<i>cis</i>‐Vaccenic acid in mango pulp lipids

Shibahara, Akira; Yamamoto, Kohei; Nakayama, Takao; Kajimoto, Gorō

doi:10.1007/bf02534933

Cited by 34 publications

(25 citation statements)

References 38 publications

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“…cis-Vaccinate occurs at high levels (more than 10% of total fatty acids) in some seed oils (Chisholm antl Hopkins, 1965;Kleimari and Payne-Wahl, 1984), fruit pulp (Shibahara et al, 1986(Shibahara et al, , 1987Hibahara et al, 1989;Yamamoto et al, 19901, and tissue cultures of Hydnocarpus anthelminthica (Spencer et al, 1974) and Petroselinum crispum (Illlenbracht et al, 1980). However, in most plants (Chisholm and Hopkins, 1965;Mukherjee and Kiewitt, 19801, as well as mammals (Holoway and Wabil, 1964;Kuemmel and Chapman, 1968;Longmuir, 1987) and microorganisms (Fulco, 1983), it i s present in low concentrations (0.52%).…”

Section: Discussionmentioning

confidence: 99%

Oleic Acid and Its Positional Isomer, cis-Vaccinic Acid, in the Appendix of Sauromatum guttatum during Anthesis

Skubatz¹,

Svee²,

Moore³

et al. 1995

Plant Physiol.

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California 9561 6 (E.R.S.); and Fairchild Tropical Garden, l h e fatty acid profiles of various organs of the thermogenic inflorescence of Sauromatum guttatum and of the sporophylls of thermogenic male cones of two cycad species (fncephalartos ferox and Dioon edule var edule and var angustifolium) were determined by gas chromatography. During anthesis, palmitate (1 6:0), oleate [18:1 (9)], cis-vaccinate [18:1 (ll)], and linoleate [18:2 (9, 12)l were the most abundant fatty acids i n the Sauromatum appendix.cis-Vaccinic acid, a positional isomer of oleic acid, was identified by comparing its retention time on a gas chromatography column and its mass spectrum to an authentic compound. The percentage of oleic acid from total fatty acids dropped from about 9 in the morning 3 d before heat production to 6 in the morning 2 d before heat production. At this time, the percentage of cis-vaccinic acid increased from 3 to 11 %, and then remained at this level until the inflorescence dried and died. Palmitoleic acid [16:1 (9)], the common precursor of cis-vaccinic acid, is a minor component of total fatty acids. In six other organs of the Sauromatum inflorescence including thermogenic organs, such as male flowers and lower spadix, palmitate, oleate, and linoleate were prevalent but cisvaccinate was not. The thermogenic male cones of the two cycad species were rich i n palmitic, oleic, and linolenic acids. The level of cis-vaccinic acid i n these organs was less than 0.5%.One striking example of a thermogenic plant organ is provided by the inflorescence of Sauromatum guttatum (the voodoo lily). On D-day, the day of inflorescence opening, the Sauromatum appendix (a 20-cm-long, slender organ) becomes hot, reaching a temperature of 32°C (Skubatz et al., 1991). The heat facilitates the vaporization of odoriferous compounds that attract pollinators; the heat loss reaches a value of 1 mW/mg dry weight . The heat is generated by the mitochondria via an alternative, cyanide-resistant pathway. The activity of this pathway, which is present in the mitochondria of many plant species, does not produce ATP, and the energy is thus released as heat (Siedow and Moore, 1993).Electron microscopic study of the Sauromatum appendix has revealed the presence of numerous lipid bodies in the cells ). It appears that the lipid bodies,

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Section: Discussionmentioning

confidence: 99%

Oleic Acid and Its Positional Isomer, cis-Vaccinic Acid, in the Appendix of Sauromatum guttatum during Anthesis

Skubatz¹,

Svee²,

Moore³

et al. 1995

Plant Physiol.

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“…Together with the ion at m/z 143, which is created from the signal at m/z 175 by the loss of methanol, they clearly establish the structure of methyl petroselinate. Besides this, the much weaker signals at m/z 217 and 173 corresponding to the typical fragmentation pattern of the DMDS adduct of methyl oleate (13,21,22) also can be found. Clearly, the oleate DMDS fragments are much less prominent, again confirming the predominance of petroselinic acid as found by GLC under special conditions (Table 1).…”

Section: Resultsmentioning

confidence: 87%

Geranium sanguineum (Geraniaceae) seed oil: A new source of petroselinic and vernolic acid

Tsevegsüren

Aitzetmüller²,

Vosmann³

2004

Lipids

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The occurrence of petroselinic acid (18:1delta6cis) in seed oils was believed to be limited to the Umbelliferae or Apiaceae, and a few other members of the Umbelliflorae. A major occurrence of petroselinic acid outside the Umbelliflorae must therefore be regarded as highly unusual and surprising. The seed oil of Geranium sanguineum, a member of the family Geraniaceae, has now been found to contain petroselinic and vernolic acids as major FA in its seed oil TAG. These unusual FA have not been reported previously as constituents of Geraniaceae seed oils. The structure and composition of the seed oil FA from G. sanguineum were determined by combined use of chromatographic (TLC, capillary GLC) and spectroscopic (IR, GC-MS) techniques. The double-bond position in petroselinic acid was located unambiguously by the characteristic mass fragmentation of its dimethyldisulfide (DMDS) adduct. The epoxy FA was identified as vernolic acid by co-chromatography and by the mass fragments formed during GC-MS of the products of the epoxy ring-opening reaction with BF3 in methanol.

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“…The internal standard (IS), 3-hydroxyhexadecanoic acid (50 lg), was added to each 50 mg sample, and then these samples were methanolyzed with 0.5 M KOH/methanol (1 mL) and successively methylated with 14% BF 3 /methanol (1.5 mL), under the same conditions as those described in our previous research [5]. After adding a saturated NaCl aqueous solution (5 mL), the resultant fatty acid methyl esters were extracted three times with hexane (3 mL each time).…”

Section: Preparation Of Derivatives From Oil Samplesmentioning

confidence: 99%

Ricinoleic Acid in Common Vegetable Oils and Oil Seeds

Yamamoto

Kinoshita

Shibahara

2008

Lipids

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An original gas chromatography/mass spectrometry method for quantifying trace amounts of ricinoleic acid (12-hydroxy-cis-9-octadecenoic acid) is detailed. Data are presented on trace amounts of ricinoleic acid found in several common vegetable oils and oils extracted from common oil seeds: e.g., ca. 30 ppm in commercial olive oil was the lowest amount; and ca. 2,690 ppm in oil extracted from cottonseeds was the highest amount.

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cis‐Vaccenic acid in mango pulp lipids

Cited by 34 publications

References 38 publications

Oleic Acid and Its Positional Isomer, cis-Vaccinic Acid, in the Appendix of Sauromatum guttatum during Anthesis

Oleic Acid and Its Positional Isomer, cis-Vaccinic Acid, in the Appendix of Sauromatum guttatum during Anthesis

Geranium sanguineum (Geraniaceae) seed oil: A new source of petroselinic and vernolic acid

Ricinoleic Acid in Common Vegetable Oils and Oil Seeds

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