Secologanin
Encyclopedia
Secologanin is a monoterpene
synthesized from geranyl pyrophosphate
in the mevalonate pathway. Secologanin then proceedes with dopamine
to form ipecac alkaloids.
(GPP) taken from the mevalonate pathway used to make terpenoid
s. The formation of secologanin begins when GPP forms either 7-deoxyloganate or 7-deoxyloganin from some currently uncharacterized enzymes. 7-Deoxyloganate and 7-deoxyloganin can then be enzymatically reacted with NADPH to form loganate and loganin respectively. Loganate can revert to loganin by the use of an S-adenosyl methionine
(SAM). Loganate and loganin can then undergo a further enzyme-catalyzed reaction to form secologanate and secologanin. Another SAM can react with secologanate to form secologanin. Secologanin is then able to proceed onto produce ipecac alkaloid
s.
Monoterpene
Monoterpenes are a class of terpenes that consist of two isoprene units and have the molecular formula C10H16. Monoterpenes may be linear or contain rings...
synthesized from geranyl pyrophosphate
Geranyl pyrophosphate
Geranyl pyrophosphate is an intermediate in the HMG-CoA reductase pathway used by organisms in the biosynthesis of farnesyl pyrophosphate, geranylgeranyl pyrophosphate, cholesterol, terpenes and terpenoids....
in the mevalonate pathway. Secologanin then proceedes with dopamine
Dopamine
Dopamine is a catecholamine neurotransmitter present in a wide variety of animals, including both vertebrates and invertebrates. In the brain, this substituted phenethylamine functions as a neurotransmitter, activating the five known types of dopamine receptors—D1, D2, D3, D4, and D5—and their...
to form ipecac alkaloids.
Biosynthesis
Secologanin biosynthesis begins from geranyl pyrophosphateGeranyl pyrophosphate
Geranyl pyrophosphate is an intermediate in the HMG-CoA reductase pathway used by organisms in the biosynthesis of farnesyl pyrophosphate, geranylgeranyl pyrophosphate, cholesterol, terpenes and terpenoids....
(GPP) taken from the mevalonate pathway used to make terpenoid
Terpenoid
The terpenoids , sometimes called isoprenoids, are a large and diverse class of naturally occurring organic chemicals similar to terpenes, derived from five-carbon isoprene units assembled and modified in thousands of ways. Most are multicyclic structures that differ from one another not only in...
s. The formation of secologanin begins when GPP forms either 7-deoxyloganate or 7-deoxyloganin from some currently uncharacterized enzymes. 7-Deoxyloganate and 7-deoxyloganin can then be enzymatically reacted with NADPH to form loganate and loganin respectively. Loganate can revert to loganin by the use of an S-adenosyl methionine
S-Adenosyl methionine
S-Adenosyl methionine is a common cosubstrate involved in methyl group transfers. SAM was first discovered in Italy by G. L. Cantoni in 1952. It is made from adenosine triphosphate and methionine by methionine adenosyltransferase . Transmethylation, transsulfuration, and aminopropylation are the...
(SAM). Loganate and loganin can then undergo a further enzyme-catalyzed reaction to form secologanate and secologanin. Another SAM can react with secologanate to form secologanin. Secologanin is then able to proceed onto produce ipecac alkaloid
Alkaloid
Alkaloids are a group of naturally occurring chemical compounds that contain mostly basic nitrogen atoms. This group also includes some related compounds with neutral and even weakly acidic properties. Also some synthetic compounds of similar structure are attributed to alkaloids...
s.