Michellamines are a group of

atropisomer Atropisomers are stereoisomers arising because of hindered rotation about a single bond, where energy differences due to steric strain or other contributors create a barrier to rotation that is high enough to allow for isolation of individual co ...

ic alkaloid which have been found to be HIV viral replication inhibitors '' in vitro''. It was discovered in the leaves of ''

Ancistrocladus korupensis ''Ancistrocladus korupensis'' is a species of liana endemic to southwestern Cameroon and the neighbouring regions of Nigeria. The type locality is Korup National Park. The plant was identified as new to science in 1993 after pharmacologically i ...

''. There are three michellamines represented as A, B, and C; however, michellamine B is the most active against the NID-DZ strain of HIV-2.

Occurrence

Michellamine A and B occur naturally in ''Ancistrocladus korupensis'' leaves. Other chemical substances including

alkaloids Alkaloids are a class of basic, naturally occurring organic compounds that contain at least one nitrogen atom. This group also includes some related compounds with neutral and even weakly acidic properties. Some synthetic compounds of similar st ...

, tannins, and

saponin Saponins (Latin "sapon", soap + "-in", one of), also selectively referred to as triterpene glycosides, are bitter-tasting usually toxic plant-derived organic chemicals that have a foamy quality when agitated in water. They are widely distributed ...

s are found in the roots, leaves, stems, flowers, or bark.

Synthesis

There are two methods explored to synthesize michellamines A and B. The first one, originally synthesized in 1994, is a retrosynthesis that leads to a biomimetic pathway that uses the construction of

naphthalene Naphthalene is an organic compound with formula . It is the simplest polycyclic aromatic hydrocarbon, and is a white crystalline solid with a characteristic odor that is detectable at concentrations as low as 0.08 ppm by mass. As an aromati ...

/ isoquinoline bonds before the naphthalene/naphthalene axis. The second method, originally synthesized only a few montes after the first method, is a complementary pathway that would use the naphthalene/naphthalene axis after it is created and add the two isoquinoline moieties.

Research

Michellamines inhibit

protein kinase C In cell biology, Protein kinase C, commonly abbreviated to PKC (EC 2.7.11.13), is a family of protein kinase enzymes that are involved in controlling the function of other proteins through the phosphorylation of hydroxyl groups of serine and t ...

and virus-induced cellular fusion. They have a broad range of effectiveness '' in vitro'' across most HIV strains, particularly the HIV-2 strain, which is found primarily in and around Cameroon.

References

{{reflist Isoquinoline alkaloids HIV/AIDS