金合欢醇的资源及其生物活性应用研究进展

根据国内外研究报道,综述了金合欢醇的主要资源及其生物活性应用。金合欢醇广 泛存在于植物体的花、叶、茎等部位之中,尤其是在一些中草药植物和香料植物中具有较高含 量。金合欢醇型细毛樟、辛夷花、枇杷叶等是具有较好开发利用前景的重要资源。金合欢醇是 中草药植物的重要活性成分之一,也是一些重要香料植物精油中的主要香料成分之一,因此,在医药、农药、化 妆品和日用化工等需要其生物活性的方面已经得到较多应用,并具有较好的前景。

金合欢醇羟基的溴取代反应研究

通过使用自行合成的高效溴取代试剂二溴三苯基膦 ,成功地从金合欢醇合成了金合欢基溴 ,并用化学分析的方法测定其含量。主要反应条件为 :苯作溶剂 ,室温反应 3h。因为二溴三苯基膦遇水极易分解 ,因此反应中使用的溶剂需要进行干燥处理。溴化反应时为了除去反应中生成的HBr ,需要加入吡啶使之成盐析出。反应完毕后 ,通过蒸除溶剂然后加入正己烷溶出金合欢基溴的方法除去反应中生成的三苯基氧化膦。本合成反应具有操作简单和得率较高的特点 。

金合欢醇合成方法的研究进展

金合欢醇存在于某些植物的花、叶子和种子的精油中,可应用于调香、抗菌、杀虫和制药等领域。金合欢醇除了可由天然原料直接分离得到外,还有多种化学合成方法和生物合成方法。由橙花叔醇、香叶基衍生物和其它多种原料经不同的化学反应手段,可以合成金合欢醇。长膜壳涤虫的代谢和穿心莲的组织培养等生物合成法,也可以得到金合欢醇。

金合欢醇和烟碱对苹果黄蚜联合毒杀作用

以苹果黄蚜AphiscitricolavanderGoot为试虫,对金合欢醇和烟碱的联合杀蚜活性进行了测定,以期为开发植物源杀蚜剂产品奠定基础。室内毒力测定采用微量点滴法;田间药效试验参照国家标准进行。金合欢醇和烟碱混用具有明显的杀蚜增效作用,在最佳质量配比(金合欢醇:烟碱=4.82:1)下,共毒系数(CTC)达151.63;经过对溶剂、表面活性剂等助剂的筛选,研制出6%烟碱·金合欢醇可溶液剂,配方为金合欢醇(5%)、烟碱(1%)、表面活性剂(10%)、溶剂(84%),质量检测符合可溶液剂国家质量标准;田间药效试验表明,以126.0 g a.i./hm^2常量喷雾,药后7 d对小麦上的麦长管蚜Sitobion avenae Fabricius和麦二叉蚜Schizaphis graminum(Rondani)混合种群的防效达87.80%,以115.5 g a.i./hm^2常量喷雾,药后7d对苹果黄蚜的防效在81%以上。可见,金合欢醇和烟碱复配具有显著的杀蚜增效作用,具有进一步开发潜力。

天然除臭剂——金合欢醇

原德威龙(现 Symrise 公司)开发了天然除臭剂——金合欢醇(Farnesol)。金合欢醇是非环式倍半萜醇的一种,在铃兰、茉莉油、柑桔类的果皮油、玫瑰油、伊兰伊兰油以及绿茶等中都含有。虽然,通过香水掩盖、防汗剂、洗涤剂以及抗菌剂都可以消除体臭,但金合欢醇对细菌的生长繁殖有阻碍和抑制的作用。经抑菌选择试验,金合欢醇对汗臭产生菌有选择性的抑制作用,而且对产生痤疮(青春痘)

催化剂对橙花叔醇异构化反应影响的研究

钒铝钨酸盐类无机催化剂、原钒酸酯类和原钒酸硅酯类有机催化剂均可对橙花叔醇 的催化异构化反应起作用。研究结果表明,3类催化剂中催化效果较好的分别是偏钒酸铵、 原钒酸丁酯和原钒酸三苯基硅酯,它们作为单一催化剂均可使橙花叔醇发生较好的异构化反 应,金合欢醇的产率分别为37．1％、37．2％和32．O％。在单一催化剂对比研究的基础上,将 偏钒酸铵、原钒酸丁酯和原钒酸三苯基硅酯等3种比较好的催化剂进行了多元复配应用试验,研究结果表明, 这3种催化剂的复配应用虽然可以轻微提高橙花叔醇异构化反应效果,但未表现出明显的增效和协同作用。

新香料植物细毛樟的研究

细毛樟是一种新香料植物,根据叶油主要成分可分为9个化学型:金合欢醇型、香叶醇型、芳樟醇型、甲基丁子香酚型、樟脑型、龙脑型、柠檬醛型、1,8-桉叶油素型和榄香素型。其中金合欢醇型含量为54％～71％,香叶醇型为86％～98％,芳樟醇型为84％～98％,甲基丁子香酚型为69％～89％。经栽培和分析,金合欢醇型有性后代50％以上、香叶醇型56％以上、芳樟醇型57％以上、甲基丁子香酚型71％以上的植株,可保持母本的特性。无性后代很少变异。

普通大蓟马聚集信息素的分离和鉴定

【目的】普通大蓟马Megalurothrips usitatus是我国华南地区重要的豆科害虫,给我国豇豆种植产业带来巨大损失。开发利用基于聚集信息素的引诱剂是普通大蓟马的绿色防控措施之一,对于普通大蓟马生物防治具有重要意义。【方法】采用Y型嗅觉仪测定普通大蓟马雌雄成虫对其雌虫和雄虫气味源的嗅觉反应;用顶空固相微萃取法(head space solid-phase microextraction, HS-SPME)和溶液浸提法提取普通大蓟马雌雄成虫挥发物;应用气质联用仪(gas chromatography-mass spectrometry, GC-MS)对收集的气体挥发物和正己烷提取物进行活性成分分离鉴定;应用Y型嗅觉仪测定人工合成聚集信息素组分对雌雄成虫的引诱效果。【结果】行为学试验结果表明,普通大蓟马雄成虫气味源对其雌雄成虫均具有显著的引诱作用,而雌成虫气味源则没有。顶空固相微萃取法和溶液浸提法均可提取雄成虫挥发物主要组分,但顶空固相微萃取法获得的TIC图基线平稳,杂峰少,提取效果优于溶剂浸提法。GC-MS分析结果表明,普通大蓟马雄成虫挥发物中主要含有1种化合物,为反式,反式-金合欢醇乙酸酯[(E,E)-farnesyl acetate],该化合物在雌成虫挥发物中不存在。室内行为学实验结果表明,特定剂量的人工合成的(E,E)-farnesyl acetate对普通大蓟马雌雄成虫均具有显著的引诱作用。【结论】本研究证明了普通大蓟马雄成虫可以释放聚集信息素,并鉴定了其主要组分(E,E)-farnesyl acetate,为应用聚集信息素开展普通大蓟马的监测和诱杀提供了基础。

气质联用追踪筛选辛夷挥发油提取工艺

采用GC-MS为追踪手段,确定辛夷挥发油提取优选工艺为:辛夷粗粉采用水蒸气蒸馏法提取3～4h,提取率约为86%。

果树叶的价值

人们常说:花的事业是美丽的,果的事业是甜蜜的,叶的事业是伟大的。叶伟大之处就在于,她与世无争,总是谦逊地垂着她的绿荫,甘作鲜花的陪衬,果熟霜染之时,又叶落归根,肥沃大地。她除了具有光合和蒸腾两大作用外。

神农香菊试种与精油提取研究初报

一种经济价值很高的新型芳香植物——香叶菊,为中国科学院武汉植物研究所植物学家们在神农架资源考察中首次发现,故定名“神农香菊”。系多年生草本,花茎多,花量大,花期香气袭人。从根、茎、叶、花提取的香精,化学性能稳定,可用于食品。

麝香秋葵籽精油的化学成分

麝香秋葵(Abelmoschus moschatus L. Medicus)又称黄葵,系锦葵科一年生或多年生草本植物,生长在热带、亚热带地区;在我省多分布于南部和西南部,并从1983年开始有了一定规模的人工种植。麝香秋葵籽具有麝香、花香香气,从中提取的精油是一种名贵香料。为新近开发之麝香秋葵籽系列产品的应用提供依据,我们对其精油进行了化学成分分析。

Influences of trans-trans farnesol,a membrane-targeting sesquiterpenoid,on Streptococcus mutans physiology and survival within mixed-species oral biofilms

Trans-trans farnesol (tt-farnesol) is a bioactive sesquiterpene alcohol commonly found in propolis (a beehive product) and citrus fruits, which disrupts the ability of Streptococcus mutans (S. mutans) to form virulent biofilms. In this study, we investigated whether tt-farnesol affects cell-membrane function, acid production and/or acid tolerance by planktonic cells and biofilms of S. mutans UA159. Furthermore, the influence of the agent on S. mutans gene expression and ability to form biofilms in the presence of other oral bacteria (Streptococcus oralis (S. oralis) 35037 and Actinomyces naeslundii (A. naeslundii) 12104) was also examined. In general, tt-farnesol (1 mmol·L-1) significantly increased the membrane proton permeability and reduced glycolytic activity of S. mutans in the planktonic state and in biofilms (P<0.05). Moreover, topical applications of 1 mmol·L-1 tt-farnesol twice daily (1 min exposure/treatment) reduced biomass accumulation and prevented ecological shifts towards S. mutans dominance within mixed-species biofilms after introduction of 1% sucrose. S. oralis (a non-cariogenic organism) became the major species after treatments with tt-farnesol, whereas vehicle-treated biofilms contained mostly S. mutans (>90% of total bacterial population). However, the agent did not affect significantly the expression of S. mutans genes involved in acidogenicity, acid tolerance or polysaccharide synthesis in the treated biofilms. Our data indicate that tt-farnesol may affect the competitiveness of S. mutans in a mixed-species environment by primarily disrupting the membrane function and physiology of this bacterium. This naturally occurring terpenoid could be a potentially useful adjunctive agent to the current anti-biofilm/anti-caries chemotherapeutic strategies.

Farnesol inhibits development of caries by augmenting oxygen sensitivity and suppressing virulence-associated gene expression in Streptococcus mutans

Streptococcus mutans is a primary etiological agent of dental caries.Farnesol,as a potential antimicrobial agent,inhibits the development of S.mutans biofilm.In this study,we hypothesized that farnesol inhibits caries development in vitro and interferes with biofilm fonnation by regulating virulence-associated gene expression.The inhibitory effects of farnesol to S.mutans biofilms on enamel surfaces were investigated by determining micro-hardness and calcium measurements.Additionally,the morphological changes of S.mutans biofilms were compared using field emission scanning electron microscopy and confocal laser scanning microscopy,and the vitality and oxygen sensitivity of S.mutans biofilms were compared using MTT assays.To investigate the molecular mechanisms of farnesol's effects,expressions of possible target genes luxS,brpA,ffh,recA,nth,and smx were analyzed using reverse-transcription polymerase chain reaction(PCR) and quantitative PCR.Farnesol-treated groups exhibited significantly higher micro-hardness on the enamel surface and lower calcium concentration of the supernatants as compared to the-untreated control.Microscopy revealed that a thinner film with less extracellular matrix formed in the farnesol-treated groups.As compared to the-untreated control,farnesol inhibited biofilm formation by 26.4%with500 μmol/L and by 37.1%with 1,000 μmol/L(P< 0.05).Last,decreased transcription levels of luxS,brpA,ffh,recA,nth,and smx genes were expressed in farnesol-treated biofilms.In vitro farnesol inhibits caries development and S.mutans biofilm formation.The regulation of luxS,brpA,ffh,recA,nth,and smx genes may contribute to the inhibitory effects of farnesol.

7,8,7,′8′-四氢番茄红素的合成

以金合欢醇为起始原料,制备了金合欢基季磷盐(3);3与2,7-二甲基-2,4,6-辛三烯-1,8-二醛发生双分子W ittig反应合成了7,8,7,′8′-四氢番茄红素,总产率64.2%。其结构经UV,1H NMR,IR和MS表征。

用一种新的混合香料做斑贴试验检测出用目前使用的混合香料未检测出的香料敏感者

The currently used 8%fragrance mix (FM I) does not identify all patients with a positive history of adverse reactions to fragrances. A new FM II with 6 frequently used chemicals was evaluated in 1701 consecutive patients patch tested in 6 dermatological centres in Europe. FM II was tested in 3 concentrations-28%FM II contained 5%hydroxyisohexyl 3cyclohexene carboxaldehyde (Lyral.), 2%citral, 5%farnesol, 5%coumarin, 1%citronellol and 10%α-hexyl-cinnamic aldehyde; in 14%FM II, the single constituents’concentration was lowered to 50%and in 2.8%FM II to 10%. Each patient was classified regarding a history of adverse reactions to fragrances:certain, probable, questionable, none. Positive reactions to FM I occurred in 6.5%of the patients. Positive reactions to FMII were dose-dependent and increased from 1.3%(2.8%FM II), through 2.9%(14%FM II) to 4.1%(28%FM II). Reactions classified as doubtful or irritant varied considerably between the 6 centres, with a mean value of 7.2%for FM I and means ranging from 1.8%to 10.6%for FM II. 8.7%of the tested patients had a certain fragrance history. Of these, 25.2%were positive to FM I; reactivity to FM II was again dose-dependent and ranged from 8.1%to 17.6%in this subgroup. Comparing 2 groups of history-certain and none-values for sensitivity and specificity were calculated:sensitivity:FM I, 25.2%; 2.8%FM II, 8.1%; 14%FM II, 13.5%; 28%FM II, 17.6%; specificity:FM I, 96.5%; 2.8%FM II, 99.5%; 14%FM II, 98.8%; 28%FM II, 98.1%. 31/70 patients (44.3%) positive to 28%FMII were negative to FM I, with 14%FM II this proportion being 16/50 (32%). In the group of patients with a certain history, a total of 7 patients were found reacting to FM II only. Conversely, in the group of patients without any fragrance history, there were significantly more positive reactions to FM I than to any concentration of FM II. In conclusion, the new FM II detects additional patients sensitive to fragrances missed by FMI; the number of false-positive reactions is lower with FM II than with FM I. Considering sensitivity, specificity and the frequency of doubtful reactions, the medium concentration, 14%FM II, seems to be the most appropriate diagnostic screening tool.

识别真假枇杷叶

枇杷叶又名巴叶,为蔷薇科植物枇杷的干燥叶,是常用中药,始载于《名医别录》,因其叶似琵琶,故名。全年皆可采收,采摘后,晒至七、八成干时,扎成小把,再晒干即可入药。枇杷叶性凉,味苦,入肺、胃经。据测定,含有挥发油,主要成分为橙花叔醇和金合欢醇,还含有月桂烯、芳樟醇、樟脑、橙花醇、多种氨基酸和多种维生素等成。

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用一种新的混合香料做斑贴试验:各组分的反应性和相关化妆品中的化学检测

A new fragrance mix (FM II), with 6 frequently used chemicals not present in the currently used fragrance mix (FM I), was evaluated in 6 dermatological centres in Europe, as previously reported. In this publication, test results with the individual constituents and after repeated open application test (ROAT) of FM II are described. Furthermore, cosmetic products which had caused a contact dermatitis in patients were analysed for the presence of the individual constituents. In 1701 patients, the individual constituents of the medium (14%) and the highest (28%) concentration of FM II were simultaneously applied with the new mix at 3 concentrations (break-down testing for the lowest concentration of FM II (2.8%) was performed only if the mix was positive). ROAT was performed with the concentration of the FM II which had produced a positive or doubtful (+or ?+) patch test reaction. Patients’products were ana-lysed for the 6 target compounds by gas chromatography-mass spectrometry (GC-MS). Results:50 patients (2.9%) showed a positive reaction to 14%FM II and 70 patients (4.1%) to 28%FM II. 24/50 (48%) produced a positive reaction to 1 or more of the individual constituents of 14%FM II and 38/70 (54.3%) to 28%FM II, respectively. If doubtful reactions to individual constituents are included, the break-down testing was positive in 74%and 70%, respectively. Patients with a positive reaction to 14%FM II showed a higher rate of reactions to the individual constituent of the 28%FM II:36/50 (72%). Positive reactions to individual constituents in pa-tients negative to FM II were exceedingly rare. If doubtful reactions are regarded as negative, the sensitivity, specificity, positive predictive value and negative predictive value for the medium concentration of FM II towards at least 1 individual constituent was 92.3%(exact 95%confidence interval 74.9-99.1%), 98.4%(97.7-99.0%), 48%(33.7-62.6%) and 99.9%(99.6-100.0%), respectively. For the high concentration, the figures were very similar. The frequency of positive reactions to the individual constituents in descending order was the same for both FM II concentrations:hydroxyisohexyl 3-cyclohexene carboxaldehyde(Lyral.)>citral>farnesol>citronellol >αhexyl-cinnamic aldehyde (AHCA). No unequivocally positive reaction to coumarin was observed. Lyralwas the dominant individualconstituent,with positive reactions in 36%of patients reacting to 14%FM II and 37.1%to 28%FM II. 5/11 patients developed a positive ROAT after a median of 7 days (range 2-10). The 5 patients with a doubtful or negative reaction to 28%FM II were all ROAT negative except 1. There were 7 patients with a certain fragrance history and a positive reaction to either 28%or 14%FM II but a negative reaction to FM I. Analysis with GC-MS in a total of 24 products obtained from 12 patients showed at least 1-5 individual constituents per product:Lyral. (79.2%), citronellol (87.5%), AHCA (58.3%), citral (50%) and coumarin (50%). The patients were patch test positive to Lyral., citral and AHCA. In conclusion, patients with a certain fragrance history and a negative reaction to FMI can be identified by FM II. Testing with individual constituents is positive in about 50%of cases reacting to either 14%or 28%FM II.