Antioxidant properties and structural analysis of phenolic glucosides from bark of <Emphasis Type="Italic">Populus ussuriensis</Emphasis> Kom.

The methanol (MeOH) extract of Populus ussuriensis Kom. bark was analyzed for antioxidant assessing by 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging potential. Among fractions using several solvents, the ethyl acetate (EtOAc) soluble fraction, which showed strong antioxidant activity (IC₅₀ 2.02 ± 0.01 μg/ml), was further purified by Thin layer chromatography (TLC) guided Sephadex LH-20 column chromatography. Three known phenolic glucosides, picein (I), salicortin (II), grandidentatin (III), and that of a new, 2-hydroxycyclohexyl-4′-O-p-coumaroyl-β-d-glucopyranoside (isograndidentatin A), were isolated and their structures were elucidated on the basis of physiochemical and spectroscopic methods. This was the first report of the chemical composition of P. ussuriensis bark. Phenolic glucosides III and IV exhibited strong antioxidant activities, with IC₅₀ values 6.73 ± 0.01 and 6.69 ± 0.01 μM, respectively, comparable to the control (α-tocopherol, IC₅₀ 6.80 ± 0.01 μM). P. ussuriensis bark EtOAc-soluble fraction and compounds III and IV could be used as biopreservatives in food applications as well as for cosmetic and medicinal preparations, to alleviate oxidative stress.     

Identification and evaluation of antioxidant activities of bamboo extracts

The antioxidant activity of solvent extracts from two main bamboo species, moso bamboo (Phyllostachys pubescens) and madake bamboo (P bambusoides) in Japan, was first evaluated by scavenging free radical of 1,1-diphenyl-2-picrylhydrazyl (DPPH), the inhibition activity for peroxidation of linoleic acid, and the reduction power. The methanol-extracts of moso bamboo culms and madake bamboo leaves presented stronger antioxidant activity compared with DPPH scavenging activity. Methanol-extract of moso bamboo culms was further fractionated by different solvents and n-butanol soluble fraction exhibited the most significant activity in the DPPH scavenging assay. The fractionation of n-butanol soluble extract was isolated by silica gel column with gradient mixture solvent of chloroform and methanol. The isolated fractions were directed by the antioxidant activity measured by scavenging the stable DPPH free radical. It was observed that most of the eluted fractions showed the antioxidative activity. Fractions acquired from elution with the mixture solvent of chloroform and methanol (10:1-5:1) showed stronger antioxidant activity than the other fractions.     

Heartwood extractives from the Amazonian trees <Emphasis Type="Italic">Dipteryx odorata,Hymenaea courbaril</Emphasis>, and <Emphasis Type="Italic">Astronium lecointei</Emphasis> and their antioxidant activities

Heartwood extracts from Amazonian trees cumaru-ferro (Dipteryx odorata), jatoba (Hymenaea courbaril), and guarita (Astronium lecointei) exhibit antioxidant activities comparable with that of α-tocopherol, a well-known antioxidant. This article reports the characterization of the antioxidant compounds in the extracts of the three heartwoods. Silica gel column chromatography of the cumaru-ferro EtOAc extract yielded (−)-(3R)-7,2′,3′-trihydroxy-4′-methoxyisoflavan and (+)-(3R)-8,2′,3′-trihydroxy-7,4′-dimethoxyisoflavan. Silica gel column chromatography followed by preparative high-performance liquid chromatography of the jatoba EtOAc extract yielded (−)-fisetinidol and (+)-trans-taxifolin. Chemical structures were assigned using electron-ionization mass spectrometry, ¹H and ¹³C nuclear magnetic resonance (NMR) spectroscopy including nuclear Overhauser effect spectroscopy (NOESY), as well as optical rotation and circular dichroism. Gas chromatography-mass spectrometry demonstrated that the isolated compounds were predominant in the EtOAc extracts. In the guarita EtOAc extract, catechin and gallic acid were identified by comparing their retention times and mass fragmentation patterns with those of authentic samples. Antioxidant activity determined by the 1,1-diphenyl-2-picrylhydrazyl assay demonstrated that all these compounds had activities comparable with that of α-tocopherol. Part of this report was presented at the 57th Annual Meeting of the Japan Wood Research Society, Hiroshima, August 2007     

Chemical constituents from Gmelina arborea bark and their antioxidant activity

Gmelina arborea Roxb. is a fast-growing species and is known to have been used in traditional Indian medicine. Chemical constituents from the bark have not been reported, although some chemical constituents from part of this plant (heartwood, leaf, and root) are known. In this study, the bark meal was successively extracted with acetone and methanol. Fractionation of the acetone extract with n-hexane, diethyl ether, and ethyl acetate and subsequent chromatographic separation of the fractions led to the isolation of four compounds. The diethyl ether-soluble fraction yielded tyrosol [2-(4-hydroxyphenyl)ethanol] (1); (+)-balanophonin (2), an 8-5′ neolignan, with opposite optical rotation to known (−)-balanophonin; and gmelinol (3), a known lignan. The ethyl acetate-soluble fraction afforded a new phenylethanoid glycoside to the best of our knowledge, which was identified as (−)-p-hydroxyphenylethyl[5′″-O-(3,4-dimethoxycinnamoyl)-β-d-apiofuranosyl(1′" → 6′)]-β-d-glucopyranoside (4). From the methanol extract, two known compounds, 2,6-dimethoxy-p-benzoquinone (5) and 3,4,5-trimethoxyphenol (6), were isolated and identified. The 1,1-diphenyl-2-picrylhydrazyl (DPPH) free radical scavenging assay of the identifi ed compounds indicated that 3,4,5-trimethoxyphenol (6) exhibited moderate activity. Part of this report was presented at the 57th and 58th Annual Meetings of the Japan Wood Research Society, Hiroshima and Tsukuba, August 2007 and March 2008, respectively     

Evaluation of biological activities of extracts from the fruiting body of <Emphasis Type="Italic">Pleurotus citrinopileatus</Emphasis> for skin cosmetics

Pleurotus citrinopileatus Singer has recently become a popular delicacy in East Asian countries. We prepared a methanol extract, soluble fractions from the methanol extract, and a hot water extract of the fruiting bodies of P. citrinopileatus. The biological activities such as melanin biosynthesis inhibition, tyrosinase inhibition, antioxidant activities [1,1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging, oxygen radical absorbance capacity (ORAC), and superoxide dismutase (SOD)-like activity], antibacterial activities, and antihyaluronidase activities of these extracts were evaluated. We found that the n-hexanesoluble, diethyl ether-soluble, and ethyl acetate-soluble fractions exhibited melanin biosynthesis inhibition in B16 melanoma cells, as well as antioxidant (ORAC) and antibacterial activities. However, the n-butanol-soluble and water-soluble fractions and the methanol and hot water extracts exhibited antioxidant (DPPH radical scavenging, SOD-like activity) and antihyaluronidase activities. These results indicate that the fruiting bodies of P. citrinopileatus have the potential to be used as an ingredient in skin cosmetics.     

12个楸树无性系叶片多酚含量与抗氧化活性

自由基具有强氧化性,机体衰老及多种疾病如肿瘤、炎症、神经退行性疾病、动脉粥样硬化等的诱发促进机制都与自由基有关[1]。自由基的减少,不仅要靠自身的清除系统,还需要外部抗氧化剂的协助。近年来,关于合成抗氧化剂的副作用受到人们更多的关注,因此,寻找安全、高效的植物源类抗氧化剂,已成为食品领域研究的热点。楸树(Catalpa bungei C.A.Mey.)为紫葳科(Bignoniaceae)梓属植物,落叶乔木,《本草纲目》记载楸树树皮、叶具有药     

Comparison of bioactive compounds content, free radical scavenging and anti-acne inducing bacteria activities of extracts from the mangosteen fruit rind at two stages of maturity

Contents of bioactive components, free radical scavenging and anti-acne producing bacteria activities of young and mature fruit rind extracts of mangosteen were compared. The young fruit rind extract contained significantly higher contents of phenolics and tannins and promoted higher free radical scavenging activity than the mature fruit rind extract, while the later extract contained higher contents of flavonoids and α-mangostin xanthone and gave higher anti-acne producing bacteria activity than the young fruit rind extract. Thus, the young and mature stages of mangosteen fruit rind should be beneficial for further development of antioxidant and anti-acne pharmaceutical preparations, respectively.     

山竹果皮提取物抗氧化活性研究

采用DPPH自由基清除能力、超氧自由基清除能力、β-胡萝卜素漂白抑制、还原力测定及抗脂质过氧化等试验方法对山竹果皮提取物及其二氯甲烷可溶部分、正丁醇可溶部分、水可溶部分进行抗氧化活性评估,同时对总酚含量进行测定。结果表明,山竹果皮提取物的各分离部位以正丁醇可溶部分的抗氧化活性最好,总酚含量也最高。因此,山竹果皮提取物正丁醇可溶部分具有极佳的抗氧化能力,有进一步开发应用的价值。     

Antioxidant properties of monomeric,oligomeric, and polymeric fractions in hot water extract from <Emphasis Type="Italic">Pinus radiata</Emphasis> bark

Hot water extract (HWE) from Pinus radiata bark was fractionated into monomeric polyphenol (MPP), oligomeric proanthocyanidin (OPA), and polymeric proanthocyanidin (PPA) fractions by monitoring the UV-visible spectrum of the eluted fractions. Nine polyphenols were identified in MPP: three phenolic acids and six flavonoids. The major compounds of MPP were taxifolin (456 μg/mg), catechins (240 μg/mg), and protocatechuic acid (46.2 μg/mg). The OPA components ranged from dimers to hexamers. PPA comprised procyanidin (PC, 94%), a small amount of prodelphinidin (PD, 6%), and also the higher trans configuration, rather than the cis configuration, of C2-C3. The average molecular weight (Mw, Mn), polydispersity (Mw/Mn), and DP of PPA were 3,800 (Mw), 1,200 (Mn), 3.2 and 13, respectively. The potential antioxidant activities of HWE and the three fractions were estimated using proton- or electron-donating assays containing 1,1-diphenyl-2-picrylhydrazyl (DPPH) free radical, 2,2′-azinobis(3-ethylbenzothiazoline-6-sulfonate) (ABTS) radical cation, superoxide anion (O₂^•−), hydrogen peroxide (H₂O₂), reducing power and lipid peroxidation. All the bark fractions exhibited potent quenching abilities against both commercially available radicals (DPPH•, ABTS^•+) and chemically induced radicals (H₂O₂, O₂^•−), as well as strong reducing power and inhibitory activity of lipid peroxidation. Particularly, OPA showed a hydrogen peroxide scavenging activity significantly higher (p < 0.05) than that of the other fractions. From 2-thiobarbituric acid reactive substances and ferric thiocyanate assays, PPA was suspected to act by essentially delaying the formation of hydroperoxide by quenching free oxygen radicals that operates in oil-in-water emulsion.     

Antioxidant activity of extracts from <Emphasis Type="Italic">Calocedrus formosana</Emphasis> leaf,bark, and heartwood

Calocedrus formosana Florin (Cupressaceae) is an endemic tree to Taiwan. To evaluate the antioxidant activity of the plant extracts from heartwood, bark, and leaf of C. formosana, assays for 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical and superoxide anion scavenging activities, as well as prevention of DNA strand cleavage were performed in this study. Similar IC₅₀ values against the DPPH radical were found for the heartwood and bark extracts at approximately 23µg/ml. Moreover, the heartwood extract exhibited the highest inhibitory activity against superoxide radicals among the test samples; a 2.3-fold lower value of IC₅₀ for superoxide radical inhibition was found in the heartwood extract relative to that of (+)-catechin. Much less effect on inhibition of DPPH and superoxide radicals was found from the leaf extract of C. formosana. More than 70% of superoxide radicals were inhibited in the presence of 10µg/ml heartwood extract, whereas only 15% inhibition was obtained from the leaf extract. The heartwood extract, at a dose of approximately 0.5mg/ml, apparently completely prevented the X174 supercoiled DNA cleavage induced by ultraviolet photolysis of H₂O₂, as judged by agarose gel electrophoresis. This report also suggests that the antioxidant activities of the plant extracts of C. formosana are in good correlation with their phenolic contents.     

Anti-inflammatory, antioxidant and antifungal furanosesquiterpenoids isolated from Commiphora erythraea (Ehrenb.) Engl. resin

The topical anti-inflammatory, free radical scavenging and antifungal activities of essential oils and extracts of Commiphora erythraea (Ehrenb.) Engl. resin were investigated. The hexane extract significantly inhibited oedema when applied topically in Croton oil-induced ear oedema assay in mice. The same extract showed antioxidant activity in DPPH radical scavenging assay. A bioguided separation of the hexane extract led to the isolation of furanosesquiterpenoids 1 and 2 that showed a weak antifungal activity, while compounds 3-5 resulted to be antioxidant (EC₅₀ 4.28, 2.56 and 1.08 mg/mL, respectively) and anti-inflammatory (30, 26 and 32% oedema reduction, respectively).     

Role of Eucalyptus globulus wound wood extractives: evidence of superoxide dismutase‐like activity

Superoxide dismutase‐like activity of crude Eucalyptus globulus extracts obtained from new wound wood was measured using the water‐soluble tetrazolium salt (WST)‐1 assay. This in vitro assay determined the activity of superoxide radicals scavenging in a xanthine oxidase system. The 50% inhibition (IC₅₀) of formazan formation was estimated for fractionated samples and purified compounds isolated from the crude wound wood extract, i.e. engelitin and pedunculagin. Standards of gallic acid and pentagalloyl glucose were also measured. Fraction II as well as the compounds pentagalloyl glucose and pedunculagin showed the highest levels of antioxidant activity. Subsequent analysis of fraction II by high‐performance liquid chromatography (HPLC) coupled with negative ion electrospray mass spectrometry revealed the fraction to be dominated by hydrolysable tannins including pedunculagin, di‐, tri‐ and tetragalloylglucoses. These preliminary results provide some evidence for an antioxidant role of secondary metabolites in tree wound repair and defence.     

Evaluation of biological activities of extracts from 22 African tropical wood species

Heartwoods of 22 African tropical wood species were extracted with methanol and the contents of total phenolic compounds in these extracts were measured. Three bioassays were conducted to evaluate the antioxidant activity, tyrosinase inhibitory activity, and antifungal activity of the methanol extracts. The results indicated that the extracts from 13 species exhibited high antioxidant potential, and their inhibitory concentrations that caused 50% scavenging of the 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical (IC₅₀) were less than 10 μg/ml. The crude extract from Cylicodiscus gabunensis showed the highest antioxidant activity, and was even higher than that of (+)-catechin, which is known as a potent antioxidant. There was a good correlation between the antioxidant activity and the content of total phenolic compounds, indicating that phenolic compounds played a predominant role in the antioxidant property of the wood extracts. Among all 22 species, only 1 species, Milicia excelsa, contained extractives that showed very high tyrosinase inhibitory activity. The extracts from 9 species showed high antifungal activity. No consistent relationship was observed between the tyrosinase inhibitory activity or antifungal activity and the content of total phenolics in the extracts. Part of this article was presented at the 56th Annual Meeting of the Japan Wood Research Society, Akita, August 2006     

Chemical composition and antioxidant capacity of the aqueous extract of <Emphasis Type="Italic">Phellodendron amurense</Emphasis>

The aqueous extract of Phellodendron amurense Rupr. (Amur Cork Tree) provides a rich source of antioxidants and chemical compounds, and can be used for food and wood preservative materials. In this study, we characterized the chemical composition of this extract by GC and GC/MS. The antioxidant capacity was evaluated using a variety of antioxidant assays (superoxide radical, hydroxyl radical, nitric oxide radical, and DPPH radical scavenging activity). Additionally, total polyphenolic content was determined. Phenolic acids and acetone derivatives were major compounds of the extract capable of scavenging the DPPH free radical and reducing ferric ions. DPPH and ferric ion reduction results were strongly correlated with total phenolic content of the extract which also exhibited strong nitric oxide, hydroxyl radical scavenging and superoxide anion radical scavenging activities.     

Screening antiacne potency of Indonesian medicinal plants: antibacterial,lipase inhibition,and antioxidant activities

Indonesian medicinal plants were screened as potential sources of antiacne agents. The screening methods were performed using antibacterial assay against Propionibacterium acnes, lipase inhibitor assay, and antioxidant assay. The results showed that from 40 plant materials extracted with methanol and 50% ethanol in water, Caesalpinia sappan was the best extract based on the combined activities: antibacterial (minimum inhibitory concentration 0.13 mg/ml; minimum bactericidal concentration 0.25 mg/ml), lipase inhibitory [50% inhibitory concentration (IC₅₀) 120.0 μg/ml], and antioxidative (IC₅₀ 6.47 μg/ml). Another prospective extract is Intsia palembanica based on its lipase inhibitory activity (IC₅₀ 4.1 μg/ml) and antioxidant activity (IC₅₀ 3.87 μg/ml). Part of this report was presented at the 58th Annual Meeting of the Japan Wood Research Society, Tsukuba, March 2008     

Structure and antioxidant activity of polysaccharide POJ-U1a extracted by ultrasound from Ophiopogon japonicus

An ultrasonic technique was employed to extract polysaccharides from Ophiopogon japonicus. The ultrasonic extracted polysaccharides (POJ-U) were purified, and POJ-U1a (a homogeneous fraction) was obtained. The structural characteristics of POJ-U1a were investigated by infrared spectra, gas chromatography, high performance liquid chromatography, periodate oxidation, Smith degradation, methylation analysis, gas chromatography–mass spectrometry and nuclear magnetic resonance spectroscopy. The results indicated that the relative molecular weight of POJ-U1a was 4.02 × 10³ Da. POJ-U1a was an α-configuration polysaccharide with a highly branched structure, and consisted of pyranoside and funanside. The backbone of POJ-U1a consisted of 1,6-α-d-glucopyranose and 1,3,6-α-d-glucofuranose in the molar ratio of 7:3, while the branched chains were mainly composed of 1,3-α-d-glucopyranose and 1-α-d-glucopyranose in the molar ratio of 1:3. The branched structure of POJ-U1a was proved intuitively by AFM. Significant antioxidant activity of POJ-U1a has been proved as shown by its DPPH radical scavenging, hydrogen radical scavenging and superoxide anion scavenging activities, which indicated that POJ-U1a showed strong antioxidant activity.     

Antioxidant activity of liquors from aqueous treatments of Pinus radiata wood

Non-isothermal, aqueous treatments of Pinus radiata wood were carried out to reach maximal temperatures in the range 210–240°C, and the liquors from the treatments were analysed for phenolic content and antioxidant activity using several tests (,-diphenyl--picrylhydrazyl (DPPH) radical scavenging, hydroxyl radical scavenging, Trolox equivalent antioxidant capacity, -carotene bleaching and reducing power). Increased severity resulted in increased yields in phenolics (up to 1.5 g phenolic compounds/100 g oven-dry wood) and improved antioxidant activity. The DPPH radical scavenging capacity of compounds present in autohydrolysis liquors and the -carotene bleaching ability of the compounds extracted with ethyl acetate from liquors were higher than those of synthetic antioxidants. The fractions solubilised in autohydrolysis treatments were also effective as hydroxyl and ABTS radical scavengers. The autohydrolysis liquors and their ethyl acetate soluble fraction showed reducing power in the range reported for extracts from other natural sources.     

印度黄檀叶多酚提取工艺优化及抗氧化活性研究

目的]印度黄檀叶含有多酚及类黄酮物质,研究印度黄檀叶多酚及其抗氧化活性,可为其利用提供依据。[方法]以印度黄檀叶为原料,乙醇为提取液,经单因素实验与正交试验设计,检测在不同乙醇浓度、提取时间、提取温度及超声功率120 w时3个因素进行响应面优化试验,确定印度黄檀多酚的提取工艺;同时,鉴定印度黄檀叶乙醇-水提取液对DPPH-自由基的清除能力。[结果]低浓度印度黄檀叶多酚能发挥更强的抗氧化能力,其提取液对清除DPPH自由基的半数抑制质量浓度(IC_(50))约为3.2 mg·L~(-1),略大于Vc的2.5 mg·L~(-1);不过,其还原能力略低于Vc。[结论]印度黄檀叶内富含多酚类物质,具有很强的体外抗氧化活性,可作为天然抗氧化植物资源开发利用。     

Composition and biological activity of essential oil of Achillea ligustica All. (Asteraceae) naturalized in central Italy: Ideal candidate for anti-cariogenic formulations

Essential oil from flowers (FL) and vegetative parts (VP) of Achillea ligustica (Asteraceae), naturalized after cultivation in central Italy, was investigated by GC–FID and GC–MS. The most abundant components were linalool, viridiflorol, β-pinene, 1,8-cineole and terpinen-4-ol. The antioxidant assays (DPPH and ABTS radical scavenging assays, and β-carotene bleaching test) demonstrated a moderate activity of essential oils. The antimicrobial activity was evaluated by the broth micro-dilution method on 6 microbial strains and showed to be quite strong against the cariogenic Gram-positive Streptococcus mutans, suggesting that this essential oil could be a valid candidate for anti-cariogenic formulations. Moderate cytotoxic activity was observed in assays on four tumour cell lines by MTT assay.     

Constitutive phenolics of Harpephyllum caffrum (Anacardiaceae) and their biological effects on human keratinocytes

Assessment of the UV protecting potential of an aqueous methanol leaf extract of Harpephyllum caffrum proved that it possesses a distinct radical scavenging effect and inhibits the production of the proinflammatory cytokine IL-6 by human keratinocytes (HaCaT cells) following UV radiation. Phytochemical investigation of this extract led to isolation and structural determination of the hitherto unknown phenolics, kaempferol 3-O-(2″-sulphatogalactopyranoside), its quercetin analogue and 3-methoxyellagic acid 4-O-galactopyranoside in addition to 18 known phenolic compounds. The structures were determined by spectroscopic and conventional methods of analysis. Flavonoid sulphatoglycosides which have been rarely found in nature were major phenolic constituents of this plant, and this is the first report of the isolation of any of them from Anacardiaceae. The extract was found to diminish UV phototoxic reaction of keratinocytes. However, the isolated kaempferol sulphatogalactopyranoside did not interact with UVB triggered IL-6 production of HaCaT keratinocytes.