Acaricidal and Insecticidal Activities of Essential Oils and Constituents of Tasmannia lanceolata (Poir.) A.C.Sm. (Canellales: Winteraceae) Against Tetranychus urticae Koch (Trombidiformes: Tetranychidae) and Myzus persicae Sulzer (Hemiptera: Aphididae).

The negative side effects of synthetic pesticides have drawn attention to the need for environmentally friendly agents to control arthropod pests. To identify promising candidates as botanical pesticides, we investigated the acaricidal and insecticidal activities of 44 plant-derived essential oils (EOs) against Tetranychus urticae Koch and Myzus persicae Sulzer. Among the tested EOs, Tasmannia lanceolata (Poir.) A.C.Sm. (Tasmanian pepper) essential oil (TPEO) exhibited strong acaricidal and insecticidal activity. Mortality rates of 100% and 71.4% against T. urticae and M. persicae, respectively, were observed with TPEO at a concentration of 2 mg/ml. Polygodial was determined to be the primary active component after bioassay-guided isolation of TPEO using silica gel open-column chromatography, gas chromatography, and gas chromatography-mass spectrometry. Polygodial demonstrated acaricidal activity against T. urticae with mortality rates of 100%, 100%, 61.9%, and 61.6% at concentrations of 1, 0.5, 0.25, and 0.125 mg/ml, respectively. Insecticidal activity against M. persicae was also evident, with mortality rates of 88.5%, 85.0%, 46.7%, and 43.3% at respective concentrations of 1, 0.5, 0.25, and 0.125 mg/ml. Insecticidal and acaricidal activities of TPEO were greater than those of Eungjinssag, a commercially available organic agricultural material for controlling mites and aphids in the Republic of Korea. These findings suggest that TPEO is a promising candidate for mites and aphids control.

Sesquiterpene Polygodial from Drimys brasiliensis (Winteraceae) Down-Regulates Implant-Induced Inflammation and Fibrogenesis in Mice.

Drimys brasiliensis (Winteraceae) has been investigated in traditional medicine for its anti-inflammatory properties to treat gastric ulcers and allergic and respiratory system diseases as well as for cancer treatment. In this work, we investigate the ability of the sesquiterpene polygodial, isolated from D. brasiliensis stem barks, to modulate the chronic inflammatory response induced by polyester-polyurethane sponge implants in C57BL/6J mice. Daily treatment with polygodial inhibited the macrophage content in the implants as determined by the activity of the N-acetyl-ß-d-glucosaminidase enzyme as well as decreased the levels of CXCL1/KC and CCL2/JE/MCP-1 pro-inflammatory chemokines and the presence of mast cells along the formed fibrovascular tissue. Similarly, the deposition of a new extracellular matrix (total collagen and type I and III collagen fibers) as well as the production of the TGF-ß1 cytokine were attenuated in implants treated with polygodial, showing for the first time its antifibrogenic capacity. The hemoglobin content, the number of newly formed vessels, and the levels of VEGF cytokine, which were used as parameters for the assessment of the neovascularization of the implants, did not change after treatment with polygodial. The anti-inflammatory and antifibrogenic effects of polygodial over the components of the granulation tissue induced by the sponge implant indicate a therapeutic potential for the treatment of inflammatory diseases associated with the development of fibrovascular tissue.

Anti-diabetic and lipid-lowering effects of drimane sesquiterpenoids isolated from Zygogynum pancheri.

Recently, it has been shown that drimane-type sesquiterpenoids isolated from Zygogynum pancheri, a species native to New Caledonia, possessed significant α-amylase inhibitory activities. To further explore their antidiabetic potential, we investigated the effect of 1ß-O-(E-cinnamoyl)-6α-hydroxy-9epi-polygodial (D) and 1ß-E-O-p-methoxycinnamoyl-bemadienolide (L), two of the most active compounds of the series, on diabetic model rats. Compounds D and L (2 mg kg/day) were daily and orally administrated for 30 days to streptozotocin (STZ) (150 mg/kg) induced male diabetic Wistar rats. Animals were allocated into five groups of six rats. Comparatively to diabetic rats, treatments with D and L compounds were able to significantly (P < 0.05) decrease Fasting Blood Glucose (FBG) (70.15%, 71.02%), serum total cholesterol (46.27% and 39.38%), triglycerides (56.60% and 58.15%), creatinine (37.31% and 36.49%) and uric acid levels (67.76% and 69.68%), respectively. Compounds D and L also restored the altered plasma enzyme (aspartate aminotransferase, AST (47.83% and 43.20%), alanine aminotransferase, ALT (49.76% and 48.35%, alkaline phosphatase, ALP (72.78% and 73.21%)) and lactate dehydrogenase, LDH (47.95% and 53.93%) levels to near normal, respectively. Administration of Glymepiride, significantly (p < 0.05) reduced FBG (73.94%) in STZ induced diabetic rats. Additionally, the compounds D and L exhibited inhibitory effects in vivo on lipase activity of diabetic rats (54.83% and 52.25%), respectively. The outcomes of this study suggested that these two drimanes could be considered as efficient hypoglycemic, hypolipidemic and antiobesity agents for diabetes management and its complications.

Gold nanoparticle-assisted enhancement in bioactive properties of Australian native plant extracts, Tasmannia lanceolata and Backhousia citriodora.

Green nanotechnology plays a significant role in developing effective treatment strategies for numerous diseases. The biological synthesis of metal nanoparticles (M-NPs) possesses suitable alternatives than chemical techniques. Using plant extract to synthesis M-NPs is an eco-friendly, non-toxic, and cost-effective that are suitable for biological applications and efforts are directed to explore the efficacy of these materials in cancer management. In this study, gold nanoparticles (Au-NPs) were synthesised by following a one-step green synthesis, a reaction between HAuCl4 and biological molecules present in Tasmannia lanceolata leaf extract as a sole agent for both reduction and stabilisation. The characterisation techniques confirmed the successful synthesis of Au-NPs. TEM photograph revealed spherical shape nanoparticles with an average size of 7.10 ± 0.66 nm. The in-vitro cytotoxicity of Au-NPs was performed by analysing the percentage inhibition of cell viability using Resazurin assay on human liver cancer (HepG2), melanoma cancer (MM418 C1) and breast cancer (MCF-7) cell lines and compared with Au-NPs synthesised by using Backhousia citriodora leaf extract. The results showed that biosynthesised Au-NPs displayed greater inhibitory activity towards MCF-7 cancer cells proliferation compared to HepG2 and MM418 cancer cells. In addition, synthesised Au-NPs@ Tasmannia lanceolata leaf extract indicated higher inhibitory activity towards cancer cells compared to Au-NPs@ Backhousia citriodora leaf extract.

Distinct Drimane Chemotypes in Tasmanian Mountain Pepper (Tasmannia lanceolata): Differences in the Profiles of Pungent Leaf Phytochemicals Associated with Altitudinal Cline.

This study assesses whether the distinct altitudinal cline in leaf morphology (decreased leaf width and length with increased altitude) in Tasmanian mountain pepper (Tasmannia lanceolata) is associated with changes in the leaf chemistry of wild populations from different ecological landscapes and altitudes. The presence of distinct pungent drimane sesquiterpenoid chemotypes was identified: subalpine woodland and wet sclerophyll forest chemotypes. Isolation studies and analysis of extracts revealed that wet sclerophyll forest T. lanceolata populations featured polygodial as the principal terpenoid, with profiles similar to the commercial cultivars sampled. In contrast, the subalpine woodland populations contained the drimane sesquiterpenoids 1ß-acetoxy-9-deoxyisomuzigadial and 3ß-acetoxydrimenin and the conspicuous absence of the pungent principle polygodial.

Inhibition of the growth of human dermatophytic pathogens by selected australian and asian plants traditionally used to treat fungal infections.

OBJECTIVE: Syzygium australe (H.L. Wnddl. ex. Link) B. Hyland, Syzygium luehmannii (F. Muell.) L.A.S. Johnson, Syzygium jambos L. (Alston), Terminalia ferdinandiana Exell. and Tasmannia lanceolata (Poir.) A.C.Sm. are used in traditional Australian Aboriginal and Asian healing systems to treat a variety of pathogenic diseases including fungal skin infections, yet they are yet to be examined for the ability to inhibit the growth of human dermatophytes. MATERIALS AND METHODS: The fungal growth inhibitory activity of extracts produced from selected Australian and Asian plants was assessed against a panel of human dermatophytes by standard disc diffusion and liquid dilution MIC methods. The toxicity of the extracts was evaluated by Artemia lethality and MTS HDF cell viability assays. The phytochemistry of the most promising extracts were examined by GC-MS headspace analysis and some interesting compounds were highlighted. RESULTS: The aqueous and methanolic extracts of all plant species were good antifungal agents, inhibiting the growth of all of the dematophytes tested. The methanolic S. australe (SA) and S. luehmannii (SL) extracts were particularly potent fungal growth inhibitors. MIC values of 39 and 53µg/mL were recorded for the methanolic SL fruit extract against T. mentagrophytes and T. rubrum respectively. Similar MICs were also noted for the methanolic SL leaf extract (88 and 106µg/mL respectively). The methanolic SL leaf extract was a particularly good fungal growth inhibitor, with MIC values≤100µg/mL against the reference C. albicans strain (96µg/mL), E. floccosum (53µg/mL), and T. mentagrophytes (88µg/mL). This extract also produced MICs≤200µg/mL against all other fungal species/strains tested. Similarly good activity was seen for the methanolic S. australe leaf and fruit extracts, as well as the S. lehmannii fruit and S. jambos leaf extracts, with MIC values 100-500µg/mL. Interestingly, these extracts had low toxicity and high therapeutic indices, indicating their suitability for clinical use. GC-MS headspace analysis highlighted several monoterpenoids and sesquiterpenoids in the methanolic SA and SL extracts. T. ferdinandiana and T. lanceolata extracts also had promising antifungal activity, albeit with substantially higher MICs. CONCLUSION: Whilst multiple extracts inhibited fungal growth, the methanolic S. australe and S. luehmannii leaf extracts and the S. luehmannii fruit extracts showed particularly potent activity against each of these dermatophytes, indicating that they are promising leads for the development of anti-dermatophytic therapeutics.

Structure-Pungency Relationships and TRP Channel Activation of Drimane Sesquiterpenes in Tasmanian Pepper (Tasmannia lanceolata).

Sensory-guided fractionation of extracts of Tasmanian pepper berries revealed 20 drimane sesquiterpens, among which polygodial, warburganal, and 1ß-acetoxy-9-deoxy-isomuzigadial exhibited the lowest pungency threshold concentrations on the tongue surface (0.6-2.8 nmol/cm2) and elicited a dose-dependent calcium influx into mTRPA1 expressing CHO cells with the lowest EC50 values (4.5 ± 1.0 to 16.7 ± 7.5 µmol/L) and a good correlation to oral pungency thresholds (R2 = 0.986, linear regression). Calcium imaging assays demonstrated these chemosensates to induce a calcium influx into cultured trigeminal neurons prepared from wildtype (TRPA1+/+) mice, whereas no calcium influx was observed in neurons from TRPA1 knockout mice (TRPA1-/-), thus confirming the α,ß-unsaturated 1,4-dialdehyde structure to be the required structural motif for a low oral puncency thresholds and activation of the Transient Receptor Potential Channel A1 (TRPA1). Time-resolved NMR experiments confirmed the pungency mediating mechanism for electrophilic drimane sesquiterpene dialdehydes to be different from that found for other electrophilic pungent agents like isothiocyanates, which have been shown to undergo a covalent binding with cysteine residues in TRPA1. Instead, the high-impact chemosensates polygodial, warburganal, and 1ß-acetoxy-9-deoxy-isomuzigadial showed immediate reactivity with the ε-amino group of lysine side chains to give pyrrole-type conjugates, thus showing evidence for TRPA1 activation by covalent lysine modification.

Composition of native Australian herbs polyphenolic-rich fractions and in vitro inhibitory activities against key enzymes relevant to metabolic syndrome.

Polyphenolic-rich fractions obtained from three native Australian herbs: Tasmannia pepper leaf, anise myrtle and lemon myrtle were characterised with regards to their composition, antioxidant capacities and inhibitory activities against α-glucosidase, pancreatic lipase and angiotensin I-converting enzyme, using in vitro models. Ellagic acid and derivatives were the dominant compounds of anise myrtle and lemon myrtle fractions, accompanied by flavonoids (catechin, myricetin, hesperetin, and quercetin). Tasmannia pepper leaf fraction comprised chlorogenic acid and quercetin derivatives, exhibited the highest oxygen radical absorbance capacity and effectively inhibited α-glucosidase (IC(50): 0.83 mg/ml) and pancreatic lipase (IC(50): 0.60 mg/ml). Anise myrtle and lemon myrtle fractions had pronounced α-glucosidase-inhibitory activities (IC(50): 0.30 and 0.13 mg/ml, respectively) and were less effective against lipase. Enzyme-inhibitory activities showed various levels of correlation with the levels of total phenolics and antioxidant capacities, indicating a specificity of individual phenolic compounds present in the isolated fractions to complex with proteins.

Distribution of drimane sesquiterpenoids and tocopherols in liverworts, ferns and higher plants: Polygonaceae, Canellaceae and Winteraceae species.

The liverwort, Porella vernicosa complex produces a very hot tasting polygodial, a drimane-type sesquiterpene dialdehyde. The same compound has been isolated from two ferns, Thelypteris hispidula and Blechnum fluviatile, as well as from the higher plants Polygonum hydropiper, P. hydropiper f. purpurascens (Polygonaceae), Cinnamosma, Caspicodendron, Canella and Warburgia species (Canellaceae), and Pseudowintera colorata, Tasmannia lanceolata, Drimys and Zygogynum species (Winteraceae). In addition, the liverworts and higher plants which elaborate polygodial and its related pungent drimane dials contain a small amount of alpha-tocopherol, gamma-tocopherol or delta-tocotrienol. The present paper gives the results of a comparative study on the drimane-type sesquiterpenoids in some liverworts, ferns and higher plants, and the role of tocopherols in these plant groups.

Influence of copigment derived from Tasmannia pepper leaf on Davidson's plum anthocyanins.

UNLABELLED: Davidson's plum (Davidsonia pruriens, F. Muell.), a native to Australian rainforests, large, crimson-red fruit, which superficially resembles plum, has been commercially cultivated in Australia since 1990s. The current production volume exceeds market demands therefore this study was designed to evaluate the suitability of Davidson's plum extract as a source of anthocyanin-based food colorant. The stability of the Davidson's plum extract towards heat treatment at 95 °C was higher than that of commercial mulberry colorant, but inferior to colorants derived from red cabbage and purple sweetpotato. An addition of a variety of phenolic acids significantly increased color intensity indicating the formation of copigmentation complexes. Commercial chlorogenic acid as well as extract from a native Australian herb rich in chlorogenic acid, Tasmannia pepper leaf (Tasmannia lanceolata, R. Br.), were both tested in model soft drink solutions subjected to light irradiation and heat treatment. In both cases, the addition of the copigment resulted in a lasting increase in color intensity. In conclusion, Davidson's plum extract can successfully be utilized as a source of natural food color. Extract from Tasmania pepper leaf can be used as a co-pigment for Davidson's plum anthocyanins. PRACTICAL APPLICATION: The color properties of an anthocyanin colorant derived from the native Australian fruit Davidson's plum are comparable to those of mulberry, which is currently applied as a food colorant in Australian food products. Utilization of Davidson's plum fruit as a source of natural color will allow the industry to increase the range of natural pigments and will create new opportunities for the emerging native food industry.

Chemical composition and antibacterial activity of the essential oil of Drimys granadensis L.f. leaves from Colombia.

Drimys granadensis L.f., a native plant from Colombia, has been included in the Vademecum de Plantas Medicinales de Colombia by the Instituto de Investigación de Recursos Biológicos Alexander von Humboldt, due to its widespread use in the folk medicine for the treatment of gastrointestinal ailments. The chemical composition of the essential oil of Drimys granadensis obtained by hydrodistillation of the leaves was analyzed by GC and GC/MS analyses. A total of 85 components were identified, with the major compounds germacrene D (1, 14.7%), sclarene (9.5%), a-cadinol (7.3%), longiborneol acetate (2, 6.3%), drimenol (4.2%), (Z)-ß-ocimene (3, 4.2%), a-pinene (4, 3.2%), and ß-elemene (5, 2.7%). The essential oil was also tested against eight bacteria using the Kirby-Bauer disk-diffusion method. Most of the Gram-positive bacteria tested were susceptible to the D. granadensis essential oil, while the Gram-negative bacteria tested were not.

Estrutura populacional e incremento corrente anual de casca-de-anta (Drimys brasiliensis Miers - Winteraceae) em Caçador, Santa Catarina, Brasil / Population structure and annual increment in "casca-de-anta" (Drimys brasiliensis Miers - Winteraceae) from Caçador Municipality, Santa Catarina State, Brazil

Drimys brasiliensis Miers, conhecida como cataia ou casca-de-anta, é árvore nativa da Mata Atlântica e as cascas tem sido utilizadas medicinalmente a partir da exploração de plantas em populações naturais. Este trabalho teve como objetivo estudar a demografia de duas populações naturais de D. brasiliensis, (1) Reserva Genética Florestal de Caçador (RGFC) e (2) Floresta Nacional de Caçador (FLONA), ambas no município de Caçador (SC), visando fundamentar estratégias de exploração sustentável e conservação deste recurso florestal não-madeireiro. A maior luminosidade no sub-bosque existente na FLONA atuou positivamente na espécie, aumentado a capacidade de incremento em diâmetro à altura do peito (DAP), altura (H) e área basal (AB), além de antecipar a reprodução em plantas de menor porte. A análise do padrão espacial das plantas reprodutivas na RGFC mostrou padrão agregado, e na FLONA até a distância de 25 metros. Esse comportamento indicou que a espécie apresenta potencial de manejo em florestas secundárias, formação sucessional em que se encontra a maioria dos remanescentes de Mata Atlântica, além de indicar potencial para cultivo em sistemas agroflorestais.

Known as "cataia" or "casca-de-anta", Drimys brasiliensis Miers is a tree native to the Atlantic Forest and its barks have been medicinally used by exploring natural populations. The present work aimed to study the demography of two D. brasiliensis natural populations, (1) Caçador Forest Genetic Reserve (RGFC) and(2) Caçador National Forest (FLONA), both located in Caçador Municipality, Santa Catarina State, Brazil, in order to establish strategies for sustainable exploration and conservation of such non-timber forest resource. The higher luminosity in FLONA understory was beneficial to the species by increasing their increment capability regarding diameter at breast height (DBH), height (H) and basal area (BA), and made the reproduction in smaller plants earlier. The spatial analysis of reproductive plants in RGFC had an aggregate pattern, whereas in FLONA until 25m distance was detected. Such results indicated that this species presents potential for management in secondary forests, the successional formation where the major Atlantic Forest remnants are found, as well as potential for cultivation in agroforestry systems.

The sesquiterpenes polygodial and drimanial in vitro affect glutamatergic transport in rat brain.

Natural products including those derived from plants, have over the years greatly contributed to the development of therapeutic drugs. Polygodial and drimanial are sesquiterpenes isolated from the bark of the plant Drymis Winteri (Winteraceae) that exhibit antinociceptive properties. Since peripheral glutamate presents nociceptive actions, in this study it was investigated the effects of hydroalcooholic extracts from Drymis winteri (polygodial and drimanial) on the glutamatergic system in rat brain. Polygodial and drimanial inhibited glutamate uptake by astrocytes, as well as by cortical, hippocampal and striatal slices, and increased synaptosomal glutamate release. These concurrent effects would predispose to an increase in the extracellular glutamate concentrations, leading to possible neurotoxic effects (excitotoxicity) of these natural compounds, which would suggest the need for some caution in their therapeutic application.

Protective effects of polygodial on gastric mucosal lesions induced by necrotizing agents in rats and the possible mechanisms of action.

The effects of polygodial isolated from the leaves of Tasmannia lanceolata on necrotizing agents-induced gastric lesions in rats were compared with capsaicin. Polygodial markedly inhibited the gastric mucosal lesions induced by several necrotizing agents, such as ethanol (ED(50)=0.029 mg/kg, p.o.), 0.6 M HCl (ED(50)=0.26 mg/kg, p.o.), and aspirin (ED(50)=0.38 mg/kg, p.o.), and partly inhibited the gastric mucosal lesions induced by indomethacin, but showed no significant effect on acid output in pylorus-ligated rats at doses of 0.05-0.5 mg/kg. The gastroprotection of polygodial was attenuated by pretreatment with indomethacin (10 mg/kg, s.c.), N(G)-nitro-L-arginine methyl ester (70 mg/kg, i.p.), N-ethylmaleimide (10 mg/kg, s.c.) and ruthenium red (3.5 mg/kg, s.c.). Polygodial (0.2 mg/kg, p.o.) increased the amount of reduced glutathione in gastric mucosa of ethanol-treated group. These results suggested that endogenous prostaglandins, nitric oxide, sulfhydryl compounds and vanilloid receptor-mediated effects are involved in the protective effect of polygodial.

Role of nitric oxide and K+ channels in relaxation induced by polygodial in rabbit corpus cavernosum in vitro.

This study examines the relaxation produced by the sesquiterpene polygodial and compares its action with those caused by acetylcholine (ACh) and sodium nitroprusside (SNP) in the rabbit corpus cavernosum (RbCC) in vitro. RbCC was set up in a 5-ml bath containing Krebs solution at 37 degrees C, at pH 7.2, and under 2 g of tension. Polygodial, ACh, and SNP elicited graded relaxation in RbCC with mean EC50 values of 46.70 microM, 0.38 microM, and 0.30 microM, respectively. The nitric oxide (NO) synthase inhibitor L-NOARG and the guanylate cyclase inhibitors LY 83583 and ODQ markedly inhibited the relaxation induced by polygodial (% of inhibition of 79, 48, and 51, respectively) and those caused by ACh (% of inhibition of 100, 49, and 32, respectively). Tetraethylammonium (TEA) and glibenclamide inhibited the relaxation induced by polygodial (52% and 43%, respectively), but only TEA caused shift to the right on ACh-mediated relaxation. In contrast, apamin, charybdotoxin, and 4-aminopyridine or the protein kinase A inhibitor KT 5720 all failed to affect either polygodial or ACh-mediated relaxation in these preparations. The authors concluded that polygodial produced graded relaxation in the RbCC in vitro via a mechanism that was partially dependent on the release of NO or a NO-derived substance through an activation of guanylate cyclase but was independent of adenylate cyclase mechanism. In addition, the opening of K+ channels sensitive to TEA and glibenclamide, but not those sensitive to apamin, 4-aminopyridine, or charybdotoxin, also contributed to the relaxant action produced by polygodial in the RbCC.