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Total synthesis of a demethoxy-egonol from Styrax obassia.

The total synthesis of a demethoxy-egonol isolated from Styrax obassia, 5-(3-hydroxypropyl)-2-(3',4'-methylenedioxyphenyl)benzofuran (9), is described. The key steps involve the construction of a 2-arylbenzofuran skeleton 7 from methyl 3-(4-hydroxyphenyl)propionate with 2-chloro-2-methylthio-(3',4'-methylenedioxy)acetophenone (6) in the presence of ZnCl2 and successive desulfurization of the resulting product 7.

Benzofurans↗

nor-Lignans from the leaves of Styrax ferrugineus (Styracaceae) with antibacterial and antifungal activity.

Chemical examination of the leaves of Styrax ferrugineus yielded 5-[3''-(beta-D-glucopyranosyloxy)propyl]-7-methoxy-2-(3',4'-dimethoxyphenyl) benzofuran, along with the known nor-lignans 5-(3''-hydroxypropyl)-7-methoxy-2-(3',4'-methylenedioxyphenyl) benzofuran, 5-(3''-hydroxypropyl)-7-methoxy-2-(3',4'-dimethoxyphenyl)benzofuran, 5-[3''-(beta-D-glucopyranosyloxy)propyl]-7-methoxy-2-(3',4'-methylenedioxyphenyl)benzofuran and the lignan, dihydrodehydrodiconiferyl alcohol. All arylpropanoids isolated showed antibacterial and antifungal activities. The structures of the isolates were established by spectroscopic analysis.

Anti-Bacterial Agents↗

Antiulcer action of Styrax camporum and Caesalpinia ferrea in rats. '.

Stem extracts of Styrax camporum Pohl and Caesalpinia ferrea Martius were administered orally and intraperitoneally to rats and effected a decrease in the acute ulceration number. The volume, pH, and hydrochloric acid concentration of gastric secretions were measured after administration of both extracts, atropine, and cimetidine. After oral administration there was a decrease in the gastric secretion volume without modification of the other gastric secretion parameters studied. There were modifications, however, when the extracts were administered intraperitoneally. Analgesy, influence on sleeping time, and spontaneous motor activity test results indicate a probable absence of central action components in the extracts.

Animals↗

Allocation of resources to reproduction in Styrax obassia in a masting year.

An analysis is presented of three possible pathways of reproductive allocation, namely, allocation of resources to reproductive organs from reproductive shoots, from non-reproductive shoots and from the main trunk. These pathways were examined by comparing the amount of storage starch in reproductive shoots, non-reproductive shoots and the main trunk in Styrax obassia, a typical masting tree species, during a year of little flowering (1999) and in a mass-flowering year (2000). In addition, we measured rates of light-saturated photosynthesis in leaves of reproductive and non-reproductive shoots to examine the contribution of photosynthetic production to reproductive costs. In both the main trunk and non-reproductive shoots the pattern of seasonal variation in the amount of starch did not differ between 1999 and 2000. However, in the mass-flowering year, the amount of starch in the reproductive shoots was less than that in non-reproductive shoots during the growing season. Thus, reproductive shoots bore most of the cost of reproduction, although non-reproductive shoots and the main trunk also bore some of the cost. Mass-based rates of light-saturated photosynthesis of the leaves of reproductive shoots were significantly higher than those of non-reproductive shoots during both the flowering and the fruiting period. However, leaves of reproductive shoots had a significantly smaller area, a lower mass per area, and lower concentrations of nitrogen than leaves of non-reproductive shoots, although the number of leaves did not differ between the two types of shoots. Therefore, the amount of photosynthate per shoot was significantly lower in reproductive shoots than in non-reproductive shoots. These results suggest that the cost of reproduction depends predominantly on storage starch in reproductive shoots, although it is still unclear how much photosynthate is allocated to reproductive organs from non-reproductive shoots.

Fertility↗

Fruit set in Styrax obassia (Styracaceae): the effect of light availability, display size, and local floral density.

Maternal reproductive success was examined in Styrax obassia (Styracaceae), a bumble-bee pollinated mass-flowering tree in a cool-temperate deciduous forest in northern Japan. The effects of flower number on the success of individual flowers at three levels (inflorescence, individual, and population) were considered. During 1995 and 1996, variations in size, light availability to branches, floral display size, and fruit set were monitored in 37 out of 211 individual S. obassia trees in a 4-ha forest plot. In addition, the locations of the 211 trees in this plot were mapped and the number of inflorescences in each tree was counted. A multiple regression analysis showed that flower number per inflorescence and inflorescence number per individual had negative effects on fruit set, and inflorescence number of aggregated clumps of flowering trees, tree size, and light resource had positive effects on fruit set although significant level were marginal. It is concluded that pollinator attraction may occur not at the individual tree level, but at the level of a clump of flowering trees. It is also suggested that geitonogamy increased with inflorescence number of tree and inflorescence size and that resource limitation was related to the light condition and variation of tree size.

Journal Article↗

Antisweet natural products. XV. Structures of Jegosaponins A-D from Styrax japonica Sieb. et Zucc.

From the fresh fruits of Strrax japonica Sieb. et Zucc., four new triterpenoid glycosides, named jegosaponins A-D (1-4), were isolated. Their structures were determined on the basis of spectroscopic data and chemical evidence. Compounds 1-4 are 3-O-tetraglycosides of barringtogenol C having an acetyl and a tigloyl or a (2Z)-hexenoyl groups at C-21, 22 and 28. The acylated saponins, 1-4, all showed antisweet activity.

Carbohydrate Sequence↗

Preparation and evaluation of pH-dependent gradient-release pellets for TCM.

This paper is designed to investigate a novel sustained release system for Traditional Chinese Medicinal Compound Recipe (TCMCR) by incorporating three kinds of pH-dependent gradient-release coated pellets into capsules. In our study, dosage reform was conducted on the TCMCR model drug--Guanxin Suhe Wan (GSW), which is in the traditional form of honey bolus, comprising Styrax, Borneolumsyntheticum, Olbanum, Radix aristolochiae and Lignum santali albi. In this study, the beta-CD inclusion complexes were prepared separately for Styrax, Borneolumsyntheticum and the volatile oil extracted from the mixture of Olbanum, Radix aristolochiae and Lignum santali albi. Pellets were prepared in a centrifugal granulator using the powder layering technique and then divided into 3 equal weight portions and coated with HPMC, HPMCP HP-55 and Eudragit L100/S100 to obtain gradient release in stomach, duodenum and jejunum or ileum respectively. On this basis, a pH-dependent sustained-release pellets system, "Guanxin Suhe Sustained-release Capsules"(GSSC), was prepared by mixing the above three kinds of coated pellets at the weight ratio of 1:1:1. Pharmacokinetic (PK) studies between GSW and GSSC were made on male volunteers and isolated guinea pig hearts by plasma drug concentration method and serum pharmacology method respectively. In plasma drug concentration method, Tmax was 0.42 h and 1.08 h for GSW and GSSC respectively, while in the serum pharmacology method, Tmax was 0.56 h and 0.52 h respectively. The relative bioavailability of GSSC to GSW was 95.62% and 121.82% separately in the above two methods, indicating a similarity between the two methods in predicting the PK behavior of GSSC.

Animals↗

The effect of erythrodiol-3-acetate on the expressions of matrix metalloproteinase-1 and type-1 procollagen caused by ultraviolet irradiated cultured primary old aged human skin fibroblasts.

Methanol and aqueous extracts of Styrax japonica used traditionally for the treatments of skin elastic materials were screened in vitro for the matrix metalloproteinase (MMP)-1 inhibitor actions. The methylene chloride soluble fraction of methanol extract from the stems of S. japonica showed significant MMP-1 inhibition in primary old aged human skin fibroblasts caused by ultraviolet (UV) irradiation. Main triterpenoids were isolated by repeated column chromatography. Among them, the triterpenoid erythrodiol-3-acetate reduced the expression of MMP-1 and induced the expression of type-1 procollagen at the protein levels in a dose-dependent manner caused by UV irradiated cultured old aged human skin fibroblasts. Taken together, our results suggest that erythrodiol-3-acetate plays an important role in the skin aging process caused by UV irradiation.

Aged↗

Allergic contact dermatitis to compound tincture of benzoin.

Nineteen cases of allergic contact dermatitis to compound tincture of benzoin are described. Patch testing to individual components revealed positive reactions to all ingredients except aloe. An alternative preparation, Mastisol, was successfully used without primarily inducing allergy. It should be considered for use before benzoin because once allergy to benzoin exists, cross-reactions to Mastisol usually occur. This is probably due to the presence of a common ingredient, styrax gum.

Adolescent↗

Two plant fish-poisons in Lebanon.

The use of a powder for poisoning sea fish off Lebanon is reported for the first time. The powder is prepared from the seeds of storax (Styrax officinalis L) and tubers of common cyclamen (Cyclamen persicum Mill.), both species growing wild in Lebanon. References to the properties of these species are provided.

Animals↗

Insecticidal effects of essential oils from various plants against larvae of pine processionary moth (Thaumetopoea pityocampa Schiff) (Lepidoptera: Thaumetopoeidae).

Along with sulfate turpentine, the essential oils obtained by steam distillation from nine plant species naturally grown in Turkish forests were tested at three different concentrations to evaluate their effectiveness against the larvae of pine processionary moth (Thaumetopoea pityocampa Schiff). The results indicated that the essential oils from the nine species and sulfate turpentine were effective against the larvae of T pityocampa. The most effective essential oil in the control of the larvae was steam-distilled wood turpentine, followed by thyme herb oil, juniper berry oil, laurel leaf oil, lavender flower oil, eucalyptus leaf oil, lavender leaf oil, cypress berry oil, essential oil of styrax and sulfate turpentine, respectively, in terms of mean mortality time. It is therefore feasible to use these essential oils as environment-friendly insecticides in the control of T pityocampa.

Animals↗

A study on inhibitory effects of Siğla tree (Liquidambar orientalis Mill. var. orientalis) storax against several bacteria.

In this study, Siğla (Liquidambar orientalis Mill.) storax (styrax) was investigated for antibacterial activity against Aeromonas hydrophila, Bacillus amyloliquefaciens, B. brevis, B. cereus, B. megaterium, B. subtilis, Corynebacterium xerosis, Enterobacter aerogenes, Enterococcus faecalis, Escherichia coli, E. coli O157:H7, Klebsiella pneumoniae, Listeria monocytogenes, Micrococcus luteus, Mycobacterium smegmatis, Proteus vulgaris, Pseudomonas aeruginosa, P. fluorescens, Staphylococcus aureus and Yersinia enterocolitica. The storax was dissolved in absolute ethanol and was tested at concentrations of 10.0%, 1.0%, 0.4%, 0.2% and 0.1%. Pure ethanol was used for the control. The antibacterial activity of the Siğla storax was determined by using the agar diffusion method. The growths of A. hydrophila, B. amyloliquefaciens, B. megaterium, E. coli, E. coli O157:H7, L. monocytogenes and Y. enterocolitica were not inhibited by any of the concentrations of Siğla storax. The results showed that Siğla storax has antibacterial activity against many bacteria at concentrations of 10.0% and against some bacteria at concentrations of 1.0%, 0.4% and 0.2%.

Anti-Bacterial Agents↗

Anti-Aspergillus activities of plant essential oils and their combination effects with ketoconazole or amphotericin B.

The essential oils from Cedrus atlantica, Styrax tonkinensis, Juniperus communis, Lavandula angustifolia, Melaleuca alternifolia, Pelargonium graveolens, Pogesternon patchouli and Rosmarinus officinalis were analyzed by GC-MS. Antifungal activities of the oils were investigated by disk diffusion assay and the broth dilution method against Aspergillus niger and A. flavus. The effects of geraniol and the essential oil fraction from P. graveolens on the antifungal activity of amphotericin B and ketoconazole were examined using a checkerboard microtiter assay against both Aspergillus fungi. Most of the tested essential oils, with the exception of C. atlantica, J. communis, and P. patchouli, significantly inhibited growth of A. niger and to a lesser extent that of A. flavus, with MICs (minimal inhibitory concentrations) in the range 0.78-12.5 mg/mL. The essential oil fraction of P. graveolens and its main components, geraniol and citronellol, exhibited additive effects with amphotericin B and with ketoconazole against both Aspergillus species, resulting in fractional inhibitory concentration (FIC) indices ranging from 0.52 to 1.00.

Amphotericin B↗