Alliacolide, a new bicyclic sesquiterpene epoxy-lactone with a novel carbon skeleton from cultures of the fungus Marasmius alliaceus(Jacques ex Fr.)Fr; X-ray structure

King, Trevor J.; Farrell, Iain W.; Halsall, T. G.; Thaller, V.

doi:10.1039/c39770000727

Cited by 30 publications

(14 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…First reported in 1977 by Thaller and co-workers, alliacol A (1) was isolated from the fungus Marasmius alliaceus. 35 In 2004 Mihelcic and Moeller accomplished the first enantioselective total synthesis by utilising an anodic coupling reaction, hence proving its usefulness in synthesis. 36 Alliacol A (1) was prepared in 9.9% overall yield from a known precursor requiring 13 steps, including an asymmetric Michael reaction, to establish the required stereochemistry and an electrochemical cyclisation, followed by Friedel-Crafts alkylation, to generate the tricyclic framework.…”

Section: Sesquiterpenesmentioning

confidence: 99%

“…Featuring an additional ester group, phellodonic acid (35) was first isolated in 1993 from Phellodon melaleucus by Anke, Steglich and co-workers. 61 Expanding the scope of their developed synthetic procedure to create triquinanes, the Banwell group reported the first total synthesis of phellodonic acid (35) in 2008. Overall 35 was produced in 16 steps with 2.6% total yield.…”

Section: Polyquinanesmentioning

confidence: 99%

See 1 more Smart Citation

Synthesis of Secondary Metabolites from Higher Fungi

Reck

Spiteller

2015

Synthesis

View full text Add to dashboard Cite

Higher fungi are a promising source of new bioactive natural products with great structural diversity, ranging from polyketides to terpenoids and alkaloids. Many of these structures are a challenge for synthetic organic chemists who have been inspired to develop new total syntheses. Nevertheless, reviews covering syntheses of fungal natural products are lacking. One aim of this review is to close this gap and to present a selection of more recent syntheses of fungal secondary metabolites from different structural classes. Secondly, this review intends to demonstrate that there are many more motivations for the synthesis of natural products than to confirm a proposed structure or to report the first total synthesis of a new natural product. Thirdly, this review is intended to stimulate the interest of organic chemists in the synthesis of fungal natural products. 1

show abstract

Section: Sesquiterpenesmentioning

confidence: 99%

Section: Polyquinanesmentioning

confidence: 99%

Synthesis of Secondary Metabolites from Higher Fungi

Reck

Spiteller

2015

Synthesis

View full text Add to dashboard Cite

show abstract

“…Hanson and Thallerl have reported a novel sesquiterpenealliacolide, from cultures of the basidiomycete Marasmius alliaceus. 4 These substrates show adequate antimicrobial activity and inhibit DNA synthesis in the ascetic form of Ehrlich carcinoma at concentrations less than 10 µg/mL. 2 Studies towards synthesis of architecturally more complex crinipellinsare limitedand there are only a few total syntheses of crinipellin B.…”

Section: Introductionmentioning

confidence: 99%

An Efficient Synthesis Towards the Core of Crinipellin and Alliacol-B Along With Their Docking Studies

Sahu¹,

Mohapatra²,

Al‐Resayes³

et al. 2020

Preprint

View full text Add to dashboard Cite

In this present work, we are reporting a novel route for the synthesis of the tetracyclic ring systems, which is a common core of crinipellin via oxidative dearomatization, cycloaddition and oxa- di-pi-methane rearrangement. We considered to exploring a route to tetracyclic core (1e) of Crinipellin and tricyclic core (1g) of Allicaol B through intermolecular diels alder reaction and photochemically 1,2 acyl shift. Moreover, docking study of compound 13 and 16has been investigated against AcrB multidrug efflux pump of Escherichia coli (PDB ID: 1T9U), main protease of SARS COV-2 (PDB ID: 6W63), DNA gyrase of Streptococcus pneumonia (PDB ID: 4Z2C), human estrogen receptor alpha (PDB ID: 3ERT), human lanosterol 14-alpha-demethylase (CYP51)(PDB ID: 3JUS) and cyclooxygenase-2 (Prostaglandin Synthase-2) (PDB ID: 1CX2). The obtained results herein are important for the exploitation of the therapeutic potential of these derivatives as antimicrobial, antiviral, anticancer, antifungal or anti-inflammatory agents.

show abstract

“…11). In addition to alliacolide (11) and alliacol B (13) Anke isolated the primary alcohol alliacol A (12). on acetylation with Ac20/ pyridine 12 undergoes rearrangement to yield the tertiary acetate 14, indicating the high strain of the endocyclic double bond.…”

mentioning

confidence: 99%

Biologically active compounds from higher fungi

Steglich¹

1981

Pure and Applied Chemistry

View full text Add to dashboard Cite

From mycelial cultures and fruiting bodies of Higher Fungi several metabolites with antibiotic and cyto= toxic activity have been isolated. Some recent progress in this field is discussed including the chemistry of sesquiter= pene antibiotics, striatals, strobilurins and hemiterpenoids. Myxomycetes appear to be a source of unusual pigments which often exhibit antibiotic properties.Fruiting bodies of Higher Fungi show many different colours, colour reactions, odors and tastes which are useful characters for their identification. The chemistry behind these phenomena opens a wide field of research, and in recent years several new types of pigments, terpenes, amino acids, alkaloids and polysaccharides have been isolated from mushrooms and toadstools.

show abstract

Alliacolide, a new bicyclic sesquiterpene epoxy-lactone with a novel carbon skeleton from cultures of the fungus Marasmius alliaceus(Jacques ex Fr.)Fr; X-ray structure

Abstract: Suminmy From a culture of the fungus Marasnzius alliaceus (Jacques ex Fr.) Fr. alliacolide, a new sesquiterpene hydroxy-epoxy-lactone, C,,H,,O,, has been isolated ; its structure, which has been established by X-ray diffraction analysis, has a new sesquiterpene carbon skeleton.

Cited by 30 publications

References 0 publications

Synthesis of Secondary Metabolites from Higher Fungi

Synthesis of Secondary Metabolites from Higher Fungi

An Efficient Synthesis Towards the Core of Crinipellin and Alliacol-B Along With Their Docking Studies

Biologically active compounds from higher fungi

Contact Info

Product

Resources

About