Aspidosperma species: A review of their chemistry and biological activities

Abstract

Ethnopharmacological relevanceSpecies of Aspidosperma are known popularly as "peroba, guatambu, carapanaúba, pau-pereiro" and "quina". The genus can be found in the Americas, mainly between Mexico and Argentina. Many species of Aspidosperma are used by the population in treating cardiovascular diseases, malaria, fever, diabetes and rheumatism. The phytochemical aspects of the species of the genus Aspidosperma have been studied extensively. The monoterpene indole alkaloids are the main secondary metabolites in Aspidosperma species, and about 250 of them have been isolated showing a considerable structural diversity. Several of them have showed some important pharmacological activities. Aspidosperma subincanum Mart. and Aspidosperma tomentosum Mart. (Apocynaceae) are Brazilian species widely used by the population to treat diabetes mellitus, hypercholesterolemia. The pharmacological activities of both species have been investigated and the biological properties described can be related to their isolated indole alkaloids. However, more pharmacological studies are needed in order to justify the use of these species in folk medicine. In this review, we present reports mainly focused on chemical and biological studies and their relationship with the ethnopharmacological use of both Aspidosperma species. Aim of the studyThe aim of this review is to present their ethnopharmacological use as correlated to their biological activities as described for the extracts and isolated compounds from Aspidosperma subincanum Mart. and Aspidosperma tomentosum Mart. In addition, some aspects related to the biosynthetic pathways are discussed, also NMR assignments and some synthesis information about indole alkaloids from both Aspidosperma species are included. Material and methodsThe bibliographic search was made in theses and dissertations using some databases such as NDLTD (Networked Digital Library of Theses and Dissertations), OATD (Open Access Theses and Dissertations) and 3 Google Scholar. More data were gathered from books, Brazilian journals and articles available on electronic databases such as, Google Scholar, PubChem, Scifinder, Web of Science, SciELO, PubMed and Science Direct.Additionally, the Google Patents and Espacenet Patent Search (EPO) were also consulted. The keywords Aspidosperma, Aspidosperma subincanum, Aspidosperma tomentosum, indole alkaloids were used in the research. The languages were restricted to Portuguese, English and Spanish and references were selected according to their relevance. Results Aspidosperma subincanumMart. and Aspidosperma tomentosum Mart. (Apocynaceae) are Brazilian species widely used by the population to treat a few diseases. Extracts and isolated compounds of both species have shown antitumor and antimalarial activities.The antitumor activity of isolated compounds has been extensively studied. However, the antiplasmodial activity needs to be investigated further as well as the antiflamatory, anti-hyperlipidemic and anorexigenic activities. From A. subincanum twenty-one indole alkaloids ...

Total Synthesis of Leuconoxine, Melodinine E, and Mersicarpine through a Radical Translocation–Cyclization Cascade

“…[9] As is evidenced by previous approaches in this area [Scheme 1, Eq. (1), (2)],t he key to building these Aspidosperma alkaloids is the creation of the indole bearing aC 2quaternary carbon. Our approach to such structures delays the formation of the substituted indole until after the N-aryl valerolactam has been assembled.…”

“…[19] We suspect the reaction involves formation of ak etene intermediate,b ut at this time we cannot explain why this set of reaction conditions is superior to others.Inany event, lactam 30 underwent transannular bromolactamization to give 31. Hydrogenolysis of 31 gave leuconoxine (2), and elimination of bromide 31 gave melodinine E( 3).…”

Calcium Chloride (CaCl2) : Characteristics and Molecular Interaction in Solution

“…Kalsium klorida ini memiliki sifat fisika (124) dan juga sifat kimia (221), diantarnya : Tabel 3. Sifat Fisika dan Sifat Kimia Kalsium Klorida (125)(126)(127)(128)(129)(130)(131)(132)(133)(134) https://id.wikipedia.org/wiki/Kalsium_klorida Optimasi (212) Molekul CaCl 2 menggunakan Molecular Mechanic (MM2) Optimasi (137) molekul CaCl 2 dilakukan dengan Molekular Mekanik (MM2) dan menghasilkan output data dalam bentuk data geometri (239) atom atom dalam molekul dan Energi optimumnya. Hasil output yang diolah dapat dilihat sebagai berikut :…”

Calcium Chloride (CaCl2) : Characteristics and Molecular Interaction in Solution

“…Kalsium klorida ini memiliki sifat fisika (124) dan juga sifat kimia (221), diantarnya : Tabel 3. Sifat Fisika dan Sifat Kimia Kalsium Klorida (125)(126)(127)(128)(129)(130)(131)(132)(133)(134) https://id.wikipedia.org/wiki/Kalsium_klorida Optimasi (212) Molekul CaCl 2 menggunakan Molecular Mechanic (MM2) Optimasi (137) molekul CaCl 2 dilakukan dengan Molekular Mekanik (MM2) dan menghasilkan output data dalam bentuk data geometri (239) (143)(144)(145)(146)(147) merupakan ukuran gesekan internal zat cair. Ketika viskositas meningkat, kecendrungan mengalir menurun.…”