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 teleocidin class of an indole alkaloid, pendolmycin (1) was synthesized from 1-(4-methylphenylsulfonyl)pyrrole in thirteen steps by way of the indole derivative (16), the amino- diester compound (6), and the ethyl carboxylate (5).
23 citations
TL;DR: The first microbial synthesis of a modified alkaloid, the first production of tetrahydrobiopterin in yeast, and the first use of a pterin-dependent mono-oxidation strategy for the synthesis of L-DOPA are presented.
Abstract: Monoterpene indole alkaloids (MIAs) have important therapeutic value, including as anticancer and antimalarial agents. Because of their chemical complexity, therapeutic MIAs, or advanced intermediates thereof, are often isolated from the native plants. The microbial synthesis of MIAs would allow for the rapid and scalable production of complex MIAs and MIA analogues for therapeutic use. Here, we produce the modified MIA hydroxystrictosidine from glucose and the monoterpene secologanin via a pterin-dependent mono-oxidation strategy. Specifically, we engineered the yeast Saccharomyces cerevisiae for the high-level synthesis of tetrahydrobiopterin to mono-oxidize tryptophan to 5-hydroxytryptophan, which, after decarboxylation to serotonin, is coupled to exogenously fed secologanin to produce 10-hydroxystrictosidine in an eight-enzyme pathway. We selected hydroxystrictosidine as our synthetic target because hydroxylation at the 10′ position of the alkaloid core strictosidine provides a chemical handle for the...
23 citations
TL;DR: The collective synthesis of glycosylated monoterpenoid indole alkaloids is reported and the transition state to induce the diastereoselectivity of the newly discovered Pictet-Spengler reaction reported here is proposed.
Abstract: A collective synthesis of glycosylated monoterpenoid indole alkaloids is reported. A highly diastereoselective Pictet-Spengler reaction with α-cyanotryptamine and secologanin tetraacetate as substrates, followed by a reductive decyanation reaction, was developed for the synthesis of (-)-strictosidine, which is an important intermediate in biosynthesis. This two-step chemical method was established as an alternative to the biosynthetically employed strictosidine synthase. Furthermore, after carrying out chemical and computational studies, a transition state for induction of diastereoselectivity in our newly discovered Pictet-Spengler reaction is proposed. Having achieved the first enantioselective total synthesis of (-)-strictosidine in just 10 steps, subsequent bioinspired transformations resulted in the concise total syntheses of (-)-strictosamide, (-)-neonaucleoside A, (-)-cymoside, and (-)-3α-dihydrocadambine.
23 citations
TL;DR: Three members of a new class of ascorbic acid-adduct indole alkaloids, a new prenylated indoles alkaloid, and five known compounds were isolated from the leaves of Flindersia pimenteliana.
Abstract: Three members of a new class of ascorbic acid-adduct indole alkaloids (1–3), a new prenylated indole alkaloid (4), and five known compounds (5–9) were isolated from the leaves of Flindersia pimenteliana. The structures of 1–4 were elucidated on the basis of their (+)-HRESIMS and 2D NMR spectroscopic data. Antiplasmodial activity was also reported for the natural products against chloroquine-sensitive (3D7) and chloroquine-resistant (Dd2) Plasmodium falciparum with IC50 values ranging from 0.19 to 3.6 μM.
23 citations
TL;DR: In this article, two indole alkaloids, angustilodine (1) with an unprecedented pentacyclic carbon skeleton, and Angustilocine (2), belonging to the seco-angustilobine-B group of alkaloid, were obtained from the leaf extract of the Malayan species Alstonia angustilioba, and their structures were established by spectroscopic analysis.
Abstract: Two new indole alkaloids, angustilodine (1), with an unprecedented pentacyclic carbon skeleton, and angustilocine (2), belonging to the seco-angustilobine-B group of alkaloids, were obtained from the leaf extract of the Malayan species Alstonia angustiloba, and their structures were established by spectroscopic analysis.
23 citations