Two new coumarins from the seeds of Solanum indicum

Two new coumarins, (E)-2-(4-hydroxy-3-methoxybenzylidene)-5-methoxy-2H-[1,4]dioxino[2,3-h]chromene-3,9-dione (indicumin E, 1) and 7-hydroxy-6,8-dimethoxy-3-(4′-hydroxy-3′-methoxyphenyl)-coumarin (2), together with two known coumarins isofraxidin (3) and fraxetin (4), were isolated from the Solanum indicum seeds. Their structures were established on the basis of 1D and 2D spectroscopic data. Compound 1 was the rarest coumarinolignoid known to date.     

Lignans from the stems of Sambucus williamsii and their effects on osteoblastic UMR106 cells

Three new lignans, sambucunol A (8) ((+)-erythro-1-(4-hydroxy-3-methoxyphenyl)-2-[4-(4-hydroxy-3-methoxycinnamoyloxypropanyl)-2-hydroxyphenoxy]-1, 3-propanediol), sambucunol B (9) ((+)-threo-1-(4-hydroxyl-3-methoxyphenyl)-2-[4-(4-hydroxy-3-methoxy-cinnamoyloxy propanyl)-2-hydroxyphenoxy]-1, 3-propanediol) and buddlenol G (10) (2-{4-[2, 3-dihydro-3-hydroxymethyl-7-hydroxy-5-(4-hydroxy-3-methoxycinnamoyloxypropanyl)-2-benzofuranyl]-2,6-dimethoxyphenoxy}-1-(4- hydroxy-3-methoxyphenyl) -1, 3-propanediol), along with seven known ones, including ( ? )-syringaresinol (1), ( ? )-pinoresinol (2), 1, 2-bis(4-hydroxy-3-methoxy phenyl)-1, 3-propanediol (3), ( ? )-erythro-1-(4-hydroxy-3-methoxyphenyl)-2-[4-(3-hydroxy propanyl)-2-methoxyphenoxy]-1, 3-propanediol (4), ( ? )-threo-1-(4-hydroxy-3-methoxyphenyl)-2-[4-(3-hydroxypropanyl)-2-methoxy phenoxy]-1, 3-propanediol (5), ( ? )-lariciresinol (6) and ( ? )-dihydrodehydrodiconiferyl alcohol (7), were isolated from the 60% ethanol extract of stems of Sambucus williamsii Hance by chromatographic methods. Their structures were established by spectral analysis. The effects of isolated compounds on the osteoblast-like UMR106 cell proliferation and ALP activities were determined. Compounds 2, 7 and 10 showed stimulating effects both on UMR106 cell proliferation and ALP activity. Compounds 1, 3, 6 and 8 stimulated UMR106 cell proliferation, while compounds 4 and 5 induced ALP activity in UMR106 cell.     

Two new aromatic compounds from the resin of Styrax tonkinensis (Pier.) Craib

Two new aromatic compounds, trans-(tetrahydro-2-(4-hydroxy-3-methoxyphenyl)-5-oxofuran-3-yl)methyl benzoate (1), 3-(4-hydroxy-3-methoxyphenyl)-2-oxopropyl benzoate (2) and one new natural product, 4-((E)-3-ethoxyprop-1-enyl)-2-methoxyphenol (3) together with five known aromatic compounds have been isolated from the resin of Styrax tonkinensis (Pier.) Craib. Their structures were determined by physical and spectroscopic methods.     

Two natural compounds – a benzofuran and a phenylpropane – from Artemisia dracunculus

The structure elucidation of three metabolites herniarin (7-methoxy-2H-chromen-2-one, 1), phytoalexin (5-acetyl-6-hydroxy-2-(1-hydroxy-1-methylethyl)benzofuran, 2), and prestragol (3-(4′-methoxyphenyl)-prop-1,2-diol, 3) isolated from Artemisia dracunculus was determined on the basis of 1D, 2D NMR methods and by an X-ray crystallographic determination.     

Norlignans from Pouzolzia zeylanica var. microphylla and their nitric oxide inhibitory activity

Five new compounds, pouzolignan F [4-hydroxy-3-(3,5-dihydroxyphenyl)-2-[bis(4-hydroxy-3-methoxyphenyl)methyl]butyl acetate] (1), pouzolignan G [4-hydroxy-3-(3,5-dihydroxyphenyl)-2-[(4-hydroxy-3,5-dimethoxyphenyl)(4-hydroxy-3-methoxyphenyl)methyl]butyl acetate] (2), pouzolignan H [1,4-dihydroxy-3-(3,5-dihydroxyphenyl)-2-[bis(4-hydroxy-3-methoxyphenyl)methyl]butane] (3), pouzolignan I [1,4-dihydroxy-3-(3,5-dihydroxyphenyl)-2-[(4-hydroxy-3,5-dime thoxyphenyl)-(4-hydroxy-3-methoxyphenyl)methyl]butane] (4), and pouzolignan J [1,4-dihydroxy-3-(3,5-dihydroxyphenyl) -2-[(3,4,5-trimethoxyphenyl)(4-hydroxy-3-methoxyphenyl)methyl]butane] (5), along with two known compounds, indolyl-3-carboxylic acid (6) and uracil (7), were isolated from the aerial parts of Pouzolzia zeylanica (L.) Benn. var. microphylla (Wedd.) W.T.Wang. The structures of these compounds were characterized based on spectroscopic methods, including IR, NMR (¹H–¹H COSY, HSQC, HMBC, and NOESY), and HR-ESI/TOF-MS experiments. All the new norlignans were assayed for inhibitory activity against lipopolysaccharide (LPS)-induced nitric oxide (NO) production in mouse peritoneal macrophages.     

Four new diarylheptanoids from Rhizoma Zingiberis

Four new diarylheptanoids, (1S, 3R, 5R, 6R)-1, 5-epoxy-3, 6 dihydroxy-1-(4-hydroxy-3, 5-dimethoxyphenyl)-7-(4-hydroxy-3-methoxyphenyl) heptane (1), (1R, 3R, 5S)-1, 5-epoxy-3-acetoxy-1-(4, 5-dihydroxy-3-methoxyphenyl)-7-(3, 4- hydroxyphenyl) heptane (2), (3R, 5S, 6R, 7S)-3, 6-epoxy-7-hydroxyl-1-(4-hydroxyphenyl)-7-(3-methoxy-4-hydroxyphenyl) heptane (3), (E)-3-keto-1-(3-methoxy-4-hydroxyphenyl)-7-(4, 5-dihydroxy-3-methoxyphenyl)-4- heptene (4), were isolated from Rhizoma Zingiberis, and their structures were determined based on HR-ESI-MS and extensive spectroscopic techniques (UV, IR, 1D-NMR and 2D-NMR). Compounds 1–4 exhibited no cytotoxicity against HepG2 cell lines.

     

Two new 8-O-4′-type lignans from the stem of Schima superba and their cell growth inhibitory activities against human cancer cell lines

Two new lignans (1 and 2) were isolated from the EtOH extracts of the stem of Schima superba, and elucidated as (7R,8S)-1-(3,4-dimethoxyphenyl)-2-O-(2-methoxy-4-omegahydroxypropylphenyl)propane-1,3-diol (1) and threo-1-(4-hydroxy-3-methoxyphenyl)-1-methoxy-2-{4-[1-formyl-(E)-vinyl]-2-methoxyphenoxy}-3-propanol (2) by spectral analysis. Compounds 1 and 2 showed cell growth inhibitory activity against HeLa, CNE, HepG-2, and HEp-2 cell lines. Compound 1 exhibited significant cytotoxicities with IC₅₀ values of less than 4 μg/ml against all the tested cell lines.     

Synthesis and antidepressant-like action of N-(2-hydroxyethyl) cinnamamide derivatives in mice

This study described the chemical synthesis and pharmacological evaluation of a series of N-(2-hydroxyethyl) cinnamamide derivatives. The structures of them were characterized by IR, ¹H-NMR, MS and elemental analysis. Their antidepressant activities were evaluated by the forced swimming test (FST) and tail suspension test (TST). Pharmacological results of these compounds showed that some of them, given orally, significantly reduced the immobility time in the FST and TST, indicating the antidepressant-like action. Among them, compounds N-(2-hydroxyethyl)cinnamamide (1g), (E)-3-(4-hydroxy-3-methoxyphenyl)-N-(2-hydroxyethyl)acrylamide (1i) and (E)-N-(2-hydroxyethyl)-3-(3-hydroxyphenyl)acrylamide (1n), active in the two models, were considered as the most promising compounds in this study.     

Antiviral activities of diarylheptanoids against influenza virus in vitro

The anti-influenza A/PR/8/34 (H1N1) virus activities of ten diarylheptanoids isolated from Alpinia officinarum were examined using the MTT method. The 50% inhibitory concentration of each diarylheptanoid examined was clearly lower than its 50% cytotoxic concentration determined by the MTT assay and/or maximum non-cytotoxic concentration (MNCC) determined by the morphological change of cells. In particular, the influenza virus was more susceptible to 7-(4″-hydroxy-3″-methoxyphenyl)-1-phenyl-4E-hepten-3-one (3) and (5S)-5-hydroxy-7-(4″-hydroxyphenyl)-1-phenyl-3-heptanone (8) than the other diarylheptanoids. Thus, all diarylheptanoids exhibited potential antiviral activity against influenza virus in vitro.     

Metabolites from endophytic fungus S20 of Cephalotaxus hainanensis

Three new C-methylated acetogenins, (2E,6Z)-9,10-dihydroxy-4-hydroxymethyl-2,6-decadiene (1), (2E,6Z)-8,9,10-trihydroxy-4-hydroxymethyl-2,6-decadiene (2), and (2E,6Z)-9-hydroxy-4-hydroxymethyl-2,6-nonadiene (3), together with two known compounds, p-hydroxybenzyl alcohol (4) and indolyl-3-carboxylic acid (5), were isolated from endophytic fungus S20 of Cephalotaxus hainanensis Li. Their structures were determined based on HR-ESI-MS and spectroscopic techniques (IR, UV, 1D, and 2D NMR). Compound 5 showed inhibitory effects on Staphylococcus aureus and methicillin-resistant S. aureus by the filter paper disc agar diffusion method.     

Aromatic acid derivatives from the lateral roots of Aconitum carmichaelii

Seven new aromatic acid derivatives (1–7), together with five known analogs, were isolated from the lateral roots of Aconitum carmichaelii. Structures of the new compounds were determined by spectroscopic and chemical methods as 4-methyl ( ? )-(R)-hydroxyeucomate (1), 4-butyl ( ? )-(R)-hydroxyeucomate (2), 4-butyl-1-methyl (+)-(R)-2-O-(4′-hydroxy-3′-methoxybenzoyl)malate (3), 1-butyl-4-methyl (+)-(R)-2-O-(4′-hydroxy-3′-methoxybenzoyl)malate (4), dimethyl (+)-(R)-2-O-(4′-hydroxy-3′-methoxybenzoyl)malate (5), dimethyl (+)-(R)-2-O-(4′-hydroxybenzoyl)malate (6), and methyl ( ± )-3-(4′-hydroxy-3′-methoxyphenyl)-3-sulfopropionate (7), respectively. Compounds 1 and 2 are 2-benzylmalates (eucomate derivatives), 3–6 belong to 2-O-benzoylmalates, and 7 is a rare phenylpropionate containing a sulfonic acid group. The absolute configurations of eucomate derivatives were confirmed by X-ray crystallographic analysis of 4-methyl eucomate (11).     

Four new glucosides from the aerial parts of Mediasia macrophylla

As part of our chemical studies on the medical plants in Uzbekistan aimed at searching for new drug leads, we have examined the aerial parts of Mediasia macrophylla. This has resulted in the isolation of four new glucosides, together with 30 known compounds. The structures of new compounds were elucidated as (1′S)-(4-hydroxyphenyl) ethane-1′,2′-diol 2′-O-β-glucopyranoside (1), 3-(4′-methoxyphenyl)-propanol 1-O-β-glucopyranoside (2), 2-methoxy-3-hydroxy-5-(E)-propenyl-phenol 1-O-β-glucopyranoside (3), 1-O-angeloyl-β-glucopyranose (4), on the basis of spectral analysis.     

Two new resorcinols from Sargassum thunbergii

Two new resorcinols, 1-(5-acetyl-2,4-dihydroxyphenyl)-3-methylbutan-1-one (1) and 1-(5-acetyl-2-hydroxy-4-methoxyphenyl)-3-methylbutan-1-one (2), have been isolated from the brown algae Sargassum thunbergii (Mert.) O'Kuntze. Their structures were elucidated on the basis of spectroscopic methods.     

Aromatic glycosides from the flower buds of Lonicera japonica

Six new glycosides (1–6) have been isolated from the flower buds of Lonicera japonica. Their structures including the absolute configurations were determined by spectroscopic and chemical methods as ( ? )-2-hydroxy-5-methoxybenzoic acid 2-O-β-d-(6-O-benzoyl)-glucopyranoside (1), ( ? )-4-hydroxy-3,5-dimethoxybenzoic acid 4-O-β-d-(6-O-benzoyl)-glucopyranoside (2), ( ? )-(E)-3,5-dimethoxyphenylpropenoic acid 4-O-β-d-(6-O-benzoyl)-glucopyranoside (3), ( ? )-(7S,8R)-(4-hydroxyphenylglycerol 9-O-β-d-[6-O-(E)-4-hydroxy-3,5-dimethoxyphenylpropenoyl]-glucopyranoside (4), ( ? )-(7S,8R)-(4-hydroxy-3-methoxyphenylglycerol 9-O-β-d-[6-O-(E)-4-hydroxy-3,5-dimethoxyphenylpropenoyl]-glucopyranoside (5), and ( ? )-4-hydroxy-3-methoxyphenol β-d-{6-O-[4-O-(7S,8R)-(4-hydroxy-3-methoxyphenylglycerol-8-yl)-3-methoxybenzoyl]}-glucopyranoside (6), respectively.     

Two new lignans from the aerial part of Vitex negundo

A new phenyldihydronaphthalene-type lignan, (3R,4S)-6-hydroxy-4-(4-hydroxy- 3-methoxyphenyl)-5,7-dimethoxy-3,4-dihydro-2-naphthaldehyde-3a-O-β-d-glucopyranoside (1), and a new phenylnaphthalene-type lignan, 6,7,4′-trihydroxy-3′-methoxy-2,3- cycloligna-1,4-dien-2a,3a-olide (2), along with 10-known lignan derivatives (3–12) were isolated from the aerial part of Vitex negundo var. heterophylla. Their structures were established by comprehensive 1D- and 2D-NMR spectroscopic analyses.     

Two new stilbenoids from Pleione bulbocodioides

Two new stilbenoids, 9-(4′-hydroxy-3′-methoxyphenyl)-10-(hydroxymethyl)-11-methoxy-5,6,9,10-tetrahydrophenanthro[2,3-b]furan-3-ol (1) and 2-(4″-hydroxybenzyl)-3-(3′-hydroxyphenethyl)-5-methoxy-cyclohexa-2,5-diene-1,4-dione (2), together with the three known stilbenoids were isolated from the tubers of Pleione bulbocodioides (Franch.) Rolfe. Their structures were elucidated by spectroscopic methods.     

Antibacterial activity of <Emphasis Type="Italic">Capsicum annuum</Emphasis> extract and synthetic capsaicinoid derivatives against <Emphasis Type="Italic">Streptococcus mutans</Emphasis>

The inhibitory effects of the ethyl acetate extract and capsaicin (1) and dihydrocapsaicin (2) isolated from fruits of Capsicum annuum chili pepper type, and synthetic capsaicinoid derivatives (N-(4-hydroxyphenylethyl)decamide (3), (E)-N-(4-hydroxy-3-methoxybenzyl)-3,7-dimethylocta-2,6-dienamide (4), 4-hydroxy-3-methoxy-N-((E)-3,7-dimethylocta-2,6-dienyl)benzamide (5) and N-(4-hydroxy-3-methoxybenzyl)decamide (6) at different concentrations were evaluated against Streptococcus mutans. The minimum inhibitory concentration at which the ethyl acetate extract prevented the growth of S. mutans was 2.5 mg/mL; those of the isolated compounds 1 and 2 were 1.25 μg/mL, while 3 was 5.0 μg/mL, and 4, 5 and 6 were 2.5 μg/mL, respectively.     

Cytotoxic stilbenes from the roots of Paphiopedilum godefroyae

Two new stilbenes, 2-(3′,5′-dimethoxyphenyl)-6-hydroxy-5-methoxybenzofuran (1) and 3′-hydroxy-2,5′-dimethoxystilbene (2), together with seven known stilbenes (3, 5–10) and one flavanone (4), were isolated from the roots of Paphiopedilum godefroyae. Their chemical structures were determined on the basis of their spectroscopic data. These isolated compounds were evaluated for their cytotoxicity against human small cell lung cancer (NCI-H187) cell lines and an arylbenzofuran derivative, 5,6-dimethoxy-2-(3-hydroxy-5-methoxyphenyl)benzofuran (6), was shown to be strongly cytotoxic with an IC₅₀ value of 5.10 μM.     

Synthesis and analgesic, anti-inflammatory activities of 3-(3-methoxyphenyl)-2-substituted amino-quinazolin-4(3H)-ones

A variety of novel 3-(3-methoxyphenyl)-2-substituted amino-quinazolin-4(3H)-ones were synthesized by reacting the amino group of 2-hydrazino-3-(3-methoxyphenyl)-quinazolin-4(3H)-one with a variety of aldehydes and ketones. The starting material 2-hydrazino-3-(3-methoxyphenyl)-quinazolin-4(3H)-one was synthesized from 3-methoxy aniline. The title compounds were investigated for analgesic, anti-inflammatory, and ulcerogenic behavior. Among these the compound 2-(1-methyl butylidene-hydrazino)-3-(3-methoxyphenyl)-3H-quinazolin-4-one (AS3) emerged as the most active compound for the analgesic activity, while the compound 2-(1-ethyl propylidene-hydrazino)-3-(3-methyoxyphenyl)-3H-quinazolin-4-one (AS2) showed most potent anti-inflammatory activity of the series and these compounds are moderately more potent when compared to the reference standard diclofenac sodium. Interestingly the test compounds showed only mild ulcerogenic potential when compared to acetylsalicylic acid.     

Cycloartanes from the red alga Galaxaura sp.

Six cycloartane triterpenes have been isolated from the red alga Galaxaura sp. The new structures (galaxaurols A–E) were determined to be methyl 3β-hydroxy-23-oxocycloart-24-en-29-oate (2), methyl 23(E)-3β-hydroxy-25-methoxycycloart-23-en-29-oate (3), methyl 23(E)-3β-hydroxycycloarta-23,25-dien-29-oate (4), 23(E)-25-methoxycycloart-23-en-3β,29-diol (5), and cycloart-24-en-3β,23α,29-triol (6), respectively.