Triterpenes from Campanula lactiflora

One new triterpene compound, 3β-acetoxylup-20(30)-en-29-al (1) and two known 3-acetylptiloepoxide (2) and 3β-acetoxylup-20(29)-ene (3) were isolated for the first time from the leaves of Campanula lactiflora and their structures were deduced by high field 1D and 2D 400 MHz NMR, EI-MS and (+) LC-MS/MS spectra.     

A new anti-HIV lupane acid from Gleditsia sinensis Lam.

A new lupane acid, 2β-carboxyl,3β-hydroxyl-norlupA (1)-20 (29)-en-28-oic acid (1), together with five known lupane acid derivatives (2-6), were isolated from the stings of Gleditsia sinensis Lam.. Their structures were elucidated on the basis of 1D and 2D NMR techniques. All these known compounds were isolated from this genus for the first time. The new compound 1 showed strong anti-HIV activity.     

ent-Kaurenoids from the roots of Cacalia pilgeriana

Two new ent-kaurenoids,19-acetoxyl-ent-3β,17-dihydroxykaur-15-ene (1), 19-acetoxyl-ent-3β-hydroxykaur-15-en-17-al (2), together with seven known ent-kaurenoids: ent-kaur-16-en-19-al (3), ent-kaur-16-en-19-oic acid (4), ent-kauran-16β,17-diol (5), ent-15β, 16β-epoxy-17-hydroxykauran-19-oic acid (6),19-acetyl-ent-3β-hydroxyl-kaur-16-ene (7), ent-3β,19-dihydroxykaur-16-ene (8), ent-17-hydroxykaur-15-ene (9), were isolated from Cacalia pilgeriana. Their structures were elucidated by spectroscopic methods including 2D NMR spectral analysis.     

A new gymnomitrane-type sesquiterpenoid from the liverwort Cylindrocolea recurvifolia

A novel gymnomitrane-type alcohol was identified from the liverwort Cylindrocolea recurvifolia. The structure of this new compound was confirmed by X-ray analysis. This is the first report on the chemical constituents of this genus.     

Antinociception Effect and Mechanisms of Campanula Punctata Extract in the Mouse

In the present study, the antinociceptive profiles of Campanula punctata extract were examined in ICR mice. The Campanula punctata contain a large dose of saponin. Campanula punctata extract administered orally (200 mg/kg) showed an antinociceptive effect as measured by the tail-flick and hot-plate tests. In addition, Campanula punctata extract attenuated the writhing numbers in the acetic acid-induced writhing test. Furthermore, the cumulative nociceptive response time for intrathecal (i.t.) injection of substance P (0.7 µg) was diminished by Campanula punctata extract. Intraperitoneal (i.p.) pretreatment with yohimbine (α₂-adrenergic receptor antagonist) attenuated antinociceptive effect induced by Campanula punctata extract in the writhing test. However, naloxone (opioid receptor antagonist) or methysergide (5-HT serotonergic receptor antagonist) did not affect antinociception induced by Campanula punctata extract in the writhing test. Our results suggest that Campanula punctata extract shows an antinociceptive property in various pain models. Furthermore, this antinociceptive effect of Campanula punctata extract may be mediated by α₂-adrenergic receptor, but not opioidergic and serotonergic receptors.     

红蓼果实中的一个新三萜皂苷

为了研究红蓼果实的化学成分，利用硅胶和反相柱色谱方法进行分离纯化，根据理化性质和光谱数据鉴定其化合物结构，分离并鉴定了3个化合物：28-O-β-D-glucopyranosyl-3β,7β-dihydroxy-lup-20(29)-en-28-oate (1)，5,7-二羟基色原酮(2)和柚皮素(3)。化合物1为新化合物，化合物2，3为首次从该植物中分离得到。     

Three new monoterpene glycosides from the roots of Paeonia lactiflora

Three new monoterpene glycosides, 2′-O-benzoylpaeoniflorin, albiflorin R₂, and albiflorin R₃ (1–3) were isolated from the roots of Paeonia lactiflora. Their structures were elucidated on the basis of spectroscopic means including one- and two-dimensional NMR experiments.     

C-27 and C-3 Glucosylation of Diosgenin by Cell Suspension Cultures of Costus Speciosus

3-O-[β-D-glucopyranosyl-(1' → 2')-β-D-glucopyranosyl], 27-O-β-D-glucopyranosyl-(25R)-spirost-5-ene-3β,27-diol was isolated from cell suspension cultures of Costus speciosus, following incubation with diosgenin, and its structure was elucidated using a combination of one- and two-dimensional ¹H and ¹³C NMR spectral data, and positive and negative ion ESMS spectral data.     

A New d-Lactone Containing Triterpene from the Flowers of Calendula officinalis

A new δ-lactone containing triterpene, 4β-methylcholest-20-en-12a-ol-3β-olide, was isolated from Calendula officinalis Linn. flowers in addition to three known compounds, lanast-20(22)-en-3β-ol, stigmast-5,22-dien-3β-ol, and stigmast-5,24(28)-dien-3β-ol. Their structures were elucidated by spectroscopic (UV, IR, NMR, and MS) methods and chemical reactions.     

Antifungal Activity of the Essential Oils of Nine Zingiberaceae Species

The rhizome oils of nine Zingiberaceae species [Zingiber officinale Rosc., Z. cassumunar Roxb., Z. zerumbet Smith, Curcuma aeruginosa Roxb., C. mangga Valeton and van Zyp, C. xanthorrhiza Roxb., Kaempferia galanga Linn., Alpinia galanga Swartz and Boesenbergia pandurata (Roxb.) Schlecht] were investigated for their antifungal activities against five dermatophytes (Trichophyton mentagrophytes, T. rubrum, Microsporum canis, M. nanum and Epidermophyton floccosum), three filamentous fungi (Aspergillus niger, A. fumigatus and Mucor sp.) and five strains of yeast (Saccharomyces cerevisiae, Cryptococcus neoformans, Candida albicans, Ca. tropicalis and Torulopsis glabrata). The antifungal testing was carried out by using the broth microdilution and the disc gel diffusion methods. Amongst the essential oils studied, only the oil of B. pandurata was effective against all the fungi, exhibiting the lowest MIC values of 0.63µgµl -1 to Mucor sp., 1.25µgµl -1 to both A. niger and A. fumigatus, and 2.5µgµl -1 to both T. rubrum and E. floccosum, and the highest inhibition zone diameter of 20.6mm against S. cerevisiae. The essential oil of K. galanga showed selective toxicity against A. fumigatus with a MIC value of 0.63µgµl -1, while the essential oils of Z. officinale and Z. cassumunar exhibited high activity against the yeasts (11.7-15.7mm). The chemical composition of the active essential oils was investigated by GC and GC-MS.     

A cyclic peroxide of clerodenoic acid from the Taiwanese liverwort Schistochila acuminata

Two minor diterpenoids, 15(16)-peroxy-3, 13-clerodadien-18-oic acid (4) and totarol (7), were isolated from the liverwort Schistochila acuminata. The former is a further oxidized cyclic peroxide from the major component. The latter is a rearranged abietane alcohol which skeleton was found in liverworts for the first time.     

Diglucosylation of salicyl alcohol by cell suspension cultures of Solanum laciniatum

A new biotransformation product, salicyl alcohol-7-O-β-D-(β-1,6-D-glucopyranosyl)-gluco-pyranoside was isolated from cell suspension cultures of Solanum laciniatum, following administration of salicyl alcohol, and its structure was elucidated using a combination of one-and two-dimensional ¹H and ¹³C-NMR data, and positive and negative ion ESMS data.     

Genetic Diversity in Fusarium graminearum from a Major Wheat-Producing Region of Argentina

The Fusarium graminearum species complex (FGSC) is a group of mycotoxigenic fungi that are the primary cause of Fusarium head blight (FHB) of wheat worldwide. The distribution, frequency of occurrence, and genetic diversity of FGSC species in cereal crops in South America is not well understood compared to some regions of Asia, Europe and North America. Therefore, we examined the frequency and genetic diversity of a collection of 183 FGSC isolates recovered from wheat grown during multiple growing seasons and across a large area of eastern Argentina, a major wheat producing region in South America. Sequence analysis of the translation elongation factor 1-α and β-tubulin genes as well as Amplified Fragment Length Polymorphism (AFLP) analyses indicated that all isolates were the FGSC species F. graminearum sensu stricto. AFLP analysis resolved at least 11 subgroups, and all the isolates represented different AFLP haplotypes. AFLP profile and geographic origin were not correlated. Previously obtained trichothecene production profiles of the isolates revealed that the 15-acetyldeoxynivalenol chemotype was slightly more frequent than the 3-acetyldeoxynivalenol chemotype among the isolates. These data extend the current understanding of FGSC diversity and provide further evidence that F. graminearum sensu stricto is the predominant cause of FHB in the temperate main wheat-growing area of Argentina. Moreover, two isolates of F. crookwellense and four of F. pseudograminearum were also recovered from wheat samples and sequenced. The results also suggest that, although F. graminearum sensu stricto was the only FGSC species recovered in this study, the high level of genetic diversity within this species should be considered in plant breeding efforts and development of other disease management strategies aimed at reducing FHB.     

Two new phenol derivatives from Stereum hirsutum FP-91666

Two new phenol derivatives, 2-(3-methyl-2-buten-1-yl)-4-methoxyethyl-phenol (1) and 5-hydroxy-4-(hydroxymethyl)-2-(3-methylbut-2-en-1-yl)cyclohex-4-en-1-one (2), together with eight known compounds consisting of phenol derivatives (3 and 4), niacinamide (5), and five ergosta type compounds (6–10), were isolated from solid fermentation products of Stereum hirsutum FP-91666. Two new structures were elucidated by extensive spectroscopic methods, including 1D NMR and 2D NMR, and HR-EI-MS experiments.     

Differences in functional cyclic AMP compartments mediating lepolysis by isoprenaline and BRL 37344 in four adipocyte types

Triglyceride mobilization and adenylyl cyclase activation in adipocytes from Wistar rats, lean Zucker (Fa/?) rats, obese Zucker (fa/fa) rats and humans were investigated in concentration-response studies with (−)-isoprenaline and the atypical β₃-adrenoceptor selective agonist BRL 37344. Maximum FFA production by both agonists was identical in Wistar rat and lean Zucker rat adipocytes, while obese Zucker rat adipocytes and human adipocytes produced significantly less FFA, especially with BRL 37344. Maximum adenylyl cyclase activation by (−)-isoprenaline was similar for all types of adipocyte ghosts, whereas BRL 37344 was a partial agonist in all cases with the lowest intrinsic activity in human adipocytes. For (−)-isoprenaline the relationship between cAMP and lipolysis was steepest with Wistar rat adipocytes, followed by human and lean Zucker rat adipocytes, while obese Zucker rat cells showed a shallow relationship. For BRL 37344, the relationship was very steep and similar for all four adipocyte types, despite the marked differences in maximal lipolysis and cyclic AMP production. The results strongly argue in favour of cyclic AMP compartmentalization, the activity ratio between the functional and the non-functional compartment being least favourable in obese Zucker rat adipocytes. The atypical β₃-adrenoceptor agonist BRL 37344 very efficiently directs the generated cyclic AMP into the functional compartment in all four adipocytes types investigated.     

Role of γ-glutamyltranspeptidase and β-lyase in the nephrotoxicity of hexachloro-1,3-butadiene and methyl mercury in mice

Male Swiss OF1 mice received a single oral dose of either 80 mg/kg hexachloro-1,3-butadiene (HCBD) or 80 mg/kg methyl mercury (MeHg). Examination of cryostat kidney sections stained for alkaline phosphatase (APP) revealed damage to about 50% of the proximal tubules after 8 h. Pretreatment with the γ-glutamyltranspeptidase (γ-GT) inactivator AT-125 (Acivin, 50 mg/kg i.p., plus 50 mg/kg p.o., reduced the number of damaged tubules by 59 and 58% in mice treated with HCBD and MeHg, respectively. Pretreatment with the two β-lyase inhibitors, amino-oxyacetic acid (AOAA, 3 × 100 mg/kg p.o.) and -propargylglycine (PPG, 300 mg/kg i.p. plus 300 mg/kg p.o), reduced HCBD nephrotoxicity by 46 and 59%, respectively, but did not protect against MeHg nephrotoxicity. The results support a role for γ-GT and β-lyase in the mouse renal toxicity of HCBD and implicate γ-GT but not β-lyase in MeHg-induced nephrotoxicity in mice.     

Isolation and structure elucidation of novel gamma-lactones from Saccopetalum prolificum

Two novel γ-lactones, saccopetrin C (1) and saccopetrin D (2), were isolated from the roots of Saccopetalum prolificum. Their structures were established by spectroscopic and chemical methods.     

A new flavone glycoside: 5,7,3',4'-tetrahydroxy-3-methoxy flavone-7-O-beta-D-galactopyranosyl-(1-->4)-O-beta-D-glucopyranoside from the stem of Acacia catechu Willd

A new bio-active flavone glycoside, m.p. C 28 H 32 O 17 , mp 283-284°C, M + 640 [EIMS] was isolated from the ethylacetate soluble fraction of the ethanolic extract of the stems of Acacia catechu and its structure was characterised as 5,7,3',4'-tetrahydroxy-3-methoxy flavone-7- O - β- d -galactopyranosyl-(1 →4)- O - β- d -glucopyranoside by various chemical degradations and spectral analyses.     

Chemokine receptor CCR5: from AIDS to atherosclerosis

There is increasing recognition of an important contribution of chemokines and their receptors in the pathology of atherosclerosis and related cardiovascular disease. The chemokine receptor CCR5 was initially known for its role as a co-receptor for HIV infection of macrophages and is the target of the recently approved CCR5 antagonist maraviroc. However, evidence is now emerging supporting a role for CCR5 and its ligands CCL3 (MIP-1α), CCL4 (MIP-1β) and CCL5 (RANTES) in the initiation and progression of atherosclerosis. Specifically, the CCR5 deletion polymorphism CCR5delta32, which confers resistance to HIV infection, has been associated with a reduced risk of cardiovascular disease and both CCR5 antagonism and gene deletion reduce atherosclerosis in mouse models of the disease. Antagonism of CCL5 has also been shown to reduce atherosclerotic burden in these animal models. Crucially, CCR5 and its ligands CCL3, CCL4 and CCL5 have been identified in human and mouse vasculature and have been detected in human atherosclerotic plaque. Not unexpectedly, CC chemokines have also been linked to saphenous vein graft disease, which shares similarity to native vessel atherosclerosis. Distinct roles for chemokine-receptor systems in atherogenesis have been proposed, with CCR5 likely to be critical in recruitment of monocytes to developing plaques. With an increased burden of cardiovascular disease observed in HIV-infected individuals, the potential cardiovascular-protective effects of drugs that target the CCR5 receptor warrant greater attention. The availability of clinically validated antagonists such as maraviroc currently provides an advantage for targeting of CCR5 over other chemokine receptors.     

Minor Saponins from the Leaves of Panax ginseng C.A. Meyer

<正> Five minor compounds isolated from the leaves of Panax ginseng C. A. Meyer were characterized as 20(R)-protopanaxatriol (1), daucosterin (2), 3β, 12β-dihydroxy-dammar-20 (22), 24-diene-3-O-β-D-glucopyranoside (3), 20 (R)-protopanaxadiol-3-O-β-D-glucopyranoside (4) and ginsenoside-Rh_2 (5), respectively, on the basis of spectral analyses and chemical evidence. The two new saponins, 3 and 4, were named as ginsenoside-Rh_3 and 20(R)-ginsenoside-Rh_2.Nine other major saponins obtained simultaneously were identical with ginsenoside-Rh_1(6),-Rg_3 (7), -Rg_2 (8), -Rg_1 (9),-Re(10),-Rd (11), -Rc (12), -Rb_2(13) and Rb_1 (14), respectively.