In vivo anti-ageing activity of cream containing niosomes loaded with purple glutinous rice (Oryza sativa Linn.) extract.

OBJECTIVE: To evaluate the anti-ageing activity of cream containing the methanolic purple glutinous rice extract loaded in niosomes. METHODS: The in vitro biological activities of the purple glutinous rice extracted by methanol maceration were determined. The extract loaded in niosomes and the cream containing the niosomes were developed. The in vivo anti-ageing activity in 20 human volunteers including skin hydration, pigmentation, roughness and elasticity after daily application for 28 days compared to at initial was evaluated by Corneometer, Mexameter, Visiometer and Cutometer, respectively. RESULTS: The purple glutinous rice extract showed free radical scavenging (SC50 ), lipid peroxidation inhibition (IPC50 ), metal ion chelating (CC50 ) and tyrosinase inhibition (IC50 ) values at 32.31 ± 1.28, 57.40 ± 2.12, 85.05 ± 5.43 and 43.89 ± 2.14 mg/mL which were 0.00031, 0.011, 0.0078 and 0.0016 times of the standards (0.01 ± 0.00, 0.62 ± 0.14, 0.66 ± 0.05 and 0.07 ± 0.01), respectively. The purple glutinous rice extract contained 0.35 µg of anthocyanin/1 mg of the extract determined by HPLC. After loaded in niosomes, the solubility of the extract was not only increased in various solvents, but also the chemical stability in different environments (weak base, reducing agent and acid salt) was improved. The cream formulation containing niosomes loaded with 1%w/v of the purple glutinous rice extract indicated the anthocyanin remaining percentages after 6 cycles of heating and cooling test at 52.28% of the initial. For in vivo anti-ageing activities, cream containing niosomes loaded with the extract gave significant decreased melanin index and skin roughness reduction of -14.05 and -9.95% of the initial, respectively. The % changes of the increased skin hydration, skin elastic extension and skin elastic recovery when applied on human volunteers' skin with this formulation were +48.73, -24.51 and +35.98%, respectively. CONCLUSION: The cream containing niosomes loaded with the 1%w/v methanolic purple glutinous rice extract gave not only the suitable in vitro antioxidant activity and physical stability of the active anthocyanin, but also the superior in vivo anti-ageing activity on human skin compared to the cream base and before application which can be further developed as a novel anti-ageing cosmeceutical product.

OBJECTIF: Evaluer l'activité anti-âge d'une crème contenant de l'extrait de riz gluant violet méthanolique chargé en niosomes. MÉTHODES: Les activités biologiques in vitro de l'extrait du riz gluant violet par macération au méthanol ont été déterminées. L'extrait chargé en niosomes et la crème contenant les niosomes ont été développés. L'activité anti-âge in vivo sur 20 volontaires humains, y compris de l'hydratation de la peau, la pigmentation, la rugosité et l'élasticité après une application quotidienne pendant 28 jours a été évaluée par comparaison avec T0 par cornéomètre, mexamètre, visiomètre et cutomètre, respectivement. RÉSULTATS: L'extrait de riz gluant violet a montré des valeurs de piégeage des radicaux libres (SC50), d'inhibition de la peroxydation lipidique (IPC50), de chélation des ions métalliques (CC50) et d'inhibition de la tyrosinase (IC50) à 32,31 ± 1,28, 57,40 ± 2,12, 85,05 ± 5,43 et 43,89 ± 2,14 mg / ml qui étaient 0,00031, 0,011, 0,0078 et 0,0016 fois des standards respectivement (0,01 ± 0,00, 0,62 ± 0,14, 0,66 ± 0,05 et 0,07 ± 0,01). L'extrait de riz gluant violet contenait 0.35 pg d'anthocyanine / 1 mg de l'extrait déterminé par HPLC. Après avoir été chargé dans les niosomes, la solubilité de l'extrait a non seulement été augmentée dans divers solvants, mais aussi la stabilité chimique dans différents environnements (base faible, agent réducteur et sel d'acide) a été améliorée. La formulation de crème contenant des niosomes chargés avec 1% p / v de l'extrait de riz gluant violet a indiqué les pourcentages d'anthocyanine restants après 6 cycles de test de chauffage et de refroidissement à 52,28% de la valeur initiale. Pour les activités anti-âge in vivo, la crème contenant des niosomes chargés de l'extrait a donné une réduction significative de l'indice de mélanine et de la rugosité cutanée de -14,05 et -9,95% de la valeur initiale, respectivement. Les pourcentages de variation de l'hydratation accrue de la peau, de l'extension élastique de la peau et de la récupération de l'élasticité de la peau lors de l'application sur la peau de volontaires humains avec cette formulation étaient respectivement de +48,73, -24,51 et + 35,98%. CONCLUSION: La crème contenant des niosomes chargée avec l'extrait de riz gluant violet méthanolique à 1% p / v a donné non seulement une activité antioxydante in vitro appropriée et une stabilité physique de l'anthocyanine active, mais également une activité anti-vieillissement in vivo supérieure sur la peau humaine par rapport à la base de la crème et avant application, qui peut être développée en tant que nouveau produit cosméceutique anti-âge. Mots clés: riz gluant violet, niosomes, antioxydant, inhibition de la tyrosinase, efficacité anti-âge in vivo, produit cosméceutique.

Investigating the effect of particle size on pulmonary surfactant phase behavior.

We study the impact of the addition of particles of a range of sizes on the phase transition behavior of lung surfactant under compression. Charged particles ranging from micro- to nanoscale are deposited on lung surfactant films in a Langmuir trough. Surface area versus surface pressure isotherms and fluorescent microscope observations are utilized to determine changes in the phase transition behavior. We find that the deposition of particles close to 20 nm in diameter significantly impacts the coexistence of the liquid-condensed phase and liquid-expanded phase. This includes morphological changes of the liquid-condensed domains and the elimination of the squeeze-out phase in isotherms. Finally, a drastic increase of the domain fraction of the liquid-condensed phase can be observed for the deposition of 20-nm particles. As the particle size is increased, we observe a return to normal phase behavior. The net result is the observation of a critical particle size that may impact the functionality of the lung surfactant during respiration.

Particle size effects on collapse in monolayers.

We report on the impact of differently sized particles on the collapse of a Langmuir monolayer. We use an SDS-DODAB monolayer because it is known to collapse reversibly under compression and expansion cycles. Particles with diameters of 1 µm, 0.5 µm, 0.1 µm, and 20 nm are deposited on the SDS-DODAB monolayer. We find a critical particle size range of 0.1 to 0.5 µm that produces a transition from reversible to irreversible collapse. The nature of the collapse is determined through optical observations and surface pressure measurements. In addition, although 20 nm particles do not cause irreversible collapse in the monolayer, they significantly decrease the collapse pressure relative to the other systems. Therefore, we observe three distinct collapse behaviors-reversible, irreversible, and reversible at a reduced surface pressure.

Inhibition of trypsin and chymotrypsin by anti-inflammatory triterpenoids from Compositae flowers.

Taraxastane, oleanane, ursane, lupane, taraxane, cycloartane, dammarane and tirucallane triterpenoids isolated from flowers of Compositae plants have been previously reported to exhibit anti-inflammatory effects and are variously competitive and non-competitive inhibitors of the serine proteases trypsin and chymotrypsin. The general features of those triterpenoids found to be protease inhibitors are having a hydroxy group and an appropriate side chain in the region of the molecule distal to the 3-hydroxy group. However, fatty acid esterification of the triterpenoid 3-hydroxy group can have a marked effect on inhibitor effectiveness. This suggests a possible means of rapid alteration of the plant defensive complement in vivo and of the bioactivity of these anti-inflammatory compounds.

Anti-tumor promoting effects of multiflorane-type triterpenoids and cytotoxic activity of karounidiol against human cancer cell lines.

Forty-nine multiflorane-type triterpenoids consisting of 11 compounds isolated from the seeds of Trichosanthes kirilowii (Cucurbitaceae) and 38 of their derivatives have been evaluated for their inhibitory effects on Epstein-Barr virus early antigen (EBV-EA) activation induced by the tumor promoter 12-O-tetradecanoylphorbol-13-acetate in Raji cells as a primary screening test for anti-tumor promoters. All of the compounds tested showed an inhibitory effect against EBV-EA activation, and among which 43 were revealed to possess remarkable activity with potencies either comparable to or stronger than that of glycyrrhetic acid, a known natural anti-tumor promoter. Their structure-activity relationship is discussed. Evaluation of the cytotoxic activity of karounidiol (27) against human cancer cell lines exhibited cytotoxicity especially against a human renal cancer.

Detecting the inseparability and distillability of continuous variable states in Fock space.

The partial transposition (PT) operation is an efficient tool in detecting the inseparability of a mixed state. We give an explicit formula for the PT operation for the continuous variable states in Fock space. We then give the necessary and sufficient condition for the positivity of Gaussian operators. Based on this, a number of criteria on the inseparability and distillability for the multimode Gaussian states are naturally drawn. We finally give an explicit formula for the state in a subspace of a global Gaussian state. This formula, together with the known results for Gaussian states, gives the criteria for the inseparability and distillability in a subspace of the global Gaussian state.

Constituents of compositae plants. 2. Triterpene diols, triols, and their 3-o-fatty acid esters from edible chrysanthemum flower extract and their anti-inflammatory effects.

The n-hexane soluble and the nonsaponifiable lipid fractions of the edible flower extract of chrysanthemum (Chrysanthemum morifolium) were investigated for triterpene diol and triol constituents. These triterpenes occur as the 3-O-fatty acid esters in the n-hexane soluble fraction from which 26 new and 6 known fatty acid esters were isolated and characterized. From the nonsaponifiable lipid fraction, 24 triterpene diols and triols were isolated, of which 3 were new compounds: (24S)-25-methoxycycloartane-3beta,24-diol (11), (24S)-25-methoxycycloartane-3beta,24,28-triol (22), and 22alpha-methoxyfaradiol (23). Faradiol (9) and heliantriol C (19), present in the nonsaponifiable lipid fraction and as the 3-O-palmitoyl esters in the n-hexane soluble fraction, were the most predominant triterpene diol and triol constituents. Fourteen triterpene diols and triols and 9 fatty acid esters were evaluated with respect to their anti-inflammatory activity against 12-O-tetradecanoylphorbol-13-acetate (TPA)-induced inflammation in mice. All of the triterpenes examined showed marked inhibitory activity, with a 50% inhibitory dose (ID50) of 0.03-1.0 mg/ear, which was more inhibitive than quercetin (ID50 = 1.6 mg/ear), a known inhibitor of TPA-induced inflammation in mice.

Inhibitory effects of triterpenoids and sterols on human immunodeficiency virus-1 reverse transcriptase.

Fifty-five triterpenoids consisting of 19 tetracyclic, 32 pentacyclic, and 4 incompletely cyclized triterpenoids, and 2 sterols, mostly isolated from various plant and fungal materials, were examined for their inhibitory effects on a purified human immunodeficiency virus type 1 (HIV-1) reverse transcriptase. Twenty triterpenoids and one sterol showed inhibitory effects with 50% inhibition concentration (IC50) values less than 5.0 microM. Among these cycloartenol ferulate (IC50 = 2.2 microM), 24-methylenecycloartanol ferulate (1.9 microM), lupenone (2.1 microM), betulin diacetate (1.4 microM), and karounidiol 29-benzoate (2.2 microM) inhibited most effectively. Some of the triterpenoids and sterols may be potential new lead compounds to find still more potent HIV-1 reverse transcriptase inhibitors.

6S,8R-Stereochemistry of the C27- and C29-alkane-6,8-diols isolated from three compositae flowers.

The Deltadelta (deltaS-deltaR) values for the C-1 methyl 1H signals in the 1H-NMR spectroscopy of the bis-MTPA esters of four synthetic stereoisomers of alkane-6,8-diols, viz., bis-MTPA esters of (6S,8R)-C27- (1a) and C29- (3a) (Deltadelta = -0.05 ppm), (6R,8S)-C27- (2a) and C29- (4a) (Deltadelta = +0.05 ppm), (6S,8S)-C27- (5a) (Deltadelta = -0.01 ppm), and (6R,8R)-C27- (6a) (Deltadelta = +0.01 ppm) alkane-6,8-diols, made it possible to differentiate unequivocally among the four stereoisomers. This allowed the determination of the (6S,8R)-stereochemistry (Deltadelta = -0.05 ppm for the bis-MTPA esters) for the natural C27- and C29-alkane-6,8-diols isolated from the flowers of three Compositae plants, Carthamus tinctorius, Cynara cardanclus, and Taraxacum platycarpum.

Triterpene alcohol and sterol ferulates from rice bran and their anti-inflammatory effects.

Six novel feruloyl esters of triterpene alcohols and sterols, viz., two trans-ferulates, cycloeucalenol and 24-methylenecholesterol trans-ferulates, and four cis-ferulates, cycloartenol, 24-methyelenecycloartanol, 24-methylcholesterol, and sitosterol cis-ferulates, besides five known trans-ferulates, cycloartenol (CAR), 24-methylenecycloartanol (24-MCA), 24-methylcholesterol, sitosterol, and stigmastanol trans-ferulates, and one known cis-ferulate, stigmastanol cis-ferulate, were isolated from the methanol extract of edible rice bran. These and eight other synthetic trans- and cis-ferulates of triterpene alcohols and sterols, along with the corresponding free alcohols, were evaluated with respect to their anti-inflammatory activity against 12-O-tetradecanoylphorbol-13-acetate (TPA)-induced inflammation (1 microg per ear) in mice. All of the ferulates showed marked inhibitory activity, and their 50% inhibitory dose (ID(50)) was 0. 1-0.8 mg per ear. On the other hand, whereas two free triterpene alcohols, CAR and 24-MCA, showed strong inhibition (ID(50) 0.2-0.3 mg/ear), eight free sterols examined showed weaker activity (ID(50) 0.7-2.7 mg/ear) than their corresponding ferulates.

Inhibitory effect of euphol, a triterpene alcohol from the roots of Euphorbia kansui, on tumour promotion by 12-O-tetradecanoylphorbol-13-acetate in two-stage carcinogenesis in mouse skin.

The anti-inflammatory activity of euphol, twelve other triterpene alcohols and sitosterol-beta-D-glucopyranoside, isolated from the dichloromethane extract of the roots of Euphorbia kansui, has been evaluated in mice with inflammation induced by 12-O-tetradecanoylphorbol-13-acetate (TPA). TPA (1.7 nmol; 1.0 microg/ear) was dissolved in acetone and 10 microL delivered to the inner and outer surfaces of the right ear of ICR mice. A triterpene alcohol, sterol glucoside or vehicle (20 microL; chloroform-methanol 1:1), was applied topically approximately 30 min before each TPA treatment. The ear thickness was measured before treatment and then oedema was measured 6 h after TPA treatment. For the two-stage carcinogenesis experiment, initiation was accomplished by administration of a single topical application of 7,12-dimethylbenz[a]anthracene (DMBA; 195 nmol; 50 microg/mouse) to the shaved backs of mice. Promotion was with 1.7 nmol (1.0 microg) TPA, applied twice weekly to the same shaved area, begun one week after the initiation. Euphol (2.0 micromol; 853 microg), or its vehicle (acetone-dimethylsulphoxide, 9:1; 100 microL), was applied topically 30 min before each TPA treatment. The number and diameter of skin tumours were measured every other week for 20 weeks. All the compounds were found to possess marked inhibitory activity and their 50% inhibitory dose for TPA-induced inflammation was 0.2-1.0 mg/ear. Topical application of euphol (2.0 micromol; 853 microg/mouse) markedly suppressed the tumour-promoting effect of TPA (1.7 nmol; 1.0 microg/mouse) in mouse skin initiated with DMBA.

Acyclic and incompletely cyclized triterpene alcohols in the seed oils of theaceae and gramineae.

The triterpene alcohol constituents of the non-saponifiable lipids of two Theaceae seed oils, sasanqua and camellia oils, and two Gramineae seed oils, wheat germ and rice bran oils, were investigated. This led to the isolation and characterization of one acyclic and eight incompletely cyclized triterpene alcohols. They are camelliol A, camelliol B, camelliol C, achilleol A, helianol, isohelianol, sasanquol, graminol A [(13R, 14R)-3,4-seco-25(10->9)abeo-8alpha,9beta,10al phapodioda-4,17,21 -trien-3-ol], and (2Z,6Z,10Z,14E,18E)-farnesyl-farnesol. Two other compounds isolated were characterized as (2Z,6Z,10E,14E)-geranylfarnesol, a sesterterpene alcohol, and phytol, a diterpene alcohol. Graminol A and (2Z,6Z,10E,14E)-geranylfarnesol are considered to be new natural products.

Camelliols A-C, three novel incompletely cyclized triterpene alcohols from sasanqua oil (Camellia sasanqua)

Three novel triterpene alcohols, camelliols A (1), B (3), and C (5), possessing a mono-, bi-, and tricyclic ring system, respectively, have been isolated, along with achilleol A, a known monocyclic triterpene alcohol, from the nonsaponifiable lipids of sasanqua oil (Camellia sasanqua). The structures of these new alcohols were determined on the basis of spectroscopic methods.

Inhibitory effect of cycloartenol ferulate, a component of rice bran, on tumor promotion in two-stage carcinogenesis in mouse skin.

Inhibitory activity against 12-O-tetradecanoylphorbol-13-acetate (TPA)-induced inflammation in mice was observed in the methanol extract of rice bran and gamma-oryzanol. The active components of rice bran, sitosterol ferulate, 24-methylcholesterol ferulate, cycloartenol ferulate and 24-methylenecycloartanol ferulate inhibited markedly the TPA-induced inflammation in mice. The 50% inhibitory dose of these compounds for TPA-induced inflammation was 0.2-0.3 mg/ear. Furthermore, cycloartenol ferulate markedly inhibited the tumor-promoting effect of TPA in 7,12-dimethylbenz[a]anthracene-initiated mice.

Sasanquol, a 3,4-seco-triterpene alcohol from sasanqua oil, and its anti-inflammatory effect.

A novel 3,4-seco-triterpene alcohol, named sasanquol, was isolated from the non-saponifiable lipid of sasanqua oil from the seeds of Camellia sasanqua. Its structure was established to be 3,4-seco-D:B-friedobacchara-4,21-dien-3-ol by spectroscopic methods. This is the first example of naturally occurring triterpene with a D:B-friedobaccharane skeleton. The 50% inhibitory dose of this compound against 12-O-tetradecanoylphorbol-13-acetate (TPA)-induced ear inflammation (1 microgram per ear) in mice was 0.4 mg per ear.

Isohelianol: A 3,4-seco-Triterpene Alcohol from Sasanqua Oil

The structure of isohelianol isolated from the seeds of Camellia sasanqua Thunb. was established to be 3,4-seco-19(10-->9)-abeo-8alpha,9beta,10alpha-eupha-4,24-dien-3-ol (1) on the basis of spectroscopic methods.

Inhibitory effect of heliantriol C; a component of edible Chrysanthemum, on tumor promotion by 12-O-tetradecanoylphorbol-13-acetate in two-stage carcinogenesis in mouse skin.

Two hydroxy taraxastane-type triterpenes, faradiol and heliantriol C, have been isolated from the ligulate flowers of Chrysanthemum morifolium Ramat. var. sinense Makino fa. esculentum Makino, the edible Chrysanthemum. These compounds showed strong inhibitory activity against 12-O-tetradecanoyl-phorbol-13-aetate (TPA)-induced inflammation in mice. At 0.2 µmol/mouse, these compounds markedly inhibited the promoting effect of TPA (1 µg/mouse) on skin tumor formation followed by 7,12-dimethylbenz[a]anthracene (50 µg/mouse).

Triterpene alcohols from camellia and sasanqua oils and their anti-inflammatory effects.

The nonsaponifiable lipids of camellia and sasanqua oils from the seeds of Camellia japonica L. and C. sasanqua THUNB., respectively, were investigated for their triterpene alcohol constituents. This led to the isolation of twenty-seven triterpene alcohols of which seven were novel naturally occurring compounds, tirucalla-5,7,24-trien-3 beta-ol (1), lemmaphylla-7,21-dien-3 beta-ol (2), isoeuphol (3), isotirucallol (4), (24R)-24,25-epoxybutyrospermol (5) and its 24S-epimer (6), and isoaglaiol (7). The structures were determined by spectroscopic and chemical methods. The inhibitory effects of 3, 4 a mixture of 5 and 6, a mixture of 7 and its 24S-epimer (aglaiol), and eight known triterpene alcohols isolated in this study were evaluated in ear inflammation in mice induced by 12-O-tetradecanoylphorbol-13-acetate (TPA). The 50% inhibitory dose of these triterpenes for TPA-induced inflammation (1 microgram per ear) was 0.2-0.9 mg/ear.

Triterpene alcohols from the flowers of compositae and their anti-inflammatory effects.

Eleven tabular and nine ligulate flowers from 15 species of Compositae plants were investigated for their triterpene alcohol constituents. This led to the isolation and identification of 11 triterpene alcohols as follows: heliaol, taraxasterol, psi-taraxasterol, alpha-amyrin, beta-amyrin, lupeol, taraxerol, cycloartenol, 24-methyl-enecycloartanol, tirucalla-7,24-dienol and dammaradienol. The tabular flowers of Calendula officinalis, Carthamus tinctorius, Cosmos bipinnatus, Chrysanthemum morifolium, Helianthus annuus and Matricaria matricarioides showed a characteristic feature by containing helianol as the most predominant component (29-86%) in the triterpene alcohol fractions. The triterpene alcohols from Compositae flowers were evaluated with respect to their anti-inflammatory activity against 12-O-tetradecanoylphorbol-13-acetate-induced inflammation (1 microgram per ear) in mice. All of these showed marked inhibitory activity, and their 50% inhibitory dose was 0.1-0.8 mg per ear.

Inhibitory effect of Di- and trihydroxy triterpenes from the flowers of compositae on 12-O-tetradecanoylphorbol-13-acetate-induced inflammation in mice.

Ten dihydroxy- and trihydroxy triterpenes, viz., four taraxastanes: faradiol, heliantriol B0, heliantriol C and arnidiol; two lupanes: calenduladiol and heliantriol B2; two oleananes: maniladiol and longispinogenin; and two ursanes: brein and uvaol, isolated from the nonsaponifiable lipids of the flower extracts of Compositae plants were evaluated with respect to their anti-inflammatory activity against 12-O-tetradecanoylphorbol-13-acetate (TPA)-induced inflammation in mice. All the triterpenes were found to possess marked inhibitory activity. The 50% inhibitory dose of these compounds with respect to TPA-inflammation (1 microgram) was 0.03-0.2 mg/ear.