Topic
Indole alkaloid
About: Indole alkaloid is a research topic. Over the lifetime, 868 publications have been published within this topic receiving 15401 citations. The topic is also known as: indole alkaloids.
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TL;DR: The first total synthesis of (±)-psychotrimine, a novel trimeric indole alkaloid isolated from Psychotria rostrata, was achieved in this paper. But this synthesis was performed with a single tryptamine unit.
Abstract: The first total synthesis of (±)-psychotrimine, a novel trimeric indole alkaloid isolated from Psychotria rostrata, was achieved. In the total synthesis, the copper-mediated intramolecular and intermolecular aminations of halobenzenes, which respectively contributed to the construction of a pyrrolidinoindoline core and the installation of a third tryptamine unit, were used as key steps.
TL;DR: In this paper , a five-step Cranwell and Saxton synthesis was used for obtaining ellipticine (Ell), and Ellipticine hydrochloride salt (Ell×HCl) was also synthesized.
Abstract: First isolated from the tropical plant Oschrosia elliptica, indole alkaloid ellipticine provoked huge interest since it demonstrated antitumor activity was demonstrated along with limited toxic side effects and a complete lack of hematological toxicity. In this work, a five-step Cranwell and Saxton synthesis was used for obtaining ellipticine (Ell). Ellipticine hydrochloride salt (Ell×HCl) was also synthesized. Detailed in vitro studies of anticancer, antimalarial, and leishmanicidal activities were performed. Antiproliferation assay using DU145 cancer cell line treated with Ell showed a consistent reduction in cell proliferation and cell viability when treated with 5 μmol Ell. Anti-proliferation activity was more pronounced for the Ell×HCl solutions. Both the Ell and Ell×HCl revealed moderate activity in vitro against Leishmania amazonensis promastigotes, which is related to insufficient solubility of the drugs. IC50 values of Ell and Ell×HCl were determined in vitro against multidrug resistant Plasmodium falciparum strain K1. The Ell×HCl was shown to be almost three times more potent than the Ell in DMSO. Upon dilution with water, Ell solubility and activity drops down, while the activity and solubility of Ell×HCl is enhanced up to 10 times in 50:50 aqueous DMSO solutions
TL;DR: In this article , a Pictet-Spengler reaction with α-cyanotryptamine followed by the removal of the cyano group and autoxidation (aromatization) efficiently constructed the β-carboline motif.
Abstract: The collective and efficient asymmetric total syntheses of five β-carboline-type monoterpenoid indole alkaloid glycosides were achieved in fewer than thirteen steps. A Pictet-Spengler reaction with α-cyanotryptamine followed by the removal of the cyano group and autoxidation (aromatization) efficiently constructed the β-carboline motif. In addition, bioinspired reactions were developed to provide different alkaloid skeletons.
TL;DR: In this paper , a comprehensive analysis on the stems of Alstonia scholaris (L.) R. R. Br. (L. Scholaris) led to the isolation and identification of 30 natural products, including sixteen alkaloids (1, 16), nine triterpenoids (17, 25), two phenols (26, 27), and three lignans (28, 30).