Secologanin

Lonicerosid

Yellowish solid

94-96 ° C

Template: Infobox chemical / molecular formula search available

Secologanin is a glycoside and a Secoiridoid, that in the biosynthesis of many alkaloids play a central role. It is a colorless oil. The Monoterpenglykosid is a key building block in the synthesis of most indole alkaloids, further cinchona, Ipecac and Pyrrolochinolinalkaloide, also simple monoterpene alkaloids. Almost a quarter of all formed in living organisms alkaloids are synthesized from him.

Biosynthesis

The biosynthesis begins secologanin originally at geraniol via several intermediate steps. Secologanin itself is then formed either from the iridoid Loganin. For this purpose, the cyclopentane ring of Loganin between the C7 and C8 atom is oxidatively cleaved. This reaction is catalyzed an secologanin synthase (EC 1.3.3.9 ), a cytochrome P450 enzyme for which NADPH and oxygen are required.

In Catharanthus roseus ( pink Catharanthe ) secologanin is synthesized from Loganat. It catalyzes a methyltransferase ( EC 2.1.1.50 ), wherein the reaction S-adenosylmethionine ( SAM) is used.

Secologanin can - catalyzed by strictosidine synthase - react further to form strictosidine.