Crocetin di-

Crocus sativus L. Shi Hong Hua (Saffron) (root) Crocetin, crocetin geniobiose glucose ester, crocetin di-glucose ester, crotin, lycopene, beta-carotene.33-450 Ameliorating effect on ethanol-induced impairment of learning and memory. 

Crocetin di-glucose ester Crocetin geniobiose glucose ester... 

MeOH gradient solution (1 0 to 0 1) to yield crocetin di-glucose ester (0.41 g), crocetin gentiobiose glucose ester (5.10 g) and crocin (5.69 g). 

Crocin of 50 mg/kg ameliorated the blocking effect of ethanol on the LTP at approximately 84% compared to the control as indicated in Fig. (10). Crocetin gentiobiose glucose ester also antagonized the blocking effect of ethanol on the LTP dose-dependently. But die intensity is not so strong, about a half of crocin when compared the intensity of 50 mg/kg. On the other hand, crocetin di-glucose ester did not remove the inhibitory effect of ethanol on the LTP. 

Saffron extract contains many carotenoids such as crocetin, crocetin di-glucose ester, crocetin gentiobiose glucose ester, and crocin (crocetin di-gentiobiose ester), whose chemical structures are shown in Figure 58.1. These carotenoids scavenge free radicals, especially superoxide anions, and so may protect cells from oxidative stress. Indeed, it has been demonstrated that these carotenoids are useful in sperm cryoconservation and in protecting heptocytes from toxins. 

For the partial synthesis, a regio- and stereoselective reaction is required, in which a bond with defined stereochemistry is formed exclusively between the carboxylic acid and the carbohydrate at the anomeric carbon atom. Due to the polyene system and the ease of the hydrolysis of the ester bond at the anomeric carbon atom, the application of protecting groups on the carbohydrate is restricted. Therefore a method using unprotected carbohydrates has been developed. Crocetin-di(P-D-glucosyl) ester (543) was synthesized in 70% yield by the reaction of crocetin-diimidazolide (4) or crocetin-di(l,2,4-triazolide) (5) and unprotected p-D-glucose in pyridine in the presence of a base [5]. The esterification takes place exclusively at the anomeric carbon atom and produces only the p-anomer [6]. The method was also applied to 8 -apo-P-caroten-8 -oic acid (486) and to other carbohydrates [7]. 

Sugiura M, Shoyama Y, Saito H, Abe K. Crocin (crocetin di-gentiobiose ester) prevents the inhibitory effect of ethanol on long-term potentiation in the dentate gyrus in vivo. J Pharmacol Exp Ther 1994 271 703-707. 

Crocin. 8,8 -Diapo-if/ -carotenedioic acid bisi6-O-0-D-glucopyranosyl-g -D -gtucopyranosyi) ester a-crocin di-gentiobiose ester nf crocetin, mol wt 977,00. 

Crodn (gardenin). Formula, see under crocetin. 4411 4024, Mr 976.98, brown-red needles, mp. 180-190°C (decomp.), soluble in hot water, poorly soluble in organic solvents, uv 464, 434 nm (CHjOH). C. is the di-j8-gentiobiosyl ester of a- cro-cetin and occurs in Crocus (Iridaceae) and Gardenia (Rubiaceae) species and as the colored principle in saffron (Crocus sativus, content 24-27%). 

Recently the application of sulphone coupling was reported for the preparation of lycopene (31) [6]. Geranyldiethylamine (21) was converted into geranylsulphone (22) by reaction with ethyl chloroformate and sodium chlorophenylsulphate. Treatment of 22 with BuLi, crocetin-dialdehyde (536), acetic anhydride and base led to the C4o-disulphone 23 with a di-cis configuration. Reduction with disodium dithionite gave (all- )-lycopene (31) (Scheme 5). 

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