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At least 253 records · Page 14Linked to original sources
PubMed2000

Inhibition of interleukin-12 and interferon-gamma production in immune cells by tanshinones from Salvia miltiorrhiza.

Pharmacological control of interleukin-12 (IL-12) and interferon-gamma (IFN-gamma) production may be a key therapeutic strategy for modulating immunological diseases dominated by Th1-derived cytokine responses. In this study, we investigated the effects of three different tanshinone pigments from Salvia miltiorrhiza (tanshinone I, dihydrotanshinone, and cryptotanshinone) on IL-12 production in mouse macrophages and on IFN-gamma production in lymph node cells. All tested tanshinones significantly inhibited IL-12 production in lipopolysaccharide (LPS)-activated macrophages and also IFN-gamma production in keyhole limpet hemocyanin (KLH)-primed lymph node cells in a dose-dependent manner. Dihydrotanshinone was more effective than tanshinone I or cryptotanshinone. Tanshinones significantly inhibited the expression of IL-12 p40 gene at the mRNA level. Furthermore, tanshinones potently inhibited the promoter activation of IL-12 p40 gene and nuclear factor (NF)-kappaB binding to the kappaB site, suggesting that tanshinones may negatively regulate IL-12 production at the transcription level. These results may explain some known biological activities of tanshinones including their anti-inflammatory effect, and suggest a possible use of tanshinones in the treatment of immunological diseases dominated by Th1-derived cytokine responses.

Abietanes↗
PubMed2002

Isolation of two highly potent and non-toxic inhibitors of human immunodeficiency virus type 1 (HIV-1) integrase from Salvia miltiorrhiza.

Water soluble extracts of the herbal plant, Salvia miltiorrhiza (Danshen) exhibited potent effect against HIV-1 integrase activity in vitro and viral replication in vivo. We have developed an extensive purification scheme to isolate effective, non-toxic inhibitors against human immunodeficiency virus type 1 (HIV-1) using the 3'-processing activity of integrase as a purification guide and assay. Two water soluble compounds, M(5)22 and M(5)32, have been discovered by isolating them from S. miltiorrhiza roots in purities of >99.5% as shown by NMR spectral analysis with yields of 0.018 and 0.038%, respectively. Structural determination revealed that M(5)22 is lithospermic acid and M(5)32 is lithospermic acid B. These two structurally related compounds are potent anti-HIV inhibitors and showed no cytotoxicity to H9 cells at high concentrations (CC(100)>297 microM for M(5)22 and >223 microM for M(5)32). The IC50 for inhibition of 3'-processing by HIV-1 integrase was found to be 0.83 microM for M(5)22 and 0.48 microM for M(5)32. In addition, M(5)22 and M(5)32 inhibited HIV-1 integrase catalytic activities of 3'-joining to the target DNA with IC50 of 0.48 microM for M(5)22 and 0.37 microM for M(5)32. Furthermore, kinetic and mechanistic studies suggested that drug binding to HIV-1 integrase and inhibition of enzymatic activity occur at a fast rate. Both M(5)22 and M(5)32 do not prevent HIV entry in H9 cells. They also show no inhibition of reverse transcriptase activity in infected cells. The levels of intracellular strong stop and full-length viral DNA remained unchanged following drug treatment. However, both inhibitors strongly suppressed the acute HIV-1 infection of H9 cells with IC50 values of 2 and 6.9 microM for M(5)22 and M(5)32, respectively. Thus these two selective integrase inhibitors hold promise as a novel class of therapeutic drugs for AIDS based on their high potencies and absence of cytotoxicity.

Benzofurans↗
PubMed1997

Tanshinone production in Ti-transformed Salvia miltiorrhiza cell suspension cultures.

Transformed cell cultures of Salvia miltiorrhiza were established by infecting sterile plantlets with Agrobacterium tumefaciens strain C58. The transformed cells in suspension formed macroscopic clumps of cell aggregates up to 2-3 cm in size rather than homogeneous cell suspensions. These transformed cells grew well in hormone-free media. It was found that the B5 mediums supported the best growth while the 6,7-V medium promoted tanshinone production in the transformed cell suspension cultures. The effect of initial sucrose concentration on cell growth was also studied. The best growth was observed when cells were cultivated in the B5 medium containing 30 g l-1 sucrose. Although low levels of tanshinones were produced in fast growing cell cultures, there existed a rapid increase in tanshinone production when the cell aggregates were transferred to the fresh yeast-extract-containing medium. By this two-stage culture method, about 22 mg tanshinones were produced in 1 liter of medium. Green cell aggregates were formed when cells were cultured under illumination. Light was found to have an inhibitory effect on tanshinone biosynthesis. A sensitive high-performance liquid chromatographic method was developed for the measurement of tanshinones. Cryptotanshinone, tanshinone I and tanshinone IIA were identified from the transformed cultures.

Abietanes↗
PubMed2001

Constituents of Salvia moorcroftiana.

A new aromatic ester, 3-oxodecan-1-o1 p-hydroxybenzoate (1) was isolated from Salvia moorcroftiana aerial parts along with four other constituents.

Alkanes↗
PubMed2002

Some effects of Salvia aegyptiaca L. on the central nervous system in mice.

Salvia aegyptiaca L. is used for treating various unrelated conditions that include nervous disorders, dizziness, trembling, diarrhoea and piles. This work examines some effects of the crude acetone and methanol extracts of the plant given at single oral doses of 0.25, 0.5, 1 or 2 g/kg, on the central nervous system (CNS) in mice. The extracts were also tested for anti-inflammatory and antipyretic actions. Several models of nociception have been used to examine the analgesic effect of the extract. In treated mice, the extracts caused dose-related inhibition of acetic acid-induced abdominal constriction, and significantly reduced formalin-induced pain. Treatment with the extracts at doses of 0.5 and 1 g/kg significantly increased the reaction time in the hot-plate test. In treated mice both extracts caused significant and dose-related impairment of the sensorimotor control and motor activity. Treatment with both extracts did not significantly affect the rectal temperature of normothermic mice. The methanol extract (0.5 and 1.0 g/kg) did not affect the rectal temperature of hyperthermic mice, but the acetone extract was effective in significantly reducing the rectal temperature of hyperthermic mice, 0.5 and 1 h after administration of the extract at doses of 0.25-2 g/kg. It is concluded that the crude methanol and acetone extracts of S. aegyptiaca have CNS depressant properties, manifested as antinociception and sedation. Both extracts have some anti-inflammatory and antipyretic actions. On the whole, the acetone extract appeared to be slightly more effective than the methanol extract in this regard.

Acetone↗
PubMed1999

Inhibitory effect of caffeic acid analogues isolated from Salviae Miltiorrhizae Radix against 1,1-diphenyl-2-picrylhydrazyl radical.

Caffeic acid and its four polymers isolated from Salviae Miltiorrhizae Radix were examined for their activity of scavenging free radicals in a 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical generating system. The results showed that the polymers of caffeic acid inhibited the DPPH radical more strongly than caffeic acid. The strongest activity was displayed by two tetramers, lithospermic acid B and its Mg2+ salt. The trimer (lithospermic acid) and dimer (rosmarinic acid) showed similar efficiency. In comparison, caffeic acid was less efficient in scavenging free radicals. Determination of the activity of caffeic acid derivatives of small molecules revealed that the o-dihydroxyl group was the most important active structure of caffeic acid derivatives for scavenging of free radicals. Lack or substitution of this structure resulted in marked reduction or even loss of the activity. Structural modification of the side chain of caffeic acid produced slight changes in activity. The present results demonstrate that a saturated group connected to the aromatic ring has slightly higher inhibitory activity against the DPPH radical than an unsaturated group.

Antioxidants↗
PubMed2003

Proposed mechanism and functional amino acid residues of malonyl-CoA:anthocyanin 5-O-glucoside-6'''-O-malonyltransferase from flowers of Salvia splendens, a member of the versatile plant acyltransferase family.

The versatile plant acyltransferase (VPAT) family is a recently identified protein family consisting of acyltransferases involved in secondary metabolism in plants along with numerous homologues with as yet unidentified biochemical functions. Malonyl-CoA:anthocyanin 5-O-glucoside-6' "-O-malonyltransferase of Salvia splendens flowers (Ss5MaT1) is a member of this family that catalyzes the regiospecific transfer of the malonyl group from malonyl-CoA to the 6' "-hydroxyl group of the 5-glycosyl moiety of anthocyanins. To elucidate the mechanism and functional amino acid residues of VPAT family enzymes, steady-state kinetic analyses and site-directed mutagenesis of Ss5MaT1 guided by sequence comparison studies were carried out. On the basis of the results of product and dead-end inhibition studies as well as sequence comparison studies, the kinetic mechanism of Ss5MaT1 could be most consistently described in terms of a ternary complex mechanism in which both substrates and the enzyme form a complex before catalysis can occur, as in the case of chloramphenicol O-acetyltransferase (CAT) and histone acetyltransferase (HAT). Eight polar or ionizable amino acid residues that are invariant among 12 VPAT family enzymes were replaced by alanine, and the mutant enzymes were kinetically characterized. A significant diminution of the k(cat) value was observed with the substitution of His167 (relative k(cat), 0.02%) and Asp390 (<0.01%), strongly suggesting that His167 and Asp390 are very important for catalytic activity. The log k(cat) versus pH plots of the Ss5MaT1-catalyzed malonyl transfer suggested that a deprotonated active site group of pK(a) = 7.0 +/- 0.1 may be involved in the catalytic steps of the "substrate to product" conversion in the ternary enzyme-substrate complex. Taking these lines of evidence together with the suggested similarity of the kinetic and catalytic mechanisms of Ss5MaT1 to those of CAT and HAT, the following Ss5MaT1 mechanism based on general acid/base catalysis was proposed: in the ternary complex, a general base deprotonates the 6' "-hydroxyl group of the anthocyanin substrate, thereby promoting a nucleophilic attack on the carbonyl of the thioester of malonyl-CoA; His167 and Asp390 appear to be involved in the general acid/base mechanism of Ss5MaT1.

Acyltransferases↗
PubMed2002

Antioxidant activity of chemical components from sage (Salvia officinalis L.) and thyme (Thymus vulgaris L.) measured by the oil stability index method.

A new abietane diterpenoid, 12-O-methyl carnosol (2), was isolated from the leaves of sage (Salvia officinalis L.), together with 11 abietane diterpenoids, 3 apianane terpenoids, 1 anthraquinone, and 8 flavonoids. Antioxidant activity of these compounds along with 4 flavonoids isolated from thyme (Thymus vulgaris L.) was evaluated by the oil stability index method using a model substrate oil including methyl linoleate in silicone oil at 90 degrees C. Carnosol, rosmanol, epirosmanol, isorosmanol, galdosol, and carnosic acid exhibited remarkably strong activity, which was comparable to that of alpha-tocopherol. The activity of miltirone, atuntzensin A, luteolin, 7-O-methyl luteolin, and eupafolin was comparable to that of butylated hydroxytoluene. The activity of these compounds was mainly due to the presence of ortho-dihydroxy groups. The 1,1-diphenyl-2-picrylhydrazyl radical scavenging activity of these compounds showed the similar result.

Anthraquinones↗
PubMed2002

Composition and antifungal activity on soil-borne pathogens of the essential oil of Salvia sclarea from Greece.

The hydrodistilled essential oils of the aerial parts of wild-growing Salvia sclarea originated from two localities in Greece were analyzed by GC-MS. Sixty-six compounds, representing 93.26-98.19% of the oils, were identified. Linalyl acetate (19.75-31.05%), linalool (18.46-30.43%), geranyl acetate (4.45-12.1%), and alpha-terpineol (5.08-7.56%) were the main components. The antifungal activity of the oil of one locality and of the main components, linalyl acetate and linalool, was evaluated in vitro against three soil-borne pathogens.

Acetates↗
PubMed2003

Essential oils produced by in vitro shoots of sage (Salvia officinalis L.).

In vitro shoots of sage (Salvia officinalis L.) were established under eight different hormonal supplementations and proliferated by subculture of nodal shoot segments. The respective essential oils, obtained by hydrodistillation, were composed of more than 75 compounds, 65 of which were identified. The 10 major compounds were, by order of retention time, alpha-pinene (4.1-5.4%), camphene (6-7.1%), beta-pinene (9.3-14.5%), limonene (2-2.3%), 1,8-cineole (3.6-5.6%), (-)-thujone (13.2-16.1%), (+)-isothujone (6.6-7.4%), camphor (19.8-24%), alpha-humulene (5.1-6.8%), and manool (4.2-7.7%). Notwithstanding the eight different hormonal supplementations tested, the percentage composition of the shoot essential oils were kept in a narrow range of variation. However, the type and concentration of growth regulators apparently influenced the accumulation of essential oils. The highest accumulation of essential oils and the highest shoot biomass growth were obtained with 2.0 mg/L kinetin and 0.05 mg/L 2,4-dichlorophenoxyacetic acid.

Bicyclic Monoterpenes↗
PubMed2003

Volatile metabolites from Salvia fruticosa as antifungal agents in soilborne pathogens.

The volatile metabolites of Salvia fruticosa plants, growing wild in 15 localities scattered across Greece, were analyzed by means of GC and GC-MS. The essential oil content ranged from 0.69 to 4.68%, and the results of the analyses showed a noticeable variation in the amounts of the five main components [1,8-cineole, alpha-thujone, beta-thujone, camphor, and (E)-caryophyllene]. The antifungal activities of the essential oils from two localities, belonging in two different groups of cluster and principal component analysis, and their main components (1,8-cineole and camphor) were evaluated in vitro against five phytopathogenic fungi. Both oils were slightly effective against Fusarium oxysporum f. sp. dianthi and Fusarium proliferatum, whereas against Rhizoctonia solani, Sclerotinia sclerotiorum, and Fusarium solani f. sp. cucurbitae the oils exhibited high antifungal activities.

Bicyclic Monoterpenes↗
PubMed2005

Diterpenes from Salvia broussonetii transformed roots and their insecticidal activity.

The new diterpenes brussonol (1) and iguestol (6alpha,11-dihydroxy-12-methoxy-abieta-8,11,13-triene) (2) with an icetexane and a dehydroabietane skeleton, respectively, have been isolated from hairy root cultures of Salvia broussonetii. Other previously known diterpenes, 7-oxodehydroabietane, 11-hydroxy-12-methoxyabietatriene, taxodione, inuroyleanol, ferruginol, deoxocarnosol 12-methyl ether, cryptojaponol, pisiferal, sugiol, isomanool, 14-deoxycoleon U, 6alpha-hydroxydemethylcryptojaponol, demethylsalvicanol, and demethylcryptojaponol, were also obtained from these roots. The insect antifeedant and toxic effects of several of these compounds were investigated against the insect pests Spodoptera littoralis and Leptinotarsa decemlineata. Additionally, their comparative cytotoxic effects were tested on insect Sf9 and mammalian CHO cells. Demethylsalvicanol (4) was a moderate antifeedant to L. decemlineata, whereas brussonol (1) was inactive. 14-Deoxycoleon U (15) was the strongest antifeedant, whereas demethylcryptojaponol (11) was toxic to this insect. None of these compounds had antifeedant or negative effects on S. littoralis ingestion or weight gains after oral administration. Demethylcryptojaponol (11) was cytotoxic to mammalian CHO and insect Sf9 cell lines, followed by the icetexane derivative brussonol (1), with moderate cytotoxicity in both cases. The remainder of the test compounds showed a strong selective cytotoxicty to insect Sf9 cells, with demethylsalvicanol (4) being the most active.

Animals↗
PubMed2002

Bioactive abietane and seco-abietane diterpenoids from Salvia prionitis.

From the roots of Salvia prionitis a new tricyclic diterpene, saprirearine (1), a new anhydride-type compound, saprionide (2), a new 7,8-seco-abietane diterpene derivative, 7,8-seco-para-ferruginone (3), and two new 4,5-seco-5,10-friedo-abietane diterpenoids, 4-hydroxysaprorthoquinone (4) and 3-keto-4-hydroxysaprorthoquinone (5), were isolated. Their structures were established by spectroscopic methods and chemical transformation. Compound 3 showed antimicrobial activities against two Gram-positive organisms, Staphylococcus aureus and Micrococcus luteus, with MIC values of 20.0 and 15.0 microM, respectively. Compound 4 showed significant inhibition against topoisomerase Iota with an IC50 value of 0.8 microM. Compound 5 exhibited cytotoxic activities against HL-60 human leukemia and the SGC-7901 and MKN-28 stomach cancer cell lines, with IC50 values of 4.6, 0.2, and 0.3 microM, respectively.

Anti-Bacterial Agents↗
PubMed2002

Semisynthesis of rosmanol and its derivatives. Easy access to abietatriene diterpenes isolated from the genus Salvia with biological activities.

The known diterpenes rosmanol (3), rosmaquinone (4), 7-methoxyrosmanol (5), 7-ethoxyrosmanol (6), galdosol (7), and epirosmanol (8) have been obtained by partial synthesis from carnosol (2), an abundant natural product present in Salvia species. The physical and spectroscopic data of these semisynthetic diterpenes were identical to those of authentic natural samples and with data reported in the literature. These abietane diterpenes have very interesting biological activities and are present in the genus Salviain low quantities; thus, the semisynthetic approach described here represents an efficient alternative method to obtain these compounds. Additionally, the known diterpene 16-hydroxyrosmanol (10) and a new aromatic diterpene 11 were obtained from 16-hydroxycarnosol (9) by reaction with Ph3P/NBS in CH2Cl2. The structure of the new compound 11 was established from its spectroscopic data as 12,16-epoxycarnosol.

Abietanes↗
PubMed2002

A new 24-nor-oleanane triterpenoid from Salvia carduacea.

A new triterpenoid (1) has been isolated from the acetone extract of the leaves of Salvia carduacea, together with other compounds described previously. The structure of 1 [2alpha,3alpha-dihydroxy-24-nor-4(23),12-oleanadien-28-oic acid] was elucidated by spectroscopic methods, particularly by extensive 1D and 2D NMR studies.

Molecular Structure↗
PubMed2003

Salvinorins D-F, new neoclerodane diterpenoids from Salvia divinorum, and an improved method for the isolation of salvinorin A.

Three new neoclerodane diterpenoids, salvinorins D-F (4-6), have been isolated from the leaves of Salvia divinorum. The structures were elucidated by chemical and spectroscopic methods, particularly 1D and 2D NMR. A simplified isolation method using chromatography on activated carbon also gave improved yields of the controlled substance salvinorin A (1) and of salvinorin C (3).

Acetylation↗
PubMed2003

Divinatorins A-C, new neoclerodane diterpenoids from the controlled sage Salvia divinorum.

Three new neoclerodane diterpenoids, divinatorins A-C (7-9), have been isolated from the leaves of Salvia divinorum. The compounds were identified by spectroscopic methods as derivatives of the antibiotic (-)-hardwickiic acid (10), which was also isolated, along with four other known terpenoids. Neither the crude extract nor 7-9 displayed antimicrobial activity.

Anti-Infective Agents↗
PubMed2004

Highly hydroxylated triterpenes from Salvia kronenburgii.

The three new triterpenes (1-3) and five known triterpenes and a sterol were isolated from the acetone extract of a Turkish collection of Salvia kronenburgii. The structures of the new triterpenes were established as 1beta,2alpha-dihydroxy-3beta-acetoxy-11-oxours-12-ene (1), 2alpha,20beta-dihydroxy-3beta-acetoxyurs-9(11),12-diene (2), and 1beta,2alpha-dihydroxy-3beta-acetoxyurs-9(11),12-diene (3) on the basis of spectral analyses, including 1D and 2D NMR and mass spectroscopy. It is probable that compounds 2 and 3 are artifacts from dehydration of the corresponding allylic alcohols. 1beta,2alpha,3beta,11alpha-Tetrahydroxyurs-12-ene (5), the most abundant compound in the extract, was found to be highly cytotoxic to renal, non-small cell lung, and breast cancer cell lines.

Antineoplastic Agents, Phytogenic↗