Kumar D. Mukherjee’s research while affiliated with Federal Agency for Agriculture and Food (Germany) and other places
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The distribution of acyl moieties at sn-1 and sn-2 positions of cholinphosphoglycerides (CPG) and ethanolaminephosphoglycerides (EPG) has been determined for neurosarcoma, sarcoma 180 and leukemia L 1210. In all the three samples, the positional distribution of acyl moieties in the two major classes of phospholipids is found to be similar to that in cellular phospholipids of most mammalian tissues. The saturated acyl moieties are located predominantly at sn-1 and polyunsaturated acyl moieties at sn-2, whereas the monounsaturated acyl moieties are randomly distributed between these two positions. Apparently, a disruption of specific positioning of acyl moieties in phospholipids, which hitherto has been considered to be a general metabolic deletion in neoplasia, does not exist in an all neoplastic cells.
Cell suspension cultures of soya were incubated with cis-[1- ¹⁴ C]octadecenoic acids and trans- [1- ¹⁴ C]octadecenoic acids, each of known composition with regard to positional isomers. Each of the positional isomers ranging from ⊿8- to ⊿15-as-octadecenoic acids and ⊿7- to ⊿16-frans-octadecenoic acids was readily incorporated into the acyl lipids of the cells, yet, the ⊿9 cis- and the ⊿9-trans-isomers were the preferred substrates, cis-trans Isomerization did not occur during the incorporation of the fatty acids into the acyl lipids.
Simple methods are described for the preparation of trans-[1-14C]monounsaturated fatty acids and cis-[1-14C]monounsaturated fatty acids, each with a fairly uniform distribution of positional isomers, which can serve as mixed substrates in biochemical studies. Methyl trans-[1-14C]octadecenoates and methyl trans-[1-14C]eicosenoates are prepared by partial catalytic hydrogenation of methyl [1-14C]linolenate and methyl [1-14C]arachidonate, respectively, followed by argentation chromatography of the partially hydrogenated products. Methyl trans-[1-14C]octadecenoates and methyl trans-[1-14C]eicosenoates, thus obtained, yield the corresponding methyl cis-[1-14C]octadecenoates and methyl cis-[1-14C]eicosenoates, respectively, after trans-cis equilibration and argentation chromatography. Hydrolysis of each of these methyl esters yields the fatty acids.
Radioactivity from cis-9-[1-14C]octadecenol, injected intravenously into rats bearing neurosarcoma, is incorporated to a significantly greater extent into tumor than into muscle. In the lipids of both tissues, radioactivity is incorporated predominantly into the acyl moieties, rather than into the alkyl or alk-1-enyl moieties, of diradylglycerophosphocholines, diradylglycerophosphoethanolamines, and triradylglycerols.
The alcoholysis of crambe and camelina oils was carried out with oleyl alcohol, alcohols derived from crambe and camelina
oils, and n-octanol using potassium hydroxide as catalyst to prepare alkyl esters. Conversions to alkyl esters were about 0% with oleyl
alcohol, 20–45% with crambe and camelina alcohols, and 60% with n-octanol. The conversion to esters for crambe and camelina oil with oleyl alcohol and n-octanol increased with increasing molar excess of alcohol. Composition of the alkyl esters formed was as expected from the
composition of the reaction partners.
Linear copolymeric polythioesters [PTE; poly(alpha,omega-alkanedioic acid-co-alpha,omega-alkanedithiols)] were formed in good yield (approximately 69%) by thioesterification of 1,12-dodecanedioic acid with 1,6-hexanedithiol and 1,8-octanedithiol, respectively, catalyzed by immobilized lipase from Rhizomucor miehei (Lipozyme RM IM) in vacuo without a solvent. Similarly, transthioesterification (thiolysis) of diethyl 1,12-dodecanedioate with 1,6-hexanedithiol led to the formation of approximately 66% PTE. Poly (1,12-dodecanedioic acid-co-1,6-hexanedithiol) and poly (1,12-dodecanedioic acid-co-1,8-octanedithiol) were extracted from the reaction mixture using methyl-t-butylether, precipitated at -20 degrees C and the precipitates extracted with boiling i-hexane to yield two fractions of PTE. The i-hexane-insoluble fraction of poly (1,12-dodecanedioic acid-co-1,6-hexanedithiol) shows an average molecular mass (Mw) of 1,212 Da, corresponding to a molecular weight range of up to 13,200 Da and a degree of polymerization of up to 38 monomer units. The i-hexane-insoluble fraction of poly (1,12-dodecanedioic acid-co-1,8-octanedithiol) shows a Mw of 2,360 Da, corresponding to a molecular weight range of up to 19,500 Da and a maximum degree of polymerization of up to 52 monomer units. The low-molecular weight (<800 Da) reaction products of thioesterification of 1,12-dodecanedioic acid with 1,6-hexanedithiol, elucidated by gas chromatography-mass spectroscopy, show the following intermediates: (1) 9,20-dioxo-1,8-dithiacycloeicosane; (2) 17,28-dioxo-1,8,9,16-tetrathiacyclooctacosane; (3) 1,12-dodecanedioic acid methyl(O)ester 6'-S-mercaptohexyl thio(S)ester; and (4) oligomeric linear thioester, formed by thioesterification of two molecules of 1,12-dodecanedioic acid with one molecule of 1,6-hexanedithiol.
Various methods have been applied for the enzymatic preparation of diacylglycerols that are used as dietary oils for weight reduction in obesity and related disorders. Interesterification of rapeseed oil triacylglycerols with commercial preparations of monoacylglycerols, such as Monomuls 90-O18, Mulgaprime 90, and Nutrisoft 55, catalyzed by immobilized lipase from Rhizomucor miehei (Lipozyme RM IM) in vacuo at 60 degrees C led to extensive (from 60 to 75%) formation of diacylglycerols. Esterification of rapeseed oil fatty acids with Nutrisoft, catalyzed by Lipozyme RM in vacuo at 60 degrees C, also led to extensive (from 60 to 70%) formation of diacylglycerols. Esterification of rapeseed oil fatty acids with glycerol in vacuo at 60 degrees C, catalyzed by Lipozyme RM and lipases from Thermomyces lanuginosus (Lipozyme TL IM) and Candida antarctica (lipase B, Novozym 435), also provided diacylglycerols, however, to a lower extent (40-45%). Glycerolysis of rapeseed oil triacylglycerols with glycerol in vacuo at 60 degrees C, catalyzed by Lipozyme TL and Novozym 435, led to diacylglycerols to the extent of </=50%. Repeated use of Lipozyme RM in the esterification of rapeseed oil fatty acids with Monomuls resulted in minor reduction of its activity. The products of esterification of rapeseed oil fatty acids with Monomuls and glycerol yielded upon short-path vacuum distillation residues (diacylglycerol oils) containing 66-70% diacylglycerols.
1- S-Mono-palmitoyl-hexanedithiol and 1- S-mono-palmitoyl-octanedithiol were prepared in high yield (80-90%) by solvent-free lipase-catalyzed thioesterification of palmitic acid with the corresponding alpha,omega-alkanedithiols in vacuo. Similarly, 1,6-di- S-palmitoyl-hexanedithiol and 1,8-di- S-palmitoyl-octanedithiol were prepared in moderate yield (50-60%) by solvent-free lipase-catalyzed thioesterification of palmitic acid with 1- S-Mono-palmitoyl-hexanedithiol and 1- S-mono-palmitoyl-octanedithiol, respectively. An immobilized lipase preparation from Rhizomucor miehei (Lipozyme RM IM) was more effective than a lipase B preparation from Candida antarctica (Novozym 435) or a lipase preparation from Thermomyces lanuginosus (Lipozyme TL IM). Lipase-catalyzed transthioesterifications of methyl palmitate with alpha,omega-alkanedithiols using the same enzymes were less effective than thioesterification for the preparation of the corresponding 1- S-mono-palmitoyl thioesters.
Plant steryl and stanyl esters are effective in lowering plasma cholesterol concentration by inhibiting the absorption of cholesterol from small intestine. They are, therefore, used as constituents of special margarines, which are commercially available as functional foods with the ability to reduce blood cholesterol levels. An enzymatic method has been developed for the preparation of oleic acid esters of sterols and stanols in high yield by transesterification of methyl oleate with the 3-hydroxy group in vacuo (20-40 hPa) at moderate temperature (80 °C) using immobilized lipase preparation from Thermomyces lanuginosus (Lipozyme TL IM®) as biocatalyst. Neither an organic solvent nor a drying agent are required. Cholesterol and stanols such as 5α-cholestanol and sitostanol have been converted at similar rates and in near-quantitative yields (>95%) to the corresponding oleic acid esters.
We report the stereospecific (sn-1, sn-2, sn-3) distribution of fatty acids in subcutaneous adipose tissue triacylglycerols of male weaned Wistar rats fed either a standard diet or diets containing, in addition to 20 g corn oil/kg feed, 120 g/kg feed, each, of canola-type rapeseed oil, olive oil, conventional or high oleic sunflower oil or high petroselinic coriander oil for 10 wk. The regiospecific distribution of the major acyl moieties in the sn-1 (3) vs. sn-2 positions of the adipose tissue triacylglycerols broadly reflected that of the dietary oils. The saturated palmitoyl and stearoyl moieties were more abundant in the sn-1 and sn-3 positions compared with the sn-2 position of the adipose tissue triacylglycerols, and both occurred at a higher proportion in the sn-1 than in the sn-3 position. Oleoyl moieties were abundant in all the three positions of the adipose tissue triacylglycerols, whereas petroselinoyl moieties were more abundant in the sn-1 and sn-3 positions compared with the sn-2 position. Linoleoyl moieties occurred predominantly in the sn-2 position compared with the sn-1 and sn-3 positions of the adipose tissue triacylglycerols; however, they were more abundant in the sn-3 than in the sn-1 position. Despite widely varying proportions of the palmitoyl, oleoyl and linoleoyl moieties at the three positions of the dietary triacylglycerols, the ratios of each of these acyl moieties at the sn-1, sn-2, and sn-3 positions in adipose tissue triacylglycerols were essentially constant for all groups, with the exception of the group fed coriander oil, indicating a rigid stereospecific incorporation.
Citations (78)
... Además, pueden catalizar la hidrólisis o síntesis de un grupo amplio de ésteres carboxílicos (Bornscheuer et al. 1994). Estas enzimas están ampliamente distribuidas en la naturaleza, y se encuentran en microorganismos, plantas y animales (Berner y Hammond, 1970;Mukherjee, 1996;Ruiz et al., 2007). Una característica peculiar de las lipasas es que son enzimas solubles en agua que actúan sobre sustratos insolubles y agregados, por lo que operan unidas a interfaces lípido-agua. ...
... For instance, a common lipid subclass is glycerolipids made by esterifying fatty acid (FA) chains to one or more of the three glycerol hydroxyls. These feature four major isomer types ( Figure 1): (i) acyl chain substitution or stereonumbering (sn-) that results from exchange of FA chains (transacylation), (ii) chain length from swapping pieces between FAs, and, for unsaturated lipids, (iii) double bond (DB) positional isomers and (iv) cis/trans (Z/E) geometry at each DB [3][4][5][6][7][8][9][10][11][12]. Permuting these variations can yield hundreds of isomers with often distinct biological activities, many present in vivo [3][4][5][6][7][8][9][10][11][12][13]. ...
... This import of IysoPtdCho into plastids and its further metabolism requires that an acyl-CoA synthetase be present in the envelope, independently of those already observed in the ER (Lessire and Cassagne, 1979;Murphy et al., 1984). The presence of plastidial acyl-CoA synthetases located in the envelope has been demonstrated (for example, Roughan and Slack, 1977;Joyard and Stumpf, 1981;Block et al., 1983b); until now they have so far been supposed to be involved in the ACP-track-CoA-track switching system (ACP = acyl carrier protein). ...
... In fact, the principal component analysis conducted using the data obtained herein (not showed here) did not reveal any geographic discrimination between the samples analyzed and the fatty acid composition was found to be fairly similar among these samples. As already suggested for other plants (Mukherjee et al., 1984;Tlili et al., 2014), the fatty acid biosynthesis in E. maritimum seeds is especially controlled by genetic rather than environmental factors. ...
... Vinyl laurate as the best acyl donor (Villeneuve et al., 1997b) presumably resulted from the irreversibility of that reaction, derived from the formation of vinyl alcohol which rapidly tautomerises to acetaldehyde, thus shifting the enzymatic reaction toward the products formation (Weber et al., 1997). Currently, applications regarding fats and oils modification, esterification in organic media, and asymmetric resolution of several chiral acids, as well as non-natural α-amino acids, have been also reported (Mukherjee and Kiewitt, 1996;Borgdorf and Warwel, 1999;Gandhi and Mukherjee, 2000a;Villeneuve et al., 2005). ...
... C-7 adducts can be formed by the oxidation of (n-390 7) monounsaturated fatty acids such as cis-vaccenic or paullinic acids, identified in the seed oils of 391 some plants (Avato et al., 2003). Mukherjee and Kiewitt (1980) observed a relatively higher abundance 392 of (n-7) cis-monounsaturated fatty acids in the seeds of Sinapis alba and especially Brassica napus 393 which was widely grown both regionally and in fields around the station. We observed the highest 394 concentrations of kC 7 and ωC 7 in July ( Fig. 2j and Fig. 3e), when Brassica napus is also harvested. ...
... Contrary to the present finding, McNeill et al. (2004) recommended a restricted use of even 00 rapeseed meal in broiler rabbit feeding and exceeding the inclusion level by more than 10% was found to reduce the intake and growth. Possibly, the process of complete feed pelleting involves the inclusion of 30% moisture, which may favour activation of the myrosinage enzyme present in rapeseed-mustard meal and responsible for TGLS degradation (Mukherjee et al., 1976). Myrosinase is deactivated at a temperature of 708C to 808C (Gil and Macleod, 1980), which was observed in the pelleting chamber of the pelletiser. ...
... from Thermomyces lanuginosus (Lipozyme TL IM) that resulted in no conversion in study [42], was used successfully to synthetize oleic acid esters of sterols and stano high yield by the transesterification of methyl oleate with the 3-hydroxy group in ano study [43]. The reason for this might be the differences in reaction conditions, as expla by the authors. ...
... Previous publications in which CPL was employed mainly focused on its strict sn-1,3 selectivity and enantioselectivity. Giordani and Gandhi used CPL for the synthesis of TAGs, which possess short acyl chains at the sn-1,3 positions and are considered to be hypocaloric (Giordani et al. 1991;Gandhi and Mukherjee 2001). Moreover, Chen successfully employed this biocatalyst for the resolution of a (R,S)-naproxen-2,2,2-trifluoroethyl ester (Chen and Tsai 2005). ...
... 42 The contents of palmitic and linoleic acids reportedly decrease during the maturation of Sinapis semen. 43 Furthermore, hierarchical cluster analysis and GC-MS conducted by Cheng et al revealed 13 FA-like constituents of Sinapis alba L. oil from different origins, which included linoleic acid and γ-sitosterol with relatively high levels of β-tocopherol and rapeseed stanols. 22 Thioglucosides and their Derivatives of Sinapis semen. ...
