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11 beta-Hydroxylupeol


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Protection against inflammation and oxidative stress is key in slowing down aging processes. The honey bee (Apis mellifera) shows flexible aging patterns linked to the social role of individual bees. One molecular factor associated with honey bee aging regulation is vitellogenin, a lipoglycophosphoprotein with anti-inflammatory and antioxidant properties. Recently, we identified three genes in Hymenopteran genomes arisen from ancient insect vitellogenin duplications, named vg-like-A, -B, and -C. The function of these vitellogenin homologs is unclear. We hypothesize that some of them might share gene- and protein-level similarities and a longevity-supporting role with vitellogenin. Here, we show how the structure and modifications of the vg-like genes and proteins have diverged from vitellogenin. Furthermore, all three vg-like genes show signs of positive selection, but the spatial location of the selected protein sites differ from those found in vitellogenin. We show that all these genes are expressed in both long-lived winter worker bees and in summer nurse bees with intermediate life expectancy, yet only vg-like-A shows elevated expression in winter bees as found in vitellogenin. Finally, we show that vg-like-A responds more strongly than vitellogenin to inflammatory and oxidative conditions in summer nurse bees, and that also vg-like-B responds to oxidative stress. We associate vg-like-A and, to lesser extent, vg-like-B to the antiaging roles of vitellogenin, but that vg-like-C probably is involved in some other function. Our analysis indicates that an ancient duplication event facilitated the adaptive and functional divergence of vitellogenin and its paralogs in the honey bee.


Apis mellifera, vitellogenin, protein structure, functional divergence, seasonality, gene expression


Ancient Duplications Have Led to Functional Divergence of Vitellogenin-Like Genes Potentially Involved in Inflammation and Oxidative Stress in Honey Bees


Heli Salmela,1 Taina Stark,1,2 Dimitri Stucki,1 Siiri Fuchs,1 Dalial Freitak,1 Alivia Dey,3 Clement F. Kent,3 Amro Zayed,3 Kishor Dhaygude,1 Heikki Hokkanen,2 and Liselotte Sundstrom1,*

Publish date

2016 Mar;




The asymmetric unit of the title compound, C10H11NO4, which was synthesized via nitration reaction of eugenol (4-allyl-2-meth­oxy­phenol) with a mixture of nitric acid and sulfuric acid, consists of three independent mol­ecules of similar geometry. Each mol­ecule displays an intra­molecular hydrogen bond involving the hydroxide and the nitro group forming an S(6) motif. The crystal cohesion is ensured by inter­molecular C?H?O hydrogen bonds in addition to π-π stacking inter­actions between the aromatic rings [centroid-centroid distances = 3.6583?(17)-4.0624?(16)?a]. The Hirshfeld surface analysis and the two-dimensional fingerprint plots show that H?H (39.6%), O?H/H?O (37.7%), C?H/H?C (12.5%) and C?C (4%) are the most important contributors towards the crystal packing.


crystal structure, nitro­eugenol, hydrogen bonds, Hirshfeld surface analysis, IR, NMR


Crystal structure and Hirshfeld surface analysis of 4-allyl-2-meth­oxy-6-nitro­phenol


Yassine El Ghallab,a,* Sanae Derfoufi,a El Mostafa Ketatni,b Mohamed Saadi,c and Lahcen El Ammaric

Publish date

2020 Mar 1;




The title compound, K11[α-Pt(μ3-OH)2(μ3-OH0.5)Mo6(μ3-O)3(μ2-O)6O12]2·12H2O (simplified chemical formula K11[H2.5PtMo6O24]2·12H2O), containing the well-known Anderson-type heteropolyoxomolybdate anion, was obtained by hydro­thermal reaction at pH = ca 6.0. The complete polyanion dimer has 2/m symmetry. The locations of the H atoms with respect to protonated O atoms were obtained from difference Fourier maps, and confirmed by the inter­polyanion hydrogen bonds, bond-length elongation and bond-valence sums (BVSs). The title heteropolyanion has two types of protonated O atoms viz. μ3-OH, {Mo2-O(H)-Pt} and μ3-OH0.5 (disordered H atom). The [H2.5α-PtMo6O24]5.5? polyanion forms a dimer, [(H2.5α-PtMo6O24)2]11?, held together by two pairs of μ3-O?H?μ1-O and of one disordered μ3-O?H?μ3-O hydrogen bonds. Three K+ ions are located on special positions (two on twofold rotation axes, one on a mirror plane), and two K+ ions are located on general positions with a reduced occupancy of 0.5. The remaining K+ ion has a reduced occupancy of 0.25 for charge balance and reasonable displacement parameters. As a result, the numbers of K+ and H+ ions in the title compound are 5.5 and 2.5, respectively.


crystal structure, platinium(IV), platinum-containing heteropolyoxometalate, short hydrogen bond, Anderson structure heteropolyoxomolybdate


Crystal structure of undeca­potassium bis­[α-hemi­penta­hydrogen hexa­molybdoplatinate(IV)] dodeca­hydrate


Hea-Chung Joo,a Ki-Min Park,b and Uk Leea,*

Publish date

2015 Aug 1;