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At least 289 records · Page 16Linked to original sources
PubMed2003

Constituents of sage (Salvia officinalis) with in vitro affinity to human brain benzodiazepine receptor.

Benzodiazepine receptor binding assay-guided fractionation of the methanol extract from sage leaves ( Salvia officinalis L.) revealed three flavones and two abietane diterpenes functioning as benzodiazepine receptor-active components. Structural elucidation of the isolated pure compounds was performed by UV, EI-MS, ESI(pos)-MS/MS, as well as 1H- and 13C-NMR techniques. The flavones apigenin, hispidulin and cirsimaritin competitively inhibited 3H-flumazenil binding to the benzodiazepine receptor with IC50 values of 30, 1.3 and 350 microM, respectively. In addition, the affinities of the newly discovered diterpene receptor ligands, i. e., 7-methoxyrosmanol and galdosol, were characterized. 7-Methoxyrosmanol exhibited an IC50 value of 7.2 microM and galdosol showed the strongest binding activity to the benzodiazepine receptor with an IC50 value of 0.8 microM.

Cerebral Cortex↗
PubMed2003

New diterpenoids from the aerial parts of Salvia candelabrum.

The new diterpenoids, candesalvoquinone, 12- O-methylcandesalvone B, candesalvone B methyl ester with the 3,4-secoabietane skeleton, and candelabroquinone with the abietane skeleton were isolated from the aerial parts of Salvia candelabrum, together with the known compound candelabrone. The structures were established by mass spectroscopy and advanced two-dimensional NMR methods, including 1H-NMR, JMOD, 1H- 1H COSY, HSQC, HMBC and NOESY experiments.

Diterpenes↗
PubMed2003

Studies on di- and triterpenoids from Salvia staminea with cytotoxic activity.

A new ursane-type triterpenoid, 3 beta,11 alpha,21 alpha-trihydroxyurs-12-ene, named salvistamineol (1), has been isolated from the methanol extract of Salvia staminea. In addition to 1, the methanol extract yielded four known compounds and the acetone extract yielded twelve known compounds consisting of two sesquiterpenes, six diterpenoids, a triterpenoid, two steroids and one flavone. DNA damaging properties of the extracts and some isolated diterpenes were investigated against three yeasts and only taxodione gave a positive response and also showed the highest cytotoxic activity against a panel of cell lines among the investigated compounds in this study.

Antineoplastic Agents↗
PubMed2003

Germacrane sesquiterpene esters from Salvia roborowskii.

From the whole plant of Salvia roborowskii, four new germacrane sesquiterpene esters, 3beta,6beta,8alpha-triacetoxy-4beta,5alpha-epoxy-1-oxogermacr-10(14)-ene, 3beta,6beta,8alpha-triacetoxy-4beta,5alpha-epoxygermacr-1 (10) E-ene, 3beta,6beta,8alpha-triacetoxy-4beta,5alpha:1alpha,10beta-diepoxygermacrane and 6beta-acetoxyglechomafuran were isolated, and their structures were elucidated by spectroscopic methods including 2D NMR techniques (1H-1H COSY and 1H-1H NOESY for 1).

Esters↗
PubMed2003

Tanshinone IIA from Salvia miltiorrhiza inhibits inducible nitric oxide synthase expression and production of TNF-alpha, IL-1beta and IL-6 in activated RAW 264.7 cells.

The inhibitory effects of tanshinone IIA, a diterpene isolated from Salvia miltiorrhiza root, on the production of nitric oxide (NO), interleukin-1beta (IL-1beta), interleukin-6 (IL-6) and tumor necrosis factor-alpha (TNF-alpha), and the expression of inducible nitric oxide synthase (iNOS) were investigated in activated RAW 264.7 cells. This compound markedly inhibited the production of NO, IL-1beta and TNF-alpha, and suppressed the expression of iNOS in a dose-dependent manner. These results suggest that the traditional use of S. miltiorrhiza as an anti-inflammatory herbal medicine may be explained, in part, by the inhibition of NO, IL-1beta, IL-6 and TNF-alpha production, and expression of iNOS.

Abietanes↗
PubMed2003

Diterpenes from the aerial parts of Salvia candelabrum and their protective effects against lipid peroxidation.

A methanolic extract of the aerial parts of Salvia candelabrum was subjected to multiple chromatographic separation under the guidance of anti-lipid peroxidation assay. From the most active fractions seven abietane and seco-abietane diterpenes were isolated by preparative TLC purification. Besides candesalvoquinone, candelabroquinone, 12- O-methylcandesalvone B, candesalvone B methyl ester and candelabrone (all reported earlier), the known candesalvone B and the new candesalvolactone were identified. The structures were established by means of mass spectroscopy and advanced 2D NMR methods. All the identified compounds were evaluated for antioxidant activity in enzyme-dependent (IC (50) values 3.49 - 10.42 microM) and enzyme-independent (IC (50) values 1.40 - 13.40 microM) systems of lipid peroxidation. All compounds displayed marked concentration-dependent effects in both tests as compared with those of authentic ascorbic, rosmarinic and caffeic acids. The differences in antioxidant capacities observed in the enzyme-independent system allowed conclusions concerning structure-activity relationships.

Antioxidants↗
PubMed2004

Extremely low bioavailability of magnesium lithospermate B, an active component from Salvia miltiorrhiza, in rat.

We assessed the bioavailability of magnesium lithospermate B (MLB), a main polyphenolic component of Salvia miltiorrhiza and a potent antioxidant having various pharmacological activities, to evaluate its action in vivo. The plasma concentrations of lithospermic acid B (LSB) showed a biexponential decrease after intravenous administration of MLB to rats at doses of 4 and 20 mg/kg. The values of area under the concentration-time curve (AUC; 87.8 +/- 10.9 and 1130 +/- 329 microg.min/mL), total body clearance (CL (tot); 55.52 +/- 7.07 and 23.51 +/- 5.98 mL/min/kg), and distribution volume at steady state (V (ss); 7.60 +/- 1.03 and 3.61 +/- 1.16 L/kg) suggested non-linear pharmacokinetics between the two doses. After oral administration of MLB at a high dose of 100 mg/kg, the mean AUC was barely 1.26 +/- 0.36 microg.min/mL. Absolute bioavailability of MLB was calculated to be 0.0002 from the AUC values after both intravenous dosing at 20 mg/kg and oral dosing at 100 mg/kg. The extremely low bioavailability was caused mainly by poor absorption from the rat gastrointestinal tract; about 65 % of the dose was retained in the tract even 4 h after oral administration, and most of the dose was retained even 20 min after infusion in an in situ jejunal loop experiment. Urinary and biliary excretion of LSB were only 0.70 % +/- 0.26 % and 5.10 % +/- 2.36 %, respectively, over a 30 h time period after intravenous injection despite the large CL (tot) and V (ss) values, and were much less (0.010 % +/- 0.001 % and 0.12 % +/- 0.04 %) after oral dosing. These findings suggest that extensive metabolism, including a first-pass effect, and wide distribution of LSB besides the poor absorption contributed significantly to the extremely low systemic bioavailability.

Administration, Oral↗
PubMed2004

Enhancement of tanshinone production in Salvia miltiorrhiza hairy root culture by Ag+ elicitation and nutrient feeding.

Ag (+) was employed as an abiotic elicitor to stimulate the secondary metabolite production in hairy root culture of Salvia miltiorrhiza, a valuable herbal plant. The addition of Ag (2)S (2)O (3) at 15 - 40 microM to the culture between 12 and 22 days post inoculation resulted in more than 2-fold increase in the yields of the three diterpenoid tanshinones, tanshinone I, tanshinone IIA and cryptotanshinone. This stimulating effect was dependent on the Ag (+) dose, the day of Ag (+) addition to the culture and the tanshinone species, while the total yield of the three tanshinones (TT) was mainly dependent on the Ag (+) dose, with the highest being attained at 30 microM. The Ag (+) treatment also caused a dose-dependent inhibition of hairy root growth. Sucrose feeding or medium renewal before the addition of Ag (+) to the culture effectively prevented the growth inhibition, and significantly increased the biomass concentration and volumetric tanshinone yield. With combined medium renewal and Ag (+) treatment, in particular, the TT yield was increased 6.6-fold relative to that of the control (55.7 mg/L versus 7.3 mg/L). The elicitor function of Ag (+) in the hairy root culture was validated by its ability to induce the characteristic elicitor responses of plants, the increase in cross-cell membrane ion fluxes and the production of reactive oxygen species.

Abietanes↗
PubMed2004

A secoisopimarane diterpenoid from Salvia cinnabarina inhibits rat urinary bladder contractility in vitro.

We have evaluated the effect of 3,4-secoisopimar-4(18),7,15-triene-3-oic acid (compound 1), isolated from the aerial parts of Salvia cinnabarina, on the contractile response elicited by electrical field stimulation (EFS) in the rat isolated urinary bladder. Compound 1 (10 ( - 7) - 10 ( - 4) M) produced a concentration-dependent inhibition of the EFS contractile response without modifying the contractions produced by exogenous acetylcholine (10 ( - 6) M). A number of antagonists/inhibitors including a combination of atropine (10 ( - 6) M), phentolamine (10 ( - 6) M), propranolol (10 ( - 6) M) and hexamethonium (10 ( - 4) M), the NK (1) receptor antagonist SR140333 (10 ( - 7) M) plus the NK (2) receptor antagonist SR48968 (10 ( - 6) M), naloxone (10 ( - 6) M), verapamil (10 ( - 7) M), capsazepine (10 ( - 5) M) and the CB (1) receptor antagonist SR141716A (10 ( - 6) M) did not modify the inhibitory effect of compound 1. However, the nitric oxide (NO) synthase inhibitor L-NAME (3 x 10 ( - 4) M), significantly reduced the inhibitory effect of compound 1. It is concluded that compound 1 inhibits rat bladder contractility with a mechanism involving, at least in part, NO production.

Acetylcholine↗
PubMed2004

Novel diterpenoid acetylcholinesterase inhibitors from Salvia miltiorhiza.

Acetylcholinesterase (AChE, EC 3.1.1.7) inhibitors are the only registered drugs used to treat Alzheimer's disease (AD). New AChE inhibitors may contribute to the design of new pharmaceuticals and supply information which will facilitate the understanding of the interaction between inhibitors and the enzyme. The dried root of Salvia miltiorhiza is called 'Danshen' in China, and has been used for the treatment of cerebrovascular disease and CNS deterioration in old age for over one thousand years. In this work, a modified Ellman method was used to guide the fractionation of the active AChE inhibitory compounds from an acetone extract. Four inhibitory compounds, dihydrotanshinone, cryptotanshinone, tanshinone I and tanshinone IIA were isolated, and the structures were identified by comparison of their spectral characteristics with previous reports. The inhibitory activities of dihydrotanshinone and cryptotanshinone were dose-dependent, their IC (50) values being 1.0 microM and 7.0 microM, respectively. These two compounds were the major inhibitory compounds in the extract as judged by HPLC analysis, forming 0.054 % w/w and 0.23 % w/w in the dried root, respectively, and in mixture they appear to be less active than as isolated compounds. The clogP values of dihydrotanshinone, cryptotanshinone, tanshinone I and tanshinone IIA were calculated as 2.4, 3.4, 4.8 and 5.8, respectively, which indicate that these compounds have potential to penetrate the blood-brain barrier. This is the first example of diterpenoids as inhibitors of AChE.

Acetylcholinesterase↗
PubMed2004

A diterpenoid from Salvia cinnabarina inhibits mouse intestinal motility in vivo.

This study was aimed to investigate the effect of 3,4 secoisopimara-4(18),7,15-trien-3-oic acid (compound 1) isolated from the aerial parts of Salvia cinnabarina, on upper gastrointestinal transit in mice in vivo. Compound 1 (10 - 100 mg/kg, i. p.) dose-dependently delayed gastrointestinal motility. Pretreatment ( i. p.) of mice with hexamethonium (10 mg/kg), naloxone (2 mg/kg), N(G)-nitro- L-arginine-methyl ester ( L-NAME) (25 mg/kg) or yohimbine (1 mg/kg) did not modify the inhibitory effect of compound 1 (50 mg/kg). However, the L-type Ca (2+) channel verapamil (5 mg/kg, i. p.) significantly reduced the antimotility effect of compound 1 (50 mg/kg). These results suggest that compound 1 inhibits gastrointestinal motility in mice. The effect could involve, at least in part, L-type Ca (2+) channels.

Animals↗
PubMed2004

Diterpenoids from Salvia wagneriana.

From the surface exudate of the aerial parts of Salvia wagneriana, three new clerodane diterpenoids, the known hardwickiic acid and 1,10-didehydrosalviarin, were obtained. Two were bis-diterpenoids. Their structures were established by 1D- and 2D-NMR spectroscopic techniques.

Diterpenes↗
PubMed2004

HPLC-based activity profiling of Salvia miltiorrhiza for MAO A and iNOS inhibitory activities.

In the course of a screening of plant extracts for potential CNS and anti-inflammatory activities, a dichloromethane extract of Salvia miltiorrhiza showed a pronounced inhibitory effect on recombinant monoamine oxidase A (MAO A) and on inducible NO synthase (iNOS) induction in Raw 267.4 cells. With the aid of HPLC-based profiling techniques, activities could be linked, to a significant extent, to peaks of tanshinone-type diterpenoids, four of which were subsequently isolated. The IC50 of the most active compound, 15,16-dihydrotanshinone I, on human recombinant MAO A was at 23 microM, and 2.4 microM on lipopolysaccharide-mediated iNOS induction in Raw 267.4 cells.

Animals↗
PubMed2005

Novel cytotoxic seco-abietane rearranged diterpenoids from Salvia prionitis.

Six novel 4,5-seco-rearranged abietane diterpenoids, including one tetracyclic diterpenoid, prionoid A (1), two tricyclic diterpenoids, prionoids B (2) and C (3), and three dicyclic diterpenoids, prionoids D (4), E (5), and F (6), were isolated from the roots of Salvia prionitis Hance (Labiatae). Their structures were elucidated using spectroscopic analysis. The structure of 1 was further confirmed by a single-crystal X-ray diffraction determination. Moreover, it was found that 4 (IC50 = 0.41 microM) and 5 (IC50 = 0.72 microM) showed significant cytotoxic activity against P-388 and A-549 cell lines, respectively.

Abietanes↗
PubMed2006

Two new abietane diterpenoids from Salvia yunnanensis.

Two new abietane diterpenoids, yunnannin A and danshenol C, were isolated from Salvia yunnanensis together with ten known diterpenoids, danshenol A, przewalskin, tanshinone IIA, tanshinone I, crypotanshinone, 1,2-dihydrotanshinone, tanshinlactone, 5,6-dehydrosugiol, 12-hydroxy-6,7-seco-8,11,3-abietatriene-6,7-dial and phytol. Their structures were established based on spectroscopic data, chemical reactions and comparison with literature data. Compounds were tested for their antitumor activity in T-24, QGY, K562, Me180 and BIU87 cell lines. Compound showed inhibited growth of K562 (IC50=0.53 microg/mL), T-24 (IC50=7.94 microg/mL), QGY (IC50=4.65 microg/mL) and Me180 (IC50=6.89 microg/mL) cell lines while compound was inactive. Compound showed moderate inhibitory activity on QGY (IC50=16.75 microg/mL) and Me180 (IC50=5.84 microg/mL) cells.

Abietanes↗
PubMed2006

New polyhydroxylated triterpenes and anti-inflammatory activity of Salvia hierosolymitana.

Salvia hierosolymitana (Lamiaceae) leaves were investigated for their topical anti-inflammatory properties following a bioassay-guided fractionation. The chloroform extract showed a strong inhibition of the Croton oil-induced ear oedema in mice, comparable to that of indomethacin. Phytochemical and pharmacological investigations of this extract led to the isolation of eight anti-inflammatory polyhydroxylated triterpenes of the ursane and oleanane series. Four of them are new compounds, whose structures were elucidated by NMR and mass spectroscopy as 3beta, 6alpha,23-trihydroxyurs-12,19(29)-dien-28-oic acid, 23-( TRANS-P-coumaroyloxy)-3beta, 6alpha,30-trihydroxyurs-12-en-28-oic acid, 2alpha,3beta-dihydroxyolean-28-oic acid and 24-nor-2alpha,3beta-dihydroxyolean-4(23),12-ene.

Animals↗
PubMed2001

Malonyl-CoA:anthocyanin 5-O-glucoside-6"'-O-malonyltransferase from scarlet sage (Salvia splendens) flowers. Enzyme purification, gene cloning, expression, and characterization.

The orange to blue coloration of flowers in nature is, in most cases, provided by anthocyanins, a class of plant flavonoids, many of which are modified by malonyl group(s). However, the identity of the enzyme catalyzing the malonylation reaction remains to be established. Here, we describe for the first time the purification, characterization, and cDNA cloning of an anthocyanin malonyltransferase from scarlet sage (Salvia splendens) flowers. The purified enzyme (termed Ss5MaT1) was a monomeric 50-kDa protein catalyzing the regiospecific transfer of the malonyl group from malonyl-CoA to the 6"'-hydroxyl group of the 5-glucosyl moiety of anthocyanins. Ss5MaT1 showed a k(cat) value of 7.8 s(-1) at 30 degrees C and pH 7.0 for the malonylation of bisdemalonylsalvianin (pelargonidin 3-(6"-O-caffeyl-beta-glucopyranoside)-5-beta-glucopyranoside) and K(m) values of 101 microm and 57 microm for bisdemalonylsalvianin and malonyl-CoA, respectively. p-Coumaric acid, which mimics an aromatic acyl group linked to the 3-glucosidic moiety of an anthocyanin substrate, was a competitive inhibitor with respect to the substrate. This strongly suggests that the presence of an aromatic acyl group at the 3-glucosidic moiety of anthocyanin is important for substrate recognition by the enzyme. On the basis of the partial amino acid sequences of the purified enzyme, we isolated a cDNA encoding Ss5MaT1. Ss5MaT1 consisted of 462 amino acids and shared motifs that are commonly found among members of a versatile plant acyltransferase family, which was recently shown to include numerous homologs of unknown biochemical functions. Northern blot analysis revealed that the transcripts of Ss5MaT1 were detected in petals, sepals, bracts, and red stems, in accordance with the pigment accumulation patterns. Phylogenetic analysis suggests that the aliphatic and aromatic acylations of anthocyanins are generally catalyzed by subfamily members of the plant acyltransferase family.

Acyltransferases↗
PubMed2003

Determination of phenolic antioxidant compounds produced by calli and cell suspensions of sage (Salvia officinalis L.).

Sage (Salvia officinalis L.) calli were established by culturing internodal segments, excised from aseptic seedlings, on MS basal medium gellied with agar and supplemented with 0.05 mg/L dichlorophenoxyacetic acid (2,4-D) in presence of benzyladenine (BA) or zeatin (ZEA) or kinetin (KIN), at 1.5 mg/L. Suspended cells were established by transferring one callus to 50 mL of liquid MS basal medium devoid of agar and containing the same type of hormonal supplementation used in respective calli growth. The highest growth of calli and suspensions occurred with 1.5 mg/L ZEA. However, with this cytokinin supplementation, as well as with 1.5 mg/L KIN, both in presence of 0.05 mg/L 2,4-D, suspensions differentiated small root shaped structures. Well shaped, majority single cell suspensions were formed under the effect of 0.05 mg/L 2,4-D and 0.5 mg/L KIN. Calli grown with 0.05 mg/L 2,4-D and 1.5 mg/L BA and suspended cells grown with 0.05 mg/L 2,4-D and ZEA or KIN at 1.5 mg/L, or KIN at 0.5 mg/L, were searched for phenolics production. Twelve phenolic compounds were identified in calli: gallic acid, 3-O-caffeoylquinic acid, 5-O-caffeoylquinic acid, caffeic acid, rosmarinic acid, hesperetin, epirosmanol, hispidulin, genkwanin, carnosol, carnosic acid, and methyl carnosate. With the exception for genkwanin and epirosmanol all of these phenolic compounds were also produced by the sage suspension cultures grown in the presence of 1.5 or 0.5 mg/L KIN. Genkwanin was the only phenolic absent in the suspensions grown with 1.5 ZEA. Suspended cells, grown with 0.5 mg/L KIN, and calli cultures showed the highest specific accumulation of the total phenolics, with rosmarinic acid representing 94-97%.

Antioxidants↗