Iridoids.pptx
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The document discusses the biosynthesis of indole alkaloids. Many indole alkaloids are derived from tryptophan, which originates from the shikimic acid pathway. Some indole alkaloids also incorporate geraniol, a terpene precursor. Serotonin and psilocybin are examples of indole alkaloids directly derived from tryptophan. Beta-carboline alkaloids are formed from tryptophan and an aldehyde or ketoacid. Terpenoid indole alkaloids incorporate both tryptophan and geraniol, with geraniol transforming into loganin and secologanin intermediates that can rearrange to form different skeletal structures.
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Learning objectives:
1. Define an electrocardiogram (ECG) and electrocardiography
2. Describe how dipoles generated by the heart produce the waveforms of the ECG
3. Describe the components of a normal electrocardiogram of a typical bipolar lead (limb II)
4. Differentiate between intervals and segments
5. Enlist some common indications for obtaining an ECG
6. Describe the flow of current around the heart during the cardiac cycle
7. Discuss the placement and polarity of the leads of electrocardiograph
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9. Define mean electrical vector (axis) of the heart and give the normal range
10. Define the mean QRS vector
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12. Comprehend the vectorial analysis of the normal ECG
13. Determine the mean electrical axis of the ventricular QRS and appreciate the mean axis deviation
14. Explain the concepts of current of injury, J point, and their significance
Study Resources:
1. Chapter 11, Guyton and Hall Textbook of Medical Physiology, 14th edition
2. Chapter 9, Human Physiology - From Cells to Systems, Lauralee Sherwood, 9th edition
3. Chapter 29, Ganong’s Review of Medical Physiology, 26th edition
4. Electrocardiogram, StatPearls - https://www.ncbi.nlm.nih.gov/books/NBK549803/
5. ECG in Medical Practice by ABM Abdullah, 4th edition
6. Chapter 3, Cardiology Explained, https://www.ncbi.nlm.nih.gov/books/NBK2214/
7. ECG Basics, http://www.nataliescasebook.com/tag/e-c-g-basics
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Iridoids.pptx
- 2. Indole alkaloids come from trytophan which originates from the shikimic acid pathway. Many are of mixed-origin using geraniol, a terpene as a precursor. Biggest single class of alkaloids - more than 1500 known. INDOLE ALKALOIDS
- 4. OH O COOH C CH2 COOH chorismic acid ANTHRANILIC ACID O COOH C CH2 COOH NH2 H H+ :B-Enz COOH NH2 anthranilic acid glutamic acid :NH3 H+ Tryptophan
- 5. TRYPTOPHAN NH2 COOH O O H OH CH2 OP O PP .. phospho- ribosyl PP anthranilic acid NH COOH O O H OH CH2 OP N OH OH OP O H H H COOH N OH OH OP O H H COOH N OH OH OP O H C O O H H+ N OH O OP H H N H - CO2 - H2O N H NH2 COOH H+ tautomers enol keto imine enamine tautomers O H NH2 COOH indole serine reverse adol TRYPTOPHAN PLP
- 9. b-CARBOLINE ALKALOIDS N H NH2 COOH C H R O aldehyde from an amino acid tryptophan N H N COOH C R H H N N H H R H N N H R H N N H H a b-carboline tryptophan + an aldehyde
- 10. b-CARBOLINE ALKALOIDS tryptophan + an a-ketoacid N H NH2 COOH C O COOH an a-ketoacid tryptophan N H N COOH C H COOH N N H H H COOH N N H H COOH N N H Mannich Arom Subst Oxidative decarboxylation N N H N N H MeO N N H MeO harman harmaline harmine
- 13. Yopo Anadenathra peregrina Cohoba snuff a legume
- 14. Virola
- 16. There are a variety of alkaloids that have tryptophan and geraniol as their precursors. The geraniol precursor can yield a variety of skeletal pieces as it rearranges readily via a pathway containing two intermediates called loganin and secologanin. OH O OGlu O H MeOOC C O OGlu O MeOOC H geraniol loganin secologanin
- 17. C O OGlu O MeOOC H secologanin Corynanthe type Aspidosperma type Iboga type SECOLOGANIN Secologanin has so much functionality that it can open bonds, rotate and make new bonds, easily rearranging the carbon skeleton. Three principal skeleton types are shown below. These combine with tryptamine to form alkaloids (some examples are given). N N H COOMe N N H COOMe N N H COOMe tabersonine akuammicine catharanthine IRIDOIDS IRIDANE SKELTON
- 19. Vinca
- 20. SUMMARY REPEAT
- 21. CHORISMIC ACID SHIKIMIC ACID PREPHENIC ACID TYROSINE PHENYLALANINE CINNAMIC ACIDS ALKALOIDS ALKALOIDS PHENYL-C3 COMPOUNDS ANTHRANILIC ACID TRYPTOPHAN ALKALOIDS Shikimate Pathways PHENYL-C1 COMPOUNDS FLAVANOIDS (+ acetogenin)
- 22. ASSIGNMENTS Read: Hesse Alkaloids - Nature’s Cure or Curse, Wiley-VCH (2000) Chapter 7 “Alkaloids and Chemotaxonomy”, pp 237-256, especially Section 7.2 which discusses the formation of secologanin and other iridoids from geraniol. Schultes, Hofmann and Ratsch, Plants of the Gods, Healing Arts Press (2001) All of these are indole-based alkaloids (b-carbolines and tryptamines) “The Magic Drink of the Amazon”, pp 124-139 (Ayahuasca) “Beans of the Hekula Spirit”, pp116-119 (Yopo) “Seeds of Civilization”, pp 120-123 (Cebil) “Semen of the Sun”, pp 176-181 (Virola, Epena) Ibogamine is fromed from an iridoid intermediate “Guide to the Ancestors”, pp 112-115 (Iboga) Psilocybin mushrooms “Little Flowers of the Gods”, pp 156-163 (Psilocybes) (Yage)