Cyanogenic glycosides linamarin

Frakes, R.A., R.P.Sharma, and C.C.Willhite. 1985. Developmental toxicity of the cyanogenic glycoside linamarin in the golden hamster. Teratology 31 241-246. 

Nitrogen-containing compounds (excluding alkaloids) Cyanogenic glycosides (linamarin)... 

A microsomal system that catalyzes the in vitro synthesis of the aglucones of the two cyanogenic glycosides linamarin... 

The cyanophoric compounds linamarin (11) (/ )-lotaus-tralin (42), (5)-epilotaustralin (43), linustatin (44), neolinus-tatin (45), and sarmentosin epoxide (46) (probable) are derived from valine and isoleucine (Fig. 16.11). The first two compounds are widespread and probably are found in more plant species than any other cyanogenic glycosides. Linamarin and lotaustralin almost always co-occur. These gluco-sides are most commonly encountered in the Asteraceae, Euphorbiaceae, Fabaceae, and Linaceae. 

The wings of bumet moths (Zygaena filipendulae) contain small amounts of histamine (11) and the cyanogenic glycoside linamarin. Furthermore, the addition of small amounts of histamine to linamarin-containing solutions resulted in the rejection of solutions normally consumed by quail (Coturnix coturnix coturnix). It was suggested that histamine plays a role in defense of the moth from predatory birds (Muhtasib and Evans, 1987). 

Figure 10.9 The biosynthesis of the cyanogenic glycosides linamarin and lotaustralin from amino-acids in the burnet moth. The dot on nitrogen and the prime and double prime on carbon represent N and respectively. Labelling showed that these atoms were retained in place during the synthesis...

Inhibition of cytochromes of electron transport system can be caused by cyanogenic glycosides, such as amygdalin (Fig. 11.14) in bitter almonds, Prunus amygdalus, linamarin and lotaustralin in clover and birdsfoot trefoil, or dhurrin (Fig. 11.14) in Sorghum vulgare. The potent effect of cyanide on cell respiration has given rise to a recent serious conservation problem. In Southeast Asia, divers stun fish on coral reefs with a blast of cyanide to collect them for the aquarium trade. In the process, many fish are killed and the corals bleached, because their symbionts die (e.g. Payne, 2001). 

Four cyanogenic glycosides (amygdalin, linamarin, prunasin, mandelonitrile) were extracted from apricots and separated on a C g column (2 = 200 nm or pulsed amperometric detection, ] = 0.00 V for 240 ms, = 0.60 V for 60 ms, ) = —0.80 V for 60 ms). For the amperometric analysis, a 0.5 M NaOH solution was fed into the effluent postcolumn. An isocratic 12 min 82/12 water/acetonitrile run or an 8-min 100/0- 40/60 water/acetonitrile gradient was used [1259]. Baseline resolution was achieved using the gradient... 

---