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Analysis of Hydroxy Fatty Acids from the Pollen of Brassica campestris L. var. oleifera DC. by UPLC-MS/MS.

Yang NY, Yang YF, Li K - J Pharm (Cairo) (2012)

Bottom Line: Ultraperformance liquid chromatography coupled with negative electrospray tandem mass spectrometry (UPLC-ESI-MS/MS) was used to determine 7 hydroxy fatty acids in the pollen of Brassica campestris L. var. oleifera DC.All the investigated hydroxy fatty acids showed strong deprotonated molecular ions [M-H](-), which underwent two major fragment pathways of the allyl scission and the β-fission of the alcoholic hydroxyl group.Compounds 3, 5, and 7 are reported for the first time.

View Article: PubMed Central - PubMed

Affiliation: Department of Traditional Chinese Medicine, Shanghai Institute of Pharmaceutical Industry, Shanghai 200040, China.

ABSTRACT
Ultraperformance liquid chromatography coupled with negative electrospray tandem mass spectrometry (UPLC-ESI-MS/MS) was used to determine 7 hydroxy fatty acids in the pollen of Brassica campestris L. var. oleifera DC. All the investigated hydroxy fatty acids showed strong deprotonated molecular ions [M-H](-), which underwent two major fragment pathways of the allyl scission and the β-fission of the alcoholic hydroxyl group. By comparison of their molecular ions and abundant fragment ions with those of reference compounds, they were tentatively assigned as 15,16-dihydroxy-9Z,12Z-octadecadienoic acid (1), 10,11,12-trihydroxy-(7Z,14Z)-heptadecadienoic acid (2), 7,15,16-trihydroxy-9Z,12Z-octadecadienoic acid (3), 15,16-dihydroxy-9Z,12Z-octadecadienoic acid (4), 15-hydroxy-6Z,9Z,12Z-octadecatrienoic acid (5), 15-hydroxy-9Z,12Z- octadecadienoic acid (6), and 15-hydroxy-12Z-octadecaenoic acid (7), respectively. Compounds 3, 5, and 7 are reported for the first time.

No MeSH data available.


Related in: MedlinePlus

Characteristic fragmentation pathways for the molecular anion of compounds 1–7.
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fig4: Characteristic fragmentation pathways for the molecular anion of compounds 1–7.

Mentions: The full MS/MS product ion spectrum of compound 1 was shown in Figure 3. Six primary product ions are observed and it is proposed that they are formed in two major fragment pathways (Figure 4). Pathway I involves the β-fission of alcoholic hydroxyl group along with the neutral loss of propionaldehyde and 2-hydroxy-butyraldehyde or 1-hydroxy-2-butanone, which results in the formation of m/z 253 and m/z 223 as the major peaks. Pathway II involves the allyl scission leading to the formation of m/z 183 as the main peak. Some other pathways indicated neutral loss of H2O or CO or H2 from the deprotonated molecular and fragments. The allyl scission of the molecular ion [M–H]− at m/z 313 of 2 leads to the formation of m/z 213, and the β -fission of OH group of 2 lost 1,3-pentadiene and 2,3-dihydoxy-octa-5-enal or 1,3-dihydoxy-octa-5-en-2-one to produce the major peaks of m/z 245 and m/z 155.


Analysis of Hydroxy Fatty Acids from the Pollen of Brassica campestris L. var. oleifera DC. by UPLC-MS/MS.

Yang NY, Yang YF, Li K - J Pharm (Cairo) (2012)

Characteristic fragmentation pathways for the molecular anion of compounds 1–7.
© Copyright Policy - open-access
Related In: Results  -  Collection

Show All Figures
getmorefigures.php?uid=PMC4595942&req=5

fig4: Characteristic fragmentation pathways for the molecular anion of compounds 1–7.
Mentions: The full MS/MS product ion spectrum of compound 1 was shown in Figure 3. Six primary product ions are observed and it is proposed that they are formed in two major fragment pathways (Figure 4). Pathway I involves the β-fission of alcoholic hydroxyl group along with the neutral loss of propionaldehyde and 2-hydroxy-butyraldehyde or 1-hydroxy-2-butanone, which results in the formation of m/z 253 and m/z 223 as the major peaks. Pathway II involves the allyl scission leading to the formation of m/z 183 as the main peak. Some other pathways indicated neutral loss of H2O or CO or H2 from the deprotonated molecular and fragments. The allyl scission of the molecular ion [M–H]− at m/z 313 of 2 leads to the formation of m/z 213, and the β -fission of OH group of 2 lost 1,3-pentadiene and 2,3-dihydoxy-octa-5-enal or 1,3-dihydoxy-octa-5-en-2-one to produce the major peaks of m/z 245 and m/z 155.

Bottom Line: Ultraperformance liquid chromatography coupled with negative electrospray tandem mass spectrometry (UPLC-ESI-MS/MS) was used to determine 7 hydroxy fatty acids in the pollen of Brassica campestris L. var. oleifera DC.All the investigated hydroxy fatty acids showed strong deprotonated molecular ions [M-H](-), which underwent two major fragment pathways of the allyl scission and the β-fission of the alcoholic hydroxyl group.Compounds 3, 5, and 7 are reported for the first time.

View Article: PubMed Central - PubMed

Affiliation: Department of Traditional Chinese Medicine, Shanghai Institute of Pharmaceutical Industry, Shanghai 200040, China.

ABSTRACT
Ultraperformance liquid chromatography coupled with negative electrospray tandem mass spectrometry (UPLC-ESI-MS/MS) was used to determine 7 hydroxy fatty acids in the pollen of Brassica campestris L. var. oleifera DC. All the investigated hydroxy fatty acids showed strong deprotonated molecular ions [M-H](-), which underwent two major fragment pathways of the allyl scission and the β-fission of the alcoholic hydroxyl group. By comparison of their molecular ions and abundant fragment ions with those of reference compounds, they were tentatively assigned as 15,16-dihydroxy-9Z,12Z-octadecadienoic acid (1), 10,11,12-trihydroxy-(7Z,14Z)-heptadecadienoic acid (2), 7,15,16-trihydroxy-9Z,12Z-octadecadienoic acid (3), 15,16-dihydroxy-9Z,12Z-octadecadienoic acid (4), 15-hydroxy-6Z,9Z,12Z-octadecatrienoic acid (5), 15-hydroxy-9Z,12Z- octadecadienoic acid (6), and 15-hydroxy-12Z-octadecaenoic acid (7), respectively. Compounds 3, 5, and 7 are reported for the first time.

No MeSH data available.


Related in: MedlinePlus