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Bioactive Compounds from Marine “Plants and Microorganisms”

Bioactive Compounds from Marine “Plants and Microorganisms”. Bioactive Compounds from Vascular Plants. Bioactive Compounds from Algae (Part 1) Macroalgae Microalgae (Part 1). Five Kingdoms of Biological Diversity. Monera (“Prokaryotes”). Protista. Plantae. Fungi. Animalia.

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Bioactive Compounds from Marine “Plants and Microorganisms”

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  1. Bioactive Compounds from Marine “Plants and Microorganisms” Bioactive Compounds from Vascular Plants Bioactive Compounds from Algae (Part 1) Macroalgae Microalgae (Part 1)

  2. Five Kingdoms of Biological Diversity Monera (“Prokaryotes”) Protista Plantae Fungi Animalia

  3. Five Kingdoms of Biological Diversity Monera (“Prokaryotes”) Protista Plantae Fungi Animalia

  4. Plant Kingdom: Transition to Land “Bryophytes” “Ferns” and Relatives Vascular Plants Gymnosperms (Conifers and Cycads) Seed Plants Lilliopsida (monocotyledons) Angiosperms a.k.a. Magnoliophyta (“Flowering Plants”) Magnoliopsida (dicotyledons)

  5. Aquatic Plants Division Magnoliophyta Class Lilliopsida Order Alismatales Family Alismataceae Family Aponogetonaceae Family Araceae Family Butomaceae Family Cymodoceaceae Family Hydrocharitaceae Family Juncaginaceae Family Limnocharitaceae Family Posidoniaceae Family Potamogetonaceae Family Ruppiaceae Family Scheuchzeriaceae Family Tofieldiaceae Family Zosteraceae

  6. Order Alismatales

  7. Aquatic Plants Division Magnoliophyta Class Lilliopsida Order Alismatales Family Alismataceae Family Aponogetonaceae Family Araceae Family Butomaceae Family Cymodoceaceae Family Hydrocharitaceae Family Juncaginaceae Family Limnocharitaceae Family Posidoniaceae Family Potamogetonaceae Family Ruppiaceae Family Scheuchzeriaceae Family Tofieldiaceae Family Zosteraceae “Seagrass”

  8. “Seagrasses”

  9. Seagrass Distribution

  10. Bioactive Compounds from Seagrasses: Antiinflammatory Constituents from Zostera japonica TNFa IL-1b Hexane Fraction (H5) from Z. japonica Inhibits Release of Tumor Necrosis Factor (TNF)and Interleukin (IL)

  11. Bioactive Compounds from Seagrasses: Antiinflammatory Constituents from Zostera japonica Fatty Acids are the Major Constituents of Fraction H5

  12. “Mangroves” 16 Plant Families Major Components: Acanthacaeae - e.g. Avicennia spp. (“Black Mangrove”) Combretaceae - e.g. Laguncularia spp. (“White Mangrove”) Rhizophoraceae - e.g. Rhizophora spp. (“Red Mangrove”)

  13. Bioactive Compounds from Mangroves: Antiinflammatory Compounds from Rhizophora mangle (Red Mangrove) Low Molecular Weight Polyphenols Extracted from R. mangle Inhibit COX-2 and PLA2

  14. Bioactive Compounds from Marine “Plants and Microorganisms” Bioactive Compounds from Vascular Plants Bioactive Compounds from Algae (Part 1) Macroalgae Microalgae (Part 1)

  15. What Are Algae? Monera (“Prokaryotes”) Protista Plantae Fungi Animalia

  16. What Are Algae? Monera (“Prokaryotes”) “Algae” Protista Plantae Fungi Animalia

  17. “Microalgae” “Macroalgae” What Are Algae? Prokaryotic Kingdom Monera (Bacteria) Cyanobacteria (“Blue-Green Algae”) Eukaryotic Kingdom Protista Dinophyta (“Dinoflagellates”) Raphidophyta (“Raphidophytes”) Bacillariophyta (“Diatoms”) Chrysophyta (“Golden Algae”) Chlorophyta (“Green Algae”) Phaeophyta (“Brown Algae”) Rhodophyta (“Red Algae”)

  18. Pigments and Algae PBs4 Chl a1bcdCar. 2Xanth.3PC5PE6 Cyanobacteria x x x Dinoflagellata x x x x Bacillariophyta x x x x Chrysophyta x x x x Chlorophyta x x x Phaeophyta x x x x Rhodophyta x x x x 1Chl = Chlorophyll; 2Car. = Carotenoids; 3Xanth. = Xanthophylls; 4PB = Phycobilins (Phycobiloproteins); 5PC = Phyocyanin; 6PE = Phycoerythrin

  19. Macroalgae Chlorophyta (“Green Algae”) Phaeophyta (“Brown Algae”) Rhodophyta (“Red Algae”)

  20. Bioactive Compounds from Chlorophyta: Capisterones A and B A R = Ac B R = H

  21. Capisterones A (1) and B (2) Reverse Fluconazole-Resistance Xing-Cong et al. (2005) J. Nat. Prod., 69: 542-6

  22. Yeast Transformed with MDR1 and CDR1 MDR1/CDR1 P-Glycoproten Pumps Drugs and Toxins out of Cell MDR1/CDR1 Gene Product is ATP-Binding Cassette (ABC) Protein

  23. Capisterones A (1) and B (2) Reverse Fluconazole-Resistance Xing-Cong et al. (2005) J. Nat. Prod., 69: 542-6

  24. Algicidal Polyunsaturated Fatty Acids (PUFAs) from Ulva fasciatus Hexadeca-4,7,10,13-Tetraenoic Acid (HDTA) Octadeca-6,9,12,15-Tetraenoic Acid (ODTA) a-Linolenic Acid

  25. Bioactive Compounds from Phaeophyta: Phloroglucinols from Ecklonia cava 8,8’-Bieckol 8,4”-Dieckol

  26. Phloroglucinol Tannins (“Phlorotannins”) Phloroglucinol

  27. Phlorotannins from Ecklonia cava Inhibit HIV Reverse-Transcriptase (RT) and Protease IC50(mM) RT Protease Eckol >100 >100 8,8’-Bieckol 0.51 81.5 8,4”-Dieckol 5.31 36.9 Phlorofucofureckol A >100 >100 Nevirapine 0.28 Not Tested Acetyl Pepstatin Not Tested 0.34 Taken from Ahn et al. (2004) Biol. Pharm. Bull., 27: 544-7

  28. Bioactive Compounds from Phaeophyta: Diterpenes from Dictyota R (6R)-6-Hydroxydichotoma-3,14-Diene-1,17-Dial (Da-1) -H (6R)-6-Acetoxydichotoma-3,14-Diene-1,17-Dial (AcDa-1) -Ac (from D. meunstralis)

  29. Da-1 and AcDa-1 Inhibit HIV-1 Replication by Inhibition of Reverse Transcriptase

  30. Bioactive Compounds from Rhodophyta: Antiviral Activity of Carrageenan k-carrageenan n i-carrageenan n l-carrageenan n

  31. Carrageenan Strongly Human Papilloma Virus (HPV) Psuedovirus (PsV)

  32. Carrageenan Resembles Sulfated Glycosaminoglycans Heparan Sulfate

  33. HPV Attaches to Host Cells by Binding Heparan Sulfate Bound to Cell Membrane

  34. Carrageenan Binds HPV Capsids

  35. Carrageenan is Found ALREADY in Number of Contraceptives Buck et al. (2006)

  36. Eukaryotic Microalgae Dinoflagellata Bacillariophyta (“Diatoms”) Raphidophyta

  37. “Harmful Algal Blooms” (HABs)

  38. HAB Toxins Typically Associated with Human Health Effects “Amnesic Shellfish Poisoning” (ASP) “Paralytic Shellfish Poisoning” (PSP) “Neurotoxic Shellfish Poisoning” (NSP)“Ciguatera Fish Poisoning” (CFP) “Diarrhetic Shellfish Poisoning” (DSP)

  39. “Amnesic Shellfish Poisoning” (ASP) Domoic Acid Pseudonitzschia spp.

  40. Domoic Acid Binds to Kainate-Type Glutamate Receptors

  41. Kainate Receptor is “Non-NMDA” Glutamate Receptor Glu

  42. Kainate Receptor is “Non-NMDA” Glutamate Receptor Ca2+ Glu 1. Free-Radicals (e.g. Nitric Oxide, Reactive Oxygen Species) 2. Damage to Membranes (e.g. Collapse of Mitochondria) 3. Loss of ATP 4. Apoptosis/Necrosis 5. Excitatory Neurotransmitters

  43. Domoic Acid Causes Lesion in the Hippocampus

  44. “Paralytic Shellfish Poisoning” (PSP) R4: R1R2R3 H H H STX GTX5 H H OSO3- GTX2 C1 H OSO3- H GTX3 C2 OH H H NeoSTX GTX6 OH H OSO3- GTX1 C3 OH OSO3- H GTX4 C4 Saxitoxin (STX), Gonyautoxins (GTX) and Other “PSP Toxins” e.g. Alexandrium tamarense

  45. = STX or TTX STX Binds Voltage-Gated Sodium Channels at the Same Site as TTX

  46. Minor Modification of Sodium Channel Leads to Resistance to STX in Shellfish

  47. Reduced Toxicity Leads to Increased Accumulation of STX in Shellfish Higher Mortality for STX-Exposed Clams (black) vs. Unexposed (white) Higher Accumulation in Resistant (black) vs. Sensitive (white) Clams

  48. “Florida Red Tide” Karenia brevis

  49. “Florida Red Tide”

  50. Brevetoxins (PbTx): The Florida Red Tide Toxin Brevetoxin A (PbTx-1) Brevetoxin B (PbTx-2)

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