Cog 2nd

• Borntrager's test


  • Involves extraction using organic solvent followed by addition of base
  • Positive test gives a red color on the lower alkaline layer
  • (-) indicates a very stable form of anthraquinone esp. the reduced types of anthranol (the sample must be hydrolyzed and oxidized first)
• Sacred bark (Cascara sagrada)


  • Synonyms: Cascara sagrada
  • Scientific Name: Rhamnus purshianus
  • Family: Rhamnaceae
  • Constituents: Barbaloin (Cascarosides A and B), chrysaloin (Cascarosides C and D) Uses:
  • Cathartic for habitual constipation restores natural tone of the colon)
  • Casanthranol is purified mixture of the anthranol glycosides, and is combined with surfactants or hydrocolloids
  • Should be aged for at least 1 year prior to use
  • To reduce its bitter taste, cure with MgO or alkaline earths
• Aloe


  • Synonyms: Sabila
  • Scientific Name: Dried latex leaves of Aloe barbadensis (Curacao aloe) Aloe ferox/ Aloe spicata (Cape aloe) Aloe perryi (Zanzibar/Socotrine aloe)
  • Family: Liliaceae
  • Constituents: Barbaloin, emodin, aloe emodin
  • Use: Cathartic, used for compound benzoin tincture
  • Aloe vera Gel: treatment of burns, abrasions, skin irritations, purgative, alopecia
  • Stabilized aloe is used for lotion or yogurt production
• Rhubarb


  • Scientific Name: Rheum officinale, R. palmatum, R. raponticum
  • Family: Polygonaceae
  • Constituents: Rhein anthrones (at 2.2%), glucorhein, glucogallic acid
  • Rhanponticin - adulterant from rhapontic rhubarb – blue fluorescence
  • Types: • High-grade (Chinghai, Shensi-type) • Medium grade (Canton-type) • Third grade
  • Use: For jaundice, kidney stones
• Sennas/ Slimming tea


  • Source: Dried leaflets of • Cassia angustifolia (Tinnevelly senna) • Cassia acutifolia (Alexandria senna)
  • Family: Fabaceae
  • Determination:
  • • Alexandria: pink w/ MgOAc in daylight, green-orange in filtered uv
  • • Tinnevelly: orange w/MgOAc in daylight, yellow-green in filtered uv
• Goa powder


  Scientific Name: Andira araroba

  Family: Fabaceae Constituents: Chrysarobin (anthranol-type)

  
  

  Use: Keratolytic agent, for psoriasis, trichophytosis, eczema Notes: • Chrysarobin is extracted by hot benzene

  • Chrysarobin is the only anthraquinone glycoside too irritating for oral use

  • Anthralin has replaced the use of chrysarobin
• St. John's Wort (SJW)


  • Scientific Name: Hypericum perforatum
  • Family: Hypericaceae Constituents: Hyperforin, hypericin
  • • Hyperforin is a prenylated ring –acts as reuptake inhibitor -> increase neurotransmitters
  • • Was once dubbed as “Nature’s Prozac”
  • • [What is Prozac?] • Claims to treat depression
  • • SJW is a well-known enzyme inducer
• Phenol glycosides


  • Aglycone is a phenolic group
  • Detected by Millon's Test
  • (+) peach/salmon/pink-colored Hg complex of nitrophenyl derivative
  • NOTE: Most tannins and flavonoids are also phenol glycosides by technicality (their structures are intrinsically phenolic too)
  • Being aromatic, it is expected they come from the Shikimic acid pathway (chorismate branch)

  
• Bearberry


  • Synonyms: Rockberry
  • Scientific Name: Arctostaphylos uva-ursi
  • Family: Ericaceae
  • Constituents: Arbutin, ericolin •
  • Hydrolysis of arbutin yields hydroquinone
  • Use: Diuretic, astringent and antiseptic •
  • Arbutin has some tyrosinase-inhibiting effect, Skin-lightening potential
• Willow


  • Scientific Name: Salix purpurea and S. fragilis
  • Family: Salicaceae
  • Constituents: Salicin (also found in poplar)
  • Salicin is hydrolyzed to yield salicylalcohol by emulsin
  • Salicylalcohol can be oxidized in the lab to yield salicylic acid
  • Antirheumatic, anti-inflammatory
• Poplar


  • Scientific Name: Populus tremuloides
  • Family: Salicaceae
  • Constituents: Populin (benzoylsalicin)
  • Use: Quinine substitute
  • Expectorant, antipyretic, analgesic
  • Common ingredient of herbal cough mixtures
• Qualitative tests for aldehydes


  • Fehling's Test - Cu2SO4, brick red ppt
  • Nessler's Test - alkaline K2HgI4, gray ppt of Hg
  • Tollen's Test - ammioniacal AgNO3, silver mirror
  • Schiff's Test - Complexation reaction, Magenta-red color restored if there’s a aldehyde
• Vanilla


  • Unripe fruit of Vanilla planifolia (Mexican/ Bourbon vanilla) or Vanilla tahitensis (Tahitian) [Orchidaceae]
  • • Contains glucovanillin (avenein) •
  • Vanilla must undergo sweating to release odor (hydrolysis of glucovanillin to yield vanillin) •
  • Vanillin can be artificially made using eugenol (clove) or more commonly today, guiacol (Pinaceae) •
  • Vastly used in food, perfumery, and cosmetics •
  • Vanilla is the SECOND most expensive spice in the world! •
  • Mexican/Vera cruz – best variety • Bourbon – coumarinlike odor • Tahiti – reddish brown, unpleasant odor
• Steps to convert prephenate to coumaric acid, and finally to vanillin

  Several steps take place

  
• Lactone glycosides


  • Aglycone contains a lactone (cyclic ester) portion
  • Involves derivatives of coumarin, phenylpropanoids that originate from cinnamic and coumaric acids

  
• Lactone glycosides: Qualitative tests


  • Kedde's Test - for unsaturated lactones, Reagent: 3,5-dinitrobenzoic acid in NaOH, (+) blue-violet/amethyst color
  • Chromatography - for saturated lactones, Folin Ciocalteau - for catechol & hydroquinone type, (+) blue spots
  • Vanillin-HCl - for resorcinol & phloroglucinol type, (+) pink spots
  • Gibb's reagent, (+) various colors of different phenols (2,6-dichloroquinone-4-chloroimide)

  
• Coumarin (compound)


  • Coumarin is hydroxycinnamic acid lactone, usually used as flavoring agents (especially of tonka)
  • Tonka is used in tobacco manufacture and in perfumery (replaced by synthetic coumarin)
  • Dicumarol, or dihydroxylated coumarin, obtained from Melilotus officinalis and used as an anticoagulant
• Sources of coumarin


  • Tonka beans (Dipteryx odorata)
  • Sweet clover (Melilotus albus)
  • Red clover (Trifolium pretense)
  • Sweet vernal grass (Anthoxanthum odoratum)
  • Sweet-scented bedstraw (Galium trifolium)
• Melilot (Melilotus officinalis, Fabaceae)


  • Yellow papilionaceous flower
  • Improperly cured leaves and flowering tops
  • Melilotoside, melilotic acid, caffeic acids
• Spanish fly


  • Synonyms: Blistering flies/ Cantharides
  • Scientific Name: Cantharis vesicatoria (Other name: Lytta vesicatoria)
  • Constituents: Cantharidin
  • Rubefacient, vesicant (for warts), urinary irritant resulting to priapism and thus usable as aphrodisiac
  • In excess, can cause renal failure and fatality
• Grapefruit juice


  • Scientific Name: Citrus paradisi
  • Family: Rutaceae
  • Constituents: Bergamottin, bergapten
  • Inhibit CYP enzymes (especially CYP3A4)
• Flavonoid glycosides


  • "C6-C3-C6 " compounds arising from the phenylpropanoid (prephenate) branch of the shikimate pathway
  • Most have the gamma-benzopyrone as nucleus
  • Exception: benzofuranone in aurones
  • Classifications: Chalcone, Aurone, Flavanone, Flavone, Flavonol (ex. quercetin), Flavan-3-ol (ex. catechin), Leucoanthocyanidin (flavan-3,4-diols), Isoflavone, Anthocyanidin

  
• Flavonoid glycosides


  • Flavonoids or bioflavonoids from Citrus fruits and Soya
  • Largest group of naturally occurring phenols
  • "Flava" – yellow (flavonoids dissolve in alkali, giving yellow solution; in acid, it becomes colorless)
  • Chalcones ("copper") are the yellow pigment in plant flowers
  • Anthocyanidins - aglycones
  • "Anthocyanins" – proper term for the glycosides
  • Sap pigments (color of plant is determined by pH of the sap)
  • Ppt in aqueous solution as Pb salts or picrates
  • Add 20% HC = hydrolyzes , crystallizes
  • Bilberry (Vaccinium myrtillus, Ericaceae) – source of anthocyanins

  
• Significant flavonoids


  • 1) Hesperitin, diosmin and naringen - Anti-H. pylori
  • 2) Isoflavonoids – richest in soy, Along with some coumestans and lignans, are called "phytoestrogens"
  • 3) Quercetin (glycoside: quercitrin) - Commonly used standard for total flavonoid content
• Vitamin P


  • "Permeability factors"
  • Originally assumed to be "citrin" in paprika/ lemon peel
  • Actually a combination of rutin + hesperidin
  • Rutin – yields quercetin, rhamnose, glucose
  • Hesperidin – yields hesperitin, rhamnose, glucose
  • For treatment of capillary bleeding and increased capillary fragility
  • For HTN, radiation injuries

  
• Flavonoid glycosides: Qualitative tests


  • Wilstatter "cyanidin" test – uses HCl, (+) orange to red to crimson & magenta occasionally green/blue
  • Bate-Smith & Metcalf test - uses HCl, (+) immediate red = presence of chalcones & aurones, If no color is produced, boil sample, Intense red color/ violet = leucoanthocyanins
  • Test for anthocyanins: extract with 1% HCl then boil, (+) at boiling point, an orange red to blue red coloration

  
• Milk thistle


  • Synonyms: Carduus marianus
  • Scientific Name: Silybium marianum
  • Family: Asteraceae
  • Silbinin (a mix of silybin A and silybin B) – flavolignans that have hepatoprotective effect
• Tea catechins (Camellia sinensis)


  • 30-42% of dry weight of tea are flavonoids
  • Controls lipid levels, prevents atherosclerosis and coronary disease
  • Epigallocatechin gallate (EGCG) - potential anticancer effects
• Cranberry


  • Contains procyanidins and other flavonoids and polyphenols
  • Prevents adhesion of UTI-causing microbes such as E. coli and H. pylori in GIT and teeth
  • Potential use in periodontal diseases
• Saponins


  • Aglycones are called the sapogenins (if toxic – "sapotoxin")
  • Neutral/ Steroidal – tetracyclic; present in monocots
  • Acidic/ Triterpenoid – pentacyclic; present in dicots

  
• Saponin glycosides


  • 3 Main Properties: Foams/lathers in aqueous solution, Hemolyzes red blood cells, Lowers surface tension of solution
  • Forms complex with metal solutions like those of barium and lead (complex has beige to brown color)
  • One of the most toxic plant principles
  • Irritating to the mucus membranes
  • Toxic to cold-blooded animals (fish poisons)
• Saponin glycosides: Qualitative tests

  • Froth test – foam / lather formation, Honeycomb froth persisting for 10 minutes above 2 cm is positive for saponins, If froth is unstable add aqueous Na2CO3 to neutralize the free acids
  • Liebermann–Burchard test - For steroidal saponins in monocots - (+) blue or green, For triterpenoidal saponins in dicots - (+) red, pink or violet, Pale yellow if saturated sterol or triterpenoid is present

  
• Yam


  • Scientific Name: Dioscorea alata, D. spiculiflora, D. floribunda (Mexican Yam)
  • Family: Dioscoreaceae
  • Constituents: Botogenin, diosgenin (steroidal saponins)
  • Uses: Diosgenin is used for production of corticosteroids (specifically sex hormones), D. floribunda is the best source of steroids
• Sarsaparilla


  • Scientific Name: Smilax aristolochiaefolia (Mexican sarsaparilla), Smilax regellii (Honduras sarsaparilla)
  • Family: Liliaceae
  • Constituents: Smilagenin, sarsasapogenin, parillin (steroidal saponins)
  • Claims of use for syphilis, rheumatism, skin diseases, psoriasis, eczema, Suggested to come from sarsaparilla's steroid content
• Ginseng


  • Scientific Name: Panax ginseng (Asian ginseng), Panax quinquefolius (American ginseng)
  • Family: Araliaceae
  • Constituents: Ginsenosides, panaxosides, chikusetsusaponins (all steroidal saponins)
  • Aphrodisiac and an adaptogen (resistance to stress)
  • Tx of anemia, diabetes, gastritis, sexual impotence
  • "Ginseng of Europe": Chamomile - leaflets of Matricaria chamomila
• Quillaja/ Soapbark


  • Dried inner bark of Quillaja Saponaria (Rosaceae)
  • Contains "quillaja saponin" (10%)
  • Detergent, emulsifier
• Gugo (Box bean, St. Thomas bean)


  • Entada phaseoloides (Fabaceae)
  • Used during historical times
• Cardiac Glycosides


  • Have specific action on the cardiac tissues; they increase force of systolic contraction
  • Inhibit Na+/K+ ATPase, thereby increasing the Ca+2 inside the heart muscles (positive inotropic effect)
• Liebermann Burchard Test


  • For unsaturated sterol
  • Reagent: Conc. H2SO4 + acetic anhydride
  • (+) green/ blue (pale yellow if saturated sterol)

  
• Foxglove


  • Scientific Name: Digitalis purpurea, Digitalis lanata (Grecian)
  • Family: Plantaginaceae
  • Constituents: Purpurea: digitoxin & gitoxin (two most active), gitaloxin
  • Lanata: digoxin and lanatosides
  • Use: For heart failure and arrhythmias
  • Digoxin: more polar, shorter half-life (30 to 40 hours), excreted via kidneys (Lanoxin®)
  • Digitoxin: very lipophilic, longer half-life (168 to 192 hours)