Mass Spectra of Trimethylsilyl Derivatives

Sharkey, A.G.; Friedel, R. A.; Langer, Stanley H.

doi:10.1021/ac60125a009

Cited by 185 publications

(70 citation statements)

References 21 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…The molecular ion m/z 365 was very weak and sometime absent. It was similar in character to the spectra of TMSi derivative of alcohol (13). The Figures 3 and 4.…”

Section: Methodssupporting

confidence: 75%

Translocation of Paclobutrazol, a Gibberellin Biosynthesis Inhibitor, in Apple Seedlings

Wang¹,

Sun²,

Faust³

1986

Plant Physiol.

View full text Add to dashboard Cite

“…The molecular ion m/z 365 was very weak and sometime absent. It was similar in character to the spectra of TMSi derivative of alcohol (13). The Figures 3 and 4.…”

Section: Methodssupporting

confidence: 75%

Translocation of Paclobutrazol, a Gibberellin Biosynthesis Inhibitor, in Apple Seedlings

Wang¹,

Sun²,

Faust³

1986

Plant Physiol.

View full text Add to dashboard Cite

“…Components 1-4, 6, and 9 were identified by their retention times and mass spectra to be a homologous series of aliphatic alcohols. The characteristic ions used for identification by mass spectra were a weak parent ion (M+), an intense fragment ion corresponding to M+-CH3, and a large fragment ion at m/e 103 corresponding to +CH2OSi(CH3)3 (19,21). Using these ions and the gas chromatographic retention times, the components were assigned the following structures: peak 1, hexadecanol; peak 2, heptadecanol; peak 3, a mixture of saturated and unsaturated C18 alcohols; peak 4, nonadecanol; peak 6, eicosanol; and peak 9, docosanol.…”

Section: Methodsmentioning

confidence: 99%

Synthesis of Suberin during Wound-healing in Jade Leaves, Tomato Fruit, and Bean Pods

Dean

Kolattukudy²

1976

Plant Physiol.

View full text Add to dashboard Cite

The structure and composition of the aliphatic monomers of the polymeric material deposited during wound-healing of tomato fruit, bean pods, and Jade leaves were examined. After removing the cuticlecontaining layer of tissue, the wounds were healed for 14 days and the resulting surface layer was excised, lyophilized, solvent-extracted, and depolymerized by hydrogenolysis with LiAIH4 or transesterified with BF3 in methanol. The products obtained by the chemical depolymerization were subjected to thin layer chromatography and combined gas chromatography and mass spectrometry. The major aliphatic components isolated from the hydrogenolysate of the wound polymer produced by tomato fruit were hexadecane-1,16-diol and octadec-9-ene-1,18-diol, which were shown to be derived from a 1:1 mixture of w-hydroxy and dicarboxylic acids of the appropriate chain length by LiAIH4 reduction.Also identified in the wound polymer were long chain (>C20) fatty acids and alcohols. This monomer composition is typical of suberin polymers and is in sharp contrast with that of the cutin of tomato fruit which contains dihydroxy C16 add as the major aliphatic component. The hydrogenolysis of the wound material from bean pods gave octadecene-1,18-diol as the major aliphatic component, and smaller amounts of hexadecane-1,16-diol and long chain alcohols. Similar treatment of the normal cuticular tissue of these pods gave hexadecane triol, as well as C16 and C18 alcohols. Hydrogenolysis of wound material from the Jade leaves gave octadecene-1,18-diol, C16 and C22 diols, as well as alcohols from C16 to C26, whereas similar treatment of the cutin-containing tissue from these leaves gave C16 triol as the major aliphatic component. Thus, the major aliphatic monomers of the polymeric material deposited during the wound-healing of bean pods and Jade leaves are very similar to those of suberin, although the natural protective polymer of these tissues is cutin. From these results, it is concluded that suberization is a fundamental process involved in wound-healing in plants, irrespective of the chemical nature of the natural protective polymer of the tissue.In recent years, the composition of the monomers of cutin and suberin, the lipid polymers which cover plants, has been studied with modern analytical techniques. The major components of cutin are dihydroxy C16 fatty acids, 18-hydroxy-9,10-epoxy C18 fatty acids, and trihydroxy C18 fatty acids. Also found are smaller amounts of w-hydroxy C16 and C18 fatty acids. The major aliphatic components of suberin are w-hydroxy fatty acids and dicarboxylic acids from C16 to C28 and fatty acids and alcohols in which aliphatic chains longer than C20 often predominate (4,6,7,10,13,17). The composition of the aliphatic monomers of the '

show abstract

“…Loss of 30 mass units from the molecular ion (giving a peak at mle 418) is typical of 18-trimethylsiloxy-17-0x0-steroids and 19-trimethylsiloxy-3-0x0-d4-steroids [14]. Prominent peaks are seen at m/e 103 and a t m/e 129; these fragments are characteristic for steroids with a primary trimethylsiloxy group [6,15] and for steroids with a 3#?-trimethylsiloxy-As structure [l6], respectively. Table 2 shows the gas-liquid chromatographic analyses of the pregnane-3,20-diol isomers found in meconium.…”

Section: /?-Hydroxy-a5 Steroidsmentioning

confidence: 99%

Steroids in Meconium from Male and Female Newborn Infants

Gustafsson

Stenberg

1971

European Journal of Biochemistry

View full text Add to dashboard Cite

The steroids in meconium from normal male and female newborn infants have been studied by gas chromatography-mass spectrometry. Practically all steroids were excreted as monoand disulphates. The approximate concentrations of steroid mono-and disulphates were 430 and 470pg per g of meconium. Twenty unsaturated and fourteen saturated steroids were completely identified. Most of the unsaturated steroids had a 3/?-hydroxy-A6 structure. I n addition, seven saturated steroids were tentatively identified. No significant qualitative differences were found in the steroid composition of meconium from male and female newborns. The results are discussed in relation to present knowledge of steroid metabolism in the foeto-placental unit.Very little information is available on the excretion of neutral steroid metabolites in meconium from newborn infants. I n a series of publications Francis et al. . In order to obtain a complete understanding of the metabolism of neutral steroid hormones in the foeto-placental unit it was considered of interest to have a detailed knowledge of the metabolites excreted in meconium. New methods of purification in combination with gas chromatographymass spectrometry (for references see [6]) have now made it possible to separate and identify even minor constituents in small amounts of biological material. MATERIALS AND METHODS Collection of MeeoniumMeconium was collected from diapers not contaminated with urine. Samples from 6 male and 9 female infants were pooled to give a meconium pool from males (70 g) and a meconium pool from females (40 g). The samples were stored a t -20 "C until analysed. SteroidsThe sources of several of the steroids used as reference compounds were given in a previous Unusual Abbreviations. Progesterone, silyl, trimethylsilyl. The terms pregnanolone and pregnanediol are used as collective names for isomers of 3-hydroxy17p-pregnan-20-one and pregnane-3,2O-diol, respectively.Enzymes. 3-a-Hydroxysteroid : NADP oxidoreductase (EC 1.1.1.50).Note. Retention times, tg, are calculated relative to 5a-cholestane.paper [7]. 3~-Hydroxy-5-androsten-l7-one was purchased from Ikapharm (Ramat-Gan, Israel). 3/?,78-Dihydroxy-5-androsten-17-one and 3B,18-dihydroxy-5-androsten-17-one were gifts from Dr. G. Johannsson and Dr. C. H. L. Shackleton, respectively. 5-Androstene-3/?,17a-diol and 5m-androstane-3a,17a-diol were obtained from Schering AG (Berlin, Germany). 38-2 1 -Dihydroxy-5-pregnen-20 one-21 -acetate (purchased from Sigma Chemical Company, St. Louis, Missouri, U.S.A.) was hydrolysed with K2C0, in methanol a t room temperature over night. The resulting 38,21 -dihydroxy-5-pregnen-ZO-one was reduced with sodium borohydride in methanol and the following compounds were found : 5-pregnene-3@,20B, 21 -trio1 (high yield) and 5-pregnene-3B,20a,21 -trio1 (low yield). 3a-Hydroxy-5a-pregnan-ZO-one, 3m-hydroxy-5B-pregnan-ZO-one and 3B-hydroxy-5-pregnen-20-one were purchased from Ikapharm (Ramat-Gan, Israel). Sodium borohydride reductions of these compounds gave the corresponding 208-and 20a-hydr...

show abstract

Mass Spectra of Trimethylsilyl Derivatives

Cited by 185 publications

References 21 publications

Translocation of Paclobutrazol, a Gibberellin Biosynthesis Inhibitor, in Apple Seedlings

Translocation of Paclobutrazol, a Gibberellin Biosynthesis Inhibitor, in Apple Seedlings

Synthesis of Suberin during Wound-healing in Jade Leaves, Tomato Fruit, and Bean Pods

Steroids in Meconium from Male and Female Newborn Infants

Contact Info

Product

Resources

About