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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.


Structural formulas of hydroxy fatty acids in the present study.
© Copyright Policy - open-access
Related In: Results  -  Collection


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fig1: Structural formulas of hydroxy fatty acids in the present study.

Mentions: Pollen contains many kinds of nutrient which are necessary to human body. It is well known as a natural nutrition, health food, and “perfect food.” The pollen preparation (Qian Lie Kang Tablets) made of Brassica campestris L. var. oleifera DC. has also been widely used in China as a good treatment for benign prostatic hyperplasia (BPH), and a chemical study has found plenty of fatty acids in the pollen [1]. Reports have shown promising therapeutic effects of fatty acids and their derivatives in treatment of BPH [2–6]. Hydroxy fatty acids contained in pollen are important bioactive substances. Various kinds of hydroxy fatty acids exhibit many pharmacological activities such as antitumor, antifungal, and prostaglandin E-like [7–9]. Although the pollen preparation has been used as phytotherapy for BPH for a long time, its active components and mechanism of action remain unclear. The effects of the supercritical fluid extract and its residue of the plant were screened so as to clarify its active constituents, and its supercritical fluid extract decreased the size of the prostate of androgen-induced prostatic rats by in vivo experiments (P < 0.01) and also demonstrated remarkable inhibitory effects on 5α-reductase and aromatase through in vitro experiments. The chemical investigation of its supercritical fluid extract has led to the isolation of some fatty acids and fatty acid derivatives [10], and the activity test experiments showed that fatty acids possessed strong inhibitory activity on 5α-reductase, which were consistent with literature reports [2–4]. The activity test experiments also displayed that fatty acid derivatives possessed strong inhibitory activity on aromatase [10]. 5α-reductase and aromatase are two important effect targets on prostate hyperplasia [11], so fatty acids and fatty acid derivatives play a coreaction role in treatment of BPH. UPLC-MS combine the efficient separation capability of UPLC and the great power in structural characterization of MS and provide new powerful approach to identify the constituents in plant extracts rapidly and accurately. In this paper, we investigated the fragmentation behaviors of hydroxy fatty acids in a Micromass Q/TOF Mass Spectrometer and emphasized on the structural determination of hydroxy fatty acids 1–7 (Figure 1) from the supercritical fluid extract by UPLC-ESI-MS/MS.


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)

Structural formulas of hydroxy fatty acids in the present study.
© Copyright Policy - open-access
Related In: Results  -  Collection

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

fig1: Structural formulas of hydroxy fatty acids in the present study.
Mentions: Pollen contains many kinds of nutrient which are necessary to human body. It is well known as a natural nutrition, health food, and “perfect food.” The pollen preparation (Qian Lie Kang Tablets) made of Brassica campestris L. var. oleifera DC. has also been widely used in China as a good treatment for benign prostatic hyperplasia (BPH), and a chemical study has found plenty of fatty acids in the pollen [1]. Reports have shown promising therapeutic effects of fatty acids and their derivatives in treatment of BPH [2–6]. Hydroxy fatty acids contained in pollen are important bioactive substances. Various kinds of hydroxy fatty acids exhibit many pharmacological activities such as antitumor, antifungal, and prostaglandin E-like [7–9]. Although the pollen preparation has been used as phytotherapy for BPH for a long time, its active components and mechanism of action remain unclear. The effects of the supercritical fluid extract and its residue of the plant were screened so as to clarify its active constituents, and its supercritical fluid extract decreased the size of the prostate of androgen-induced prostatic rats by in vivo experiments (P < 0.01) and also demonstrated remarkable inhibitory effects on 5α-reductase and aromatase through in vitro experiments. The chemical investigation of its supercritical fluid extract has led to the isolation of some fatty acids and fatty acid derivatives [10], and the activity test experiments showed that fatty acids possessed strong inhibitory activity on 5α-reductase, which were consistent with literature reports [2–4]. The activity test experiments also displayed that fatty acid derivatives possessed strong inhibitory activity on aromatase [10]. 5α-reductase and aromatase are two important effect targets on prostate hyperplasia [11], so fatty acids and fatty acid derivatives play a coreaction role in treatment of BPH. UPLC-MS combine the efficient separation capability of UPLC and the great power in structural characterization of MS and provide new powerful approach to identify the constituents in plant extracts rapidly and accurately. In this paper, we investigated the fragmentation behaviors of hydroxy fatty acids in a Micromass Q/TOF Mass Spectrometer and emphasized on the structural determination of hydroxy fatty acids 1–7 (Figure 1) from the supercritical fluid extract by UPLC-ESI-MS/MS.

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.