Indole alkaloids are a class of alkaloids containing a structural moiety of indole; many indole alkaloids also include isoprene groups and are thus called terpene indole or secologanin tryptamine alkaloids. Containing more than 4100 known different compounds, it is one of the largest classes of alkaloids. Many of them possess significant physiological activity and some of them are used in medicine. The amino acid tryptophan is the biochemical precursor of indole alkaloids.
Spirotryprostatin B is an indolic alkaloid found in the Aspergillus fumigatus fungus that belongs to a class of naturally occurring 2,5-diketopiperazines. Spirotryprostatin B and several other indolic alkaloids have been found to have anti-mitotic properties, and as such they have become of great interest as anti-cancer drugs. Because of this, the total syntheses of these compounds is a major pursuit of organic chemists, and a number of different syntheses have been published in the chemical literature.
In enzymology, a polyneuridine-aldehyde esterase (EC 3.1.1.78) is an enzyme that catalyzes the chemical reaction:
Aspergillus sydowii is a pathogenic fungus that causes several diseases in humans. It has been implicated in the death of sea fan corals in the Caribbean Sea.
Gelsemine (C20H22N2O2) is an indole alkaloid isolated from flowering plants of the genus Gelsemium, a plant native to the subtropical and tropical Americas, and southeast Asia, and is a highly toxic compound that acts as a paralytic, exposure to which can result in death. It has generally potent activity as an agonist of the mammalian glycine receptor, the activation of which leads to an inhibitory postsynaptic potential in neurons following chloride ion influx, and systemically, to muscle relaxation of varying intensity and deleterious effect. Despite its danger and toxicity, recent pharmacological research has suggested that the biological activities of this compound may offer opportunities for developing treatments related to xenobiotic- or diet-induced oxidative stress, and of anxiety and other conditions, with ongoing research including attempts to identify safer derivatives and analogs to make use of gelsemine's beneficial effects.
Stephacidin A and B are antitumor alkaloids isolated from the fungus Aspergillus ochraceus that belong to a class of naturally occurring 2,5-diketopiperazines. This unusual family of fungal metabolites are complex bridged 2,5-diketopiperazine alkaloids that possess a unique bicyclo[2.2.2]diazaoctane core ring system and are constituted mainly from tryptophan, proline, and substituted proline derivatives where the olefinic unit of the isoprene moiety has been formally oxidatively cyclized across the α-carbon atoms of a 2,5-diketopiperazine ring. The molecular architecture of stephacidin B, formally a dimer of avrainvillamide, reveals a complex dimeric prenylated N-hydroxyindole alkaloid that contains 15 rings and 9 stereogenic centers and is one of the most complex indole alkaloids isolated from fungi. Stephacidin B rapidly converts into the electrophilic monomer avrainvillamide in cell culture, and there is evidence that the monomer avrainvillamide interacts with intracellular thiol-containing proteins, most likely by covalent modification.
Apparicine is a monoterpenoid indole alkaloid. It is named after Apparicio Duarte, a Brazilian botanist who studied the Aspidosperma species from which apparicine was first isolated. It was the first member of the vallesamine group of alkaloids to be isolated and have its structure established, which was first published in 1965. It has also been known by the synonyms gomezine, pericalline, and tabernoschizine.
Aspergillus tubingensis is a darkly pigmented species of fungus in the genus Aspergillus section Nigri. It is often confused with Aspergillus niger due to their similar morphology and habitat. A. tubingensis is often involved in food spoilage of fruits and wheat, and industrial fermentation. This species is a rare agent of opportunistic infection.
Aspergillus assulatus is a species of fungus in the genus Aspergillus. It is from the Fumigati section. The species was first described in 2014. It has been reported to produce indole alkaloids and apolar metabolites.
Aspergillus heteromorphus is a species of fungus in the genus Aspergillus. A. heteromorphus belongs to the group of black Aspergilli which are important industrial workhorses. A. heteromorphus belongs to the Nigri section. The species was first described in 1957. The species has been found in Brazil. It has been isolated from both rice straws, wheat straws, and sugarcane bagasse. This species can produce sclerotia and some mid-polar indole compounds. It produces a series of other not well-characterized exometabolites.
Aspergillus kanagawaensis is a species of fungus in the genus Aspergillus. It is from the Cervini section. The species was first described in 1951. It has been reported to a few extrolites, including two polar indol-alkaloids and one polar indol-alkaloid.
Aspergillus vitricola is a species of fungus in the genus Aspergillus. It is from the Robusti section. The species was first described in 1962 by Ohtsuki. It has been isolated from binocular lenses in Japan and house dust in Canada.
Aspergillus domesticus is a species of fungus in the genus Aspergillus. It is from the Robusti section. The species was first described in 2017. It has been isolated from wallpaper and a museum piece in the Netherlands. It has been reported to produce asperphenamate.
Aspergillus glabripes is a species of fungus in the genus Aspergillus. It is from the Robusti section. The species was first described in 2017. It has been isolated from office folders in the United States. It has been reported to produce mycophenolic acid and asperphenamate.
Aspergillus magnivesiculatus is a species of fungus in the genus Aspergillus. It is from the Robusti section. The species was first described in 2017. It has been isolated from katsuobushi in Japan, and from air and dried corn in the United States. It has been reported to produce asperglaucide, cristatin A, echinulin, indole alkaloid A, and antarone A.
Aspergillus reticulatus is a species of fungus in the genus Aspergillus. It is from the Robusti section. The species was first described in 2017. It has been isolated from a lung biopsy in the United States, air in Puerto Rico and elsewhere in the United States, dust in Belgium, oil paintings in Slovenia, and a leather shoe in the Czech Republic. It has been reported to produce asperglaucide, aurantiamide, indole alkaloid A, and clavatol D.
Aspergillus villosus is a species of fungus in the genus Aspergillus. It is from the Robusti section. The species was first described in 2017. It has been isolated in the UK and from a painting in France. It has been reported to produce asperphenamate, indole alkaloid A, and asperphenamate.
Tabernaemontanine is a naturally occurring monoterpene indole alkaloid found in several species in the genus Tabernaemontana including Tabernaemontana divaricata.
Dregamine is a naturally occurring monoterpene indole alkaloid found in several species in the genus Tabernaemontana including Ervatamia hirta and Tabernaemontana divaricata.
Vobasine is a naturally occurring monoterpene indole alkaloid found in several species in the genus Tabernaemontana including Tabernaemontana divaricata.
