Isolement et identification de composés phénoliques et monoterpéniques de la mousse de chêne (Evernia prunastri (L.) Ach.)

The composition of different oakmoss extracts was investigated by combined gas chromatography/mass spectrometry. A series of 38 compounds – especially phenol derivatives and monoterpenes – was identified, 22 of which have not yet been reported as constituents of oakmoss.     

Identification et synthèse de nouveaux depsides isolés de la mousse de chêne (Evernia Prunastri (L.) ACH.). 4e Communication

Identification and synthesis of new depsides isolated from oakmoss (Evernia Prunastri (L .) ACH .) Lecanoric acid 5 and 4 new depsides have been isolated from oakmoss (Evernia Prunastri (L .) ACH .) extracts by means of silicagel column chromatography. Various spectral methods including ¹³C-NMR. were used in determining the structure of 4,2″-O-methylgyrophoric acid ( 1 ), lecanoric acid ( 5 ), 2′-O-methylevernic acid ( 2 ), 3′-methylevernic acid ( 3 ) and methyl 3′-methyllecanorate ( 4 ).     

Triterpènes de la «mousse de chêne» (Evernia Prunastri (L.) ACH.). 5e Communication

Triterpenoids from ‘Oakmoss’ (Evernia Prunastri (L .) ACH .) Seven triterpenoids have been isolated from ‘oakmoss’ (Evernia Prunastri (L .) ACH .) extracts by column chromatography and identified as friedelin ( 1 ), taraxerol ( 2 ), 29-nor-21 α-hopan-3,22-dione ( 3 ), moretenone ( 4 ), ursolic acid ( 5 ), lupeol ( 6 ) and lanosterol ( 7 ).     

GC-MS分析大叶金花草中挥发性成分和脂肪酸

应用 GC-MS 联用技术对大叶金花草(Stenoloma chusana(L.)Ching)的挥发性成分和脂肪酸进行了检测,共检测出7种挥发性成分和32种脂肪酸,脂肪酸检出量为87.65%,其中饱和脂肪酸占脂肪酸总量的53.13%,不饱和脂肪酸占脂肪酸总量的46.87%.该研究为大叶金花草的进一步开发利用提供了科学依据.     

(22S)-6-O-acetyl-21betaH-hopane-3beta,6beta,22,29-tetrol from oakmoss (Evernia prunastri)

A novel hopanoid triterpene, (22S)-6-O-acetyl-21betaH-hopane-3beta,6beta,22,29-tetraol, was isolated from oakmoss (Evernia prunastri (L.) Ach.), as identified from 1H, 13C, DEPT, COSY, NOESY, HSQC and HMBC NMR, MS and IR spectroscopy. During recrystallisation a new compound, 30-nor-6-O-acetyl-3beta,6beta-dihydroxy-21alphaH-hopan-22-one, was formed by a formal loss of methanol from the dihydroxypropyl moiety. No biological activity was found for the naturally occurring compound upon testing against a series of fish and human pathogenic bacteria.     

Sesquiterpene-rich volatile constituents of Ipomoea obscura (L.) Ker-Gawl.

The hydro-distilled essential oil from flowering aerial parts of Ipomoea obscura (L.) Ker-Gawl. (Convolvulaceae) was investigated by using gas chromatography equipped with a flame ionisation detector GC-FID and gas chromatography coupled with a mass spectrometry (GC/MS). Forty-two components, representing 97.1% of the total oil, were identified. The major constituents of the essential oil were α-bulnesene (23.8%), α-humulene (13.7%) and seychellene (11.2%). The other minor constituents were α-guaiene (8.3%), β-caryophyllene (7.1%), γ-terpinene (4.2%), hexadecanoic acid (3.0%) and β-elemene (2.7%). The oil was found to be rich in sesquiterpene hydrocarbon type constituents (78.4%).     

Identification of atranorin and related potential allergens in oakmoss absolute by high-performance liquid chromatography-tandem mass spectrometry using negative ion atmospheric pressure chemical ionization

This paper describes the first high-performance liquid chromatographic-tandem mass spectrometric method for the identification of atranorin and related potential allergens in oakmoss absolute. Oakmoss absolute is ubiquitous in the fragrance industry and is a key component in many fine perfumes. However, oakmoss absolute causes an allergic response in some individuals. Research is focused toward establishing the identity of the compounds causing the allergic response so a quality controlled oakmoss with reduced allergenic potential can be prepared. Consequently a highly selective and specific analytical method is necessary to support this effort. This is not available with the existing HPLC methods using UV detection.     

Volatile components from Anthriscus sylvestris (L.) Hoffm

The volatile components of fresh leaves and roots from Anthriscus sylvestris (L.) Hoffm., obtained through hydrodistillation, were analysed by GC and GC-MS. This was compared to dichloromethane extracts of both fresh and dried leaf and root material. The monoterpene fraction (69-70%) dominated, while beta-phellandrene (39-45%) was the main component in both the leaf and the root oil. Other components in the leaf oil were beta-myrcene (17%), sabinene (6.2%), Z-beta-ocimene (5.4%) and benzene acetaldehyde (4.1%). In the roots we found Z-beta-ocimene (16.9%) and alpha-pinene (4.6%) as other major components. These principle constituents of both essential oils were also present in the dichloromethane extracts of the fresh and dried leaves and the roots, although in much smaller percentages. Comparing hydrodistillation of fresh plant material with a dichloromethane extract, the latter yielded a considerably lower amount of constituents. In addition, air drying and freeze drying resulted in a significant loss of volatile constituents as compared to fresh material (dichloromethane extract).     

Analysis of the volatile components of Argyranthemum adauctum (Link.) Humphries by gas chromatography-mass spectrometry

The volatile constituents of the essential oil of Argyranthemum adauctum (Link.) Humphries extracted by steam distillation have been studied by GC-MS. A total of 60 compounds have been identified representing the 89.8% of the oil. The major constituents were found to be beta-pinene (27.4%) and santolinatriene (22.6%). This is the first report on the chemical compounds of the oil of this species.     

New Hydroxylated Spermidine Alkaloids from Pleurostylia opposita(WALL.) MERILL-METCALF

The leaves of a New Caledonian celastraceae, Pleurostylia opposita (WALL .) MERRILL -METCALF , have yielded three new spermidine alkaloids, 7-hydroxypleurostyline ( 1 ), 7-hydroxycelacinnine ( 2 ), and 7′-hydroxy-7′,8′-dihydropleurostyline ( 3 ), as minor basic constituents, together with three related alkaloids pleurostyline ( 4 ), celacinnine ( 5 ), and celallocinine ( 6 ).     

Sur les constituants odorants de l'essence absolue de Cassie (Acacia farnesiana WILLD.)

The absolute oil of cassie (Acacia farnesiana WILLD. ) has been thoroughly investigated by using several combined chromatographic techniques. Among the 38 new constituents which were thus identified in this oil, four deserve a particular mention, namely, the cis-3-methyldec-3-en-1-ol (I), the related acid III, the trans-3-methyl-dec-4-enoic acid (IV), and the homoterpene lactone dihydroactinidiolide (II). With the exception of the last one, these unusual C₁₁ compounds play a prominent role in the characteristic fragrance of cassie oil.     

A new lignan and a new sesquiterpene from Eurotia ceratoides (L.)

A new lignan, rayalinol (1) and a new sesquiterpene kairatene (2) were isolated from Eurotia ceratoides (L.) along with four hitherto unreported syringaresinol, dehydrodiconiferyl aldehyde, dihydrodehydrodiconiferyl alcohol, and dehydrodiconiferyl alcohol and two previously reported constituents ferulic acid and β-sitosterol. The structures of the new constituents were elucidated by extensive spectroscopic means and chemical evidences. Rayalinol is a biogenetically interesting compound with a hitherto unreported 9a homolignane skeleton. Its biosynthetic origin is suggested.     

Fingerprint chemotaxonomic GC–TOFMS profile of wood and bark of mangrove tree Sonneratia caseolaris (L.) Engl.

The bark and wood of Sonneratia caseolaris (L.) Engl. have been analyzed for chemical profile by GC–TOFMS. Overall thirty-two compounds from bark and twenty-eight compounds from wood have been detected. Sixteen constituents have been found to be common in both the extracts. GC–TOFMS chemical profile may be a significant finger print chemotaxonomic marker as an identity of this plant.     

香粉叶挥发性成分提取和分析

采用水蒸汽蒸馏法提取香粉叶的挥发组分,用乙醚萃取蒸馏溶液的挥发性成份,利用气相色谱-质谱联用仪分别定性定量分析了它们的化学成分。 结果表明,挥发油的提取率为0.75%(质量百分数,以下同),主要成分有：1,8-桉叶素28.94%、α-甲基香豆酮15.75%、4-松油醇5.13%、α-松油醇11.22%、2-羟基肉桂酸7.97%、愈创木醇2.87%。 水层乙醚萃取物得率为0.25%,主要成分有：2-甲基苯并呋喃8.47%、2H-1-苯并吡喃-2-酮24.13%、2H-1-苯并吡喃-3-醇-3,4-二氢乙酸酯18.07%、p-羟甲苯基缩水甘油醚2.09%、1-苯基苯乙基-3,3-二乙酯4.50%、丙三醇二乙酸酯17.19%、乙酸金合欢酯11.80%。     

Analysis of the Volatile Constituents of Schisandra chinesis (Turz.) Bail by Gas Chromatography-Mass Spectrometry, Using Headspace Solid-Phase Microextraction

Summary Headspace solid-phase microextraction (HS-SPME) with gas chromatography-mass spectrometry was developed for the analysis of the volatile constituents of a traditional Chinese medicine, the fruits of Schisandra chinensis (Turz.) Bail. Two different fibers of polydimethylsiloxane and carbowax-divinylbenzene were used for the absorption of the volatile constituents of the fruits. Thirty-three volatile compounds were separated and identified. The optimum absorption and desorption conditions were also studied. Relative standard deviation values less than 6.5% showed that the method has a good reproducibility. The volatile constituents were also analyzed by steam distillation and thirty-five compounds were identified. The similar results obtained by the two methods showed that SPME is a simple, rapid and solvent-free method for the analysis of volatile constituents of plant materials.     

Essential oil composition of Rydingia michauxii (Briq.) Scheen & V.A. Albert endemic of Iran

The chemical composition of the essential oil (EO) obtained from the aerial parts of Rydingia michauxii (Briq.) Scheen & V.A. Albert was analysed by gas chromatography and gas chromatography/mass spectrometry (GC/MS). Eighty components were identified in the oil with caryophyllene oxide (20.1%), trans-verbenol (10.2%), linalool (5.3%) and humulene epoxide II (4.6%) as main constituents. We reported here the chemical compositions of R. michauxii EOs from southern Zagros of Iran with a distinct chemical profile for the first time.     

Quality evaluation of Rhizoma Belamcandae (Belamcanda chinensis (L.) DC.) by using high-performance liquid chromatography coupled with diode array detector and mass spectrometry

A high-performance liquid chromatography coupled with diode array detector and mass spectrometry (HPLC-DAD-MS) method was developed to evaluate the quality of Rhizoma Belamcandae (Belamcanda chinensis (L.) DC.) through establishing chromatographic fingerprint and simultaneous determination of seven phenolic compounds. The analysis was achieved on an Alltima C(18) analytical column (250 mm x 4.6 mm i.d. 5 microm) using linear gradient elution of acetonitrile-0.1% trifluoroacetic acid. The correlation coefficients of similarity were determined from the HPLC fingerprints, and they shared a close similarity. By using an online APCI-MS/MS, twenty phenols were identified. In addition, seven of these phenols including mangiferin, 7-O-methylmangiferin, tectoridin, resveratrol, tectorigenin, irigenin and irisflorentin were quantified by the validated HPLC-DAD method. These phenols are considered to be major constituents in Rhizoma Belamcandae, and are generally regarded as the index for quality assessment of this herb. This developed method by having a combination of chromatographic fingerprint and quantification analysis could be applied to the quality control of Rhizoma Belamcandae.     

Synthèses dans la série des constituants odorants caractéristiques de l'essence absolue de cassie (Acacia farnesiana WILLD.): Les acides méthyl-3-décène-3-oïques cis et trans,méthyl-3-décène-4-oïques cis et trans,et les quatre méthyl-3-décénols-1 correspondants

Three new fragrant compounds formerly isolated from the absolute oil of cassie (Acacia farnesiana WILLD .) have been synthesized through stereospecific reactions, and their respective structures thus confirmed. These unusual C₁₁ constituents are cis-3-methyl-dec-3-enoic acid (Ia), trans-3-methyl-dec-4-enoic acid (IIa) and cis-3-methyl-dec-3-en-1-ol (Ib). The related ‘non natural’ stereomers, namely, trans-3-methyl-dec-3-enoic acid (X) and cis-3-methyl-dec-4-enoic acid (XIX), have also been synthesized, as well as the 3-methyl-decen-1-ols IIb, XVII and XX.     

藏药柳茶叶乙醇水提取物中化学成分的鉴定

采用多种色谱分离技术对藏药柳茶叶80%乙醇提取物进行分离纯化,得到了9个化合物。 根据其理化性质与NMR谱数据对化合物进行了结构鉴定,分别为金丝桃苷（hyperoside,Ⅰ）、槲皮素（quercetin,Ⅱ）、芸香苷（rutin,Ⅲ）、槲皮素3-O-β-D-吡喃葡萄糖苷（quercetin-3-O-β-D-glucopyranoside,Ⅳ）、儿茶素（catechin,Ⅴ）、香草酸（vanillic acid,Ⅵ）、熊果苷（arbutin,Ⅶ）、异阿魏酸（isoferulic acid,Ⅷ）和胡萝卜苷（daucosterol,Ⅸ）。 化合物中除Ⅳ、Ⅷ和Ⅸ外,其余6个化合物为首次从该属植物中分离鉴别。     

Composition of the essential oil of Geocaryum cynapioides (Guss.) L. Engstrand

Volatile constituents from two fresh samples of the subendemic Geocaryum cynapioides (Guss.) L. Engstrand (Apiaceae) obtained by hydrodistillation were analyzed by GC and GC-MS. Forty four and one hundred-twenty three constituents identified in the oils accounted for 98.7 % and 98.4 % of the total oils, respectively. The major component of both oils was (E)-β-farnesene (73.3 % and 57.7 %) while the other major contributors were: (E,E)-α-farnesene (4.8 % and 14.6 %) and trans-sesquisabinene hydrate (12.2 % and 3.0 %). The constituents endo-fenchyl acetate, and three sesquiterpene lactones belonging to the selinane (callitrisin) and guaiane (grilactone and jalcaguaianolide) series, with a rather restricted natural occurrence, were present in only one of the samples (4.7 %, trace amount, 0.1 %, 0.5 %, respectively) and completely absent from the other distinguishing so the two samples. A chemotaxonomic discussion of the results is presented.