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

DOI: 10.1155/2013/874875

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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. 1. Introduction 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 and also demonstrated remarkable inhibitory effects on 5 -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 5 -reductase, which were consistent with literature reports [2–4]. The activity test experiments also displayed

References

[1]  J. G. Pang, Y. Duan, and H. Q. Wu, “Analysis of the chemical constituents of rape pollen,” Chinese Journal of Instrumental Analysis, vol. 22, pp. 74–76, 2003.
[2]  L. Y. Pérez, R. Menéndez, R. Má, and R. M. González, “In vitro effect of D-004, a lipid extract of the fruit of the cuban royal palm (Roystonea regia), on prostate steroid 5α-reductase activity,” Current Therapeutic Research, vol. 67, no. 6, pp. 396–405, 2006.
[3]  M. L. Arruzazabala, R. Mas, D. Carbajal, and V. Molina, “D-004, a lipid extract from royal palm fruit, exhibits antidepressant effects in the forced swim test and the tail suspension test in mice,” Drugs in R&D, vol. 6, pp. 281–289, 2005.
[4]  H. J. Niederprum, H. U. Schweikert, and K. S. Zanker, “Testosterone 5 alpha-reductase inhibition by free fatty acids from Sabal serrulata fruits,” Phytomedicine, vol. 1, pp. 127–133, 1994.
[5]  Y. M. H. Younis, S. Ghirmay, and S. S. Al-Shihry, “African Cucurbita pepo L.: properties of seed and variability in fatty acid composition of seed oil,” Phytochemistry, vol. 54, no. 1, pp. 71–75, 2000.
[6]  Y. H. Li, Y. F. Yang, and D. Y. Kong, “Advances in studies on active components for 5α-reductase inhibitors isolated from plants,” Chinese Traditional and Herbal Drugs, vol. 37, no. 11, pp. 1740–1744, 2006.
[7]  R. W. Jiang, M. E. Hay, C. R. Fairchild et al., “Antineoplastic unsaturated fatty acids from Fijian macroalgae,” Phytochemistry, vol. 69, no. 13, pp. 2495–2500, 2008.
[8]  H. Ohigashi, K. Kawazu, and H. Egawa, “Antifungal constituent of Sapium japonicum,” Agricultural and Biological Chemistry, vol. 36, pp. 1399–1403, 1972.
[9]  A. G. Panossian, G. M. Avetissian, and V. A. Mnatsakanian, “Unsaturated polyhydroxy acids having prostaglandin-like activity from Bryonia alba II. Major components,” Planta Medica, vol. 47, no. 1, pp. 17–25, 1983.
[10]  N. Y. Yang, K. Li, Y. F. Yang, and Y. H. Li, “Aromatase inhibitory fatty acid derivatives from the pollen of Brassica campestris L. var. oleifera DC.,” Journal of Asian Natural Products Research, vol. 11, no. 2, pp. 132–137, 2009.
[11]  L. L. Jin, K. Li, Y. F. Yang, and N. Y. Yang, “Advance in the research of drug targets on prostate hyperplasia,” Chinese Pharmaceutical Journal, vol. 49, pp. 161–165, 2009.
[12]  J. L. Zhang, J. Kubanek, M. E. Hay, W. Aalbersberg, W. C. Ye, and R. W. Jiang, “Rapid identification of triterpenoid sulfates and hydroxy fatty acids including two new constituents from Tydemania expeditionis by liquid chromatography-mass spectrometry,” Journal of Mass Spectrometry, vol. 46, pp. 908–916, 2011.
[13]  T. Caruso and A. Spinella, “First total synthesis of natural aplyolides C and E, ichthyotoxic macrolides isolated from the skin of the marine mollusc Aplysia depilans,” Tetrahedron Asymmetry, vol. 13, no. 19, pp. 2071–2073, 2002.
[14]  M. Hamberg and G. Hamberg, “15(R)-hydroxylinoleic acid, an oxylipin from oat seeds,” Phytochemistry, vol. 42, no. 3, pp. 729–732, 1996.

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