The isolation and synthesis of chanoclavine-I acid

Choong, Tung-Chung; Shough, H. Richard

doi:10.1016/s0040-4039(01)83180-4

Cited by 9 publications

(4 citation statements)

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“…Our research has uncovered new knowledge of its function by establishing an in vitro biochemically relevant reaction system and performing molecular docking and site mutation analysis. We confirmed that EasD af directly converts both CC 1 and CC aldehyde 2 to produce CC acid 3 , a well-known compound isolated from Ipomoea violacea (Choong and Shough 1977 ). This discovery establishes EasD af ’s dual functionality, enabling the transformation of both CC and CC aldehyde into CC acid in vitro.…”

Section: Discussionsupporting

confidence: 74%

“…Compound 2 was identified as CC aldehyde and verified by comparison with a synthetic sample in our lab (Figure S 4 ). Although 3 was previously isolated and characterized from Ipomoea violacea (Choong and Shough 1977 ), the catalytic function of EasD af in its biosynthesis had not been reported. To confirm this newly observed product, a large-scale EasD af -reaction was performed, and the mixture was purified and identified using HPLC and analyzed with LC-MS (Fig.…”

Section: Resultsmentioning

confidence: 99%

“…The chemical structure of CC acid (CC acid, 3 ) was initially identified in the seeds of Ipomoea violacea (Choong and Shough 1977 ), and the first total synthesis of CC acid 3 was achieved chemically using 3-indolecarboxaldehyde (Somei et al 1990 ). However, no reports exist on the transformation of CC aldehyde 2 to CC acid 3 in literature.…”

Section: Introductionmentioning

confidence: 99%

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An unexpected role of EasDaf: catalyzing the conversion of chanoclavine aldehyde to chanoclavine acid

Yu,

An,

Yao

et al. 2024

Appl Microbiol Biotechnol

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Ergot alkaloids (EAs) are a diverse group of indole alkaloids known for their complex structures, significant pharmacological effects, and toxicity to plants. The biosynthesis of these compounds begins with chanoclavine-I aldehyde (CC aldehyde, 2), an important intermediate produced by the enzyme EasDaf or its counterpart FgaDH from chanoclavine-I (CC, 1). However, how CC aldehyde 2 is converted to chanoclavine-I acid (CC acid, 3), first isolated from Ipomoea violacea several decades ago, is still unclear. In this study, we provide in vitro biochemical evidence showing that EasDaf not only converts CC 1 to CC aldehyde 2 but also directly transforms CC 1 into CC acid 3 through two sequential oxidations. Molecular docking and site-directed mutagenesis experiments confirmed the crucial role of two amino acids, Y166 and S153, within the active site, which suggests that Y166 acts as a general base for hydride transfer, while S153 facilitates proton transfer, thereby increasing the acidity of the reaction. Key points •EAs possess complicated skeletons and are widely used in several clinical diseases •EasDafbelongs to the short-chain dehydrogenases/reductases (SDRs) and converted CC or CC aldehyde to CC acid •The catalytic mechanism of EasDaffor dehydrogenation was analyzed by molecular docking and site mutations

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Section: Discussionsupporting

confidence: 74%

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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An unexpected role of EasDaf: catalyzing the conversion of chanoclavine aldehyde to chanoclavine acid

Yu,

An,

Yao

et al. 2024

Appl Microbiol Biotechnol

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“…Pharmacological studies on the Convolvulaceae genera, Ipomoea, Rivea, Argyreia, Stictocardia and Cuscuta suggested that they have psychotropic properties (Chao and Der Marderosian, 1973;Bailin, 1975;Evans and Hofmann, 1980) due to ergot-type alkaloids present in the seeds of several species (Hofmann, 1972;Der Marderosian et al, 1974;Choong and Shough, 1977;Ikhiri et al, 1987). Most of these alkaloids are well known as antiserotonergic agents and some of them selectively antagonize the serotonin action in the uterine rat tissue (Colpaert et al, 1982;Bradley, 1984).…”

Section: Introductionmentioning

confidence: 99%

Effect of Ipomoea intrapilosa Methanol Extract on the Serotonergic Response in Rat Uterus

Osuna¹,

Ponce‐Monter

Campos

et al. 1996

Phytother. Res.

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Alkaloids

Mascavage

Jasmin

Sonnet

et al. 2010

Ullmann's Encyclopedia of Industrial Chemistry

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The article contains sections titled: 1. Introduction 2. Alkaloids Derived from Polyketides and the Amino Acids Ornithine and Lysine 2.1. Alkaloids Derived by the Insertion of Nitrogen into a Polyketide 2.1.1. ( S )‐(+)‐Coniine, γ‐Coniceine and Related Alkaloids 2.1.2. Solenopsin Family (Fire Ant Alkaloids) 2.1.3. Perhydroazaphenalenes: Defensive Alkaloids of the Coccinellidae 2.1.4. Cyanobacteria Alkaloids 2.1.5. Additional Polyketide‐Derived Alkaloids 2.2. Alkaloids Derived from Ornithine and/or Arginine 2.2.1. Tropane Alkaloids 2.2.2. Pyrrolizidine Alkaloids 2.3. Alkaloids Derived from Ornithine (and/or Arginine) and Nicotinic Acid 2.4. Alkaloids Derived from Lysine (Lys, K) and Nicotinic Acid 2.5. Purine Alkaloids 2.6. Imidazole Alkaloids 2.7. Pepper Alkaloids 3. Alkaloids Derived from the Shikimate Pathway 3.1. Alkaloids Derived from Anthranilate 3.2. Alkaloids Derived from Phenylalanine and Tyrosine 3.2.1. Biosynthesis of Dopamine, Mescaline and Capsaicin 3.2.2. Biosynthesis of Tetrahydroisoquinoline Alkaloids 3.2.3. Cryptostyline (Orchidaceae) and Alkaloids of the Amaryllidaceae 3.2.4. Ephedra Alkaloids 3.3. Alkaloids Derived from Tyrosine 3.4. Alkaloids Derived from Tryptophan and/or Tryptamine (Indole Alkaloids) 3.4.1. Alkaloids Derived from Tryptamine and an Unrearranged Monoterpene Unit 3.4.2. Mold Metabolites 3.4.3. Ergot Alkaloids 3.4.4. Corynantheine–Heteroyohimbine Structural Types 3.4.5. Corynantheine‐Type Alkaloids 3.4.6. Ajmalicine‐Type Alkaloids 3.4.7. Heteroyohimbine Oxindole Type 3.4.8. Glucoalkaloids 3.4.9. Yohimbine–Reserpine Structural Types 3.4.10. Akuammidine–Quebrachidine–Ervatamine–Gelsemine–Akuammiline Structural Types 3.4.11. Uleine–Ellipticine–Vallesamine–Ngouniensine Structural Types 3.5. The Cinchona Structural Type 3.6. The Camptothecin Structural Type 3.7. Terpene, Sesquiterpene, Diterpene and Steroidal Alkaloids (→ ((anchor interlink a26_205.xml Terpenes))) 3.7.1. Overview of Terpenoid Biosynthesis 3.7.2. Monoterpene Alkaloids 3.7.3. Sesquiterpene Alkaloids 3.7.4. Diterpene Alkaloids 3.7.5. Sesterterpene and Triterpene Alkaloids 3.7.6. Steroidal Alkaloids 4. Summary

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The isolation and synthesis of chanoclavine-I acid

Cited by 9 publications

References 9 publications

An unexpected role of EasDaf: catalyzing the conversion of chanoclavine aldehyde to chanoclavine acid

An unexpected role of EasDaf: catalyzing the conversion of chanoclavine aldehyde to chanoclavine acid

Effect of Ipomoea intrapilosa Methanol Extract on the Serotonergic Response in Rat Uterus

Alkaloids

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