Geranyl geraniol

A total of 21 compounds present in the surface and cephalic extracts of the queen bumblebee, Bomhus terrestris, evoked responses in male antennae. These included saturated and unsaturated fatty acids, ethyl and methyl esters of the fatty acids, heptacosene, 2-nonanone, and geranyl geraniol. A blend of synthetic versions of these compounds elicited typical male mating behavior. 

A synthesis of all-tran -geranylgeraniol and the assignment of its C n.m.r. spectrum has been recorded. A highly oxygenated derivative of geranyl-geraniol, ligantrol (183), has also been synthesized. " ... 

Im Rahmen der Geranylgeraniol-Synthese aus Geraniol fiihrt im letzten Schritt die re-duktive Spaltung von 16-Benzyloxy-8-phenylthio-2,6,10,14-tetramethyl-hexadecatetra-en-(2,6,10,14) mit Lithium in Athylamin zu 16-Hydroxy-2,6,10,14-tetramethyl-hexade-catetraen-(2,6,10,14) (Geranyl-geraniol) (88% d.Th.)4 durch ... 

Diterpenoids. Two acyclic diterpenoids have been reported to be present in the alcohol fraction isolated from olive oil. These are phytol (at a concentration of 120-180 mg/kg) which probably originates from chlorophyll, and geranyl-geraniol (Figure 9.9). 

Zdero, C., F. Bohlmann, and G.M. Mungai Clerodanes, Secoclerodanes, Geranyl Geraniol Derivatives and Unusual Sesquiterpenes from Conyza hypoleuca. Phytochem., 30, 575 (1991). 

Figure 8 Thin-layer chromatography of prenylquinones and prenols. Adsorption chromatography on (A) silica gel plates, solvent light petroleum-diethyl ether (9 1), and (B) on silica gel plates impregnated with AgN03, solvent light petroleum-chloroform-acetone (50 10 17) Ki, phylloquinone, vitamin Ki MKa, menaquinone-4 PQ-9, plastoquinone-9 Q-9 and Q-10, ubiquinone-9 and -10 a-T, a-tocopherol a-Ts, a-tocotrienol 3-C, P-carotene GG, geranyl-geraniol (Source From Ref. 18, with permission of the copyright owner).

The sequential cross-coupling strategy was used to generate the natural product geranyl geraniol (Scheme 5-90). ... 

Scheme 5-90. Sequence of cross-coupling reactions including zinc reagents to generate geranyl geraniol. ...

Recent studies have suggested that MK-4, in particular, has a transcriptional regulatory function, for example, in osteosarcoma cell cultures, in which it binds to and activates the SXR steroid and xenobiotic receptor. This in turn increases mRNA levels for osteoblast markers bone alkaline phosphatase, osteoprotogerin, osteopontin, and MGP. MK-4 and its isolated geranyl-geraniol side chain was also able to suppress the synthesis of prostaglandin Ei, which is a potent bone resorption catalyst. These observations have led to speculation (i) that some of the menaqui-nones may possess some functions that are not shared by phylloquinone, and (ii) that there may be implications for cell proliferation and for cancer risk from variations in the supply of vitamin K and in its speciation. 

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