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Questions and Answers
What compound results from opening the oxetane ring in Taxol?
What compound results from opening the oxetane ring in Taxol?
20-O-secotaxol
What is the main type of alkaloids discussed in Lecture 9?
What is the main type of alkaloids discussed in Lecture 9?
Terpenoid Alkaloids
What effect did removal of the 4-acetyl moiety at the C-4 position in Taxol have?
What effect did removal of the 4-acetyl moiety at the C-4 position in Taxol have?
Match the following: Alkaloid - Pharmaceutical Use
Match the following: Alkaloid - Pharmaceutical Use
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Where is Taxol mainly found?
Where is Taxol mainly found?
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Taxol is mainly used for treating skin cancer.
Taxol is mainly used for treating skin cancer.
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Taxol binds to the β-subunit of the tubulin heterodimer protein, thus stabilizing the heterodimer and enhancing polymerization of tubulin into stable non-functional ____________.
Taxol binds to the β-subunit of the tubulin heterodimer protein, thus stabilizing the heterodimer and enhancing polymerization of tubulin into stable non-functional ____________.
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Study Notes
Here are the study notes in detailed bullet points, focusing on key facts with context:
Quinoline Alkaloids to Steroidal Alkaloids
- Alkaloids are categorized into several types, including Quinoline, Isoquinoline, Indole, β-Carboline, Imidazole, Purine, Terpenoid, Pyridine, Piperidine, Pyrrolizidine, Quinolizidine, Steroidal, Tropane/Ecgonine, and Marine Alkaloids.
Terpenoid Alkaloids
- Terpenoid Alkaloids are derived from the isoprenoid pathway and can be classified into monoterpenoids (C10), sesquiterpenoids (C15), diterpenoids (C20), and triterpenoids (C30).
- Paclitaxel (Taxol) is a diterpene alkaloid obtained from the Pacific Yew tree (Taxus brevifolia).
- Paclitaxel is used to treat ovarian and breast cancer and is administered via I.V. infusion.
- The mechanism of action of Paclitaxel involves binding to the β-subunit of tubulin, stabilizing microtubules, and inducing apoptosis.
Structure Activity Relationship (SAR) of Taxol
- The SAR of Taxol involves modifying the side chain and taxane nucleus to simplify synthetic studies and create more active analogues.
- Modifications to the side chain include changing the C-2' and C-3' positions, while modifications to the taxane nucleus involve changes to the C-7, C-10, and oxetane ring positions.
Related Compounds of Pharmaceutical Importance
- Taxotere is a water-soluble, semi-synthetic derivative of Taxol used to treat ovarian and breast cancer.
- 10-Deacetylbaccatin III and Baccatin III are obtained from tissue cultures of Taxus baccata and used as starting materials for semi-synthetic Taxol and Taxotere.
Steroidal Alkaloids
- Steroidal Alkaloids are based on a C-27 cholestane skeleton and are nitrogen analogues of steroidal saponins.
- They occur in glycosidal combination with sugars and are found in Solanum and Veratrum species.
Solanum Alkaloids
- Solanine and Solasonine are two major steroidal glycoalkaloids found in Solanum species.
- Solanine contains solanidine as the aglycone and solanose as the sugar part.
- Solasonine contains solasodine as the aglycone and solanose as the sugar part.
- Solanidine is used as a starting material for the synthesis of steroidal drugs, while Solasonine is used as an agricultural insecticide and as a starting material for the synthesis of sexual hormones and corticosteroids.
Marine Alkaloids
- Marine Alkaloids are obtained from marine organisms and are known for their cytotoxic, antiviral, antimicrobial, insecticidal, and fungicidal activities.
- Examples of Marine Alkaloids include Pyridoacridines, Pyrroloacridines, Manzamines, and Indoles.### Marine Alkaloids
- Alkaloids are derived from marine organisms.
Indoles
- Dragmacidin: an alkaloid from the deep-water Caribbean sponge Dragmacidon sp.
- Inhibits growth of several cancer cell lines.
- Chemical structure: 5,6-Dibromo-tryptamine.
Pyrroles
- A tetrabromo-pyrrole was isolated from a purple-colored bacterium of the genus Alteromonas.
- Displays moderate antimicrobial activity.
- Chemical structure: Tetrabromo-pyrrole.
- 4,5-Dibromopyrrole-2-carboxylic acid: shows in vitro immunosuppressive activity.
Manzamines
- A unique class of β-carboline marine alkaloids with an unusual tetra- or pentacyclic system.
- Exhibits a variety of bioactivities against:
- Infectious diseases.
- Cancer.
- Inflammatory diseases.
- Manzamine A:
- A cytotoxic compound.
- Shows great potential against malaria, with improved potency relative to chloroquine and artemisinin.
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Description
This quiz covers the classification and types of alkaloids, including quinoline, isoquinoline, indole, and more, as part of Phytochemistry II for PharmD students.
