Compositions of Royal Jelly II. Organic Acid Glycosides and Sterols of the Royal Jelly of Honeybees (Apis mellifera)

Abstract

Royal jelly is a secretion from the hypopharyngeal and mandibular glands of worker bees, and it is the exclusive food of the queen bee for the entire span of both her larval and adult lives. With regard to the constituents of this material, it contains remarkably high amounts of organic acids in the total lipid fraction.1) Many organic acids mainly consisting of 8 to 11 carbon atoms such as 10-hydroxy-2-decenoic 2,3) and 10-hydroxydecanoic acids have been isolated. Among them, a minor component, 9-hydroxy-2-decenoic acid, 4) is known to be a queen honeybee pheromone with swarm-stabilizing activity, 5) and it is also regarded as a precursor of the so-called queen substance, 9-keto-2-decenoic acid, which controls the caste of honeybee colonies.6) Recently, we have isolated mono-or diesters of 10-hydroxy-2-decenoic acid in which the hydroxyl group was esterified by another organic acid residue from the total lipid fraction of the royal jelly of the honeybees (Apis mellifera). 7) In view of these findings, it seems that other unknown compounds including pheromones or their precursors exist in royal jelly. The present study was undertaken to examine the constituents of royal jelly in the hope of discovering the biologically active compounds that control the hierarchy of honeybee colonies. By application of the recycling HPLC technique for the isolation of minor constituents from a complex mixture, two glycosides (1, 2) together with 16 compounds (3-18) were obtained in the pure state. The former two were fatty acid monoglucosides and the latter were sterols mainly composed of 28 or 29 carbons. This paper deals with the isolation and structural elucidation of these compounds. Results and DiscussionThe total lipid fraction obtained from lyophilized royal jelly powder (6.0 kg) was separated repeatedly on silica gel column chromatography with a mixture of CHCl 3 -MeOH to yield crude glycoside and sterol fractions (see Experimental). Both fractions were further separated with HPLC including a recycling mode, and two (1, 2) from the former and 16 (3-18) compounds from the latter were isolated in pure form. Among them, compounds 7-18 were identified as the known sterols 24-methylenecholesterol (7), 8) isofucosterol (8), 9) cholesta-5,24(24Ј)-dien-3b-ol-7-one (9), 10,11) cholesta-5,24(24Ј)-diene-3b,7b-diol (10), 10,12) cholesta-5,24(24Ј)-diene3b,7a-diol (11), 10,12) b-sitosterol (12), 13) stigmast-5-en-3b-ol-7-one (13), 13) stigmast-5-ene-3b,7b-diol (14), 13) stigmast-5-ene-3b,7a-diol (15), 13) cholest-24(24Ј)-ene-3b,5a,6b-triol (16), 14) stigmastane-3b,5a,6b-triol (17), 15) and desmosterol (18) 16) by comparison of their 1 H-and 13 C-NMR spectroscopic data with those described in the literature. Structures of Compounds 1 and 2 Negative-ion FAB-MS of 1 gave an [MϪH]Ϫ ion peak at m/z 347, and HR-FAB-MS revealed the molecular formula of 1 to be C 16 H 28 O 8 . The 1 H-NMR spectrum showed one anomeric proton signal at d 4.87 ppm, in addition to typical signals ascribable to a 10-hydroxy-2-decenoyl group. 7) Based on the couplin...

Oocyte maturation with royal jelly increases embryo development and reduces apoptosis in goats

“…In agreement with our results, Valiollahpoor et al (2016) has reported higher maturation rates of sheep oocytes when cultured in the presence of royal jelly at various concentrations. The positive effect of royal jelly in improving COC maturation could be due to the various active compounds like proteins, essential amino acids (cystine, lysine and arginine), sugars (fructose, glucose, and sucrose), vitamins (A, B5, C, D and E), and lipids (Howe et al, 1985;Boselli et al, 2003;Kodai et al, 2007;Tamura et al, 2009). An early study observed increased errors in chromosomal segregation due to high oxidative stress during IVM, which compromises oocyte developmental potential after IVF in mice (Tarin et al, 1996).…”

“…2018 125 feed the queen honeybee throughout the larval period (Viuda-Martos et al, 2008;Isidorova et al, 2009). It contains the following: water (50-60%), proteins (18%), carbohydrates (15%), lipids (3-6%), mineral salts (1.5%), and vitamins, in addition to various bioactive substances (Howe et al, 1985;Boselli et al, 2003;Nagai and Inoue 2004;Kodai et al, 2007;Tamura et al, 2009). The antioxidative capacity of royal jelly was shown to be effective in protecting female and male gametes (Guo et al, 2009) and cryopreserved semen (Moradi et al, 2013;Shahzad et al, 2016).…”

Royal Jelly: An ancient remedy with remarkable antibacterial properties

“…Approximately 90% of lipids is constituted by fatty acids; the rest are neutral lipids, steroids, hydrocarbons and phenols (Nabas et al, 2014;Ramadan and Al-Ghamdi, 2012). The fatty acids of RJ have 8-10 carbon atoms, usually either hydroxy fatty acids or dicarboxylic acids, unlike organic acids of most animal and plant materials (Kodai et al,2007;Noda et al,2005;Ramadan and Al-Ghamdi, 2012). The analysis of the lipid components can be a criterion of the genuineness of the RJ, because an adulteration with honey or sugars, decrease the protein and lipid component, increase the concentration of minor sugars and makes RJ insoluble in alkaline medium (Boselli et al, 2003;Lercker et al,1981;Li and Chen, 2003).…”

Study of the chemical constituents of Pruni Cortex and its related parts

“…PFL-4 and PFL-10 were identified as mandelic acid b-D-glucopyranoside [27] and its methyl ester [27], respectively. PFL-11 was identified as 10-hydroxydecanoic acid 10-O-b-D-glucopyranoside [28].…”