Pub Date : 1999-02-01DOI: 10.1002/(SICI)1521-4133(19992)101:2<71::AID-LIPI71>3.0.CO;2-Z
M. Guillén, N. Cabo
Twelve sets of olive oil mixed with various edible seed oils in different proportions were made. The seed oils used were sunflower, corn, walnut, rapeseed, soybean, safflower, peanut, wheat germ, and sesame oil. These samples have very different proportions of saturated, mono- and polyunsaturated acyl groups, and of minor components. Fourier transformed infrared spectra of these blends were recorded from films of the oil samples between two discs of KBr. Taking into account the close relationships found previously between the frequency data of some specific bands and the composition of the oil samples, frequency data of all samples were collected and used in equations that relate frequency and composition predicting the percentage by weight of saturated, mono- and polyunsaturated acyl groups in the samples. The predicted values were compared with those derived from the combination of chemical and gas-chromatographic methods and a high degree of agreement was found. The presence of small amounts of seed oil in olive oil is shown by a small variation in the values of the frequencies of specific bands of the spectra, resulting from a smaller proportion of mono-unsaturated acyl groups than in pure olive oil. On the other hand, the frequency of the maximum absorbance between 915 cm–1 and 904 cm–1 also indicates the proportion of seed oil in the blend up to levels of 5% or up to 8% of seed oil in olive oil, depending on the nature of the seed oil. This methodology could give information about the composition of blends of edible oils in a very fast and simple way. Die Nutzlichkeit mancher Frequenzen aus Fourier-transformierten Infrarot-spektroskopischen Banden fur die Bestimmung der Zusammensetzung von esbaren Olmischungen Zwolf Serien von Olivenol gemischt mit einigen esbaren Pflanzenolen wurden in verschiedenen Verhaltnissen hergestellt. Die Pflanzenole waren Sonnenblumenol, Maisol, Walnusol, Rapsol, Sojaol, Farberdistelol, Erdnusol, Weizenkeimol und Sesamol. Diese Proben hatten unterschiedliche Anteile an gesattigten, einfach und mehrfach ungesattigten Acylgruppen und an Minorverbindungen. Fourier-transformierte Infrarotspektren dieser Mischungen wurden aus Filmen von Olproben zwischen zwei KBr-Scheiben aufgenommen. Die Frequenzdaten aller Proben wurden gesammelt, um den prozentualen Gewichtsanteil von gesattigten, mono- und polyungesattigten Acylgruppen in den Proben vorauszusagen; dabei wurden die fruher gefundenen Beziehungen zwischen der Frequenz einiger spezifischen Banden und der Zusammensetzung der Olproben berucksichtigt. Die vorausgesagten Werte wurden mit denjenigen aus chemischen und gaschromatographischen Methoden verglichen, und ein hoher Grad an Ubereinstimmung wurde festgestellt. Die Anwesenheit einer kleinen Pflanzenolmenge im Olivenol wurde durch eine kleine Anderung der Frequenzwerte von spezifischen Banden des Spektrums gezeigt, was durch den kleineren Anteil an einfach gesattigten Acylgruppen verglichen mit reinem Ol
将各种食用籽油按不同比例混合制成12套橄榄油。使用的种子油有向日葵、玉米、核桃、油菜籽、大豆、红花、花生、小麦胚芽和芝麻油。这些样品的饱和、单不饱和和多不饱和酰基以及少量成分的比例差别很大。在两个KBr圆盘之间的油样薄膜上记录了这些混合物的傅里叶变换红外光谱。考虑到之前发现的某些特定波段的频率数据与油样组成之间的密切关系,收集了所有样品的频率数据,并将其用于预测样品中饱和、单不饱和和多不饱和酰基的重量百分比的频率和组成的方程中。将预测结果与化学气相色谱法相结合得到的结果进行了比较,结果吻合度较高。橄榄油中存在少量的种子油,这可以通过光谱特定波段的频率值的微小变化来证明,这是由于单不饱和酰基的比例比纯橄榄油小。另一方面,最大吸光度在915 cm-1和904 cm-1之间的频率也表明混合油中种子油的比例高达橄榄油中种子油的5%或8%,这取决于种子油的性质。该方法可以快速、简便地给出食用油混合物的成分信息。在傅里叶变换变换中,傅里叶变换变换的频率与频率是一致的;在傅里叶变换中,傅里叶变换变换的频率与频率是一致的。pflanzenol包括Sonnenblumenol, Maisol, Walnusol, Rapsol, Sojaol, Farberdistelol, Erdnusol, Weizenkeimol和Sesamol。常见的疾病有:先天性先天性先天性疾病、先天性先天性疾病、先天性先天性疾病、先天性先天性疾病、先天性先天性疾病、先天性先天性疾病和先天性先天性疾病。傅里叶变换红外光谱分析[j], [m], [m], [m], [m]。Die Frequenzdaten allen wurden gesammelt, um den prozentalen Gewichtsanteil von gesattigten, single and polyungesattigten, acylgrouppen den Proben vorauszusagen;在德国,有两种不同的方法:一种是基于频率的方法,一种是基于频率的方法,一种是基于频率的方法。在化学和气相色谱仪方面的研究进展,以及在其他方面的研究进展。Die Anwesenheit einer kleinen Pflanzenolmenge im Olivenol wurde durch ine kleine Anderung der Frequenzwerte von spezifischen Banden des spectrumgetight,即为durch den kleenen Anteil和einch gesattiten Acylgruppen verglichen mitreinem Olivenol bedingist。样品的重量、频率和最大吸收值分别为915 cm-1和904 cm-1,样品中含含5%、8%的蒽醌和含橄榄醇的蒽醌,样品中含天然蒽醌。《疾病防治方法》,《疾病防治方法》,《疾病防治方法》,《疾病防治方法》,《疾病防治方法》。
{"title":"Usefulness of the frequencies of some Fourier transform infrared spectroscopic bands for evaluating the composition of edible oil mixtures","authors":"M. Guillén, N. Cabo","doi":"10.1002/(SICI)1521-4133(19992)101:2<71::AID-LIPI71>3.0.CO;2-Z","DOIUrl":"https://doi.org/10.1002/(SICI)1521-4133(19992)101:2<71::AID-LIPI71>3.0.CO;2-Z","url":null,"abstract":"Twelve sets of olive oil mixed with various edible seed oils in different proportions were made. The seed oils used were sunflower, corn, walnut, rapeseed, soybean, safflower, peanut, wheat germ, and sesame oil. These samples have very different proportions of saturated, mono- and polyunsaturated acyl groups, and of minor components. Fourier transformed infrared spectra of these blends were recorded from films of the oil samples between two discs of KBr. Taking into account the close relationships found previously between the frequency data of some specific bands and the composition of the oil samples, frequency data of all samples were collected and used in equations that relate frequency and composition predicting the percentage by weight of saturated, mono- and polyunsaturated acyl groups in the samples. The predicted values were compared with those derived from the combination of chemical and gas-chromatographic methods and a high degree of agreement was found. The presence of small amounts of seed oil in olive oil is shown by a small variation in the values of the frequencies of specific bands of the spectra, resulting from a smaller proportion of mono-unsaturated acyl groups than in pure olive oil. On the other hand, the frequency of the maximum absorbance between 915 cm–1 and 904 cm–1 also indicates the proportion of seed oil in the blend up to levels of 5% or up to 8% of seed oil in olive oil, depending on the nature of the seed oil. This methodology could give information about the composition of blends of edible oils in a very fast and simple way. \u0000 \u0000 \u0000 \u0000Die Nutzlichkeit mancher Frequenzen aus Fourier-transformierten Infrarot-spektroskopischen Banden fur die Bestimmung der Zusammensetzung von esbaren Olmischungen \u0000 \u0000 \u0000 \u0000Zwolf Serien von Olivenol gemischt mit einigen esbaren Pflanzenolen wurden in verschiedenen Verhaltnissen hergestellt. Die Pflanzenole waren Sonnenblumenol, Maisol, Walnusol, Rapsol, Sojaol, Farberdistelol, Erdnusol, Weizenkeimol und Sesamol. Diese Proben hatten unterschiedliche Anteile an gesattigten, einfach und mehrfach ungesattigten Acylgruppen und an Minorverbindungen. Fourier-transformierte Infrarotspektren dieser Mischungen wurden aus Filmen von Olproben zwischen zwei KBr-Scheiben aufgenommen. Die Frequenzdaten aller Proben wurden gesammelt, um den prozentualen Gewichtsanteil von gesattigten, mono- und polyungesattigten Acylgruppen in den Proben vorauszusagen; dabei wurden die fruher gefundenen Beziehungen zwischen der Frequenz einiger spezifischen Banden und der Zusammensetzung der Olproben berucksichtigt. Die vorausgesagten Werte wurden mit denjenigen aus chemischen und gaschromatographischen Methoden verglichen, und ein hoher Grad an Ubereinstimmung wurde festgestellt. Die Anwesenheit einer kleinen Pflanzenolmenge im Olivenol wurde durch eine kleine Anderung der Frequenzwerte von spezifischen Banden des Spektrums gezeigt, was durch den kleineren Anteil an einfach gesattigten Acylgruppen verglichen mit reinem Ol","PeriodicalId":12304,"journal":{"name":"Fett-lipid","volume":"59 19 1","pages":"71-76"},"PeriodicalIF":0.0,"publicationDate":"1999-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"90479619","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 1999-02-01DOI: 10.1002/(SICI)1521-4133(19992)101:2<64::AID-LIPI64>3.0.CO;2-J
P. Bogaert, Wilfred P. C. Langezaal, J. V. Haveren, T. Slaghek, P. Meeren
A new class of alkyl glycosylamines, using methyl 9- (1) or methyl 12-aminooctadecanoate (2) and carbohydrates (glucose (3a), galactose (3b), lactose (3c), and maltose (3d)), has been synthesized. In order to accomplish the binding of the amino fatty acid esters 1-2 with carbohydrates 3a-d the method described by Helferich, which is using peracetylated carbohydrate bromides, was employed. The yields ranged between 26 and 55%. The chemical structures were identified using 'H and 13 C NMR-spectroscopy including 2D techniques and FT-IR. The critical micelle concentrations and the surface tension profiles of these N-Alkyl-D-glycosides in water were determined.
以甲基9-(1)或甲基12-氨基十八酸甲酯(2)和碳水化合物(葡萄糖(3a)、半乳糖(3b)、乳糖(3c)和麦芽糖(3d))为原料合成了一类新的烷基糖胺。为了完成氨基酸酯1-2与碳水化合物3a-d的结合,采用了Helferich描述的使用过乙酰化碳水化合物溴化物的方法。收益率在26%至55%之间。化学结构通过H和13c核磁共振光谱(包括2D技术和FT-IR)鉴定。测定了这些n -烷基- d -糖苷在水中的临界胶束浓度和表面张力分布。
{"title":"Non-reductive coupling of branched amino fatty acid esters with mono and disaccharides: synthesis of a new class of alkyl glycosylamines.","authors":"P. Bogaert, Wilfred P. C. Langezaal, J. V. Haveren, T. Slaghek, P. Meeren","doi":"10.1002/(SICI)1521-4133(19992)101:2<64::AID-LIPI64>3.0.CO;2-J","DOIUrl":"https://doi.org/10.1002/(SICI)1521-4133(19992)101:2<64::AID-LIPI64>3.0.CO;2-J","url":null,"abstract":"A new class of alkyl glycosylamines, using methyl 9- (1) or methyl 12-aminooctadecanoate (2) and carbohydrates (glucose (3a), galactose (3b), lactose (3c), and maltose (3d)), has been synthesized. In order to accomplish the binding of the amino fatty acid esters 1-2 with carbohydrates 3a-d the method described by Helferich, which is using peracetylated carbohydrate bromides, was employed. The yields ranged between 26 and 55%. The chemical structures were identified using 'H and 13 C NMR-spectroscopy including 2D techniques and FT-IR. The critical micelle concentrations and the surface tension profiles of these N-Alkyl-D-glycosides in water were determined.","PeriodicalId":12304,"journal":{"name":"Fett-lipid","volume":"58 6 1","pages":"64-70"},"PeriodicalIF":0.0,"publicationDate":"1999-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"77756241","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 1998-07-01DOI: 10.1002/(SICI)1521-4133(199807)100:7<308::AID-LIPI308>3.0.CO;2-#
K. Aitzetmüller, E. Ngoy-Kihuya, Irène Kitwa-Kabila
Sumbi oil is the seed oil of Aporrhiza nitida Gilg (Sapindaceae), a tropical tree growing in the Eastern provinces of the D. R. Congo. Sumbi oil has a very good storage stability and is rather resistant against oxidation, an important advantage for use as an edible oil in a tropical climate. The fatty acid composition, with high levels of 20:0 and 20:1n-9, is typical for a member of the Sapindaceae. Although Aporrhiza is closely related to cyanolipid-containing genera, cyanolipids were not found in this investigation of sumbi oil. However, a careful examination of different accessions seems necessary. The tocopherols consist primarily of γ-tocopherol.
{"title":"Sumbi oil from Katanga and South Kivu Province, Democratic Republic of Congo","authors":"K. Aitzetmüller, E. Ngoy-Kihuya, Irène Kitwa-Kabila","doi":"10.1002/(SICI)1521-4133(199807)100:7<308::AID-LIPI308>3.0.CO;2-#","DOIUrl":"https://doi.org/10.1002/(SICI)1521-4133(199807)100:7<308::AID-LIPI308>3.0.CO;2-#","url":null,"abstract":"Sumbi oil is the seed oil of Aporrhiza nitida Gilg (Sapindaceae), a tropical tree growing in the Eastern provinces of the D. R. Congo. Sumbi oil has a very good storage stability and is rather resistant against oxidation, an important advantage for use as an edible oil in a tropical climate. The fatty acid composition, with high levels of 20:0 and 20:1n-9, is typical for a member of the Sapindaceae. Although Aporrhiza is closely related to cyanolipid-containing genera, cyanolipids were not found in this investigation of sumbi oil. However, a careful examination of different accessions seems necessary. The tocopherols consist primarily of γ-tocopherol.","PeriodicalId":12304,"journal":{"name":"Fett-lipid","volume":"1993 1","pages":"308-312"},"PeriodicalIF":0.0,"publicationDate":"1998-07-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"88191389","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 1998-05-01DOI: 10.1002/(SICI)1521-4133(19985)100:4/5<152::AID-LIPI152>3.0.CO;2-P
B. Winter, K. Titze, V. Marschner
Microbial hydrolytic enzymes with phospholipase activites were found in Aspergillus strains, suitable for the hydrolysis of phospholipids in soybean, rapeseed, and sunflower oil during the enzymatic degumming of edible oils. The microbial enzyme is significantly different from pancreatic phospholipase. Calcium is not essential, but enhances the activity.
{"title":"Application of phospholipases in the edible oil industry","authors":"B. Winter, K. Titze, V. Marschner","doi":"10.1002/(SICI)1521-4133(19985)100:4/5<152::AID-LIPI152>3.0.CO;2-P","DOIUrl":"https://doi.org/10.1002/(SICI)1521-4133(19985)100:4/5<152::AID-LIPI152>3.0.CO;2-P","url":null,"abstract":"Microbial hydrolytic enzymes with phospholipase activites were found in Aspergillus strains, suitable for the hydrolysis of phospholipids in soybean, rapeseed, and sunflower oil during the enzymatic degumming of edible oils. The microbial enzyme is significantly different from pancreatic phospholipase. Calcium is not essential, but enhances the activity.","PeriodicalId":12304,"journal":{"name":"Fett-lipid","volume":"210 1","pages":"152-156"},"PeriodicalIF":0.0,"publicationDate":"1998-05-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"76107390","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 1998-05-01DOI: 10.1002/(SICI)1521-4133(19985)100:4/5<96::AID-LIPI96>3.0.CO;2-Z
F. Carrière, C. Withers-Martinez, H. Tilbeurgh, A. Roussel, C. Cambillau, R. Verger
The classical human pancreatic lipase (HPL) and the guinea pig pancreatic lipase-related protein 2(GPLRP2) illustrate interesting steps in the molecular evolution of the pancreatic lipase gene family towards different substrate selectivities. Based on the known 3D structures of HPL and a GPLRP2 chimera, we review here the structural features and the kinetic properties of these two enzymes for a better understanding of their structure-function relationships. HPL displays a significant activity only on triglycerides, whereas GPLRP2 displays high phospholipase and galactolipase activities. together with a comparable triglyceride lipase activity. GPLRP2 shows a high structural homology with HPL with the exception of the lid domain, which is made of five amino acid residues (mini-lid) instead of 23 in HPL. The lid domain deletion in GPLRP2 allows a free access to the active site and reduces the steric hindrance towards large substrates such as galactolipids. The role of the lid domain in substrate selectivity has been investigated by site-directed mutagenesis and the substitution of HPL and GPLRP2 lid domains. The addition of a large lid domain in GPLRP2 increases the substrate selectivity for triglycerides by depressing the phospholipase activity. However, the phospholipase activity is not restored in the case of the HPL mutant with GPLRP2 mini-lid. Therefore, the presence of a full-length lid domain is not the unique structural feature explaining the absence of phospholipase activity in HPL. The 3D structure of the GPLRP2 chimera reveals a higher hydrophilic/lipophilic balance (HLB) of the surface loops (β5 loop. β9 loop, lid domain) surrounding the active site. as compared to the homologous loops in HPL. This observation provides a tentative explanation for the ability of GPLRP2 to hydrolyze polar lipids such as phospholipids. In conclusion, the β5 loop, the β9 loop, and the lid domain play an essential role in substrate selectivity towards triglycerides. phospholipids and galactolipids.
{"title":"Structure‐function relationships of pancreatic lipases","authors":"F. Carrière, C. Withers-Martinez, H. Tilbeurgh, A. Roussel, C. Cambillau, R. Verger","doi":"10.1002/(SICI)1521-4133(19985)100:4/5<96::AID-LIPI96>3.0.CO;2-Z","DOIUrl":"https://doi.org/10.1002/(SICI)1521-4133(19985)100:4/5<96::AID-LIPI96>3.0.CO;2-Z","url":null,"abstract":"The classical human pancreatic lipase (HPL) and the guinea pig pancreatic lipase-related protein 2(GPLRP2) illustrate interesting steps in the molecular evolution of the pancreatic lipase gene family towards different substrate selectivities. Based on the known 3D structures of HPL and a GPLRP2 chimera, we review here the structural features and the kinetic properties of these two enzymes for a better understanding of their structure-function relationships. HPL displays a significant activity only on triglycerides, whereas GPLRP2 displays high phospholipase and galactolipase activities. together with a comparable triglyceride lipase activity. GPLRP2 shows a high structural homology with HPL with the exception of the lid domain, which is made of five amino acid residues (mini-lid) instead of 23 in HPL. The lid domain deletion in GPLRP2 allows a free access to the active site and reduces the steric hindrance towards large substrates such as galactolipids. The role of the lid domain in substrate selectivity has been investigated by site-directed mutagenesis and the substitution of HPL and GPLRP2 lid domains. The addition of a large lid domain in GPLRP2 increases the substrate selectivity for triglycerides by depressing the phospholipase activity. However, the phospholipase activity is not restored in the case of the HPL mutant with GPLRP2 mini-lid. Therefore, the presence of a full-length lid domain is not the unique structural feature explaining the absence of phospholipase activity in HPL. The 3D structure of the GPLRP2 chimera reveals a higher hydrophilic/lipophilic balance (HLB) of the surface loops (β5 loop. β9 loop, lid domain) surrounding the active site. as compared to the homologous loops in HPL. This observation provides a tentative explanation for the ability of GPLRP2 to hydrolyze polar lipids such as phospholipids. In conclusion, the β5 loop, the β9 loop, and the lid domain play an essential role in substrate selectivity towards triglycerides. phospholipids and galactolipids.","PeriodicalId":12304,"journal":{"name":"Fett-lipid","volume":"26 1","pages":"96-102"},"PeriodicalIF":0.0,"publicationDate":"1998-05-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"81967786","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 1998-05-01DOI: 10.1002/(SICI)1521-4133(19985)100:4/5<121::AID-LIPI121>3.0.CO;2-4
E. Blée
Although plants lack the intricate defense mechanisms provided by the immune system in mammals, plant cells are capable of resisting against attack by constitutive defenses and induced responses. which tend to limit the invasion but also to weaken and/or even destroy the aggressor. During the past several years, increasing interest in phytooxylipins (oxygenated fatty acids) has been generated as these metabolites are considered to be involved in such plant responses. Such phytooxylipins derive mainly from C18 unsaturated fatty acids through the so-called oxylipin or lipoxygenase pathway. Lipoxygenases catalyze oxidation of unsaturated C18 fatty acids into either 9- or 13-hydroperoxyoctadecadi(tri)enoic acids, or a mixture of both. depending on the source of the enzymes: these highly reactive aliphatic molecules are then rapidly metabolized by plant cells into a variety of physiologically active derivatives. Two well characterized enzymes have been shown to cut or dehydrate the carbon skeleton. respectively, a lyase and an allene oxide synthase. We have established a new fate for fatty acid hydroperoxides: the peroxygenase pathway, which involves two enzymes i) a peroxygenase, which catalyzes an intramolecular transfer of oxygen from hydroperoxides yielding epoxyalcohols, and (or) intermolecular oxygen transfer (cooxidation reactions) resulting for example in the epoxidation of double bonds of unsaturated fatty acids, ii) an epoxide hydrolase, which hydrates preferentially the epoxides formed by the peroxygenase. The products resulting from these latter reactions are also involved in the response of the plant to aggression, since they are cutin monomers (cutin is the framework of cuticle), or natural pesticides, called phytoalexins.
{"title":"Biosynthesis of phytooxylipins: the Peroxygenase pathway","authors":"E. Blée","doi":"10.1002/(SICI)1521-4133(19985)100:4/5<121::AID-LIPI121>3.0.CO;2-4","DOIUrl":"https://doi.org/10.1002/(SICI)1521-4133(19985)100:4/5<121::AID-LIPI121>3.0.CO;2-4","url":null,"abstract":"Although plants lack the intricate defense mechanisms provided by the immune system in mammals, plant cells are capable of resisting against attack by constitutive defenses and induced responses. which tend to limit the invasion but also to weaken and/or even destroy the aggressor. During the past several years, increasing interest in phytooxylipins (oxygenated fatty acids) has been generated as these metabolites are considered to be involved in such plant responses. Such phytooxylipins derive mainly from C18 unsaturated fatty acids through the so-called oxylipin or lipoxygenase pathway. Lipoxygenases catalyze oxidation of unsaturated C18 fatty acids into either 9- or 13-hydroperoxyoctadecadi(tri)enoic acids, or a mixture of both. depending on the source of the enzymes: these highly reactive aliphatic molecules are then rapidly metabolized by plant cells into a variety of physiologically active derivatives. Two well characterized enzymes have been shown to cut or dehydrate the carbon skeleton. respectively, a lyase and an allene oxide synthase. We have established a new fate for fatty acid hydroperoxides: the peroxygenase pathway, which involves two enzymes i) a peroxygenase, which catalyzes an intramolecular transfer of oxygen from hydroperoxides yielding epoxyalcohols, and (or) intermolecular oxygen transfer (cooxidation reactions) resulting for example in the epoxidation of double bonds of unsaturated fatty acids, ii) an epoxide hydrolase, which hydrates preferentially the epoxides formed by the peroxygenase. The products resulting from these latter reactions are also involved in the response of the plant to aggression, since they are cutin monomers (cutin is the framework of cuticle), or natural pesticides, called phytoalexins.","PeriodicalId":12304,"journal":{"name":"Fett-lipid","volume":"60 1","pages":"121-127"},"PeriodicalIF":0.0,"publicationDate":"1998-05-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"85054191","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 1998-05-01DOI: 10.1002/(SICI)1521-4133(19985)100:4/5<173::AID-LIPI173>3.0.CO;2-D
A. Kinney
The major uses of soybean oils world-wide are for food products such as frying oils, shortenings and margarine. Refined soybean oil is usually chemically hydrogenated to increase storage life, stability during frying, and to increase its melting point for use in solid fat applications. Hydrogenation results in the formation of monounsaturated trans fatty acids, the consumption of which has been associated with an increased risk of coronary heart disease in humans. It is nutritionally desirable, therefore, to produce trans-free soybean oils rich in monounsaturated fatty acids for cooking and trans-free oils rich in stearic and oleic acids for shortenings and margarine. Cloned genes may be introduced into soybeans to create transgenic lines with improved oil traits. The design of transgene constructs has been assisted by the use of soybean somatic embryos in suspension culture as a model system for soybean seed transformation. This system has allowed the selection of the right genes and promoters to achieve the desired phenotypes in transgenic soybeans. By manipulating the expression of fatty acid desaturase genes we have produced lines with 85% oleic acid in their seed oil and lines with up to 30% stearic acid. Commercialization of high-oleic acid transgenic soybeans has demonstrated that it is possible to drastically alter the fatty acid composition of a soybean seed without affecting the yield or environmental sensitivity of the soybean plant. We have demonstrated that high-oleic soybean oil is also useful for non-food applications such as biodegradable lubricants. We have now cloned a number of fatty acid desaturase-related genes from species which produce unusual and industrially useful fatty acids. By expressing these genes it will be possible to produce new fatty acids in soybean seeds, which could potentially replace petrochemicals as raw material for many industrial processes.
{"title":"Plants as industrial chemical factories – new oils from genetically engineered soybeans","authors":"A. Kinney","doi":"10.1002/(SICI)1521-4133(19985)100:4/5<173::AID-LIPI173>3.0.CO;2-D","DOIUrl":"https://doi.org/10.1002/(SICI)1521-4133(19985)100:4/5<173::AID-LIPI173>3.0.CO;2-D","url":null,"abstract":"The major uses of soybean oils world-wide are for food products such as frying oils, shortenings and margarine. Refined soybean oil is usually chemically hydrogenated to increase storage life, stability during frying, and to increase its melting point for use in solid fat applications. Hydrogenation results in the formation of monounsaturated trans fatty acids, the consumption of which has been associated with an increased risk of coronary heart disease in humans. It is nutritionally desirable, therefore, to produce trans-free soybean oils rich in monounsaturated fatty acids for cooking and trans-free oils rich in stearic and oleic acids for shortenings and margarine. Cloned genes may be introduced into soybeans to create transgenic lines with improved oil traits. The design of transgene constructs has been assisted by the use of soybean somatic embryos in suspension culture as a model system for soybean seed transformation. This system has allowed the selection of the right genes and promoters to achieve the desired phenotypes in transgenic soybeans. By manipulating the expression of fatty acid desaturase genes we have produced lines with 85% oleic acid in their seed oil and lines with up to 30% stearic acid. Commercialization of high-oleic acid transgenic soybeans has demonstrated that it is possible to drastically alter the fatty acid composition of a soybean seed without affecting the yield or environmental sensitivity of the soybean plant. We have demonstrated that high-oleic soybean oil is also useful for non-food applications such as biodegradable lubricants. We have now cloned a number of fatty acid desaturase-related genes from species which produce unusual and industrially useful fatty acids. By expressing these genes it will be possible to produce new fatty acids in soybean seeds, which could potentially replace petrochemicals as raw material for many industrial processes.","PeriodicalId":12304,"journal":{"name":"Fett-lipid","volume":"13 1","pages":"173-176"},"PeriodicalIF":0.0,"publicationDate":"1998-05-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"87772932","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 1998-05-01DOI: 10.1002/(SICI)1521-4133(19985)100:4/5<161::AID-LIPI161>3.0.CO;2-P
M. Frentzen
Different discrete acyltransferases are involved in glycerolipid biosynthesis, which occurs in plastids, mitochondria and endomembranes, mainly in the endoplasmic reticulum of plant cells. In each compartment a glycerol-3-phosphate and 1-acylglycerol-3-phosphate acyltransferase catalyze the stepwise acylation of glycerol-3-phosphate to 1,2-diacylglycerol-3-phosphate, the key intermediate in the biosynthesis of the various glycerolipids. These acyltansferases play an important role in establishing the typical fatty acid patterns of the major polar membrane lipids. This also holds true for the microsomal acyltransferases involved in triacylglycerol synthesis where a 1,2-diacylglycerol acyltransferase catalyzes the third acylation reaction. Consequently, the activities of plant acyltransferases are indispensable for the formation of both membrane and storage lipids, and their properties can be decisive determinants of certain plant traits. Recently, the importance of acyltransferases, especially of 1-acylglycerol-3-phosphate acyltransferases, in determining oil quality and usability for specific markets has been confirmed by genetic engineering. Chimeric 1-acylglycerol-3-phosphate acyltransferase genes have been successfully utilized to achieve the synthesis of rapeseed oil with homogeneous fatty acid distributions, such as trierucin and trilaurin, desired for industrial applications. Moreover, evidence has been provided that expression of acyltransferase genes in transgenic rapeseed plants can improve not only oil quality but also oil yield.
{"title":"Acyltransferases from basic science to modified seed oils","authors":"M. Frentzen","doi":"10.1002/(SICI)1521-4133(19985)100:4/5<161::AID-LIPI161>3.0.CO;2-P","DOIUrl":"https://doi.org/10.1002/(SICI)1521-4133(19985)100:4/5<161::AID-LIPI161>3.0.CO;2-P","url":null,"abstract":"Different discrete acyltransferases are involved in glycerolipid biosynthesis, which occurs in plastids, mitochondria and endomembranes, mainly in the endoplasmic reticulum of plant cells. In each compartment a glycerol-3-phosphate and 1-acylglycerol-3-phosphate acyltransferase catalyze the stepwise acylation of glycerol-3-phosphate to 1,2-diacylglycerol-3-phosphate, the key intermediate in the biosynthesis of the various glycerolipids. These acyltansferases play an important role in establishing the typical fatty acid patterns of the major polar membrane lipids. This also holds true for the microsomal acyltransferases involved in triacylglycerol synthesis where a 1,2-diacylglycerol acyltransferase catalyzes the third acylation reaction. Consequently, the activities of plant acyltransferases are indispensable for the formation of both membrane and storage lipids, and their properties can be decisive determinants of certain plant traits. Recently, the importance of acyltransferases, especially of 1-acylglycerol-3-phosphate acyltransferases, in determining oil quality and usability for specific markets has been confirmed by genetic engineering. Chimeric 1-acylglycerol-3-phosphate acyltransferase genes have been successfully utilized to achieve the synthesis of rapeseed oil with homogeneous fatty acid distributions, such as trierucin and trilaurin, desired for industrial applications. Moreover, evidence has been provided that expression of acyltransferase genes in transgenic rapeseed plants can improve not only oil quality but also oil yield.","PeriodicalId":12304,"journal":{"name":"Fett-lipid","volume":"11 1","pages":"161-166"},"PeriodicalIF":0.0,"publicationDate":"1998-05-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"89845198","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 1998-05-01DOI: 10.1002/(SICI)1521-4133(19985)100:4/5<103::AID-LIPI103>3.0.CO;2-4
J. Broadwater, J. Haas, B. Fox
Diiron enzymes catalyze many essential O 2 -dependent reactions required for eukaryotic and bacterial metabolism. Both membrane bound and soluble classes are now known. The integral membrane class of diiron enzymes contains desaturases. hydroxylases. and other oxidative enzymes involved in the synthesis of nutritionally or commercially desirable unsaturated fats, steroids. and other hydrophobic molecules. The soluble class of diiron enzymes has essential roles in DNA biosynthesis. desaturation of various acyl-ACPs, and the oxidation of hydrocarbons including toxic environmental pollutants. Biochemical, spectroscopic, and crystallographic studies of these enzymes have provided structures for the active sites and proposals for the mechanism of action. Two key features of the reaction cycles are the flexibility of the diiron coordination environment and the activation of O 2 to generate a series of related but not identical intermediates used for diverse catalytic processes. Most recently, the alpha helical bundle containing the diiron center has proven to be a robust scaffold for mutagenesis studies. allowing the relationship between protein structure and catalytic function to be further refined and adapted.
{"title":"The fundamental, versatile role of diiron enzymes in lipid metabolism","authors":"J. Broadwater, J. Haas, B. Fox","doi":"10.1002/(SICI)1521-4133(19985)100:4/5<103::AID-LIPI103>3.0.CO;2-4","DOIUrl":"https://doi.org/10.1002/(SICI)1521-4133(19985)100:4/5<103::AID-LIPI103>3.0.CO;2-4","url":null,"abstract":"Diiron enzymes catalyze many essential O 2 -dependent reactions required for eukaryotic and bacterial metabolism. Both membrane bound and soluble classes are now known. The integral membrane class of diiron enzymes contains desaturases. hydroxylases. and other oxidative enzymes involved in the synthesis of nutritionally or commercially desirable unsaturated fats, steroids. and other hydrophobic molecules. The soluble class of diiron enzymes has essential roles in DNA biosynthesis. desaturation of various acyl-ACPs, and the oxidation of hydrocarbons including toxic environmental pollutants. Biochemical, spectroscopic, and crystallographic studies of these enzymes have provided structures for the active sites and proposals for the mechanism of action. Two key features of the reaction cycles are the flexibility of the diiron coordination environment and the activation of O 2 to generate a series of related but not identical intermediates used for diverse catalytic processes. Most recently, the alpha helical bundle containing the diiron center has proven to be a robust scaffold for mutagenesis studies. allowing the relationship between protein structure and catalytic function to be further refined and adapted.","PeriodicalId":12304,"journal":{"name":"Fett-lipid","volume":"46 1","pages":"103-113"},"PeriodicalIF":0.0,"publicationDate":"1998-05-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"91385544","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 1998-05-01DOI: 10.1002/(SICI)1521-4133(19985)100:4/5<128::AID-LIPI128>3.0.CO;2-D
H. Lichtenthaler
Isoprenoid biosynthesis in plants proceeds via two independent pathways: 1) the cytosolic classical acetate/mevalonate pathway (biosynthesis of sterols, sesquiterpenes, triterpenoids) and 2) via the non-mevalonate 1-deoxy-D-xylulose-5-phosphate (DOX-P) pathway for the biosynthesis of plastidic isoprenoids such as carotenoids, phytol (side-chain of chlorophylls), plastoquinone-9, isoprene, mono- and diterpenes. Both pathways form isopentenyl-diphosphate (IPP) as precursors, from which all other isoprenoids are formed via head-to-tail addition. The present knowledge of the novel 1-deoxy-D-xylulose-5-phosphate (DOX-P) pathways for isopentenyl-diphosphate biosynthesis, which is apparently located in plastids, is reviewed in this contribution. It provides a new insight into chloroplast metabolism.
{"title":"The plants' 1-deoxy-D-xylulose-5-phosphate pathway for biosynthesis of isoprenoids","authors":"H. Lichtenthaler","doi":"10.1002/(SICI)1521-4133(19985)100:4/5<128::AID-LIPI128>3.0.CO;2-D","DOIUrl":"https://doi.org/10.1002/(SICI)1521-4133(19985)100:4/5<128::AID-LIPI128>3.0.CO;2-D","url":null,"abstract":"Isoprenoid biosynthesis in plants proceeds via two independent pathways: 1) the cytosolic classical acetate/mevalonate pathway (biosynthesis of sterols, sesquiterpenes, triterpenoids) and 2) via the non-mevalonate 1-deoxy-D-xylulose-5-phosphate (DOX-P) pathway for the biosynthesis of plastidic isoprenoids such as carotenoids, phytol (side-chain of chlorophylls), plastoquinone-9, isoprene, mono- and diterpenes. Both pathways form isopentenyl-diphosphate (IPP) as precursors, from which all other isoprenoids are formed via head-to-tail addition. The present knowledge of the novel 1-deoxy-D-xylulose-5-phosphate (DOX-P) pathways for isopentenyl-diphosphate biosynthesis, which is apparently located in plastids, is reviewed in this contribution. It provides a new insight into chloroplast metabolism.","PeriodicalId":12304,"journal":{"name":"Fett-lipid","volume":"89 1","pages":"128-138"},"PeriodicalIF":0.0,"publicationDate":"1998-05-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"80357744","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}