Antitumour-promoting and cytotoxic constituents of etlingera elatior.

Phytochemical studies on rhizome of Etlingera elatior have resulted in the isolation of 1,7-bis(4-hydroxyphenyl)-2,4,6-heptatrienone (1), demethoxycurcumin (2), 1,7-bis(4-hydroxyphenyl)-1,4,6-heptatrien-3-one (3), 16-hydroxylabda-8(17),11,13-trien-16,15-olide (4), stigmast-4-en-3-one (5), stigmast-4-ene-3,6-dione (6), stigmast-4-en-6b-ol-3-one (7), 5α,8α-epidioxyergosta-6,22-dien-3ß-ol (8). 1 and 4 were new compounds. Compounds 5 and 7 displayed high antitumour-promoting activity. Ethyl acetate extract showed a very significant cytotoxic activity against CEM-SS and MCF-7 cell lines (4 µg/ml and 6.25 µg/ml respectively). The antitumour-promoting activity was determined by EBV-EA assay and cytotoxic activity was determined by MTT assay.

Apianane terpenoids from Salvia officinalis.

Three apianane terpenoids, rel-(5S, 6S, 7S, 10R, 12S, 13R)-7-hydroxyapiana-8,14-diene-11,16-dion-(22,6)-olide, rel-(5S, 6S, 7R, 10R, 12S, 13R)-7-hydroxyapiana-8,14-diene-11,16-dion-(22,6)-olide and rel-(5S, 6S, 7S, 10R, 12R, 13S)-7-hydroxyapiana-8,14-diene-11,16-dion-(22,6)-olide were isolated from the leaves of Salvia officinalis, together with 15 known compounds, salvigenin, lupeol, beta-sitosterol, stigmasterol, physcion, carnosol, rosmadial, rosmanol, epirosmanol, isorosmanol, columbaridione, atuntzensin A, miltirone, carnosic acid and 12-O-methyl carnosic acid. Their structures were established on the basis of spectral evidence.

Furanosesquiterpenoids of Commiphora myrrha.

An investigation on the gum exudates of Commiphora myrrha has led to the isolation of six sesquiterpenoids. On the basis of spectroscopic data interpretation, they were determined as two new furanosesquiterpenoids, rel-1S,2S-epoxy-4R-furanogermacr-10(15)-en-6-one (1) and rel-2R-methyl-5S-acetoxy-4R-furanogermacr-1(10)Z-en-6-one (2), and four known furanosesquiterpenoids, rel-3R-methoxy-4S-furanogermacra-1E,10(15)-dien-6-one (3), rel-2R-methoxy-4R-furanogermacr-1(10)E-en-6-one (4), furanogermacra-1(10)Z,4Z-dien-6-one, and curzerenone [6,7-dihydro-5beta-isopropenyl-3,6beta-dimethyl-6-vinylbenzofuran-4(5H)-one]. This is the first report of the relative stereochemistry for the known compounds 3 and 4. Compound 1 exhibited weak cytotoxic activity against a MCF-7 breast tumor cell line in a clonogenic assay, while the other five compounds were inactive in this assay.

Antioxidative activity of carbazoles from Murraya koenigii leaves.

The antioxidative properties of the leaves extracts of Murraya koenigii using different solvents were evaluated based on the oil stability index (OSI) together with their radical scavenging ability against 1-1-diphenyl-2-picrylhydrazyl (DPPH). The methylene chloride (CH(2)Cl(2)) extract and the ethyl acetate (EtOAc) soluble fraction of the 70% acetone extract significantly prolonged the OSI values comparable to those of alpha-tocopherol and BHT. Five carbazole alkaloids were isolated from the CH(2)Cl(2) extract and their structures were identified to be euchrestine B (1), bismurrayafoline E (2), mahanine (3), mahanimbicine (4), and mahanimbine (5) based on (1)H and (13)C NMR and mass (MS) spectral data. The OSI value of carbazoles at 110 degrees C decreased in the order 1 and 3 > alpha-tocopherol > BHT > 2 > 4, 5 and control. It is assumed that compounds 1 and 3 contributed to the high OSI value of the CH(2)Cl(2) extract of M. koenigii. The DPPH radical scavenging activity for these carbazoles was in the order ascorbic acid > 2 > 1, 3 and alpha-tocopherol > BHT > 4 and 5.

Antibacterial compounds of licorice against upper airway respiratory tract pathogens.

The antibacterial activity of compounds obtained from licorice was measured against upper airway respiratory tract bacteria such as Streptococcus pyogenes, Haemophilus influenzae and Moraxella catarrhalis. Among the tested compounds, licoricidin exhibited the highest activity against all tested microorganisms with an MIC of 12.5 microg/mL. Three coumarin derivatives, glycyrol, glycyrin and glycycoumarin also showed antibacterial activity.

1,1-Diphenyl-2-picrylhydrazyl radical-scavenging active compounds from greater cardamom (Amomum subulatum Roxb.).

Constituents of the fruits of greater cardamom (Amomum subulatum) were fractionated into three fractions, the dichloromethane extract, and the ethyl acetate-soluble and water-soluble fractions of the 70% aqueous acetone extract. The ethyl acetate-soluble fraction showed a high radical-scavenging activity against 1,1-diphenyl-2-picrylhydrazyl (DPPH). Four compounds were isolated from the ethyl acetate-soluble fraction, and their structures were ascribed to protocatechualdehyde (1), protocatechuic acid (2), 1,7-bis(3,4-dihydroxyphenyl)hepta-4E,6E-dien-3-one (3) and 2,3,7-trihydroxy-5-(3,4-dihydroxy-E-styryl)-6,7,8,9-tetrahydro-5H-benzocycloheptene (4) on the basis of spectroscopic evidence. This is the first isolation of these compounds from greater cardamom. In particular, 4 was a new type of cyclic diarylheptanoid. DPPH radical-scavenging activity of these compounds was measured by colorimetric analysis. Compounds 1 and 3 showed stronger activity than such natural antioxidants as alpha-tocopherol and L-ascorbic acid. Compounds 2 and 4 were comparable to alpha-tocopherol and L-ascorbic acid.

Ecdysteroids of quinoa seeds (Chenopodium quinoa Willd.).

Quinoa (Chenopodium quinoa) is a hardy and nutritious Latin American pseudo-cereal. Studies on the seeds led to the isolation of five ecdysteroids using column chromatography. Their structures were determined as ecdysterone, makisterone A, 24-epi-makisterone A, 24(28)-dehydromakisterone A, and 20,26-dihydroxyecdysone by spectroscopic methods. This study demonstrates that quinoa seeds are a source of ecdysteroids, which were reported to be molting hormones in insects.

New constituents of the leaves of Alpinia flabellata.

Two new compounds were isolated from the leaves of Alpinia flabellata. The structures of these compounds were determined by a combination of NMR techniques and HREIMS as 4-hydroxy-2-(2,4,5-trimethoxyphenyl)-2E-butenal (1) and rel-labd-12-en-15(16)-olid-7-one-8R-spiro-1'-[2S-(2,4,5-trimethoxyphenyl)-3-cyclohexene] (2).

Phenylbutanoid dimers from the leaves of Alpinia flabellata.

Three phenylbutanoid dimers, cis- and trans-1-(2,4,5-trimethoxy-E-styryl)-2-(2,4,5-trimethoxy-Z-styryl)cyclobutane and 1,2-bis(2,4,5-trimethoxy-Z-styryl)- cyclobutane, were isolated from the leaves of Alpinia flabellata Ridley, together with three known compounds (2,4,5-trimethoxybenzaldehyde, 2,4,5-trimethoxycinnamaldehyde and 3,5-dihydroxy-7,4'-dimethoxyflavone). The structures of these compounds were determined by spectroscopic analysis.

Identification, quantitative determination, and antioxidative activities of chlorogenic acid isomers in prune (Prunus domestica L. ).

Neochlorogenic acid (3-CQA) and cryptochlorogenic acid (4-CQA), isolated from prune (Prunus domestica L.), were identified by NMR and MS analyses. In addition, the quantity of chlorogenic acid isomers in prune were measured by HPLC. These isomers, 3-CQA, 4-CQA, and chlorogenic acid (5-CQA), were contained in the ratio 78.7:18. 4:3.9, respectively. 4-CQA was identified and quantified in prune for the first time, and relatively high amounts of this isomer were characteristic. Antioxidative activities of the chlorogenic acid isomers, such as scavenging activity on superoxide anion radicals and inhibitory effect against oxidation of methyl linoleate, were also evaluated. Each isomer showed antioxidative activities which were almost the same.

Screening of Zingiberaceae extracts for antimicrobial and antioxidant activities.

Dichloromethane and methanol extracts of 13 Zingiberaceae species from the Alpinia, Costus and Zingiber genera were screened for antimicrobial and antioxidant activities. The antimicrobial activity of most of the extracts was antibacterial with only the methanol extract of Costus discolor showing very potent antifungal activity against only Aspergillus ochraceous (MID, 15.6 microg per disc). All the extracts showed strong antioxidant activity comparable with or higher that of alpha-tocopherol.

Novel glycosides from noni (Morinda citrifolia).

Three new glycosides were isolated from the fruits of noni (Morinda citrifolia). Their structures were determined to be 6-O-(beta-D-glucopyranosyl)-1-O-octanoyl-beta-D-glucopyranose (1), 6-O-(beta-D-glucopyranosyl)-1-O-hexanoyl-beta-D-glucopyranose (2), and 3-methylbut-3-enyl 6-O-beta-D-glucopyranosyl-beta-D-glucopyranoside (3) using MS and NMR methods.

Chemopreventive effects of coumaperine from pepper on the initiation stage of chemical hepatocarcinogenesis in the rat.

This study was designed to investigate the chemopreventive action of three natural products, coumaperine, aurapten and an extract from rosemary, against the initiation stage of rat hepato-carcinogenesis. Coumaperine has been isolated from white pepper as a naturally occurring antioxidative agent, but its potential modifying effects on carcinogenesis remain unclear. In experiment 1, a modification of the model developed by Tsuda et al. was applied, with assessment of numbers and areas of induced glutathione S-transferase placental form (GST-P)-positive hepatocellular foci in male F344 rats. Coumaperine, aurapten and the extract from rosemary were administered i.g. at 100 mg / kg / day once daily for 5 days with initiation by diethylnitrosamine (DEN) on day 4 (20 mg / kg, i.p.). Numbers and areas of GST-P-positive foci in each group given test chemicals tended to be decreased as compared to the vehicle control group values, significance being achieved for number with coumaperine. Experiment 2 was planned to investigate the mechanism of the inhibitory effects of coumaperine. Livers at 8 h after initiation by DEN were examined with coumaperine administered at 100 mg / kg / day once daily for 3 days. Proliferating cell nuclear antigen (PCNA)-positive cells tended to be decreased as compared to the vehicle control, but no effects on apoptosis or cytochrome P-450 (CYP) 2E1 expression were apparent. Our results suggest that coumaperine provides protection against initiation of hepatocarcinogenesis, and that this is related to inhibition of cell proliferation.

Galloylglucosides from berries of Pimenta dioica.

Three new galloylglucosides, (4S)-alpha-terpineol 8-O-beta-D-(6-O-galloyl)glucopyranoside (1); (4R)-alpha-terpineol 8-O-beta-D-(6-O-galloyl)glucopyranoside (2), and 3-(4-hydroxy-3-methoxyphenyl)propane-1,2-diol 2-O-beta-D-(6-O-galloyl)glucopyranoside (3), were isolated from the berries of Pimenta dioica together with three known compounds, gallic acid (4), pimentol (5), and eugenol 4-O-beta-D-(6-O-galloyl)glucopyranoside (6). The structures of 1-3 were elucidated on the basis of MS and NMR spectral data and enzymatic hydrolysis. These galloylglucosides (1-3, 5, and 6) showed radical-scavenging activity nearly equivalent to that of gallic acid (4) against 1,1-diphenyl-2-picrylhydrazyl radical.

Isolation and structural elucidation of two new glycosides from sage (Salvia officinalis L.).

Six compounds, 1-O-(2,3, 4-trihydroxy-3-methyl)butyl-6-O-feruloyl-beta-D-glucopyranoside, ethyl beta-D-glucopyranosyl tuberonate, p-hydroxybenzoic acid, (-)-hydroxyjasmonic acid, caffeic acid, and 4-hydroxyacetophenone 4-O-[5-O-(3, 5-dimethoxy-4-hydroxybenzoyl)-beta-D-apiofrunosyl]-(1-->2)-beta-D- glu copyranoside, were isolated from the n-butanol-soluble fraction of sage leaf extracts. Their structures were determined by spectral methods (MS, NMR, and 2D-NMR), and their antioxidant activities were measured. Among them, two new glycosides were elucidated. All of these compounds showed DPPH free radical scavenging activity at the concentration of 30 mM, and caffeic acid was the most active compound.

Novel trisaccharide fatty acid ester identified from the fruits of Morinda citrifolia (Noni).

Two known glycosides and a novel trisaccharide fatty acid ester were isolated from the n-butanol-soluble fraction of the fruits of Morinda citrifolia (noni). Structure determination was carried out by spectral techniques such as MS, IR, NMR, and 2D-NMR. The novel trisaccharide fatty acid ester was elucidated as 2, 6-di-O-(beta-D-glucopyranosyl)-1-O-octanoyl-beta-D-glucopyranose. The known compounds were identified as rutin and asperulosidic acid.

Acetophenone glycosides from thyme (Thymus vulgaris L.).

Four acetophenone glycosides were isolated from the butanol-soluble fraction of thyme extracts. Their structures were determined by spectral methods (MS, NMR, and 2D-NMR). Among them, two new compounds, 4-hydroxyacetophenone 4-O-[5-O-(3, 5-dimethoxy-4-hydroxybenzoyl)-beta-D-apiofuranosyl]-(1-->2)-beta-D -gl ucopyranoside (1) and 4-hydroxyacetophenone 4-O-[5-O-(4-hydroxybenzoyl)-beta-D-apiofuranosyl]-(1-->2)-beta-D-+ ++gluc opyranoside (2), were determined. Compound 1 showed weak cytotoxicity, inhibiting DNA synthesis of human leukemia cells.

Two C21-steroidal glycosides isolated from Cynanchum stauntoi.

Studies on the roots of Cynanchum stauntoi led to the isolation of two C21-steroidal glycosides, formally named stauntosides A and B. Their structures were elucidated on the basis of spectroscopic evidence, especially that from analysis of 2D-NMR spectra. They were found to possess an unusual skeleton and were identified as stauntogenin 3-O-alpha-L-diginopyranosyl-(1-4)-beta-L-cymaropyranosyl-(1- 4)-beta-D- digitoxopyranosyl-(1-4)-beta-D-thevetopyranoside and stauntogenin 3-O-alpha-L-cymaropyranosyl-(1-4)-beta-D-digitoxopyranosyl-( 1-4)-beta-D-3- demethyl-2-deoxy-thevetopyranoside.

New Bitter Diterpenes, Rabdosianone I and II, Isolated from Isodon japonicus Hara.

The new bitter diterpenes, rabdosianone I (C20H24O5) and II (C22H28O6), were isolated from Isodon japonicus (Japanese name, enmeiso), and their structures were elucidated by spectroscopic methods. Electrophysiological experiments were performed to compare rabdosianone I with quinine. The taste responses of chorda tympani nerves to rabdosianone I were smaller than those to quinine in Wistar rats.

Spasmolytic activity of aurapten analogs.

Seven coumaric compounds analogous to aurapten were synthesized. Their spasmolytic activity against Ba2+, acetylcholine and histamine was evaluated to investigate their structure-activity relationship. The results of the bioassay demonstrated the important roles of the cis type of double bond at C-2' and the epoxide between c-6' and 7'.