phytopharmacology class 4 (primary metabolism in plants)
TRANSCRIPT
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Phytopharmacology:
Primary Metabolism in Plants
Alejandro Pino, PhD.
Class 4
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Lectins: Derivatives From Proteins
Glycoproteins
Specific binding to cell glycoproteins
Phytoaglutinines
Mitogenic activity
Cytostatic activity
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Mistletoe (Viscum album L.)
Parasitic plant on trees
Branches might be as long as 1 m
Leaves of 8 cm
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History of Mistletoe
First used by original civilizations in Germany
Ornamental in Europe
In 1917 the anticancer effect wasdemonstrated
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Chemical Composition
Lectin: Viscumin or ML-1
Viscotoxins I,II,III,IV (Proteins)
Alkaloids:
Viscalbina
Phenylpropanes
Lignans
Flavonoids
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Viscumin (ML-1)
Mr = 60,000 (by gel electrophoresis)
Two chains 34,000 (B) and 28,000 (A)
Inhibit protein synthesis in cell free systems
Chain A is responsible of inhibition
Ribosomal subunit 60 S is selectively inactivated by
chain A
Chain B is responsible of binding to cells
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Viscotoxins
Basic proteins
Low molecular weight
Agonists of acetyl-choline receptors
Capable to interact with DNA
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Medical Applications and Dosage Forms
Treatment of Cancer
Iscador: Fermented plant juice administered
orally (2 ml BID, 2.5 mg of Viscumin)
Eurixor: Viscumin (ML-1) administered
intravenously or SC close to the place of
tumor (No reported dose) (Twice a week)
Under clinical trial in Europe
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Toxicities and Adverse Effects
GIT effects
Cardiovascular toxicity by interfering Ca2+ ions at the
membrane
Viscotoxins LD50 in rats = 0.7 mg/Kg
Iscador LD50 in rats = 276 mg/Kg
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Polysaccharides
Homo-polysaccharides
Hetero-polysaccharides
Glucans (glucose)
Mannans (mannose)
Hemicellulose (Xylose)
Levans (Fructose)
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Glucose isomers
Hemiacetal forms
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Xanthan gum
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Aloe (Aloe vera L.)
Succulent plant growing to 1 m tall
Leaves are lanceolate, thick and fleshy
Flowers on a spike up to 90 cm tall
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History
Egipt: Evers Papyrus, Century XVI b.C. = Long life
elixir
Used by soldiers to heal wounds
Century I: Dioscorides refers to the internal andexternal use of aloe juice
Century XV: Barbados.
1932: Declared officinal drug in England 1973: Declared protected spice in USA
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Chemical Composition
Anthraquinones: Aloins
Nataloins
Barbaloins
Polysaccharide Gel Mucopolysaccharides: Acemannan (Acetylated mannans)
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Pharmacology of Mannans
Inhibit cholesterol absorption (Orally)
Mannose binding proteins in cell surface
macrophage activation and interleukin-l release
inhibit viral replication
stimulate bone marrow activity
promote wound healing
inhibit tumor growth
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Effects on Skin and Mucoses
Restorative effect on the skin
Wound healing (Activation of fibroblasts)
Anti-inflammatory effect (Inhibition of
phospholipases = less release of araquidonic acid).
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Mode of action
Activation of membrane mannan receptors
influences the activity of T-lynphocytes, fibroblasts,
B-lynphocytes, and endothelial cells.
Stimulates phagocytosis. Increases antibody production
Inhibit the enzyme lipooxygenase
Possible activation of beta-cells in pancreas.
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Applications of the Gel
Cosmetic applications (Topic)
Wound healing (Topic)
Ulcers and gastritis (Orally)
Diabetes (Orally)
Treatment of Fibrosarcoma in dogs and cats
(Acemannan) (IV)
Inhalation solutions of acemannan in asthma (understudy)
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Toxicities and Adverse Effects
Anthraquinones:
Irritation of mucoses
Diarrhoea
Hypokalemia
Colon cancer
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Doses and Dosage Forms
Gel orally 30 ml/dose BID
Gel topically 2 10 %
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Sulfoxides
S-Propyl-cysteine sulfoxide
S-Propenyl-cysteine sulfoxide
S-Methyl-cysteine sulfoxide
Alliin (S-Allyl-cysteine sulfoxide)
Zwiebelane
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Thiosulfinates
Allyl-methane-thiosulfinate
Methyl-methane-thiosulfinate
Diallyl-thiosulfinate (Allicin?)
Dipropenyl-thiosulfinate (Allicin)
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Derivatives from Allicin
Ajoenes
Z-ajoene
E-ajoene
Dithiins 2-vynyl-1,3-dithiin
3-vynyl-1,2-dithiin
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Pharmacology of sulfur compounds
Hypocholesterolemic effect
Anti-atherosclerosis
Inhibit platelet aggregation, anti-thrombotic
Anti-infections, antibiotic activity
Hypoglycemic effect
Antitumoral effect
Antioxidant effect
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Garlic (Allium sativum)
Food and medicine for 4000 years
Egyptian Codex Evers year 1550 b.C. indicating
garlic remedies for heart, headache, bites,
worms and tumors
Dioscorides century I, vermifuge
Louis Pasteur 1858, antibacterial
Effective against Atherosclerosis and platelet
aggregation
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Top supplements used in USA in 1997
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Garlic plant
Leaves long, narrow and flat
Bulb consisting of numerous bulblets (cloves),
enclosed within a whitish skin, which holds them as
in a sac Flowers placed at the end of a stalk, grouped in a
globular head or umbel
Plant 50 cm tall
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Allium sativum L
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Chemical composition
Gamma-glutamyl-cysteine
Alliin (80 % of sulfated compounds)
Alliinase
Allicin
Other sulfoxides
Other thiosulfinates
Saponins
Flavonoids
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T1=diallylsulfide, T2=allicin, T3=dipropylthiosulfinate, T4=dimethylthiosulfinate
1=Allium sativum, 2=Allium ursinum, 3=Allium cepa
Toluene:Ethylacetate
(100:30)
Paladium II chloride
reagent
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T1=diallylsulfide, T2=allicin, T3=dipropylthiosulfinate, T4=dimethylthiosulfinate
1=Allium sativum, 2=Allium ursinum, 3=Allium cepa
Vanillin-Acetic acid
reagent
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Pharmacology of garlic
Anticoagulant and thrombolytic
Decrease the synthesis of cholesterol
Prevents atherosclerosis
Antithrombotic
Chemopreventive and antitumoral
Antimutagenic activity
Antimicrobial effect
Prevents nephrotoxicity
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Mode of action
Inhibition of lipooxigenase and cyclooxigenase Increase superoxide dismutase activity
Increase glutathione peroxidase activity
Increase catalase activity in vascular endothelial cells
Inhibition of platelet aggregation (Aggregin, ADP)
Increase of HDL cholesterol level in blood
Allicin scavenges free radicals
Inhibition of OH-Methyl-glutaryl-Co-A reductase
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TOXICITY OF GARLIC (The dose makes the poison)
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GLUCOSINOLATES
Glucotropaeolin4-Methoxybenzyl glucosinolate
Glucoalyssin
4-Hydroxybenzyl glucosinolate
Glucobrassicanapin
Glucobrassicin
4-Methoxyindolyl-3-methyl glucosinolate
3-Methoxyglucotropaeolin
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AROMATIC ISOTHIOCYANATES
Benzylisothiocyanate
4-Methoxybenzylisothiocyanate
3-Methoxybenzylisothiocyanate
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End of presentation
Thank you!