science

Oudemansin A

Oudemansin A is a science topic covered in the lgStudy science library. This page brings together a partial reference excerpt, illustrations, worked examples, real-world applications and a short study plan, so you can understand Oudemansin A rather than just read about it. In short: Oudemansin A is a natural product first isolated from the basidiomycete fungus Oudemansiella mucida. Its chemical structure was determined by X-ray crystallography in 1979 and absolute stereochemistry by total synthesis.

Key takeaways

Oudemansin A belongs to science; place it in that map before memorising details.
Learn the definition first, then one example that makes the definition concrete.
Connect Oudemansin A to a quantity you can measure, compute or draw — that is where exam questions come from.
Reproduce the core statement of Oudemansin A from memory before moving on to harder problems.

Reference excerpt

Oudemansin A is a natural product first isolated from the basidiomycete fungus Oudemansiella mucida. Its chemical structure was determined by X-ray crystallography in 1979 and absolute stereochemistry by total synthesis. Two closely related derivatives, oudemansin B and X have also been isolated from other basidiomycetes. They are all biologically active against many filamentous fungi and yeasts but with insufficient potency and stability to become useful commercial products. However, their discovery, together with the strobilurins led to agricultural fungicides including azoxystrobin with the same mechanism of action.

Isolation and characterization

Oudemansin A (initially known simply as oudemansin) with R1 = R2 = H was first described in 1979, after being isolated from mycelial fermentations of the basidiomycete fungus Oudemansiella mucida. Its structure, including the relative configuration of the methoxy and adjacent methyl groups, was established by both spectroscopic methods and single crystal X-ray analysis but its absolute stereochemistry was at that time undetermined. Later it was found in cultures of the basidiomycete fungi Mycena polygramma and Xerula melanotricha. The latter fungus also produces oudemansin B, with R1 = MeO and R2 = Cl. Oudemansin X, with R1 = H and R2 = MeO was isolated from Oudemansiella radicata.

Chemical synthesis The oudemansins have been targets for total synthesis and in 1983, the synthesis of (-)-oudemansin A established that all three compounds have the (9S,10S)-configuration. Routes to oudemansins B and X have also been reported.

Mechanism of action as fungicides The fungicidal effects were shown to stem from what was then a novel mode of action, QoI inhibition. This was related to the β-methoxyacrylic acid sub-structure which this and related natural products, the strobilurins have in common. Intensive research by several agrochemical companies led to the development of useful agricultural fungicides based on the same mode of action, of which azoxystrobin is a typical example.

References

Further reading Anke, Timm; Steglich, Wolfgang (1999). "Strobilurins and Oudemansins". In Grabley, S.; Thiericke, R. (eds.). Drug Discovery from Nature. Springer. pp. 320–334. ISBN 3540648445. Morton, V.; Staub, T. (2008). "A Short History of Fungicides". Apsnet Feature Articles. doi:10.1094/APSnetFeature-2008-0308. Reddy, P.Parvatha (2013). "Chapter 12: Strobilurin fungicides". Recent advances in crop protection. Springer. pp. 185–200. doi:10.1007/978-81-322-0723-8. ISBN 978-81-322-0722-1. S2CID 13212055.

Illustrations

Worked examples

Example 1 — a first encounter with Oudemansin A

Start with the simplest possible case. Write down what Oudemansin A claims or describes in one sentence, then invent the smallest concrete situation in which that sentence is true. In science, the smallest case is usually a single object, a single equation or a single measurement. Check that every symbol or term in your sentence has a meaning in that case.

Example 2 — changing one variable

Take the situation from Example 1 and change exactly one quantity: double it, halve it, or set it to zero. Predict what should happen to Oudemansin A before you calculate. Comparing your prediction with the result is the fastest way to find out whether you understand the idea or only the words.

Example 3 — an exam-style question

Typical questions about Oudemansin A ask you to (a) state it precisely, (b) apply it to given data, and (c) explain a limitation. Practise writing all three answers in under five minutes; the third part is what separates a full-mark answer from an average one.

Applications of Oudemansin A

In research: Oudemansin A appears in science research whenever the underlying quantities have to be modelled precisely. Papers usually cite it as a starting assumption and then explore where it breaks down.
In technology and industry: Engineering practice reuses Oudemansin A in design rules, simulations and safety margins. Knowing the idea lets you read a specification sheet and understand why the numbers look the way they do.
In the classroom: Oudemansin A is common in secondary-school and first-year university syllabi. It links to neighbouring topics Complex III inhibitors, Fungicides, Methyl esters, so understanding it makes those chapters shorter.
In everyday life: Look for Oudemansin A outside the textbook — in sport, cooking, traffic, electronics or the sky above you. An example you found yourself is remembered far longer than one you were given.

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How to study Oudemansin A in 20 minutes

Read the reference excerpt below once, without taking notes.
Close the page and write down what Oudemansin A means in your own words.
Compare your version with the excerpt and mark what you missed.
Work through the three examples above with pen and paper.
Explain Oudemansin A out loud to somebody else — or to Teacher Smith in the lgStudy chat.

Frequently asked questions

What is Oudemansin A in simple terms?

Why does Oudemansin A matter?

Because it connects several science ideas at once: it gives you a definition you can apply, a quantity you can calculate, and a way to check whether a result is plausible.

How should I study Oudemansin A?

Read the excerpt, restate it from memory, then work through the examples and applications listed on this page. The five-step study plan above takes about twenty minutes.

What does this page cover?

It gives you a compact reference excerpt plus original lgStudy explanations, examples, applications and study material on Oudemansin A.