chemistry

Taxodone

Taxodone is a chemistry 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 Taxodone rather than just read about it. In short: Taxodone is a naturally occurring diterpenoid found in Taxodium distichum (bald cypress), Rosmarinus officinalis (rosemary), several salvia species and other plants, along with its oxidized rearrangement product, taxodione. Taxodone and taxodione exhibit anticancer, antibacterial, antioxidant, antifungal, insecticide, and antifeedant activities.

Key takeaways

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

Reference excerpt

Taxodone is a naturally occurring diterpenoid found in Taxodium distichum (bald cypress), Rosmarinus officinalis (rosemary), several salvia species and other plants, along with its oxidized rearrangement product, taxodione. Taxodone and taxodione exhibit anticancer, antibacterial, antioxidant, antifungal, insecticide, and antifeedant activities.

Discovery Taxodone was first isolated in 1968 from the seeds of Taxodium distichum (Bald Cypress) by S. Morris Kupchan and coworkers. They reported the structure determination and basic chemistry of taxodone and its oxidized rearrangement product, taxodione. Taxodone occurs naturally in the form of (+)-taxodone.

Occurrence Taxodone and/or taxodione have been identified in several plants besides Taxodium distichum including: Rosmarinus officinalis (Rosemary), Salvia barrelieri, Metasequoia glyptostroboides (Dawn Redwood), Salvia munzii (San Diego Sage), Salvia moorcroftiana, Salvia staminea, Salvia clevelandii (Cleveland Sage), Salvia hypargeia, Salvia broussonetii, Salvia montbretii, Salvia nipponica, Salvia verbenaca (Wild Clary), Salvia lanigera, Salvia prionitis, Salvia deserta, Salvia phlomoides, and Plectranthus hereroensis Taxodone, taxodione and their reaction products have been used as archeological and geological biomarkers. Analogs of taxodone and taxodione have also been isolated. 2-hydroxy taxodone and 2-hydroxy-taxodione have been found in Salvia texana (Texas Sage). 5,6-Didehydro-7-hydroxy-taxodone was found in Salvia munzii. 7-Hydroxytaxodione, 7,7‘-bistaxodione, and 11,11‘-didehydroxy-7,7‘-dihydroxytaxodione were found in Salvia montbretti.

Activity Taxodone and taxodione possess in vivo activity against Walker intramuscular carcinosarcoma 256 in rats (25 and 40 mg/kg, respectively) and in vitro activity against cells derived from human carcinoma of the nasopharynx (KB) (ED50 = 0.6 and 3 ug/ml respectively). Taxodone and taxodione exhibit antifungal activity against wood decay fungi, with taxodione being especially active against Trametes versicolor and Fomitopsis palustris. Taxodione exhibited the highest antioxidant activity among the tested diterpenoids from the roots of Salvia barrelieri. Taxodone showed potent antibacterial effects against foodborne pathogenic bacteria, such as Listeria monocytogenes ATCC 19166, Salmonella typhimurium KCTC 2515, Salmonella enteritidis KCTC 2021, Escherichia coli ATCC 8739, Escherichia coli O157:H7 ATCC 43888, Enterobacter aerogenes KCTC 2190, Staphylococcus aureus ATCC 6538 and Staphylococcus aureus KCTC 1916 Taxodone showed potent termicidal activity against the subterranean termite, Reticulitermes speratus Kolbe. Taxodione depresses neuronal GABAA receptor-operated Cl-current (IGABA). Taxodione may have potential in treatment of cardiovascular disease. The use of taxodone and taxodione to inhibit hair growth has been patented. Treatment of benign prostate enlargement with taxodone has also been patented.

Chemistry Taxodone was the first isolated example of a quinone methide with a labile hydrogen adjacent to this reactive chromophore. Kupchan demonstrated that taxodone aromatizes to a catechol ketone upon exposure to mild acid. Air oxidation of this catechol ketone affords taxodione.

Synthesis Taxodone rearranges easily in the presence of mild acids and reacts readily with nucleophiles. Although taxodone shows higher anticancer and antibacterial activity than taxodione it eluded creation in the laboratory for over 25 years because of its inherent instability. During this time several different groups reported syntheses of the more stable taxodione. In 1993 taxodone was synthesized for the first time in a 16 step sequence utilizing a unique phenol benzylic epoxide electron reorganization in the final step. As taxodone readily decomposes into taxodione this synthesis of taxodone also constitutes a formal synthesis of taxodione as well.

Since the synthesis of taxodone there have been additional syntheses of taxodione and analogs.

See also Taxodium distichum Quinone methide Diterpenoid Salvia

References

External links The First Total Synthesis of (±)-Taxodone Sanchez, Anthony J.; Konopelski, Joseph P. (1994). "Phenol Benzylic Epoxide to Quinone Methide Electron Reorganization: The Synthesis of (±)-Taxodone". J. Org. Chem. 59 (18): 5445–5452. doi:10.1021/jo00097a057. Taxodone, Pubchem entry Quinone methides, Steven Edward Rokit Biological and toxicological consequences of quinone methide formation Recent Advances in the Chemistry of Terpenoid Tumor Inhibitors

Illustrations

Worked examples

Example 1 — a first encounter with Taxodone

Start with the simplest possible case. Write down what Taxodone claims or describes in one sentence, then invent the smallest concrete situation in which that sentence is true. In chemistry, 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 Taxodone 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 Taxodone 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 Taxodone

In research: Taxodone appears in chemistry 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 Taxodone 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: Taxodone is common in secondary-school and first-year university syllabi. It links to neighbouring topics Diols, Diterpenes, Enols, so understanding it makes those chapters shorter.
In everyday life: Look for Taxodone 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 Taxodone in 20 minutes

Read the reference excerpt below once, without taking notes.
Close the page and write down what Taxodone 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 Taxodone out loud to somebody else — or to Teacher Smith in the lgStudy chat.

Frequently asked questions

What is Taxodone in simple terms?

Why does Taxodone matter?

Because it connects several chemistry 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 Taxodone?

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 Taxodone.