The oleic acid esterification of policosanol increases its bioavailability and hypocholesterolemic action in rats

Haim, Daniela; Valenzuela, Alfonso; Brañes, M. C.; Fuenzalida, Marcela; Videla, Luis A.

doi:10.3989/gya.010612

Cited by 11 publications

(11 citation statements)

References 40 publications

(49 reference statements)

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“…42) Γ-Oryzanol has several important physical effects, including hypocholesterolemic, anti-inflammatory, and antioxidant activities. 43) More than 50 studies indicate that policosanol decreases serum cholesterol, while other studies failed to reproduce this effect, 44) and tocotrienol possess po- tent antioxidant activity. 45) Upon examining the hair growth-promoting effects of the major components in RB-SCE, LA and OZ exhibited outstanding hair growth-promoting potential, showing similar results to that of 3% minoxidil based on macroscopic and histological evaluation (Fig.…”

Section: Discussionmentioning

confidence: 99%

<i>In Vivo</i> Hair Growth-Promoting Effect of Rice Bran Extract Prepared by Supercritical Carbon Dioxide Fluid

Choi

Jeon²,

Moon³

et al. 2014

Biological & Pharmaceutical Bulletin

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The potential hair growth-promoting activity of rice bran supercritical CO 2 extract (RB-SCE) and major components of RB-SCE, linoleic acid, policosanol, γ-oryzanol, and γ-tocotrienol, were evaluated with the histological morphology and mRNA expression levels of cell growth factors using real-time reverse transcriptase-polymerase chain reaction (PCR) in C57BL/6 mice. RB-SCE showed hair growth-promoting potential to a similar extent as 3% minoxidil, showing that the hair follicles were induced to be in the anagen stage. The numbers of the hair follicles were significantly increased. In addition, mRNA expression levels of vascular endothelial growth factor (VEGF), insulin-like growth factor-1 (IGF-1), and keratinocyte growth factor (KGF) were also significantly increased and that of transforming growth factor-β (TGF-β) decreased in RB-SCE-treated groups. Among the major components of RB-SCE, linoleic acid and γ-oryzanol induced the formation of hair follicles according to examination of histological morphology and mRNA expression levels of cell growth factors. In conclusion, our results demonstrate that RB-SCE, particularly linoleic acid and γ-oryzanol, promotes hair growth and suggests RB-SCE can be applied as hair loss treatment. Key words rice bran supercritical CO 2 extract; hair growth-promoting activity; in vivoAlthough hair loss is not a mortal disorder, it has a great impact on a person's self-respect, mental health, and overall quality of life. Approximately 50-60 hairs are normally lost per day, which does not have a noticeable effect on appearance; however, excess loss (>100) results in baldness. Androgenetic alopecia is the most common type of hair loss, affecting millions of both men and women.1) There are many causes of hair loss in men and women, including diseases, nutritional deficiency, aging, hormone imbalance, and stress. Androgenetic alopecia may occur as early as the teenage years, but typically begin in the later decades of life. 2,3) Hair loss affects at least half of all men by the age of 50 and up to 70% of 70-year-old men. 4)

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Section: Discussionmentioning

confidence: 99%

<i>In Vivo</i> Hair Growth-Promoting Effect of Rice Bran Extract Prepared by Supercritical Carbon Dioxide Fluid

Choi

Jeon²,

Moon³

et al. 2014

Biological & Pharmaceutical Bulletin

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“…Some studies found that 31-33 % of the administered radioactivity was in the feces by examining tissue distribution of radiolabelled octacosanol in rats, indicating the low bioavailability of the free policosanols [6]. In a previous in vivo study concerning octacosanol metabolism, only 30 ng octacosanol mL −1 plasma was detected after a 60 mg/kg dose, thus indicating a rather low absorption of policosanols given as the free form [15].…”

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“…Esterification of policosanols with fatty acids can decrease their melting point and improve their bioavailability in vivo [5,15]. Zhao et al modeled the lipase-catalyzed esterification of policosanols with conjugated linoleic acid in a solvent-free system to produce wax esters and optimized the reaction conditions by response surface methodology.…”

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confidence: 99%

“…The corresponding melting point was decreased from 79 to 57 °C by esterification with conjugated linoleic acid [5]. Haim et al investigated and compared the bioavailability of the free and esterified policosanols in relation to their hypocholesterolemic effects in Sprague-Dawley rats [15]. The results showed that esterification of policosanols with oleic acid enhanced their bioavailability and significantly improved the serum lipid profile in normocholesterolemic rats [15].…”

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confidence: 99%

“…Haim et al investigated and compared the bioavailability of the free and esterified policosanols in relation to their hypocholesterolemic effects in Sprague-Dawley rats [15]. The results showed that esterification of policosanols with oleic acid enhanced their bioavailability and significantly improved the serum lipid profile in normocholesterolemic rats [15]. Esterification of polyunsaturated fatty acids with policosanols improves their oxidative stability, thereby making them more bioavailable [5,16].…”

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Efficient Synthesis of Octacosanol Linoleate Catalyzed by Ionic Liquid and Its Structure Characterization

Qiao

et al. 2016

J Americ Oil Chem Soc

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IntroductionPolicosanols are a kind of primary aliphatic long-chain alcohol with chain lengths varying from 24 to 34 carbons, and octacosanol is one of the major components of policosanols with 28 carbons [1,2]. The most common sources of policosanols are sugar cane, bees wax, wheat germ, rice bran, sorghum kernel and sunflower seed [3][4][5]. Policosanols are also found in the leaves, fruits, nuts, and seeds of many foods [6].In recent years, policosanols have attracted much attention due to their potential beneficial effects for human health. Policosanols provided various physiological effects in the prevention or treatment of cardiovascular diseases and dermatological diseases [7,8]. Policosanols acted as a cholesterol-lowering agent by inhibiting endogenous cholesterol biosynthesis and enhancing low density lipoprotein (LDL) catabolism [7]. Daily intake of 5-20 mg policosanols decreased the LDL level by 19-31 % and total cholesterol (TC) concentration by 13-23 %, increased high density lipoprotein (HDL) cholesterol level in the range of 8-29 % [9, 10]. Daily supplement of 40 mg policosanol was also found to be effective in lowering the serum triglyceride concentration [9]. Moreover, previous studies reported that policosanols decreased endothelial damage, platelet aggregation and the development of foam cells [7,11]. Octacosanol was considered to be the major active policosanols responsible for efficacy since it was present in the largest quantity [6,12]. Octacosanol improved oxygen usage by strengthening the heart, keeping low LDL and high HDL levels, thereby maintaining healthy heart function [9,13].Currently, policosanols including octacosanol are mainly produced by saponification of a by-product from the dewaxing process. And policosanols are commercially Abstract Octacosanol, as the major active policosanol, has attracted much attention due to the potential beneficial effects for human health. However, free octacosanol has a high melting point, poor oil solubility and low bioavailability, which greatly restricts its practical application. In this study, we report a highly efficient method for an ionic liquids (IL)-catalyzed synthesis of octacosanol ester by direct esterification with linoleic acid. The synthesized product was purified, subsequently characterized by FT-IR, MS and NMR and finally confirmed to be octacosanol linoleate. The reaction parameters were investigated and the conversion reached 91.3 ± 4.8 % under the optimum conditions: IL 1-butylsulfonate-3-methylimidazolium hydrogen sulfate ([BSO 3 HMim][HSO 4 ]) as catalyst, IL dose 1.5 % (related to the mass of both reactants), 1:1 molar ratio of octacosanol to linoleic acid, 80 °C, and 1 h. The melting point and oil solubility of octacosanol were greatly improved by esterification with linoleic acid, facilitating the incorporation into a variety of oil-based systems.

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Chemoenzymatically synthesized policosanyl phenolates as autoxidation inhibitors

Wang

Hwang

Lim

2014

Euro J Lipid Sci & Tech

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In this study, ten policosanyl phenolates were synthesized via a two‐step chemoenzymatic route. The intermediate vinyl esters were first chemically produced and subsequently esterified with policosanols catalyzed by Novozyme 435 (Candida antarctica lipase B). The conversion yields of the policosanyl phenolates were in the range of 4.20–37.14%. Their antioxidant activities were evaluated. Results showed that, compared with the corresponding phenolic acids, all synthesized policosanyl phenolates had better activities for peroxide value, but worse for 2,2'‐azinobis(3‐ethylbenzothiazoline‐6‐sulfonic acid) assay; policosanyl p‐coumarate and policosanyl 5‐phenylvalerate showed a moderate and durable inhibition effect on lipid oxidation both in a linoleic acid system and a cooked pork system. Practical applications: It is important to develop antioxidants from natural sources. The lipophilization of phenolic acids with fatty alcohols can improve the hydrophobicity and change the antioxidant capacity of phenols. This study focuses on policosanol, which is a food‐grade mixture of long‐chain aliphatic primary alcohols, having development and application potential as a cost‐effective food additive. According to our results, policosanyl phenolates, which are a new range of amphiphilic antioxidant molecules, have the potential for use as alternative food antioxidants in the food industry. The policosanyl phenolates were synthesized via a two‐step route as shown in the figure. The intermediate vinyl esters were first chemically produced and subsequently esterified with policosanols catalyzed by Novozyme 435 (Candida antarctica lipase B).

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The oleic acid esterification of policosanol increases its bioavailability and hypocholesterolemic action in rats

Cited by 11 publications

References 40 publications

<i>In Vivo</i> Hair Growth-Promoting Effect of Rice Bran Extract Prepared by Supercritical Carbon Dioxide Fluid

<i>In Vivo</i> Hair Growth-Promoting Effect of Rice Bran Extract Prepared by Supercritical Carbon Dioxide Fluid

Efficient Synthesis of Octacosanol Linoleate Catalyzed by Ionic Liquid and Its Structure Characterization

Chemoenzymatically synthesized policosanyl phenolates as autoxidation inhibitors

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