Results 11 to 20 of about 559 (86)

Biosynthetic Origin of the Methoxy Group in Quinine and Related Alkaloids. [PDF]

Angew Chem Int Ed Engl
Two substrates, tryptamine and 5‐methoxytryptamine, are used in parallel by Cinchona to generate the naturally occurring mixtures of methoxy and non‐methoxy Cinchona alkaloids. Discovery of the genes responsible for methoxylation allows reconstitution of biosynthetic intermediates in tobacco. Abstract Quinine is a historically important natural product
Lombe BK, Zhou T, Caputi L, Ploss K, O'Connor SE.   +4 more
europepmc   +3 more sources

Combined Transcriptomic and Metabolomic Analysis Reveals an Ethylene-Activated Regulatory Model on Monoterpenoid Indole Alkaloid Biosynthesis in Catharanthus roseus. [PDF]

Plant Biotechnol J
ABSTRACT Catharanthus roseus contains nearly 200 bioactive monoterpenoid indole alkaloids (MIAs) that are effective in treating cancer and other diseases. Ethylene plays a significant role in enhancing MIA biosynthesis, and we have found that it greatly induces the accumulation of anhydrovinblastine.
Deng B, Miao Q, Ou C, Pan Y, Liu H, Fu X, Li L, Wang Y, Tang K, Pan Q.   +9 more
europepmc   +2 more sources

A cell-type-specific regulon controlling monoterpene indole alkaloid biosynthesis with feedback and feedforward activation loops. [PDF]

New Phytol
Summary Monoterpene indole alkaloids (MIA) are a diverse class of plant natural products produced by a subset of lineages within the Asterid clade of eudicots. The diversity of MIAs provides a unique opportunity to study not only the evolution of biosynthetic genes but also their regulation.
Li C, Wood JC, Vaillancourt B, Hamilton JP, Jones SL, Bui VH, Dang TT, Buell CR.   +7 more
europepmc   +2 more sources

Total Synthesis and Structural Plasticity of Kratom Pseudoindoxyl Metabolites**

Angewandte Chemie, Volume 135, Issue 35, August 28, 2023., 2023
Although opioids have been used in the treatment of pain for centuries, they cause various adverse effects and addiction. Recently, kratom alkaloids emerged as promising analgesic alternatives for pain management with considerably fewer side effects. The first scalable total synthesis of mitragynine pseudoindoxyl, the most potent atypical opioid kratom
Péter Angyal, Kristóf Hegedüs, Bence Balázs Mészáros, János Daru, Ádám Dudás, Anna Rita Galambos, Nariman Essmat, Mahmoud Al‐Khrasani, Szilárd Varga, Tibor Soós   +9 more
wiley   +2 more sources

Synthetic Modulation of an Unstable Dehydrosecodine‐type Intermediate and Its Encapsulation into a Confined Cavity Enable Its X‐ray Crystallographic Observation

Angewandte Chemie, Volume 135, Issue 32, August 7, 2023., 2023
The X‐ray crystallographic analysis of a labile dehydrosecodine‐type intermediate was achieved by designing a functionally modulated analogue, enabling its inclusion within a self‐assembled coordination cage. The unique folded conformation of this intermediate, stabilized inside the hydrophobic cavity, was supported by DFT calculations and supports the
Gavin Tay, Toshiaki Wayama, Hiroki Takezawa, Satoshi Yoshida, Sota Sato, Makoto Fujita, Hiroki Oguri   +6 more
wiley   +2 more sources

Enantioselective Total Synthesis of (−)‐Limaspermidine and (−)‐Kopsinine by a Nitroaryl Transfer Cascade Strategy

Angewandte Chemie, Volume 134, Issue 42, October 17, 2022., 2022
2‐Nitrobenzenesulfonamides can be exploited as functional protective groups by their use in a long‐range nitroarene transfer cascade reaction. Using a suitably functionalized precursor, this process was used as the key step in the enantioselective total synthesis of the monoterpene indole alkaloids (−)‐limaspermidine, (−)‐kopsinilam, and (−)‐kopsinine ...
Brendan Horst, Daniël S. Verdoorn, Sven Hennig, Gydo van der Heijden, Eelco Ruijter   +4 more
wiley   +2 more sources

Oxidation of four monoterpenoid indole alkaloid classes by three cytochrome P450 monooxygenases from Tabernaemontana litoralis. [PDF]

Plant J
SUMMARY Cytochrome P450 monooxygenases (CYPs) are well known for their ability to catalyze diverse oxidation reactions, playing a significant role in the biosynthesis of various natural products. In the realm of monoterpenoid indole alkaloids (MIAs), one of the largest groups of alkaloids in nature, CYPs are integral to reactions such as hydroxylation,
Mai Z, Kim K, Richardson MB, Deschênes DAR, Garza-Garcia JJO, Shahsavarani M, Perley JO, Njoku DI, Deslongchamps G, De Luca V, Qu Y.   +10 more
europepmc   +2 more sources

Total Synthesis of Ophiorrhine A, G and Ophiorrhiside E Featuring a Bioinspired Intramolecular Diels–Alder Cycloaddition**

Angewandte Chemie, Volume 134, Issue 38, September 19, 2022., 2022
A late stage bioinspired intramolecular Diels–Alder cycloaddition of the indolopyridone of ophiorrhiside E was deployed to access the spirocyclic azabicyclic[2.2.2]octanone ring system of ophiorrhiside A and achieve its total synthesis. The indolopyridone of ophiorrhiside E was synthesized by the cyclodehydration of ophiorrhine G which was formed by ...
Wei Cao, Yingchao Dou, Cyrille Kouklovsky, Guillaume Vincent   +3 more
wiley   +2 more sources

Elucidation of the mescaline biosynthetic pathway in peyote (Lophophora williamsii)

The Plant Journal, Volume 116, Issue 3, Page 635-649, November 2023., 2023
Significance Statement Peyote (Lophophora williamsii) has long been used for medicinal and ceremonial purposes by the Indigenous peoples of the American southwest deserts owing to its hallucinogenic properties, and the cactus remains a popular recreational drug. We report the isolation and characterization from peyote of six biosynthetic genes involved
Jacinta L. Watkins, Qiushi Li, Sam Yeaman, Peter J. Facchini   +3 more
wiley   +1 more source

An improved Nicotiana benthamiana bioproduction chassis provides novel insights into nicotine biosynthesis

New Phytologist, Volume 240, Issue 1, Page 302-317, October 2023., 2023
Summary The model plant Nicotiana benthamiana is an increasingly attractive organism for the production of high‐value, biologically active molecules. However, N. benthamiana accumulates high levels of pyridine alkaloids, in particular nicotine, which complicates the downstream purification processes. Here, we report a new assembly of the N. benthamiana
Katharina Vollheyde, Quentin M. Dudley, Ting Yang, Mehmet T. Oz, Davide Mancinotti, Mariano Olivera Fedi, Darren Heavens, Gareth Linsmith, Monika Chhetry, Mark A. Smedley, Wendy A. Harwood, David Swarbreck, Fernando Geu‐Flores, Nicola J. Patron   +13 more
wiley   +1 more source