula papyrifera

Phytochemical investigations of the MeOH extract of Betula papyrifera inner bark led to the isolation of ten phenolic compounds of the following types: diarylheptanoid glycosides ( 1– 4), a diarylheptanoid ( 5), a lignan ( 6), flavonoids ( 7– 8) and chavicol glycosides ( 9– 10). Among them, the diarylheptanoid glycoside, ( S)-1,7-bis-(4-hydroxyphenyl)-heptan-3-one-5- O-α- l-arabinofuranosyl-(1 → 6)-β- d-glucopyranoside, papyriferoside A ( 1), was isolated and its structure was determined on the basis of 1D and 2D NMR, HPLC-MS, as well as high resolution mass spectroscopic data. Platyphylloside ( 4) exerted the strongest cytotoxic activity of all isolated compounds with IC 50 values ranging from 10.3 to 13.8 μM.

Chemical Constituents from Alnus formosana Burk. II. Polar Constituents from the Leaves

This study was aimed to explore the n-BuOH soluble constituents of the leaves of Alnus formosana Burk. A total of 13 compounds were isolated and characterized. Of these, 2″'-cinnamoyloregonin is a new diaryl heptanoid glycoside. Ten of the remaining twelve known compounds, i.e. platyphylloside, aceroside VII, myzodendrone, quercetin, kaempferol-3-O-rhamnoside, quercetin-3-O-rhamnoside, quercetin-3-O-glucoside, rhamnetin-3-O-rhamnoside, inositol, and shikimic acid, are reported for the first time for an Alnus species. The structures were characterized by spectral analysis.

Inhibitors of nitric oxide production from the bark of Myrica rubra: structures of new biphenyl type diarylheptanoid glycosides and taraxerane type triterpene

Three new biphenyl type diarylheptanoid glycosides, myricanol 11- O-β- d-glucopyranoside, myricanone 5- O-β- d-glucopyranoside, and neomyricanone 5- O-β- d-glucopyranoside, and a new taraxerane type triterpene, myricetrione, were isolated from the bark of Chinese Myrica rubra. Their structures were elucidated on the basis of chemical and physicochemical evidence. Biphenyl type diarylheptanoids, triterpene, and their polyphenols showed potent inhibitory effects on nitric oxide production in lipopolysaccharide-activated macrophages. Furthermore, diarylheptanoids, myricanol and myricanone, were found to inhibit induction of inducible nitric oxide synthase.

ChemInform Abstract: Bioactive Constituents of Chinese Natural Medicines. Part 7. Inhibitors of Degranulation in RBL‐2H3 Cells and Absolute Stereostructures of Three New Diarylheptanoid Glycosides (I)—(III) from the Bark of Myrica rubra.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

Bioactive constituents of Chinese natural medicines. VII. Inhibitors of degranulation in RBL-2H3 cells and absolute stereostructures of three new diarylheptanoid glycosides from the bark of Myrica rubra.

Three new diarylheptanoid glycosides, named (+)-S-myricanol 5-0-beta-D-glucopyranoside, myricanene A 5-O-alpha-L-arabinofuranosyl(1-->6)-beta-D-glucopyranoside, and myricanene B 5-0-alpha-L-arabinofuranosyl(1-->6)-beta-D-glucopyranoside, were isolated from the bark of Chinese Myrica rubra, together with twenty known compounds. The absolute stereostructures of the new diarylheptanoid glycosides were elucidated on the basis of chemical and physicochemical evidence, including the application of the modified Mosher's method. The inhibitory effects of isolated constituents on the release of beta-hexosaminidase from RBL-2H3 cells were examined, and several diarylheptanoids, myricanol, (+)-S-myricanol, myricanone, and myricanenes A and B, and a flavonol, myricetin, were found to show the inhibitory activity.

Minor diarylheptanoid glycosides of Alnus rubra bark

The diarylheptanoid ( S)-1,7-bis-(4-hydroxyphenyl)-heptan-3-one-5- O-β- D-xylopyranoside, and two known compounds, 1,7-bis-(3,4-dihydroxyphenyl)-heptan-3-one-5- O-β- D-glucopyranoside and platyphylloside were isolated from Alnus rubra bark. Structures were established by application of spectrometric techniques.

Four New Diarylheptanoid Glycosides From Alnus Rubra Bark

Four new diarylheptanoid glycosides, rubranosides A,B,C and D (1–4), were isolated from red alder (Almus rubra) bark. All contain the common aglycone moiety, rubranol (5).

Two acylated diarylheptanoid glycosides from red alder bark

Two novel acylated diarylheptanoid glycosides, oregonosides A and B (3, 4, respectively), were isolated from red alder bark and their structures established by spectrometric techniques. The compounds were identified as (5S)-1,7-bis(3, 4-dihydroxyphenyl)-5-O-(6-O-benzoyl-beta-D-glucopyranosyl)-heptan-3-o ne and (5S)-1,7-bis(3, 4-dihydroxyphenyl)-5-O-(6-O-vanilloyl-beta-D-glucopyranosyl)-heptan-3 -one.

The New Diarylheptanoid Glycosides from Alnus japonica.

Two new diarylheptanoid glycosides, hirsutanonol 5-O-(6-O-galloyl)-β-D-glucopyranoside and 3-deoxo-hirsutanonol 5-O-β-D-glucopyranoside, were isolated from fresh leaves of Alnus japonica together with three known diarylheptanoids [hirsutanonol, hirsutanonol 5-O-β-D-glucopyranoside and hirsutenone], five known triterpenes [β-amyrin, 3-O-acetyl-β-amyrin, 3-O-acetyltaraxerol, glutinone and lupenone] and quercitrin. One more new diarylheptanoid glycoside, 3-deoxohirsutanonol 5-O-(6-O-β-D-apiosyl)-β-D-glucopyranoside, was also isolated from bark together with 3-deoxohirsutanonol 5-O-β-D-glucopyranoside, two known diarylheptanoids [hirsutoside and hirsutanonol 5-O-β-D-glucopyranoside] and four known triterpenes [glutinol, glutinone, lupenone and taraxerone].Their structures were determined on the basis of spectroscopic and chemical evidence.

Studies on the Constituents of Aceraceae Plants. XII. Two New Diarylheptanoid Glycosides from Acer triflorum.

Two new diarylheptanoid glycosides, named aceroside XII (7), C30H42O12, [α]D 70.3°, and aceroside XIII (8), C25H34O8, [α]D -40.2°, were isolated along with triterpenoids and caffeoyl esters from the branches of Acer triflorum KOM. (Aceraceae). On acid hydrolysis, 7 yielded (-)-centrolobol (9), glucose and apiose. On partial hydrolysis, 7 gave 8 and apiose. Acerosides XII (7) and XIII (8) were determined to be the 4''-O-β-D-apiofuranosyl-(1→6)-β-D-glucopyranoside and the 4''-O-β-D-glucopyranoside of (-)-centrolobol, respectively, on the basis of chemical and spectral evidence.

Arylbutanoid and diarylheptanoid glycosides from inner bark of Betula pendula

From the inner bark of Betula pendula, four new disaccharide glycosides, two of (−)-rhododendrol and two of platyphyllone, were isolated along with a new trisaccharide glycoside of (−)-centrolobol and several known compounds. The structures were elucidated by high field 1H and 13C NMR spectroscopy. Assignments of 1H and 13C NMR spectra were made by H,H- and C,H-COSY.