Malvalic Acid Research Articles

<i>Sterculia striata</i> seed kernel oil: Characterization and thermal stability

The objective of the present work was to characterize sterculia seed kernel oil. The chemical composition of the seeds, physicochemical properties as well as the fatty acid composition of the kernel oil was determined. The chemical composition of kernel flour presented about 25.8% lipid content. The physicochemical parameters such as acid, iodine, peroxide and saponification values were 0.82 (% as oleic acid), 69.2 (g iodine/100 g oil), 4.20 (m eq./kg) and 136.1 (mg. KOH/g oil), respectively. With respect to fatty acid composition, the oil contained 36.2, 43.7 and 10.9% saturated, monounsaturated and polyunsaturated fatty acids, respectively. Palmitic acid (31.9%), oleic acid (41.7%) and linoleic acid (10.73%) were the principal saturated, monounsaturated and polyunsaturated fatty acids. Two cyclopropanoid fatty acids i.e. sterculic and malvalic acid were identified at a concentration of 5.3 and 2.3%, respectively. With regards to the thermal stability of the oil, a thermogravimetric analysis (TGA) has shown that the oil was stable until about 284 °C, above that the oil started loosing mass, while a differential thermogravimetric analysis (DTGA) revealed three stages of degradation with an increase in temperature. These stages corresponded to the degradation of polyunsaturated, monounsaturated and saturated fatty aids. The Differential Scanning Calorimetric (DSC) analysis showed the existence of two exothermic events of energy transition, one of which is related to the oxidation reactions and another to the decomposition of the oil. Exothermic transitions in the oil were initiated at a temperature (Ti) of 287.79 °C, and terminated at 347.81 °C, with an enthalpy variation of 11.69 joules.g –1 and at initial temperature (Ti) of 384.87 °C, peak temperature (Tp) 415.71 °C, final temperature (Tf) 448.9 °C and an enthalpy of 200.83 Joules. G –1

A Quantitative Method for the Determination of Cyclopropenoid Fatty Acids in Cottonseed, Cottonseed Meal, and Cottonseed Oil (Gossypium hirsutum) by High-Performance Liquid Chromatography

Cyclopropenoid fatty acids (CPFAs), found in cottonseed, have been shown to have detrimental health effects to susceptible livestock. Previous quantitative analytical methods for the determination of CPFAs expressed these acids in terms of their relative abundance with respect to other fatty acids in the oil, necessitating the concurrent analysis of other fatty acids. The proposed analytical method describes the quantitation of three relevant CPFAs for cotton (malvalic acid, sterculic acid, and dihydrosterculic acid) in cottonseed in micrograms per gram fresh weight of sample. The method involves extraction of the oil, saponification, and derivatization of the free fatty acids with 2-bromoacetophenone to give the phenacyl esters. These esters are then separated by dual-column reverse-phase high-performance liquid chromatography and quantitated via external standards. This is the first method to include external calibration standards for CPFAs and, as such, is capable of direct quantification with no further data conversion required. CPFA data generated from the analysis of cottonseed, cottonseed meal, and cottonseed oil produced in the United States in 2002 are presented.

Unique occurrence of unusual fatty acids in Ochrocarpus africanus seed oil

The seed oils containing unusual fatty acids are being exploited for industrial utilization and are highly important to the production of oleochemicals. Ochrocarpus africanus belongs to Guttiferea plant family which is a rich source of viscous, non-edible and renewable crude oil (30.0%) containing ricinoleic acid (20.0%), vernolic acid (12.0%), malvalic acid (6.0%) and sterculic acid (4.0%) as its unusual fatty acids along with the other normal fatty acids like lauric acid (1.1%), myristic acid (1.3%), palmitic acid (28.2%), stearic acid (27.4%), oleic acid (trace) and linoleic acid (trace). The present investigation describes the unique occurrence of unusual fatty acids in O. africanus seed oil as well as in Guttiferea plant family. These fatty acids have been characterized by UV, FTIR, 1H NMR, 13C NMR, MS, GLC-techniques and chemical degradations.

Occurrence of unusual fatty acids in Ficus benghalensis seed oil

Ficus benghalensis is a rich source of oil containing unusual fatty acids which could be used for industrial utilization. F. benghalensis seed oil is found to contain vernolic acid (8.2%), malvalic acid (3.7%) and sterculic acid (1.6%) along with the other normal fatty acids like lauric acid (1.5%), myristic acid (1.3%), palmitic acid (35.2%), stearic acid (4.2%), oleic acid (20.3%), linoleic acid (15.4%) and linolenic acid (8.7%). Vernolic, malvalic, sterculic and other normal fatty acids have been identified and characterized by UV, FTIR, 1H NMR, MS, TLC, GLC-techniques and chemical degradations.

Industrial utilization of Triumfetta pilosa, Roth seed oil: A moderate source of oil and cyclopropenoid fatty acids

Triumfetta pilosa contain malvalic acid (2.4%) and sterculic acid (6.6%) along with the other normal fatty acids like palmitic (16.7%), stearic (10.8%), oleic (20.1%) and linoleic (43.4%). The cyclopropenoid (malvalic and sterculic) and other normal fatty acids have been determined by FTIR, 1H NMR, gas liquid chromatographic-techniques and chemical degradations.

Analysis of Cassia marginata and Cassia corymbosa seed oils: An approach for the industrial utilization

Cassia marginata, Roxb and Cassia corymbosa, Linn seed oils contain unusual fatty acids like vernolic acid (8.5 and 9.2%), malvalic acid (3.5 and 3.2%) and sterculic acid (2.6 and 2.8%). They also contain palmitic acid (17.3 and 17.2%), palmitoleic (trace and 7.4%), stearic acid (4.5 and 4.2%), oleic acid (14.2 and 14.8%) and linoleic acid (49.4 and 41.2%), respectively. These fatty acids were determined and characterized by UV, FTIR, 1H NMR, MS, GLC-techniques and chemical degradations.

Acacia arabica varieties— Telia babul, Vediana and Cupressiformis seed oils: a moderate source of coronaric and cyclopropene fatty acids

The seed oils from Acacia arabica varieties— Telia babul, Vediana and Cupressiformis were found to contain unique occurrence of unusual fatty acids, 9,10-epoxy-octadec- cis-12-enoic acid (coronaric acid, 9.0%, 7.0% and 7.5%), 7-(2-octacyclopropen-1-yl)heptanoic acid (malvalic acid, 2.5%, 2.1% and 2.2%) and 8-(2-octacyclopropen-1-yl)octanoic acid (sterculic acid, 2.1%, 1.1% and 1.8%), respectively along with the other normal fatty acids. These fatty acids were determined and characterized by UV, FTIR, 1H NMR, MS, GLC-techniques and chemical degradations.

Unusual fatty acids from Crotalaria striata Syn. Crotalaria mucronata seed oil

The unique occurrence of unusual fatty acids like 12-hydroxy-octadec- cis-9-enoic acid (ricinoleic acid, 15.8%), 7-(2-octacyclopropen-1-yl)heptanoic acid (malvalic acid, 2.1%) and 8-(2-octacyclopropen-1-y1)octanoic acid (sterculic acid, 4.3%) along with the other normal fatty acids like myristic (3.6%), palmitic (32.1%), stearic (4.1%) oleic (8.0%), linoleic (15.0%) and linolenic (15.0%) have been detected in the seed oil of Crotalaria striata Syn. Crotalaria mucronata. These fatty acids have been determined and characterized by UV, FTIR, 1H NMR, MS, TLC, GLC and chemical transformations.

Cyclopropenoic fatty acids in gymnosperms: The seed oil of Welwitschia

AbstractThe seed oil of the gymnosperm Welwitschia mirabilis was found to contain malvalic acid, a cyclopropenoic fatty acid. This is in sharp contrast to most other gymnosperms, which contain Δ5cis‐fatty acids as well as the normal set of fatty acids. The importance of this finding in relation to questions of the evolution of the Gymnospermae and Angiospermae, the two main branches of higher plants, is briefly discussed.

Unique Occurrence of Unusual Fatty Acids and Their Industrial Utilization

Ebenaceae plant family consists of 7 genera and more than 320 species. The present investigation describes the unique occurrence of hitherto unknown 9-keto-cis-13-octadecenoic acid (29.0%) and the cyclopropenoid fatty acids (malvalic acid 12.7% and sterculic acid 8.7%) in the seed oil of Diospyros melanoxylon as well as in the Ebenaceae plant family. Other normal fatty acids are also detected. The identification and characterization were based on FTIR, 1H NMR, 13C NMR, MS, and GLC techniques and chemical degradations.

A minor source of vernolic, malvalic, and sterculic acids inPithecollobium dulce (syn.Inga dulcis ) seed oil

Pithecollobium dulce, Benth (syn.Inga dulcis, Willd) seed oil, belonging to the Leguminosae plant family, contains minor amounts of vernolic acid (12,13-epoxy-octadec-cis-9-enoic acid, 10.0%), malvalic acid [7-(2-octacyclopropen-1-yl)heptanoic acid, 3.2%], and sterculic acid [8-(2-octacyclopropen-1-yl)octanoic acid, 2.0%]. The other normal fatty acids are palmitic (12.1%), stearic (4.2%), behenic (10.6%), oleic (34.1%), and linoleic (23.8%). These fatty acids have been characterized by Fourier transform infrared,1H nuclear magnetic resonance, mass spectrometry and gas-liquid chromatography techniques and by chemical degradations.

Component Fatty Acids of Delonix regis Seed Oil — A Source of 7‐(2‐Octacyclopropen‐1‐yI)heptanoic Acid and 8‐(2‐OctacycIopropen‐1‐yl)octanoic Acid

AbstractDelonix regia. Raffin Svn. Poinaana regia, Bojer ex Hook seed oil belonging to the Leguminosae plant family which contains an appreciable amount of 7‐(2‐octaeyclopropcn‐1‐yl)heptanoic acid (malvalic acid. 6.3%) and 8‐(2‐octacyclopropen‐1‐yl)octanoic acid (sterculic acid. 4.2%) along with the other normal fatty acids like myristic (1.1 %). palmitic (14.0%). stearic (11.0%), oleic (12.7%) and linoleic (50.7%,). These fatty acids were characterized by FTIR, H NMR. GLC‐techniques and chemical transformations.

Inhibition of fatty acid Δ6- andΔ5-desaturation by cyclopropene fatty acids in rat liver microsomes

Δ 6-Desaturation of linoleic acid and Δ 5-desaturation of dihomo-γ-linolenic acid were measured in liver microsomes from ra fresh Baobab seed oil containing cyclopropene fatty acids (malvalic acid and sterculic acid) or heated Baobab seed oil practically devoid of these fatty acids or control oil. The presence of cyclopropene fatty acids in the fresh Baobab oil diet highly depressed both desaturations, but Δ6- more than Δ 5-desaturation. The decreased capacity of microsomes to desaturate was reflected in the lower arachidonic acid content in microsomal phospholipids from rats fed this oil. However it was also lower in rats fed heated oil although in vitro Δ 6- and Δ 5-desaturation were not depressed. When liver microsomes prepared from rats fed the control diet were used for the desaturation assays, the presence of free malvalic or sterculic acid in the medium, also highly depressed Δ 6- and Δ 5-desaturation. The incorporation of arachidonic acid, the product of Δ 5-desaturation, into phospholipids was also highly depressed, while that of the precursor dihomo-γ-linolenic acid was not. This suggests that cyclopropene fatty acids specifically inhibit incorporation of the Δ 5-desaturation product into phospholipids or that they specifically inhibit desaturation of the substrate previously incorporated into a membrane phospholipid.

Influence of cyclopropene fatty acids (Baobab seed oil) feeding on the in vitro Δ9 desaturation of stearic acid in rat liver microsomes

Δ9 desaturation of [1− 14 C] stearic acid to oleic acid was studied in liver microsomes of rats fed either fresh Baobab seed oil, containing cyclopropene fatty acids (malvalic acid and sterculic acids), or heated Baobab oil, containing only minor amounts of these acids. This was compared with rats fed a control oil mixture or a fat-free diet. Up to 50 nmol of substrate, Δ9 desaturation rate was the same in rats fed the three fat diets. From 50 to 150 nmol, the desaturation rates were practically constant in rats fed fresh Baobab seed oil. It increased in heated oil-fed rats at the same rate as in the control group, but more slowly than in the fat-free diet group. Fatty acid composition of liver microsomal lipids did not reflect the in vitro observed desanturation rate because monounsaturated fatty acids were in the same percentages in fresh and heated Baobab seed oil-fed rats. Moreover, the proportion of arachidonic acid was lower, and that of linoleic acid higher for both diets, in comparison with controls, suggesting a decreased Δ6 and/or Δ5 desaturation rate.

Fatty acid composition of Sterculia seeds and oils from Madagascar

The percentage contents of oil and protein in the seeds of 17 species belonging to 9 genera of the Sterculiaceae family, growing in Madagascar, were determined. The major fatty acids were palmitic (11.6-27.5%), oleic (8.3-32.6%), linoleic (4.2-45.8% ), malvalic (tr-53.7961, and sterculic (1.3-24.876) acids. Heritiera littoralis seed oil was characterized by a high content of malvalic (53.7 %) and sterculic acids (12.4 % ). Cyclopropene fatty acids were identified and determined by using a combination of gas chromatographic and 'H and 13C NMR analyses. Dihydrosterculic acid was also detected in all samples at a low concentration.

In Vivoandin VitroEffects of a Cyclopropenoid Fatty Acid on Ovine Corpus Luteum Function*

Experiments were conducted to examine the effect of a cyclopropenoid fatty acid (CPFA) on progesterone (P4) production by the ovine corpus luteum (CL) during the estrous cycle. Ewes in Exp 1 and 2 were laparotomized on day 2 of the estrous cycle, and animals with CL in both ovaries were subjected to unilateral ovariectomy. Ewes with CL in one ovary only were not ovariectomized. During surgery, ewes were injected with a mixture of fatty acids (sterculic acid, 39%; palmitic, 29%; linoleic, 12%; malvalic acid, 9%; oleic, 8%; stearic, 3%) containing 500 micrograms sterculic acid (SA; Exp 1), 750 micrograms SA, or 750 micrograms oleic acid (Exp 2) via the artery supplying the ovary bearing the CL. Control ewes were similarly injected with vehicle only (0.1-0.2 ml dimethylsulfoxide; Exp 1 and 2, respectively). Sera from blood samples collected at 15-min intervals for 1 h after injection or once daily on alternate days of the cycle after surgery were analyzed for LH and P4, respectively. In Exp 3, slices of CL removed from five ewes on day 10 of the cycle were incubated for 90 min in medium containing 100 ng/ml SA or vehicle (10 microliters dimethylsulfoxide). Slices were then reincubated for 90 min in medium containing 10 ng/ml oLH or saline (10 microliters). Tissue and medium were analyzed for P4. Injection of 500 micrograms SA suppressed serum levels of P4 (P less than 0.01), but did not alter mean cycle length. Injection of 750 micrograms SA reduced serum concentrations of P4 and shortened estrous cycle duration (P less than 0.005). Oleic acid (750 micrograms) or as much as 1.9 mg of a mixture of fatty acids devoid of CPFA had no effect on cycle length or serum levels of P4, suggesting that altered luteal function was due to the type and not the quantity of fatty acid injected. Treatments had no effect on serum concentrations of LH. Preincubation with SA interfered with the ability of luteal slices to synthesize P4 when subsequently incubated alone or with ovine LH (P less than 0.01). It is concluded that SA acts on the CL to impair steroidogenesis and ultimately cause luteal regression.

Cyclopropenoid fatty acids in leguminosae oils

AbstractSeed oils ofCassia grandis, Linn andDelonix elata, Gamble, Syn.Poinciana elata, Linn, belonging to the Leguminosae family contain small amounts of sterculic and malvalic acids as determined by conversion of esters with AgNO3/MeOH, NMR and IR.

Cyclopropenoid fatty acids ingnetum scandens and itsterculia pallens seed oils

AbstractSeed oils ofGnetum scandens (Gnetaceae) andSterculia pattens (Sterculiaceae) were found to contain sterculic (28.57,6.97) and malvalic (11.27,3.87) acids, respectively. Gas Chromatographic analysis of silver nitrate/meth‐anol‐treated methyl esters was used to establish the co‐occurrence of these two acids.Sterculia foetida methyl esters were used as a reference standard.

The fatty acid composition of Hibiscus sabdariffa seed oil

AbstractAnalysis of Hibiscus sabdariffa seed oil from different seed collections (or cultivars), representing different growing areas, showed differences in the fatty acid pattern, especially with respect to linoleic (30.1‐37.45%) and epoxyoleic (trace to 5.3%). The results showed different values from those previously reported for the cyclopropenoid fatty acid, found to be malvalic acid (0.4‐2.0%), responsible for the positive Halphen response of the oil. It is now also established that the oil contains dihydrosterculic acid (1.0‐1.6%) which has been reported previously in other species of the genus Hibiscus. The results of the rest of fatty acids showed ranges for myristic 0.2‐0.5%, palmitic 17.4‐22.6%, stearic 3.9‐5.2% and oleic acid 34.6‐39.8%.

Cyclopropenoid Acid and Fatty Acid Content of Ten Varieties of Hybrid Cotton Seed Oils

AbstractThe cyclopropenoid (Malvalic acid) fatty acid content of oils from ten varieties of cotton seeds has been determined range (0.7 to 1.3). Iodine values varied from 32.9 to 114.0. The fatty acid composition was in the following range: Myristic, 0.9‐3.0; palmitic, 18.3‐34.1; stearic, 2.2‐4.5; arachidic, 0.8‐1.4; behenic, 0.9‐1.2; oleic, 9.7‐22.1; linoleic, 42.4‐52.5. The oil content varied from 22.5% to 24.5%.