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PubMed2005

Unsaturated diterpenoids with a novel carbocyclic skeleton from Salvia xalapensis.

Two diterpenoids with an unprecedented carbocyclic skeleton, salvixalapadiene (3) and isosalvixalapadiene (4), have been obtained from the leaves of Salvia xalapensis. The rearranged skeleton of these products may be derived biogenetically from a salvigenane precursor. In addition, two new rearranged diterpenoids (1 and 2) belonging to already known skeletons were isolated. The structures of the new compounds (1-4) were elucidated on the basis of spectroscopic data interpretation.

Diterpenes↗
PubMed2005

Nitrogen-containing compounds from Salvia miltiorrhiza.

Five new N-containing compounds, neosalvianen (1), salvianen (2), salvianan (3), salviadione (4), and 5-(methoxymethyl)-1H-pyrrole-2-carbaldehyde (5), were isolated from Salvia miltiorrhiza. Their structures were mainly established by spectroscopic methods. Neosalvianen (1) and its analogues (6a, 6b) were synthesized for spectroscopic data comparison. Compounds 1, 2, 4, and 6a were evaluated for their cytotoxic activities against selected cancer cell lines. Among these components, salvianen (2) exhibited the most potent cytotoxicity with a CD50 range of 30.4-39.5 microM against HeLa (cervical epitheloid carcinoma), HepG2 (hepatocellular carcinoma), and OVCAR-3 (ovarian adenocarcinoma) cell lines in a dose-dependent manner. The cytotoxicities of the tested compounds were not specific and showed similar activities to the selected cancer cell lines.

Antineoplastic Agents, Phytogenic↗
PubMed2006

Abietane diterpene alkaloids from Salvia yunnanensis.

Nine new abietane diterpene alkaloids containing an oxazole ring, salviamines A-F (1-6) and isosalviamines C-E (7-9), together with 17 known abietane diterpenes, were isolated and characterized from the roots of Salvia yunnanensis. The structures of 1-9 were elucidated by interpretation of their spectroscopic data.

Abietanes↗
PubMed2006

Synthetic studies of neoclerodane diterpenes from Salvia divinorum: semisynthesis of salvinicins A and B and other chemical transformations of salvinorin A.

Salvinorin A (1) is a hallucinogenic neoclerodane diterpene isolated from the widely available psychoactive plant Salvia divinorum and is the first example of a non-nitrogenous opioid receptor ligand. At present, there is little information available as to why this compound is selective for kappa opioid receptors. One approach to better understanding the mode of binding of 1 at kappa receptors is to systematically alter the structure of 1 and examine the effects on opioid receptor affinity and activity. Currently, there is a paucity of methods described for the preparation of analogues derived from 1. Here, we report the investigation of several chemical transformations of 1 isolated from S. divinorum. In particular, this work provides a semisynthesis of salvinicins A (2) and B (3) and has identified 10a as the first neoclerodane diterpene with delta opioid antagonist activity.

Diterpenes↗
PubMed2006

Abietane diterpenoids from Salvia pachyphylla and S. clevelandii with cytotoxic activity against human cancer cell lines.

A phytochemical study has been carried out on the aerial parts of Salvia pachyphylla and S. clevelandii. From S. pachyphylla, the known diterpenes carnosol (2), rosmanol, 20-deoxocarnosol (3), carnosic acid, isorosmanol (4), 7-methoxyrosmanol, 5,6-didehydro-O-methylsugiol (5), 8beta-hydroxy-9(11),13-abietadien-12-one (6), 11,12-dioxoabieta-8,13-diene, and 11,12-dihydroxy-20-norabieta-5(10),8,11,13-tetraen-1-one were isolated, together with the new diterpene pachyphyllone (1). From S. clevelandii, the known diterpenes rosmadial (7), 16-hydroxycarnosol (8), abieta-8,11,13-triene, and taxodone were obtained, together with carnosol (2), rosmanol, and carnosic acid. The structure of the new compound (1) was identified on the basis of spectroscopic data analysis. Several of these compounds (1-8) were evaluated against a small panel of human cancer cell lines.

Abietanes↗
PubMed2006

Neo-clerodane diterpenes from the hallucinogenic sage Salvia divinorum.

Seven new neo-clerodane diterpenes, salvidivins A (2), B, (3), C (4), and D (5), salvinorins H (6) and I (7), and divinatorin [corrected] F (8), along with eight known neo-clerodane diterpenes, salvinorins A (1)-F, divinatorins A and B, and seven other constituents, were isolated from the hallucinogenic sage Salvia divinorum. The structures of 1-7 were elucidated on the basis of 2D NMR spectroscopic studies.

Diterpenes, Clerodane↗
PubMed2006

Clerodane diterpenoids from Salvia splendens.

Four new clerodane diterpenoids, salvisplendins A-D (1-4), have been isolated from an acetone extract of the flowers of Salvia splendens, together with an artifact (5), arising from salvisplendin D (4) by addition of diazomethane, and the already known clerodane olearin (6). The structures of the new compounds (1-5) were established mainly by 1D and 2D NMR spectroscopic studies and, in the case of salvisplendin A (1), by chemical correlation with splenolide B (7). Complete 1H and 13C NMR assignments for olearin (6), not published hitherto, are also reported.

Diterpenes, Clerodane↗
PubMed2001

Salvinorin C, a new neoclerodane diterpene from a bioactive fraction of the hallucinogenic Mexican mint Salvia divinorum.

Salvinorin C (1), a minor component from a biologically active TLC fraction, was isolated from the leaves of the Mexican mint Salvia divinorum. Its structure was elucidated on the basis of extensive proton and C-13 NMR experiments, as well as by comparison of the NMR data with those of the mono- and diacetate derivatives 5-7 of the major NaBH(4)-reduction product of salvinorin A (2). [structure: see text]

Diterpenes↗
PubMed2005

Salvinicins A and B, new neoclerodane diterpenes from Salvia divinorum.

[reaction: see text] Two new neoclerodane diterpenes, salvinicins A (4) and B (5), were isolated from the dried leaves of Salvia divinorum. The structures of these compounds were elucidated by spectroscopic techniques, including (1)H and (13)C NMR, NOESY, HMQC, and HMBC. The absolute stereochemistry of these compounds was assigned on the basis of single-crystal X-ray crystallographic analysis of salvinicin A (4) and a 3,4-dichlorobenzoate derivative of salvinorin B.

Crystallography, X-Ray↗
PubMed2006

Przewalskin A: A new C23 terpenoid with a 6/6/7 carbon ring skeleton from Salvia przewalskii maxim.

Przewalskin A (1), a novel C23 terpenoid with a 6/6/7 carbon ring skeleton, was isolated from Salvia przewalskii. Its structure was determined by comprehensive 1D NMR, 2D NMR, and MS spectroscopic analysis and subsequently confirmed by a single-crystal X-ray diffraction study of its PDC oxidation derivative (2). Compounds 1 and 2 showed modest anti-HIV-1 activity with EC50 = 41 and 89 microg/mL, respectively.

Carbon↗
PubMed2007

Przewalskin B, a novel diterpenoid with an unprecedented skeleton from Salvia przewalskii maxim.

Przewalskin B (1), a novel diterpenoid possessing a unique skeleton, was isolated from a Chinese medicinal plant Salvia przewalskii. Its structure and relative stereochemistry were elucidated by extensive NMR analysis and a single-crystal X-ray study. A possible biosynthetic pathway for 1 was proposed. Compound 1 exhibited modest anti-HIV-1 activity with EC50 = 30 microg/mL. [structure: see text].

Anti-HIV Agents↗
PubMed2004

Salviae miltiorrhizae radix inhibits superoxide generation by activated rat microglias and mimics the action of amphetamine on in vitro rat striatal dopamine release.

Salviae miltiorrhizae Radix (SMR), an eminent herb in the treatment of cardiovascular disorder (called blood stasis in traditional Chinese medicine), is widely used in China, Japan, Taiwan and Korea. SMR is also herbal medicines used in the treatment of drug addiction without scientific support for their mechanism of action. We evaluated the effect of SMR on superoxide production by rat microglias using a 2-methyl-6-(p-methoxyphenyl)-3,7-dihydroimidazo[1,2-a]pyrazin-3-one-dependent chemiluminescence assay. SMR dose-dependently inhibited superoxide production by microglias stimulated with phorbol myristate acetate or opsonized zymosan, while it had no effect on superoxide production by a hypoxanthinexanthine oxidase system. These results indicate that SMR does not have a scavenging effect, but has an inhibitory effect on superoxide generation by microglias. Although SMR is commonly used for treating chronic cerebral infarction, it may also have a protective effect on progression of Parkinson's disease or Alzheimer's disease. On the other hand, the present study investigated the effect of the medicinal plant on dopaminergic neurotransmission in comparison with amphetamine. The effect of crude water extracts (0.1 g/ml) of SMR on K+ (20 mM)-stimulated dopamine release from rat striatal slices was compared with amphetamine (10(-4) M) using high-performance liquid chromatography with electrochemical detection to measure endogenous dopamine. Amphetamine and SMR significantly increased K+-stimulated dopamine release (P<0.001) from rat striatal slices when compared with K+-stimulated alone. SMR potentiated the effect of amphetamine on K+-stimulated dopamine release (P<0.001) when compared with amphetamine alone. The results indicate that SMR may stimulate dopamine release in the same manner as amphetamine. It remains to be determined whether the effect of this extract on dopamine function is important in its therapeutic use in the treatment of drug addiction.

Amphetamine↗
PubMed2006

Effects of cholinesterase inhibiting sage (Salvia officinalis) on mood, anxiety and performance on a psychological stressor battery.

Salvia officinalis (sage) has previously been shown both to possess in vitro cholinesterase inhibiting properties, and to enhance mnemonic performance and improve mood in healthy young participants. In this double-blind, placebo-controlled, crossover study, 30 healthy participants attended the laboratory on three separate days, 7 days apart, receiving a different treatment in counterbalanced order on each occasion (placebo, 300, 600 mg dried sage leaf). On each day mood was assessed predose and at 1 and 4 h postdose. Each mood assessment comprised completion of Bond-Lader mood scales and the State Trait Anxiety Inventory (STAI) before and after 20 min performance of the Defined Intensity Stress Simulator (DISS) computerized multitasking battery. In a concomitant investigation, an extract of the sage leaf exhibited dose-dependent, in vitro inhibition of acetylcholinesterase and, to a greater extent, butyrylcholinesterase. Both doses of sage led to improved ratings of mood in the absence of the stressor (that is, in pre-DISS mood scores) postdose, with the lower dose reducing anxiety and the higher dose increasing 'alertness', 'calmness' and 'contentedness' on the Bond-Lader mood scales. The reduced anxiety effect following the lower dose was, however, abolished by performing the DISS, with the same dose also being associated with a reduction of alertness during performance. Task performance on the DISS battery was improved for the higher dose at both postdose sessions, but reduced for the lower dose at the later testing session. The results confirm previous observations of the cholinesterase inhibiting properties of S. officinalis, and improved mood and cognitive performance following the administration of single doses to healthy young participants.

Adult↗
PubMed2007

Enhancement of tanshinone production in Salvia miltiorrhiza Bunge (red or Chinese sage) hairy-root culture by hyperosmotic stress and yeast elicitor.

The present study evaluates the use of hyperosmotic stress and a biotic elicitor YE (yeast elicitor; polysaccharide fraction of yeast extract) to stimulate diterpenoid tanshinone production in hairy-root culture of Salvia miltiorrhiza Bunge (Lamiaceae). Sorbitol was applied as an osmoticum at various concentrations (30-100 g/l) to the hairy-root culture in MS (Murashige and Skoog) medium [Murashige and Skoog (1962) Physiol. Plant. 15, 473-497] containing 30 g/l sucrose, and it increased the TT (total tanshinone) content of roots most dramatically at 50-70 g/l (medium osmolality 410-500 mmol/kg; 1 mol/kg approximately 1 osmol/kg), to 4.5-fold of that in the control. The hairy roots showed strong tolerance to hyperosmotic stress, retaining a stable or higher dry weight of roots at osmolality up to 500 mmol/kg. Most remarkably, the combined use of sorbitol (50 g/l) and YE (100 mg/l) increased the TT content 10-fold (1481.6 versus 146.4 microg/g dry root) and the volumetric tanshinone yield 9-fold (16.3 versus 1.77 mg/l) compared with the control. The results suggest that the combined use of hyperosmotic stress and a biotic elicitor can effectively enhance secondary metabolite production in hairy-root cultures.

Abietanes↗
PubMed2001

Cardioactive diterpenoids from the roots of Salvia amplexicaulis.

Five diterpenoids, three steroids, four triterpenoids and one flavonoid were isolated from the roots of Salvia amplexicaulis Lam. (Lamiaceae). Structures of these compounds were elucidated by spectroscopic analysis. The crude extract and the pure compounds were tested for cardiovascular parameters using Wistar Albino rats. The crude extract, and 7-oxo-abieta-9,12,14-triene, ferruginol, stigmast-4-en-3-one showed a vasodepressor effect.

Animals↗
PubMed2002

Cardioactive diterpenes from the roots of Salvia eriophora.

From the roots of Salvia eriophora (Lamiaceae), a new compound, 4,14-dihydroxysaprorthoquinone, was isolated in addition to ten known diterpenoids. The structure of the new compound was established by spectroscopic analysis. The crude extract of the plant and the isolated diterpenoids were tested for their cardiovascular activities using Wistar Albino rats. Activity was demonstrated in the crude extract and in 4,14-dihydroxysaprorthoquinone, aethiopinone, ferruginol, 4,12-dihydroxysapriparaquinone, and 6,7-dehydroroyleanone.

Abietanes↗
PubMed2003

Crude extract of Salvia miltiorrhiza and salvianolic acid B enhance in vitro angiogenesis in murine SVR endothelial cell line.

Salvia miltiorrhiza (SM) has been used clinically in Asian countries to improve the microcirculation in the human body. Although a pure compound extracted from SM, salvianolic acid B (Sal B), has been reported to be effective against fibrosis and ischemia-reperfusion injury, possibly through its anti-lipid peroxidation action, the effect of SM on angiogenesis remains unclear. It is our interest to investigate the role of SM on the regulation of the angiogenic process. By using the SVR endothelial cell line as an in vitro system, the effects of Sal B on the gene expression of vascular endothelial growth factor (VEGF) and its receptors VEGF-R1, VEGF-R2 were evaluated by morphology, differentiation assay, reverse-transcribed polymerase chain reaction (RT-PCR) and Western blot analysis. The results showed that both the crude extract of SM and the pure compound Sal B had enhancing effects on cell growth and differentiation. The gene expression of matrix metalloproteinase-2 (MMP-2) was up-regulated after Sal B treatment for 2 h, while VEGF and VEGF-R2 gene expression were up-regulated 40 min after Sal B treatment. We conclude that the crude extract of SM and Sal B enhance angiogenic processes on SVR cells through up-regulation of VEGF and VEGF receptors genes.

Animals↗