Two new triterpenoid saponins and two new goodyerosides isolated from the whole plant of Tournefortia sibirica.

Two new triterpenoid saponins (oleanolic acid 2ß-hydroxyl-3-O-ß-D-glucuronopyranoside-6'-O-buthyl ester (1) and oleanolic acid 2ß-hydroxyl-3-O-[ß-D-glucuronopyranosyl-6'-O-methylester]-28-O-ß-D-glucopyranoside (2)) and two new goodyerosides (4-methylenefuran-2(5H)-one (6'-O-vanilloyl)-ß-D-glucopyranoside (3), 3-hydroxy-2(5H)-furanone, 4-(6'-O-vanilloyl)-ß-D-glucopyranoside (4)), together with seven known compounds (5-11) were isolated from the whole plant of Tournefortia sibirica L. The chemical structures of the compounds were determined by spectroscopic analysis (1D and 2D NMR) and HR-ESI-MS. Compounds 1, 6 and 9 showed significant cytotoxicity towards A549, SK-Hep1 and HeLa cells, with IC50 values ranging from 1.68 ± 0.09 to 6.87 ± 0.13 µM.

A new megastigmane glycoside, a new organic acid glycoside and other constituents with anticomplementary activity from Artemisia halodendron.

A new megastigmane glycoside, (1R,5R,6S,7E)-megastigman-3,9-dione-7-en-6,11-diol 11-O-ß-D-glucopyranoside (1), and a new organic acid glycoside, methyl (4 R)-4-O-ß-D-glucopyranosyl-decanoate (2), together with eight known compounds (3-10), were isolated from the aerial parts of Artemisia halodendron Turcz. ex Bess. (Asteraceae). Their chemical structures were elucidated by 1 D and 2 D NMR and HR-ESI-MS spectra and DP4+ probability analysis. Among the identified compounds, compounds 5, 6 and 10 were isolated from the family Asteraceae, and compounds 3, 4 and 7-9 were identified from the genus Artemisia for the first time. All of the compounds were evaluated for their anticomplementary activity against the classical pathway (CP) and the alternative pathway (AP). Compounds 7 and 9 showed anticomplementary activity with the CH50 values of 0.31 ± 0.08 and 0.50 ± 0.09 mM, respectively.

Four new terpenoids and other metabolites with potential anti-complementary activities from the aerial parts of Dracocephalum moldavica (Lamiaceae).

In the course of our continuing search for biologically active compounds from medicinal herbs, four undescribed terpenoids including one monoterpenoid glycoside, (1 R, 3S, 4S, 5 R)-(-)-1,8-epoxy-p-menthan-5-ethoxycarbonyl-3-O-ß-D-glucopyranoside (1), one iridoid glycoside, 3'-O-ß-D-glucopyranosyl-melampyroside (2), one sesquiterpene, 1-(2-methylbutanol)-2-pentyl-1,3-cyclohexadiene (3), and one triterpenoid, 28-nor-3ß,18ß-dihydroxyurs-12-ene (4), together with nine known terpenoids (5-13) were isolated from the dried aerial parts of Dracocephalum moldavica (Lamiaceae). Their chemical structures were elucidated by detailed spectroscopy (1 D and 2 D NMR), HRESIMS data analysis and acid hydrolysis. Among them, compounds 9 and 10 were isolated from the family Lamiaceae, compounds 5, 6 and 11-13 were identified from the genus Dracocephalum and compounds 7 and 8 were reported from the D. moldavica for the first time. The biological evaluation of anti-complementary activity revealed that some compounds, 4, 6 and 12 exhibited anti-complementary activity with CH50 and AP50 values ranging from 0.67-1.43 and 1.12-1.55 mM, respectively.

Two new iridoid glycosides from Odontites vulgaris.

Two new iridoid glycosides, named 3'-O-benzoyl-dolichocymboside D (1) and dolichocymboside E (2), along with ten known glycosides (3-12), were isolated from the ethanol extract of the whole plants of Odontites vulgaris Moench. The structures of the isolated compounds were elucidated by 1D and 2D NMR and HR-ESI-MS spectra and by comparison with those reported in the literature. This is the first report on compounds 11 and 12 isolated from the family Scrophulariaceae, and compounds 8-10 were isolated from the genus Odontites.

Two new stilbene glucosides and a new benzoic acid derivative from Tournefortia sibirica.

Two new stilbene glucosides, trans-3,5-dihydroxy-4-methoxystilbene 3-O-ß-D-glucopyranoside (1), cis-3,5-dihydroxy-4-methoxystilbene 3-O-ß-D-glucopyranoside (2), one new benzoic acid derivative, cis-4-hydroxy-3-hydroxymethyl-2-butenyl benzoate 4-O-ß-D-glucopyranoside (3), and four known compounds (4 - 7) were isolated from Tournefortia sibirica L. The structures of these compounds were elucidated on the basis of spectral data. Anti-inflammatory effects of compounds (1 - 7) were evaluated in terms of inhibition on production of NO, TNF-α and IL-6 in LPS-induced RAW 264.7 cells. Compounds 1, 2 and 5 - 7 could inhibit the levels of NO, TNF-α and IL-6 in LPS-induced RAW264.7 cells with IC50 values ranging from 40.96 to 88.76 µM.

Two new quinones and six additional metabolites with potential anti-inflammatory activities from the roots of Juglans mandshurica.

Two new quinones, 4-(5-hydroxy-1,4-dioxo-1,4-dihydronaphtha-len-3-ylamino)-butyric acid methyl ester (compound 1) and 1,3-dimethoxycarbonyl-8-hydroxy-9,10-anthraquinone (2), and six known compounds (3-8) were isolated from the roots of Juglans mandshurica Maxim., a member of the Juglandaceae family. The chemical structures of the compounds were elucidated by nuclear magnetic resonance spectroscopy and compared with data from the literature. The isolated compounds were evaluated for their ability to inhibit the production of nitric oxide, tumour necrosis factor-α, and interleukin-6 by the mouse macrophage RAW 264.7 cell line after lipopolysaccharide stimulation in vitro. We found that compounds 1-4 exhibited potent anti-inflammatory effects, as indicated by suppression of lipopolysaccharide-stimulated nitric oxide and cytokine production with 50% inhibitory concentrations between 20.09 µM and 27.63 µM. These results identify two novel quinones from J. mandshurica with potential utility as anti-inflammatory compounds.

Synthesis, antitumor and antibacterial activities of cordycepin derivatives.

Twelve novel cordycepin derivatives were designed and synthesized with modification at positions of 2', 5'-hydroxyl and N6 amino groups of cordycepin. The results showed that the inhibitory activities of 3, 4b, 6c and 6d on A549 were comparable to the positive control gefitinib, and the inhibitory activity of 6a on A549 was better than that of gefitinib. Also, the inhibitory activities of twelve cordycepin derivatives against E. coli 1924, S. aureus 4220 and S. mutans 3289 were studied. Among them, 4b showed certain inhibitory on S. mutans 3289, while 6b showed certain inhibition on S. aureus 4220.

Isolation of a new natural kingiside aglucone derivative and other anti-inflammatory constituents from Syringa reticulata.

A new secoiridoid, (1R,5S,8S,9R)-1-methyl-kingiside aglucone (1), along with nine known compounds (2-10), were isolated from the ethanol extract of the stem bark of Syringa reticulata (Bl.) Hara. The structure of compound 1 was elucidated using HR-ESI-MS, 1D and 2D NMR spectroscopy. Compounds 1-10 were evaluated for their inhibitory activity against NO, TNF-α and IL-6 production. Compounds 1, 3, 5 and 7-10 significantly inhibited the levels of NO, TNF-α and IL-6 in LPS-induced RAW264.7 cells from concentrations of 3 to 30 µM.

A new flavanone glycoside isolated from Tournefortia sibirica.

A new flavanone glycoside, (2S)-dihydrooroxylin A 7-O-[ß-D-apiosyl(1→2)]-ß-D-glucoside (1), and four known compounds (2-5) were isolated from Tournefortia sibirica L. The chemical structures of these compounds were determined by 1 D and 2 D NMR and HR-ESI-MS spectra, and results were compared with data from the literature. These five compounds (1-5) were isolated from the family Boraginaceae for the first time. Anti-inflammatory effects of compounds (1-5) were evaluated in terms of inhibition of production of NO, TNF-α, and IL-6 in LPS-induced RAW 264.7 cells.

Anti-inflammatory activities of the chemical constituents isolated from Trametes versicolor.

Twenty-seven compounds including nine triterpenoids (1-9), eight sterols (10-17), two ribonucleotides (18, 19), four phenols (20-23), three glycosides (24-26), and one furan (27) were isolated from the fruiting bodies of Trametes versicolor (L.) Lloyd. This study is the first confirmation of the presence of the 11 compounds (3, 5, 6, 8, 18, 20, 21, 23-25, and 27) isolated from the Polyporaceae family, with six of these (2 and 12-16) from the genus Trametes. Compounds 3, 4, 10, 11, 16 and 17 were found to significantly inhibit the production of NO, TNF-α and IL-6 in a dose-dependent manner.

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-ß-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-ß-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.

One new 1,4-napthoquinone derivative from the roots of Juglans mandshurica.

A new 1,4-napthoquinone derivative, namely (S)-(-)-3-(8-hydroxy-1,4-dioxo-1,4-dihydro-naphthalen-2-yl)-3-(4-hydroxy-3-methoxyphenyl)-propionic acid methyl ester (1), was isolated from the roots of Juglans mandshurica Maxim. The structure was identified based on HR-ESI-MS, 1D and 2D NMR spectroscopic methods.

A new ribonucleotide from Cordyceps militaris.

One new ribonucleotide, 5'-(3''-deoxy-ß-D-ribofuranosyl)-3'-deoxyadenosine (1), and 14 known compounds (2-15) were isolated from an ethanol extract of Cordyceps militaris. The chemical structures of these compounds were determined from 1D and 2D NMR (1H-1H COSY, HMBC, HMQC and NOESY) and HR-ESI-MS spectra, and results were compared with data from the literature. The effects of all isolated compounds were measured on NF-κB activation, with compound 2 exhibiting significant inhibitory activity against TNF-α-induced NF-κB reporter gene expression in HeLa cells from 3 to 100 µM.

Two new quinones from the roots of Juglans mandshurica.

Two new quinones, 1-hydroxy-5-pentyl-anthraquinone (1) and 4-(5-hydroxy-1,4-dioxo-1,4-dihydro-naphthalen-2-ylamino)-butyric acid methyl ester (2), together with two known quinones, 5-hydroxy-2-(2-hydroxy-ethylamino)-(1,4) naphthoquinone (3) and juglone (4) were isolated from the roots of Juglans mandshurica (Juglandaceae). Their structures were elucidated on the basis of spectral data. Compound 3 was isolated from the Juglans genus for the first time. Compounds 1-4 exhibited significant cytotoxicity towards cultured MDA-MB231, HepG2 and SNU638 cells with IC50 values ranging from 4.46 to 88.47 µM.

Two new diarylheptanoids isolated from the roots of Juglans mandshurica.

Two new diarylheptanoids, ( - )-threo-3',4″-epoxy-1-(4-hydroxyphenyl)-7-(3-methoxyphenyl)heptan-2,3-diol (1) and (1α,3ß,5α,6α)-1,5-epoxy-3,6-dihydroxy-1,7-bis(3-methoxy-4-hydroxy-phenyl)-heptane (2), along with one known diarylheptanoid, rhoiptelol B (3), were isolated from the roots of Juglans mandshurica. The structures of compounds 1 and 2 were identified based on HR-ESI-MS, 1D and 2D NMR including (1)H-(1)H COSY, HMQC, HMBC and NOESY spectroscopic methods.