Actinophyllic Acid, a Potent Indole Alkaloid Inhibitor of the Coupled Enzyme Assay Carboxypeptidase U/Hippuricase from the Leaves of Alstonia actinophylla (Apocynaceae).

Abstract

Alkaloids U 0600 Actinophyllic Acid, a Potent Indole Alkaloid Inhibitor of the Coupled Enzyme Assay Carboxypeptidase U/Hippuricase from the Leaves of Alstonia actinophylla (Apocynaceae). -The structure of the novel title acid (I) is determined by spectroscopic means. -(CARROLL*, A. R.; HYDE, E.; SMITH, J.; QUINN, R. J.; GUYMER, G.; FORSTER, P. I.; J.

Indoles and Indolizidines

“…Actinophyllic acid 1 , (Scheme 7.1 ) is a structurally unique indole alkaloid isolated from the leaves of the Alstonia actinophylla tree collected on the Cape York Peninsula of Australia by Quinn, Carroll, and co -workers [18] . It was discovered in 2005 as part of an ongoing effort to unearth natural products that would inspire the development of new therapeutics for cardiovascular disease [18] .…”

“…Actinophyllic acid 1 possesses an unprecedented skeleton comprised of 1 -azabicyclo [4.4.2]dodecane and 1 -azabicyclo[4.2.1]nonane fragments, which together are not found in any other indole alkaloid [18] . The challenges associated with assembling the multiply bridging polycyclic structure and installing fi ve contiguous stereocenters render 1 an intriguing target for total synthesis.…”

“…18 Installation of the epidisulfi de moieties and completion of the total synthesis of ( + ) -11,11 ′ -dideoxyverticillin 5 . To achieve this, bis(dithiepanethione) 101 is fi rst treated with ethanolamine.…”

Antibacterial activity of Alstonia angustifolia leaf extract against Staphyloccoccal and Bacilli

“…It is rich in biologically active alkaloids that act as antimalarial agents to treat malaria disease, which is caused by Plasmodium falciparum [6]. It has also shown the cytotoxic activity against several human cancer cell lines [7] and has been found to assist in the fibrinolysis process by inhibiting the enzymes carboxypeptidase U (CPU) [8].…”

Arylation of Carbonyl Compounds via Photoredox Catalysis

“…21 These compounds were isolated in 2005 from the aqueous extract of Alstonia actinophylla leaves and showed great activity as carboxypeptidase U inhibitor. 22 The first key step of their plan was based on asymmetric α-alkylation of the aldehyde 42…”