HETEROGLYCANS (POLYSACCHARIDES)

Anthraquinone Glycosides

• Aglycone: anthracene • Use: cathartics (drastic) • Derivatives color: Orange • Bortrager's Test: official identification test

[Cardenolides] Adonis

• Adonis vernalis; Peasant's Eye • Adinotoxin

[Lactone] Psoralens

• Amni majus; Bishop's Flower • Photosensitizng furocoumarins • For patients with psoriasis/vitiligo (non-communicable disease) • Methoxsalen (repigmentation in vitiligo); Trioxsalen o C/I: Direct exposure to sunlight activates melanin skin cancer

Cyanophore/Cyanogenic Glycosides

• Amygdalin (H2O and amygdalase) mandelonitrile glucose (H2O and prunase) mandelonitrile + glucose benzaldehyde + HCN • Rosaceae species (Prunus) • Amygdalase and Prunase are collectively known as Emulsin (glycoside) APE o Composite enzymes: amygdalase and prunase o Composite acids for tannic acid: gallic acid and ellagic acid

[Cardenolides] Apocynum

• Apocynum cannabinum; Dogbane • Cyamarin (anti-arrythmia/cardiotoxic)

[Plant Exudates] Acacia

• Botanical source: Acacia senegal (Gum Arabic) • Gum constituent arabin • Use: Suspending agent at 33-35%, stable with alcohol at 60%

[Plant Exudates] Indian

• Botanical source: Anogeissus latifolia (Ghatti Gum) • Use: Substitute for acacia

[Plant Exudates] Tragacanth

• Botanical source: Astralagus gummifer (Gum Tragacanth) • Gum constituent: tragaacnthin (1/3 dissolve) and bassorin (2/3 swell) • Use: suspending agent at 6-6% • Tragacanth grades o Vermiform - worm-like; yellowish brown o Sorts - tear-shaped; yellowish brown o Flakes - man made; clear; preferred grade

[Plant Exudates] Karaya

• Botanical source: Sterculia urens (Sterculia Gum) • Use: bulk laxative • Most fetid gum (unpleasantly smelling)

[Isothiocyanate] White Mustard

• Brassica alba; Sinapis Alba • Sinalbin

[Isothiocyanate] Black Mustard

• Brassica nigra; Sinapis Nigra • Sinigrin Sinigrin ------------------------> allyl isothiocyanate "myrosinase"(glycosidase)

[Cardenolides] Convallaria

• Convallaria majalis; Lily of the Valley • Convallatoxin

[Aldehyde] Vanilla

• Cured fruit of Vanilla planifolia; Mexican/Vera Cruz/Bourbon • Constituent: vanillin • Use: flavoring agent • Ethylvanillin: substitute for natural vanilla

[Cardenolides] Foxglove

• Digitalis purpurea (Foxglove) • Digitalis lanata (Grecian Foxglove) • Digoxin (water soluble); digitoxin (lipophilic) • Deslanoside: digitalization required rapid digitalis loading

[Saponin] Diocorea/Yam

• Dioscorea spiculiflora - contains diosgenin which is a glucocorticoid precursor • Dioscorea florbunda - best source of steroids in the market (Mexican Yam) • Diosgenin: anti-inflammatory

[Anthraquinone] Aloe/Sabila

• Dried latex or juice of Aloe barbadensis or Aloe vera (Curacao aloe) • Hybrids of Aloe ferox with Aloe Africana and Aloe spicata (Cape aloe) • Constituents: Barbaloin and aloe emodin • Commercial source: Curacao • Uses: Moisturizer, 2% for burn preparations, Compound Benzoin Tincture

[Phenol] Uva ursi

• Dried leaf of Arctostaphylos uva ursi; Bearberry • Constituent: arbutin • Use: astringent and diuretic • Cosmetics: whitening property is studied

[Anthraquinone] Senna

• Dried leaflet of Cassia acutifolia - Alexandria senna (broken leaflets) • Cassia angustifolia - Tinnevelly senna (full leaflets used for preparation) Cute si Alex; Angas si Tin • Cultivated in wet lands resembling rice paddies • Constituents: Sennosides A, B, C, and D • Senokot, Senna Lax

[Saponin] Glycyrhizza/Licorice

• Dried roots of Glycrrhiza glabra • Increases the foaminess of beer • Masks bitter of Quinine (also Yerba santa) due to its sweet taste • Constituents: glycrhhizin, glycrrhizic acid • Males should not eat more than 100 g glycrrhiza/day risk of male sterility • Steroidal: used in treatment of Addison's disease o CI in patients with CHF (inc. Na and H2O retention)

Saponin Glycosides

• Foam upon shaking; Froth Test (stand for 1-2 minutes) • Bitter, acrid taste • Sternutatory (irritate the mucus membrane; stimulate sneeze) • Destroys RBCs of cold blooded animals Fish poisons • Aglycone: sapogenin; Toxic aglycone: sapotoxin • Steroidal in nature

[Lactone] Coumarin

• From Dipteryx odorata - Tonka beans • Aromatic burning taste • Constituents: dicoumarol, bishydroxycoumarin anticoagulant; Warfarin (Coumadin) • Dicoumarin: first oral anticoagulant - dicumarol

[Anthraquinone] Chrysarobin

• From Goa powder, Andira araroba • Only anthraquinone glycoside that is NOT used as cathartic because it is very irritating • Used as keratolytic (treat skin abnormalities) • Hot benzene is used to extract this substance

[Lactone] Cantharides

• From the dried insect Cantharis vesicatoria • Spanish/Russia/Blistering Fly • Mature insect: brilliant/shiny green with metallic luster o Wings are treated with CH3Cl3/dilute acid fumes or soaked in acetic acid • Constituent: Cantharidin • Uses: Irritant, vesicant, and rubefacient; for aphrodisiac • Causes priapism - prolonged and painful erection of the male organ (6-24 hrs)l dilation is due to the production of nitrous oxide (N2O) o metabolite of cantharides

[Flavonol] Gingko

• Gingko biloba • Constituents: ginkolides, bilobides (enough dilation of blood vessels in brain) • Use: memory enhancement • Glutaphos first memory enhancer in the PH; peptides based

[Cardenolides] Black Hellebore

• Helleborus niger; Christmas Rose • Hellebrin

Glycosides

• Heteroglycans; "sugar ethers" • N-, S-, C-, O-, alpha or beta; beta forms occur in plants • Regulatory, protective, and sanitary compunds • Glycone - sugar portion; base • Aglycone - "genin" dictates classification of glycoside; steroidal structure (cyclopentanoperhydrophenanthrene) • R - defines the class; differentiates • Cardioactive group, aldehyde group, anthraquinone group, alcohol groupm saponin group, cyanophore group, lactone group, isothiocyanate group, phenol group, flavonol group, tannins

Pectin

• Intercellular cementing material • Partially methoxylated galacturonic acid • From the extract of the inner portion of rind of citrus fruits and apple pomace; Rutaceae • Pectin Sources: o Citrus grandis - pomelo, suha, lukban o Citrus paradisi - grapefruit o Citrus aurantium - orange, kahel o Citrus sinensis - ponkan o Citrus nobilis - dalanghita o Citrus microcarpa - calamansi o Citrus limon - lemon o Pyrus malus - apple • Protopectin - unripe • Pectin - just ripe o Mango: smells sweet o Avocado: hearing seeds separate o Banana: cover with freckles (TNF) • Pectinic acid - overripe • Polymagma (Attapulgite) o Antidiarrheal agent • Kaopectate: Kaolin + Pectin o Antidiarrheal preparation

Gums and Mucilages

• Natural plant hydrocolloids that may be classified as anionic or non-ionic polysaccharides • Produced by plants as a protective after injury (counterpart = platelets) • Upon hydrolysis, they yield arabinose, galactose, glucose, mannose, xylose and other uronic acid derivatives • Pb acetate and alcohol - soluble • Gum and water - dissolution • Mucilages and water - paste • Pectin and water - gel

[Saponin] Ginseng

• Panax ginseng (Asian, medicinal); Panax quinquefolius (American) • Aphrodisiac (sex stimulant) and an adaptogen (to cope with up stress - mooooooood) • Constituents: Panaxosides, ginsenosides, chikutsusaponins • Drug interaction with Azathioprine (Immunosuppressant) Hindi masusupress ang feelings kung hanggang ngayon umaAZA na THIOPRINE

[Cyanophore] Bitter Almonds

• Prunus amygdalus

[Cyanophore] Apricots

• Prunus armeniaca • Amygdalin - source of Laetrile or Vit B17, a controversial treatment for sickle cell anemia • Muntingia calabura: Aratiles/Jamaican cherry/Strawberry Tree - studied for antioxidant property

[Cyanophore] Wild Cherry

• Prunus serotinina • Uses: flavored vehicle, expectorant, and sedative

[Anthraquinone] Frangula

• Rhamnus frangula; Buckthorn bark • Present in Movicol (Cathartic laxative) - Karaya (laxative) + Frangula (cathartic)

[Anthraquinone] Cascara sagrada

• Rhamnus purshianus; Sacred bark • Constituents o Cascarosides A and B Optical isomers of barbaloin o Cascaroides C and D Optical isomers of chrysaloin • Lane's Pill - easanthol, purified mix of anthranol glycosides

[Anthraquinone] Rhubarb

• Rheum officinale, Rheum palmatum - Rheum or Chinese Rhubarb o Use: medicinal • Rheum emodi, Rheum webbianum - Indian Rhubarb or Himalayan Rhubarb o Use: ornamental

[Phenol] Poison Ivy and Poison Oak

• Rhus radicans - Poison ivy (Toxicodendronis radians) • Rhus toxidendron - Poison oak (T. toxicaria) • Urushiol: causes delayed contact dermatitis (Type 4, T-cell mediated)

[Alcohol] Salix and Populus

• Salix purpurea, Salix fragilis - Weeping Willow/Willow Tree (Barks) • Populus candicans, Populus tacahamacca - Willow buds • Aglycone: saligenin • Salicin: anti-inflammatory, antirheumatic

[Flavonol] Milk Thistle

• Silybium morianum • Constituents: silbinin, silymarin • Use: hepatoprotective

[Marine Gums] Danish Agar

• Source: Furcellaria fastigiata • Constituent: Kappa

[Marine Gums] Agar/Japanese Isinglass

• Source: algae (Geldium cartilageneum, Gracilaria confervoides) • Constituent: agarose, agaropectin (highly sulfated compounds)

[Marine Gums] Algin

• Source: brown seaweeds (Macrocystis pyrifera) • Constituent: mannuronic acid (pharmaceutic necessity)

[Seed Gums] Guar Gum/Guaran

• Source: endosperm of Cyamopsis tetragonobulus

[Seed Gums] Locust Bean Gum/Carob Pulp/St. John's Bread

• Source: endosperm of the seed of Ceratonia siliqua • St. John's Bread: substitute for chocolate o St. John's Wort: alternative medicine; hypericin (anti-anxiety)

[Microbial Gum] Xanthan Gum

• Source: metabolite in the action of Xanthomonas campestris on carbohydrates has a pseudoplastic activity that enables toothpastes and ointments to spread readily

[Marine Gums] Carageenan/Irish Moss

• Source: red algae (Chondrus crispus, Gigartina mamillosa) • Constituents o Kappa: gelling component; stable helix; straight chain o Iota: gelling component; stable helix; straight chain o Lambda; nongelling component; unstable helix; no straight chain

[Seed Gums] Cydonium/Quince Seed

• Source: ripe seed of Cydonia vulgaris • Use: thixotropic agent for lotion

[Seed Gums] Psyllium/Plantago

• Source: seed coat of Plantago psyllium (Spanish), Plantago ovate (Blonde) • C-Lium - bulk laxative (7.5 g)

[Cardenolides] Strophantus

• Strophantus kombe, Strophantus hispidus, Acokantheria shimperi • K-strophantin (beneficial), G-strophantin (oubain - toxic)

[Flavonol]Hesperitin, Diosmin, and Naringin

• Treatment of symptoms of common colds • Naringin (Echinaceae) - prophylactic agent for colds

Cardiac Glycosides

• Unsaturated steroidal aglycone tests o Leibermann-Burchard test Most sensitive (blue green) o Salkowski test (red) o Keller Killiani test 2-deoxy sugar aglycone test Digitalis (blue green) Squill (red) o Cardenolides vs. Bufadienolides Cardenolides - active cardiac glycosides; common in nature Bufadienolides - inactive; source is frog species

[Bufadienolides] Squill

• Urginea maritima - White squill, Red squill • Urginea indica - Indian squill • Scillarenin (red)

[Flavonol] Rutin and Hesperidin

• Vitamin P/Permeability Factors; used in the treatment of capillary bleeding secondary to capillary fragility

[Flavonol] . Rutin and Quercetin

• Yellow pigments