IPS Pharmacognosy Plant Chemistry | JZDavid

INTRODUCTION
Pharmacognosy (Definition) Crude Drugs
• Biological, biochemical and economic features • Undergone the process of collection and drying
of biological origin. o Menstruum – solvent or liquid mixture
• Deals with medicinal products in their crude or which dissolves the chief constituents
unprepared form o Marc – undissolved portion of the drug that
• This knowledge is based on the incantations of remains after extraction process
voodoo tribes that is passed from one o Indigenous Plants – plants in native region
generation to another. o Naturalized – they grow in a foreign land

Focuses of Pharmacognosy Preparation of Crude Drugs

• Identification of plants and animals 1. Collection
• Chemistry • Ensuring the true natural source of the drug
• Evaluation, preservation, use and application of • Improper collection results to partial or
crude drugs complete substitution
• Toxicology • Collection time – time wherein the drug in a
• History, distribution, collection and selection part of the plant is high
• Preparation of commerce
2. Harvesting
Brief History • Gather the samples on a specific and proper
• Babylonians period or season
o Clay models Flowers – dawn
o Medicinal effects of plants Bark – between spring and summer
• Indians Root crops – when upper grounds are
o Ayurveda – traditional medicines; “science withered
of life”; mother of healing arts • Manual labor or mechanical device
o Charaka – text on internal medicine Manual – berries, coffee, digitalis
o Sushruta – book of symptoms (184 Mechanical – Apples and oranges
chapters)
• Egyptians 3. Drying
o Practice embalming • Removes the moisture to prevent fungal
o Papyrus Ebers and bacterial growth
• Greeks • Fixes the active ingredient and stops the
o Dioscorides – De Materia Medica (600 action of enzymes
plants) • Grinding and milling
▪ Belladonna, Ergot, Aloe, Colchicum • Converts drug into a more convenient form
• Claudius Galen • Involves (1) control of temperature and (2)
o Galenical Pharmacy – methods/process of regulation of airflow
preparing formula containing plant and
animal drugs 4. Curing
o Father of Pharmaceutical Compounding • Special drying process
• German • Enhances the property of active ingredient
o CA Seydler • e.g. Cascara sagrada (anthraquinone
▪ Introduced the term “pharmacognosy”: glycoside)
pharmakon *drug) + gnosis o Reduced glycoside (irritating); - dried
(knowledge) in Analecta and cured with MgO for 1 year →
Pharmacognostica Oxidized glycoside (non-irritating)
▪ Lehrbuch de Materia Medica • e.g. Vanilla planifolia
o Fluckinger o Pods turn from green to red due to its
▪ Scientific disciplines curing process known as sweating
o Friedrich Serturner – Morphine
• French 5. Garbling
o Pelletier and Caventou – Quinine • Final step
• Carl Linnaeus - Father of Taxonomy • Removing of extraneous materials (dirt, soil,
o (DKPCOFGS) plant parts, insects, other plants)

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IPS Pharmacognosy Plant Chemistry | JZDavid
6. Packaging, Storage and Preservation BIOGENESIS/DRUG BIOSYNTHESIS
• Protection and marketability of crude drugs • Process of producing secondary metabolites
• To avoid insect attacks: used as drugs
o Simplest method: expose the drug to • Active constituents – secondary metabolites
65°C (alkaloids, volatile oils)
o Fumigation with methyl bromide
o Add a drop of chloroform (CHCl3) and Biogenesis is influenced by:
carbon tetrachloride (CCl4) 1. Ontogeny or Stage of Development
Ex. Cannabis sativa
Classification of Drugs Cannabidiol – plant is still young
1. Morphologic – according to the part of the Cannabinol – plant matures
plant or animal used (roots, leases, organs, or 1-9-Tetrahydrocannabinol (THC)
glands)
2. Taxonomic – natural relation of phylogeny 2. Hereditary or Genetic
3. Pharmacologic or Therapeutic – based on Ex. Peppermint vs. Japanese peppermint
their effect on the body Japanese peppermint has 50% more
4. Chemical – Chemical Class of constituent; menthol content
preferred method
3. Environment
Evaluation of Drugs Ex. Vinca rosea (Periwinkle/Chichirika)
1. Organoleptic Contents vinca alkaloids
• Organs or senses (odor, taste, sound of Domesticated (purplish pink) vs.
fracture, feel of drug to touch) wild (blue-violet)
• Macroscopic appearance of drugs
Adulteration – debasement of an article
2. Microscopic • Inferiority – any substandard drug/article
• Observation under microscope regardless of cause
• Identity and purity of drug • Spoilage – impaired by action of fungi/bacteria
• Can detect adulterants • Deterioration – destruction of active
constituents due to aging
3. Pharmacologic • Admixture – unintentional addition of article
• Bioassays: uses living animals or excised to another
organs to evaluate the effect of drugs: • Sophistication – true adulteration; intentional
Pigeons – Digoxin • Substitution – worst kind of adulteration; total
Cats – Atropine (dilation of eyes) replacement
Chicken – Oxytocin (dilation of blood
vessel, uterine contraction)
Dog – PTH (Ca2+)

4. Chemical
• Assays of active constituent using chemicals
• Titration – best method of determining Old Name New Name
official potency Labiatae Lamiaceae
Compositae Asteraceae
5. Physical Umberlliferae Apiaceae
• Uses of physical constants Leguminosae Fabaceae
• e.g. Specific rotation of camphor Cruciferae Brassicaceae
o Synthetic camphor is racemic Graminae Poaceae
o Natural camphor is dextrorotatory Palmae Areacaceae

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IPS Pharmacognosy Plant Chemistry | JZDavid
CARBOHYDRATES

• Carbohydrates are the most abundant organic Aldose

primary metabolites and on plants, are the first • Hydroxyacetaldehyde – does not occur free in
product of their photosynthesis. nature
• These are polyhydroxyketones or • Glyceraldehyde – intermediate product in
polyhydroxyaldehydes composed of carbon, glycolysis
hydrogen and oxygen atoms, with a general • Erythrose – not found free in nature important
formula of (CH2O)n. intermediate in the PPP. It is also used in
• Sugar moieties are linked with each other phenylalanine, tyrosine and tryptophan
through a glycosidic linkage, which is biosynthesis, and it plays a role in vitamin B6
hydrolyzed to breakdown complex sugars into metabolism
simpler, utilizable form of energy. • Ribose – product of gum hydrolysis; the sugar
present in the RNA
Functions: • Arabinose – inhibits sucrase, which breaks down
• These group of compounds are necessary for sucrose into glucose and fructose in the small
they are the most significant source of intestine
energy for living organisms, can also be in a • Xylose – wood sugar; simplest sugar found in
stored form of energy, an important cellular plants; found as xylan polymer (hydrolysis of
and structural component in organisms. xylan in corn cobs and straw with dilute acid);
diagnostic aid for intestinal absorption
Classification • Glucose – dextrose/grape sugar/physiologic
A. Simple sugars sugar/blood sugar/corn sugar; β-D-glucose (the
1. Monosaccharides most abundant type of glucose in nature -grape)
2. Disaccharides • Linear configuration: Fischer projection
3. Oligosaccharides o L-glucose: less active
B. Polysaccharides o D-glucose: more active
1. Homoglycans • Use: Nutrient (Dextrose via PO, SC, IV, enema)
1. Starch o Parenteral – purified (D5W, D5NSS, D5LR)
2. Inulin • Related compounds:
3. Cellulose o Liquid glucose – thick, syrupy liquid from
2. Heteroglycans incomplete hydrolysis of starch: contains
1. Gums and Mucilages mainly dextrose but with maltose, dextrin,
2. Glycosides water
o Dextrose excipient – crystalline
1. Monosaccharides sweetening agent
• Simplest carbohydrate o Dextrates - purified mixture of saccharides
• Cannot be hydrolyzed to simpler sugars developed from the controlled enzymatic
• 8-9 carbon atoms hydrolysis of starch; contains 93-99%
• Classified based on functional group: dextrose
o Aldose (Aldehyde) o Calcium gluconate – electrolyte
o Ketose (Ketone) replensiher
o Ferrous gluconate – hematinic; given for
# of C Name Aldose (-ose) Ketose (-ulose) Iron Deficiency Anemia (IDA)
2 Diose Hydroxyacetaldehyde -
3 Triose Glyceraldehyde Dihydroxyacetone • Galactose
4 Tetrose Erythrose Erythrulose o C4 epimer of glucose
5 Pentose Ribose, Arabinose, Ribulose, Xylulose
Xylose
o Found in milk (lactose) and in neuronic
6 Hexose Glucose, Galactose, Fructose fibers (galactosides)
Mannose o Gaucher’s Disease – inability to breakdown
7 Heptose - Sedoheptulose glucose
8 Octose - D-manno-octulose
9 Nonose - Neuraminic acid
(Sialic acid) • Mannose – used for preventing urinary tract
infections and treating carbohydrate-deficient
glycoprotein syndrome

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Ketose o Invert sugar – equimolar amount of glucose
• Dihydroxyacetone – intermediate product in and fructose (darken)
glycolysis o Only disaccharide that occurs in free state
• Erythrulose – used in self-tanning cosmetics o Uses:
with DHA ▪ Pharmaceutical necessity in making syrup
• Ribulose – sugar important in formation of ▪ At 85% w/w or 65% w/w –
bioactive substance in the pentose phosphate bacteriostatic, self-preserving
pathway (PPP) ▪ Preservative
• Fructose ▪ Retard oxidation
o Levulose, “Fruit sugar” ▪ Coating agent
o Sweetest monosaccharide; bitter after-taste ▪ Demulcent
o Natural source – fruits and honey ▪ Nutrient
o Product of inversion of aqueous solution of ▪ Sweetening agent
sucrose and hydrolysis of inulin
o Reducing sugar • Maltose
▪ Barfoed’s Test o glucose + glucose (α-1,4)
▪ Benedict’s Test o malt sugar
▪ Seliwanoff’s Test o major degradation product of starch
o Uses: hydrolysis during germination of barley
▪ Nutrient for DM patient – beneficial in o Found in beer and cereals
acidosis
▪ Nutrient in infant formulas • Lactose
o High fructose sweeteners – from o glucose + galactose (β-1,4)
isomerization of glucose by glucose o milk sugar
isomerase Streptomyces sp. o Main source - cow’s milk (Bos taurus)
• Sedoheptulose – vital in the non-oxidative o Uses:
branch of the PPP ▪ Tablet diluent, less sweet than sucrose
• Neuraminic acid – sialic acid; substrate for ▪ Infant feeding, important to establish
neuraminidase enzyme intestinal flora, Lactobacillus sp.

2. Disaccharides Milk Products

• Composed of 2 monosaccharides linked by • Butter – fat globules unite by churning
a glycosidic bond • Buttermilk – liquid left after fat globules unite
• Skimmed milk – milk after separation of cream
• Formed by dehydration synthesis • Coagulum – formed when skimmed milk is
o Sucrose treated with renin
o Maltose • Cheese – treated coagulum
o Lactose • Whey – liquid separated from coagulum
o Lactulose • Condensed milk – formed by partial
o Isomaltose evaporation of milk in a vacuum with
o Trehalose consequent sterilization in hermetically-sealed
container by autoclaving
• Malted milk – evaporation of milk with malt
• Sucrose
extract
o glucose + fructose (α-1,2)
o “table sugar” • Lactulose
o a non-reducing sugar (no free carbonyl o fructose + galactose (β-1,4)
group) o Uses:
o Sources: ▪ Laxative (Duphalac®) for MI patients –
▪ Beet (Beta vulgaris) not absorbed, metabolized by colonic
▪ Sugarcane (Saccharum officinarum) – boil flora to lactic and acetic acid
with dilute acit to precipitate albumin and ▪ Decreases blood ammonia concentration
protein = pure sucrose; add H2SO4 to in portal-systemic encephalopathy
decolorize
▪ Sugar maple (Acer saccharum) • Trehalose
▪ Molasses – residual dark-colored syrup o Mycose- Found in brown seaweed, widely
after complete crystallization of sucrose, distributed in fungi
used in food preparation and o Glucose + glucose; (α-1,1)
manufacture of ethanol

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3. Oligosaccharides ▪ Uses:
• 3-10 sugar units • Dusting powder
o Maltotriose • Diluent
o Dextrins • Binder (as paste)
o Gentianose = gluc + gluc + fruc • Disintegrant in tablets
o Raffinose = gluc + galac + fruc • Antidote for iodine poisoning
o Stachyose = gluc + galac + galac + fruc ▪ Starch preparations:
• Pre-gelatinized starch – starch that is
• Maltotriose chemically or mechanically processed
o 3 glucose units to rupture all or part of the grabules;
o Intermediate product of starch hydrolysis tablet binder
• Sodium starch glycolate –
• Dextrins disintegrant agent
o Limiting dextrins • Hetastarch - Hydroxyethyl starch;
▪ Products of partial hydrolysis of starch plasma expander (used when blood
(amylose, glucoside) volume is low, i.e., shock); >90%
▪ Browning of bread amylopectin
o α-glucosidase inhibitors
▪ inhibit post-prandial increase of glucose o Glycogen
▪ Acarbose, Miglitol (AE: Flatulence, ▪ Storage polysaccharide in animals
hepatotoxicity) ▪ More branched than starch (every 10
units)
4. Polysaccharides ▪ Red color with iodine test
• a.k.a. glycans ▪ Stored in the liver (8-12hr supply0 and
• Complex, high MW polymers of skeletal muscles
monosaccharides linked by glycosidic ▪ Von Gierke disease
bonds • Type 1 Glycogen Storage Disease
o Homoglycans • Deficient in Glucose-6-phosphatase in
o Heteroglycans the liver (not found in muscles)
needed for the conversion of G6P to
• Homogylcans - one type of monosaccharide free glucose
o Starch • Most common type
▪ Temporary storage form of
photosynthetic products o Inulin
▪ Components: ▪ Polyfructan of fructofuranose (β-2,1
Amylose Amylopectin bonds)
Linearity Linear, helical Branched every 25-30 ▪ Chicory root (Cichorium intybus)
(α-1,4) units (α-1,4 and α-1,6) ▪ Abundant in members of family
Solubility Insoluble Soluble Asteraceae
in water ▪ Improves digestion
Size 250-300 units Above 600 units; Paste- ▪ Uses:
forming • Ingredient in culture media
Iodine Dark/Deep blue Blue-violet/Purple • Evaluation of renal function
Ratio 25% 75%
▪ Enzymes that breakdown starches: o Dextran
• α amylase – present in pancreatic juice ▪ Homopolyglycan (α-1,6 bond)
and saliva (human) ▪ Formed from sucrose by the action of
• β amylase – hydrolyses starch to transglycolase enzyme system (dextran
nearly pure maltose (fungi) sucrose in Leuconostoc mesenteroides)
▪ May contain gluten – tacky proteins which ▪ Used as a plasma expander
impede the free flow of starch • Iron dextran – parenteral (IV/IM);
▪ Official Sources (USP) hematinic when oral preparation
• Corn (Zea mays) cannot be tolerated
• Potato (Solanum tuberosum)
• Rice (Oryza sativa)
• Wheat (Triticum aestivum)
• Arrowroot (Maranta arundinacea)
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IPS Pharmacognosy Plant Chemistry | JZDavid
o Cellulose GUMS AND MUCILAGES
▪ Structural polysaccharide in plants • Gums are natural plant hydrocolloids that
▪ Most abundant organic matter maybe classified as anionic or non-ionic
▪ Homopolyglycan (β-1,4 bonds) polysaccharides or their salts.
a. Purified Cotton • Produced by salts as protection after injury
▪ From the hair of the seeds of • Upon hydrolysis, they yield arabinose,
Gossypium hirsutum galactose, glucose, mannose, xylose and other
▪ Surgical dressing uronic acid derivatives.
b. Soluble guncotton/Pyroxylin • Readily dissolve in water
▪ Formed by the action of nitric and
• Precipitated from solution by alcohol or Lead
sulfuric acid on cotton
acetate
▪ Other ingredients: 3% castor oil
(flexibility), 2% camphor
Linear hydrocolloids Branched hydrocolloids
(waterproof)
▪ Use: topical protectant Less soluble More soluble
c. Other soluble derivatives Less stable More stable
▪ Cellulose Acetate Phthalate Viscosity enhancers Gelating agents
(CAP) – coating agent
▪ Methylcellulose, Ethylcellulose General Uses:
– artificial tears • Ingredient in dental and other adhesives
• Visine – active component: • Bulk laxatives
Tetrahydrozoline • Pharmaceutic necessity: tablet binder,
emulsifiers, gelating agents, suspending agents,
• Eye-Mo: (Red Eyes Formula)
solubilizers and thickeners
Recalled due to
noncompliance to cGMP
requirements (2014) GUMS MUCILAGE PECTIN
o Chitin Readily-soluble Form slurry Gel-like
▪ Structural polysaccharide in animals in water masses with
▪ Exoskeleton: mollusks, crustaceans, water
arthropods and fungi Pathologic-injury Physiologic –
▪ Homoglycan of N-acetylglucosamine products natural products
(NAG)
1. Plant Exudates
• Heteroglycans –yield more than one type of Plant Exudate Botanical Source
monosaccharide units upon hydrolysis Karaya Sterculia urens
o Hyaluronic acid Acacia Acacia Senegal
▪ from “hyalos” which means glass Tragacanth Astralagus gummifer
▪ present in vitreous humor & synovial Indian sumac/Axlewood Anogeissus latifolia
fluid tree
o Chondroitin sulphate
▪ from “chondros” which means cartilage Karaya Gum
▪ present in cartilage, tendons and • a.k.a. Stercula Gum
ligaments • Constituent: O-galacturonic acid and O-
o Dermatan sulphate – present in skin glucoronic acid
o Keratan sulphate – present in nails • Galactomannan
o Heparan sulphate – an anticoagulant • Fetid odor
o Agarose – found in seaweeds • Bulk laxative
o Peptidoglycan – protein-containing
carbohydrates present in the cell wall of Acacia Gum
gram-negative bacteria; • a.k.a. Egyptian Gum, Gum Arabic
repeating/alternating units of N- • Contains arabin, a compex mixture of Ca, Mg, K
acetylmuramic acid and N-acetylglucosamine salts of Arabic acid
▪ This compound is rich in galacturonic acid • Stable below 60% alcohol
and is used as gelling agents, thickening • Contains 12-15% water
agents and stabilizers in food. • Low viscosity, stable at pH 2-10: used as
▪ Pectin can be classified into the following: emulsifying agent

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• Uses: Suspending agent at 33-35%, demulcent, 4. Microbial Gums
emollient, adhesive, binder • Xanthan Gum
Tragacanth Gum o High MW gum from the action of
• a.k.a. Gum Tragacanth Xanthomonas campestris on
• Contain bassorin/tragacanthic acid (water- carbohydrates
swellble) and tragacanthin (water-soluble) o Exhibits pseudoplastic flow: enables
• Most acid-resistant hydrocolloid toothpaste and ointments to hold shape
• Use: suspending agent at 5-6% and spread readily
Tragacanth Grades: • Dextran Gum
Vermiform Sorts Ribbon & flakes
From natural From natural From manmade 5. Plant Extractives
injuries injuries transverse • Pectin
incision of main o Intracellular cementing material
stem or o From dilute acids hydrolysis of fruit rind
branches o Contains partially methoxylated
Worm-like Ireegular tear- Ribbon-shaped galacturonic acid (responsible for
shaped or flaked swelling property)
Yellowish/brown Yellowish/brown Clearer, o Sources:
preferred grade • Pomelo (Citrus grandis)
• Orange (C. aurantium)
Indian Sumac • Dalanghita (C. nobilis)
• a.k.a. Ghatti gum • Ponkan (C. sinensis)
• Branched hydrocolloid, forms more viscous • Kalamansi (C. microcarpa)
dispersion in cold water than acacia • Grapefruit (C. parades)
• Use: substitute for acacia, bulk laxative • Lemon (C. limon)
o Forms:
2. Marine Gums • Protopectin: unripe fruits
Gums Source Constituents • Pectin: soluble, just ripe fruits by the
Agar Algae (Gellidium Agarose, action of protopectase, heat and dilute
cartilagineum; Agaropectin acid on protopectin
Gracilaria (rich in sulfate) • Pectinic acid: overripe fruits
confervoides) o Uses:
Algin Brown seaweeds/Giant • Protectant
kelp (Macrocystis • Suspending agent
pyrifera) • Kaopectate – antidiarrheal agent
Carrageenan Red algae (Chondrus Kappa and (comination of Kaolin and Pectin)
or Irish moss crispus; Gigartina Iota-gelling
mammillosa) component
Lambda – non
gelling
component
Danish agar Furcellaria fastigiata Kappa

3. Seed Gums
Gums Source
Plantago/Psyllium/ Seed coat of:
Plantain seed Plantago psyllium (Spanish
psyllium)
Plantago ovata (Blonde psyllium or
Indian psyllium)
Cydonium / Ripe seed of Cydonia vulgaris
Quince seed
Guar gum or Endosperm of Cyamopsis
Guaran tetragonoloba
Locust Bean Gum Endosperm of the seed of
/ Carob Pulp or St. Ceratonia siliqua
John’s Bread
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IPS Pharmacognosy Plant Chemistry | JZDavid
GLYCOSIDES

• Plant constituents, which produce sugars as b. Convallaria

product of hydrolysis o Lily of the valley (Convallaria majalis)
• Organic compounds in which a hemiacetal o Convallatoxin
linkage usually connects the anomeric carbon c. Apocynum
of a sugar (glycone) with an alcohol or phenolic o Black Indian hemp , Dogbane (Apocynum
hydroxyl of a second non-sugar molecule cannabinum)
(aglycone). o Cymarin
o Hemiacetal linkage – this type of linkage d. Adonis
rise to the so-called o-glycosides o Pheasant’s eye (Adonis vernalis)
(e.g.,salicin) the most common type of o Adonitoxin, Cymarin, K-strophanthin
glycosides found in plants. e. Cactus grandiflorus
1. May be O, N, C, S-linakges o Night-blooming cereus (Selenicereus
Glycone Aglycone grandifloras)
Sugar component Non-sugar component f. Black hellebore
“genin” o Christmas rose (Helleborus niger)
Base Basis of Classification (CPPP) o Hellebrin
Inactive Active g. Strophantus
o S. kombe, S. hispidus, Acokanthera
Glycosides: schimperi
Cardiac Flavonol o K-strophanthin - beneficial
Anthraquinone Alcohol o G-strophanthin (Ouabain) - Toxic
Saponins Aldehyde h. Squill
Cyanoophore Lactone o Mediterranean or White Squill (Urginea
Isothiocyanate Phenol maritima) should not contain red variety
o Indian squill (Urginea indica)
1. Cardiac Glycosides o Scillarenin – bufadienolide
• Unsaturated steroidal aglycone test o Use: Expectorant, emetic, cardiotonic,
o Liberman-Burchard test: most sensitive diuretic
(blue-green)
o Salkowski’s test (red) 2. Anthraquinone Glycosides
• 2 deoxy sugar glycone test • Commonly used as cathartic
o Keller-Killiani Test • Borntrager test – derivatives are colored
▪ Digitalis (blue-green) orange
▪ Squill (red) • Sources:
• Cardenolides vs Bufadienolides o Cascara sagrada
Cardenolides Bufadienolides o Frangula or Buckthorn bark
o Aloe
More common (Active) Rare (Bufo sp.); inactive
o Rhubarb/Rheum or Chinese Rhubarb
C-23 α and β unsaturated C-24 doubly unsaturated 6-
o Indian Rhubarb/Himalayan
5-membered lactone ring membered lactone ring
o Senna
a. Digitalis
a. Cascara Sagrada
D. purpurea D. lanata
o Sacred cascara or bark (Rhamnus
Other name Foxglove Grecian foxglove purshiana)
Constituents Digitoxin, gitoxin, Digoxin, o Cascarosides A, B: optical isomer of
gitaloxin deslanoside barbaloin
o Narrow therapeutic index o Cascarosides C, D: optical isomer of
o Digitoxin – very lipophilic, longer t ½ chrysaloin
(168-192 h) o Hydrolysis produces equal amounts of
o Digoxin – more polar, short t ½ (30-40h) rhamnose and glucose
excreted via kidneys o Lane’s pill: casanthrol – purified mixture
o Deslanoside – digitalization required of anthranol glycosides of Cascara
(rapid digitalis loading) sagrada
▪ Digitalis (blue-green)

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b. Frangula a. Glycyrrhiza/Licorice
o Buckthorn bark (R. frangula) o Sources: Dried rhizome and roots
o Present in Movicol ® - Karaya gum ▪ Spanish licorice (G. glabra)
(laxative) + Frangula (Cathartics) – used ▪ Russian licorice (G. glabra var.
for constipation gladulifera)
c. Aloe o Sweetener, flavorant – 50x sweeter than
o Sources: Dried latex juice of leaves sugar
▪ Curacao aloe (Aloe barbadensis, A. vera) o Used in the treatment of Addison’s
▪ Cape aloe (A. spicata, A. ferox) disease (Hypoaldosterinism) – CI: CHF
o Barbaloin – chief cathartic, aloe emodin and HTN, promotes water and Na+
(O-glycoside), aloin (C-glycoside) retention
o Uses: b. Dioscorea/Yam
▪ Cathartic o Mexican yam (D. floribunda) – best source
▪ Pharmaceutical for compound benzoin of steroids
tincture o Dioscorea spiculiflora – contains
▪ Management of burn wounds diosgenin which is a glucocorticoid
d. Rhubarb precursor
o Sources: Dried rhizome or root o Diosgenin – anti-inflammatory
▪ Chinese “medicinal” rhubarb (Rheum c. Ginseng
officinale, R. palmatum) – Therapeutic o Source:
▪ Indian or Himalayan rhubarb (R. ▪ American ginseng (Panax
emodi, R. webbianum) quinquefolius)
▪ Ornamental rhubarb (R. rhponatum) ▪ Asian ginseng (P. ginseng)
o Rhein anthrones – drastic cathartic o Constituents: Panaxosides, ginsenosides,
e. Senna and chikusetsusaponins
o Sources: Dried leaflets o Uses: Adaptogen, aphrodisiac
▪ Tinnevelly sienna (Cassia angustifolia)
- full leaves are used 4. Cyanophore Glycosides
▪ Alexandria senna (C. acutifolia) – • Cyanogenic – produces cyanide upon
broken leaves are used hydrolysis
▪ Constituents: Sennosides A and B • Found in Rosaceous plants
▪ Senokot ® • Amygdalin (H2O + amygdalase) →
f. Chrysarobin mandelonitrile glucose (H2O + prubase) →
o Mixture of neutral principles from Goa mandelonitrile + glucose → benzaldehyde +
powder (Andira araroba) HCN
o Not used as cathartic, but a keratolytic • Amygdalin and Prunase are collectively
(psoriasis, trichophytoses, eczema) when known as Emulsin (glycoside)
dissolved in a solvent like benzene. • Amygdalin - Source of Laetrile (Vit. B17):
controversial tx for sickle cell anemia
3. Saponins • Guignard’s Test – brick red/red coloration
• Form colloidal solutions in water that foam • Sources of amygdalin:
upon shaking (Froth test) o Bitter Almond (Prunus amygdalus)
• Bitter, acrid taste o Wild Cherry (P. seratina) / Black cherry –
• Sternutatory – irritating to mucous flavoring agent, expectorant and sedative
membranes o Apricot (P. armeniaca)
• Destroys RBCs of cold-blooded animals
(Blood agar plate hemolysis) – used as fish 5. Isothiocyanate Glycosides
poison • a.k.a. mustard glycosides
• Upon hydrolysis yield sapogenin • Found in Cruciferous plants (Brassicaceae)
• Types of sapogenin: • Odor test – mustard smell (volatile)
o Steroidal (neutral) – found in monocot • Ferric chloride test – Blood red (non-
o Triterpenoids (acid) – found in dicot volatile)
• Readily crystallizable upon acetylation • Sources:
• Sapotoxins – toxic, used for controlling o Black mustard/Sinapis nigra (Brassica
schistosomiasis snails nigra)
• Precursor of steroidal hormones like ▪ Contains sinigrin (Potassium
cortisone myrosinate)
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▪ Hydrolyzed by myrosinase to allyl • Cantharides
isothiocyanate (volatile mustard oil) o Spanish flies, Russian flies, blistering flies
o White mustard/Sinapis alba (B. alba) (Cantharis vesicatoria)
▪ Contains sinalbin (Parahydroxybenzyl o Mature insects with brilliant green with
isothiocyanate) metallic luster
▪ Hydrolyzed by myrosinase to acrinyl o Wings are treated with chloroform/dilute
isothiocyanate (less volatile) acid fumes or soaked in acetic acid
o Constituent: Cantharidin (vesicating
6. Flavonol Glycosides principle)
• Flavonoids or bioflavonoids from citrus fruits o Uses:
and soya ▪ Irritant
o Rutin and Hesperidin – Vitamin P or ▪ Vesicant – if taken internally, it is
Permeability Factor: used in the tx of excreted via the kidneys and irritate
capillary bleeding secondary to capillary the urinary tract
fragility ▪ Aphrodisiac – urinary tract infection
o Hesperidin, Diosmin, and Naringen – can cause priapism (prolonged and
treatment of symptoms of common colds painful erection: 6-24h; dilation is due
o Yellow Pigment – rutin and quercetin to nitrous oxide production)
o Source: ▪ Topical wart removal
▪ Milk Thistle (Silybum marianum) –
silibinin, silymarin (hepatoprotective) • Psoralens
▪ Ginkgo (Ginkgo biloba) -ginkolides and o Bishop’s flower (Ammi majus) merocarps
bilobalides (enough dilation for blood o Photosensitizing furocoumarins
vessels in the brain); memory o Family Apiaceae and Rutaceae
enhancement o For patient with psoriasis/vitiligo (non-
communicable disease)
7. Alcohol Glycosides o Methoxsalen (8-methoxypsoralen or
• Salicin – salix and populus xanthotoxin)
• Source: Weeping willow/willow tree (S. o Uses:
purupurea, S. fragilis) bark ▪ Repigmentation in idiopathic vitiligo
• Uses: Antirheumatic, anti-inflammatory, (leukoderma)
same as salicylic acid ▪ Symptomatic control of sever psoriasis
• Aglycone: saligenin ▪ CI: direct exposure to subnlight
• Tests: ▪ Risks: Carcinogenesis, cataract, Actinic
o Fehling’s – brick red degradation of skin
o Nessler’s – gray ▪ Trioxsalen (Trisoralen ®)
o Tollen’s – silver mirro
o Schiff’s – recolorization • Viburnum
o Blackhaw (V. prunifolium)
8. Aldehyde Glycosides o Scopoletin (6-methoxy-7-
• Vanilla nydroxycoumarin)
o Mexican or vera cruz or Bourbon vanilla o Antispasmodic
(V. planifolia)
o Tahitian Vanilla (V. tahitensis) 10. Phenol Glycosides
o Constituent – Vanillin (4-hydroxy-4- • Uva ursi
methoxy benzaldehyde) o Bearberry (Arctostaphylos uva-ursi),
o Flavoring agent Cjimaphila and other Ericaceous plants
o Constituent: Arbutin (hydroquinone +
9. Lactone Glycosides sugar)
• Coumarin o Uses: Diuretic and astringent
o From Tonka benas (Dipteryx odorata) • Poison ivy and oak
o Constituents: Dicoumarol – first oral o Poison ivy (Rhus radicans, Toxicodendron
anticoagulant, precursor of warfarin radicans)
o Test for unsaturated lactone – Kedde’s o Poison oak (R. toxicodendron, T. toxicaria)
test (blue-violet lactone) o Uroshiol – delayed contact dermatitis

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TANNINS

• Complex substances or polypeptides that are 2. Nutgall

difficult to separate because they do not • Hardened excrescence from the young twigs
crystalize of Quercus infectoria (Fagaceae) when Cynips
• Phenolic in nature; non-crystallizable tinctoria bores a hole to deposit its ova
polyphenols; protein precipitant (astringent); • Tannic Acid (Nutgall is the most important
found in barks and leaves source)
• Characteristics: o Composite acids that make up tannic acid:
o Forms colloidal solutions in water Gallic Acid, Ellagic acid
o Acidic o Solvent Extraction of powdered galls-
o Sharp puckering taste aqueous: gallotannin, ethereal: free gallic
• Deep red color with ferricyanide, dark blue or acid
green color with ferric salts (used in the o Component of Universal Antidote
manufacture of inks)
• Precipitated by copper, lead, tin dichromate 3. Japanese and Chinese Galls
• Precipitates gelatin • Formed in (Rhus chinensis) by the strings of a
• Precipitates alkaloid to form insoluble tannates plant lice (Aphis)
(used to detect alkaloids and manage their • Used in manufacture of gallic acid
poisoning
• Astringent – can precipitate proteins in living
tissues (GI, skin, abrasions, or burn wounds)
from solution renderring them resistant to
proteolytic enzymes.
• Carcinogenic potential – the habitual chewing
of betel num (Areca catechu) has been linked to
oral/esophageal cancer
• Converts animal hide to leather

Hydrolyzable Non-hydrolyzable
Other name Pyrogallotannins Phlobatannins / Condensed
tannins
Chemically Gallic acid or Phenolic nuclein linked to CHO
related and CHON condensation of
polyphenol flavan 3-ols (catechin) or flavan-
esterified with 3,4-diols (leucocyanin)
sugar
Hydrolytic Pyrogallol, Phlobaphenes - red colored
Products phenolic acids, insoluble polymerization
sugar products (responsible for diff.
colors of corn kernels)
Leather Bloom leather Tanner’s red
FeCl2 Test Blue-black Green-black
Br2 Test (-), no ppt. (+), with ppt.

True Tannins Psueudotannins

Gold beater’s (+) (-)
Test
MW 1000-5000 <1000

Pseudotannins
1. Hamamelis
• Distilled Witch Hazel extract (H. viriniana)
• Uses: Astringent in
o Hemorrhoidal products
o Insect bites and sting preparations
o Teething preparations

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LIPIDS

• Fixed oils, fats, waxes Reaction of Lipids

• Esters of long fatty acids and alcohols or • Hydrogenation
closely related derivatives o Liquid oils to semi-solid fats, used as
• Primarily for food or energy storage (fats and cooking fats and as shortening
fixed oils) o Done by passing hydrogen in the presence
Fixed Oils Fats Waxes of Ni or Pb at 160-200°C
Ester of fatty acid Ester of fatty acid Esters of fatty acid • Sulfation
and glycerol and glycerol and high MW o Reacting with sulfuric acid
monohydric o Temperature kept down by chilling
alcohols o Washed and neutralized
From plants From animals Plants and animals
o Sulfated or sulfonated: sulfate adds to the
Liquid (except Solid/Semi-solid Solid/semisolid
Myristica and (except cod liver (except Jojoba oil)
double bonds, surfactants
Theobroma) oil)
Mainly unsaturated Mainly Saturated General Uses of Lipids
FAs FAs • Emollient
Energy storage Energy storage Protectant • Lubricant laxative as emulsions
• Vehicles for other medicaments
USP Tests: • Manufacture of soaps
• Acid value or Acid number – mg of KOH • Manufacture of paints, varnishes and
required to neutralize free FAs in 1g lubricants
• Saponification value – mg of KOH needed to • Drying of oils
neutralize the free FAs and saponify the esters • Parenteral nutrient in hyperalimentation
in 1g (TPN): due to high caloric value but low
• Iodine value – g of iodine absorbed under osmotic pressure
prescribed conditions by 100g
1. Fatty Acids
*Seeds generally contain the largest amounts of • Saturated
liquids CN Shorthand Abbrev. MP (°C)
Notation
Extraction: Caproic 6:0 C5H11COOH
• Expression – uses hydraulic processes usually Capryllic 8:0 C7H15COOH
for vegetable sources Capric 10:0 C9H17COOH
o Cold-pressed oil – virgin oils, carried out in Lauric 12:0 C11H23COOH 44
the old Myristic 14:0 C12H27COOH 52
o Hot-pressed oil – carried out in heat Palmitic 16:0 C15H31COOH 63
Stearic 18:0 C17H37COOH 70
• Renderring – usually for fats
Arachidic 20:0 C19H39COOH 77
o Steamed with or without pressure Behenic 22:0 C21H43COOH 82
o Fats melt and rises to the top Lignoceric 24:0 C23H47COOH 86
o Separation by decantation Cerotic 26:0 C25H49COOH 89
o Clarified by filtration
o Bleached with ozone • Unsaturated
• Solvent extraction CN Abbreviation
Palmitoleic acid C15H29COOH
Types of oils Oleic acid C17H35COOH
• Ability to absorb oxygen; oxygen saturates Linoleic acid C17H31COOH
double bonds forming oxides that polymerize Linolenic acid C17H29COOH
to form films; paint industry Arachidonic acid C19H31COOH
• Important in the paint industry
Iodine Value Examples o Undecylenic Acid:
Non-drying <100 Olive, Almond ▪ From pyrolysis of castor oil (Ricinus
Semi-drying 100-120 Cottonseed, communis)
Sesame ▪ Antifungal, usually as zinc salt
Drying >120 Linseed, Cod Liver

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o Sodium morrhuate: d. Almond oil
▪ Sodium salts of mixture of fatty acids o From Sweet almond or bitter almond
from cod liver oil (Gadus morhua) (Prunus amygdalus)
▪ Sclerosing agent for varicose veins o Oleic acid
o Azelaic acid
▪ 9C: Saturated dicarboxylic acid e. Persic oil
▪ Form ozonolysis of castor oil (linoleic o Apricot or Peach kernel
acid)
▪ Anti-acne f. Coconut oil
o Cocos nucifera
2. Fixed oils o 80-85% lauric and myristic acids
a. Castor oil (Tangan-tangan) o Medium chain triglycerides (MCT) –
o Castor bean (Ricinus communis) glycerides of caprylic (C8) and capric (C10)
o 75% triricinolein
o Ricinoleic acid – stimulant cathartic g. Palm kernel oil
o Ricin – toxic principle o Elaeis guineensis
o Aromatic castor oil – contains suitable o Lauric and myristic acids
flavoring agents, not less than 95% o Manufacture of soaps
castor oil
o Hydrogenated castor oil – castor wax h. Safflower oil
for polishes and cosmetics o Carthamus tinctorius
o Trinoleic
b. Olive oil o Amtilipemic
o Sweet oil, oil of Europe o High calorie dietary supplement
o Olive ripe fruits (Olea europea)
o Forms: i. Sunflower oil
▪ Virgin-pressed – cold or low heat o Helianthus annus
▪ Technical form – from boiling water o Linoleic and oleic acids
▪ Tournant – from fallen or o Alternative to corn oil and safflower oil;
decomposing fruits dietary supplement
▪ Sulfur – via solvent extraction with
carbon disulfide j. Linseed or Flaxseed oil
o ID: Millon’s test – contaminated with o Linum usitatissimum
tea tree or camellia oil
o Oleic acid k. Ethiodized oil Injection
o Used as pharmaceutical aid o Iodine addition product of ethyl esters
▪ Retardant for dental cement of the fatty acids from poppy seed oil
▪ Preparation of soaps, plasters, and (Papaver somniferum)
liniments o Radiopaque, diagnostic aid

c. Soybean oil (Glycine soja) l. Theobrama oil

o 50% linoleic, 30% oleic acid o Cacao seeds (Theobrama cacao)
o Nutrient in diabetic patients and TPS o “Food for the gods”
o Lecithin – used to control deranged o Solid fixed oil
lipid and cholesterol metabolism o Nibs – broken cacao kernels
o Stigmasterol – precursor of steroid o Cacao butter – paste with 30% fat
synthesis o Bitter chocolate – cacao butter
o Partially dehydrogenated soybean congealed at room temperature
oil – dietary supplements o Sweet chocolate – bitter chocolate with
o Soybean cake – residue after sugar and flavoring
expression; contains protein, potassium o Prepared cacao or breakfast cacao
and phosphorus ▪ Powdered expressed marc
o Soybean meal – flour sifted from the ▪ Used in making cocoa syrup
decorticated ground seed, used for o Uses: Suppository base (melts at 30-
detecition of urea in serum by the 35°C
enzymatic action of urease o Contains oleopalmitostearin

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m. Hydrogenated vegetable oil 3. Fats and Related Compounds
o Refined, bleached, and decolorized a. Lanolin
vegetable oil o Purified fat like substance from sheep
o TGs of stearic and palmitic acids wool (Ovis aries)
o Serger test: test for vegetable oil o a.k.a. Hydrous woolfat
Official Fixed Oils o Ointment base
a. Peanut oil o 25-30% water
o Arachis oil (Arachis hypogea) b. Anhydrous Lanolin
o 50-65% oleic acid, 18-30% linoleic acid o a.k.a. wool fat
o Peanut butter – ground peanuts o Water absorbable ointment base,
o Peanut oil cake – residue upon expression emollient
given to livestock o Contains 0.25% water
c. Lanolin Alcohols
b. Seasme oil (Linga) o Contains > 30% cholesterol
o Sesame seed oil, Teel oil, Benne oil, (Sesame o Aliphatic, triterpenoid & steroid alcohol
indicum) o Emulsifying agent
o 43% oleic acid, 43% linoleic acid d. Cod Liver Oil
o Sesamol o Liquid fat
▪ Phenolic constituent o Rich source of oleovitamins A and D
▪ Confers excellent stability e. Butterfat (Bos taurus)
▪ By hydrolysis of lignan, sesamolin in the o Palmitic and oleic acid
unsaponifiable fraction, used as o Food
synergist to pyrethrum insecticides. f. Lard (Sus scrofa)
o Baudouin test o Food
▪ To test if an oil is adulterated with o Oleic, palmitic, stearic acid
sesame oil (+) pink color with fuming g. Suet
HCl and furfural o Beef tallow (Bos taurus)
o Uses o Mutton tallow (Ovis aries)
▪ Solvent for IM injection o Oleic, palmitic, pamitoleic, stearic acid
▪ Nutritive
▪ Laxative 4. Waxes
▪ Demulcent • Esters of HMW straight chain acids & alcohols
• In plants: epidermal walls of fruits and leaves
c. Corn oil • Protection vs penetration and loss of water
o Zea mays • Used in ointment and cosmetics
o 50% linoleic, 37% oleic acid
o Corn oil cake – residue upon expression, a. Spermaceti
given livestock o Head of sperm whale (Physter
o Uses: macrocephalus) – endangered species
▪ Solvent for IM injection o Cetyl esters of fatty acids
▪ Edible oil b. Beeswax
▪ High-calorie dietary supplement o From honeycomb of bee (Apis mellifera)
(Lipomul oral ®) o Yellow wax – unbleached
o White wax – bleached
d. Cottonseed oil o Chiefly myricyl palmitate
o Gossypium hirsutum o Ointment base
o Linoleic, oleic, malvalic acid c. Jojoba oil
o Winterchilling – done to remove stearn o Liquid wax from the seeds of
o Uses: Simmondsia chinensis
▪ Solvent for IM injection o Esters of eicosanoic acid and eicosenol
▪ Hydrogenated CSO – substitute for lard and docosenol
▪ Manufacture for soap
o Cottonseed cake d. Carnauba wax
▪ Contains gossypol, a toxic principle that o Leaves of Copernicia prunifera
causes male sterility o Chiefly myricyl cerotate
o Halphen or Bevan Test o For candles, wax, varnish, polishes
▪ Test for cottonseed oil o Substitute for beeswax

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VOLATILE OIL

• Essential or ethereal oils • Obtaining Volatile Oils:

• Odorous principle in various plants o Wet distillation
• Colorless and photosensitive 1. Water – for dried, not subject to injury
• Undergoes autooxidation and resinification with boiling (turpentine)
• Must be stored in light-resistant tight 2. Water and steam – dried (cinnamon or
containers in a dry and cold place clove) or fresh, may be injured with
• Plant Families: boiling
o Rutaceae – Schizogenous and lysigenous 3. Steam – fresh plant drugs (peppermint,
ducts spearmint)
o Pinaceae - Schizogenous and lysigenous o Destructive or Dry distillation
ducts 1. Empyreumatic oils
o Apiaceae – oil tubes called vittae 2. Pinaceae and Cupressaceae
o Piperaceae – modified parenchyma cells 3. Resultant mass is charcoal
o Lamiaceae – glandular trichomes 4. Volatile matter has 3 layers: (1)
• From petals, barks, leaves, druits of plants or naphtha=menthol, (2) pyroligneous acid
hydrolysis of glycosides = crude acetic acid, (3) pine tar or
• Chemical constituents: juniper tar
o Terpenes: from acetate-mavalonate o Expression
pathways; building blocks of isoprene (C5) 1. Cannot be distilled without
units decomposition
o Aromatic compounds: from shikimic 2. Ecuelle a piquer: puncturing the oil
pathways glands with sharp projections piercing
Class # of Carbons # of isoprene the rind.
units o Enfleurage
Monoterpenes 10C 2 1. Flower petals placed on a fatty pomade
Sesquiterpenes 15C 3 2. Extraction with alcohol
Diterpenes 20C 4 3. Production of perfumes and products
Triterpenes 30C 6 o Solvent extraction
Tetraterpenes 40C 8 1. Petroleum ether, benzene
2. Advantage over distillation – uniform
• Chemical characteristics: (50°C), more natural odor
o High refractive index: ability to bend light o Enzymatic hydrolysis - myrosinase
o Optically active: rotates plane-polarized 1. Sinalbin: acrinyl isothiocyanate
light 2. Sinigrin: allyl isothiocyanate
o Immiscible in water: but not soluble enough
to impart odor in water (aromatic water) • Components of Volatile Oils:
Volatile Oils Fixed Oils o Stereoptene
Terpenoids Ester of FAs and glycerol 1. Solid, oxidized hydrocarbon portion
No rancidity Rancidification 2. Menthol, thymol, anethole
Resinification No resinification o Eleoptene
(-) grease spot (+) grease spot
1. Liquid, hydrocarbon portion
Can be distilled Cannot be distilled
2. Eucalyptol, eugenol, methylsalicylate
Cannot be saponified Can be saponified

• Components of Perfumes:
• General Uses:
o Top notes (minute to hour)
o Spices and condiments – anise, clove,
1. Highly volatile
nutmeg
2. Lemon, clove, anise oils
o Flavoring and colorants – perfumes and
o Middle notes (3-6 hours)
food
1. Intermediate volatility and tenacity
o Carminative – peppermint, eucalyptus,
2. Thyme, rose, neroli oils
wintergreen
o Base notes (long hours)
1. Low volatility, fixative (staying power)
2. Vanillin, musk (Musk deer), ambergris
from sperm whale

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1. Hydrocarbon 3. Aldehyde
• Classification: • Classification:
o Monocyclic – limonene, p-cymene o Acyclic – citronellal, citral – a mixture of
o Dicyclic – pinene, solanine 3:1 ratio of geranial and neral
o Acyclic – myrcene o Aromatic – cinnamaldehyde, vanillin
o Sesquiterpene – cardinene, β- a. Cinnamon oil
caryophyllene o Sources:
a. Turpentine oil ▪ Ceylon cinnamon: Cinnamomum
o Pinus palustris zeylanicum
o α- and β-pinene ▪ Saigon cinnamon: C. loureiroi
b. Rectified Turpentine oil ▪ Cassia cinnamon: C. cassia (Souce of
o Distribution of turpentine oil from cassia oil)
aqueous solution of NaOH o Cinnamaldehyde
o For internal use as o Flavoring, carminative, antiseptic
stimulant/expectorant b. Lemon peel oil
c. Terpinhydrate or TerpinolTurpentine o Citrus lemon
oil o Limonene, citral
o From the action of HNO3 on rectified c. Sweet orange oil
turpentine oil o Citrus aurantium
o Stimulant expectorant o Limonene, decanal
d. Citronella oil
2. Alcohol o Cymbopogon winterianus, C. nardus, C.
• Classification: citratus
o Acyclic – geraniol, linalool, citronella o Citronellal
o Monocyclic – menthol, α-terpinol e. Hamamelis oil
o Dicyclic – borneol o Hamamelis virginiana
o Sesquiterpene – zingiberol o 2-hexanal
a. Peppermint oil o For hemorrhoidal preparations
o Mentha piperata
o Japanese peppermint – Arvensis 4. Ketone
o Contains menthol a. Camphor
▪ (-) menthol – natural o Cinnamomum camphora
▪ (+) menthol – synthetic, racemic o (+) camphor – natural
mixture o (-) camphor – Synthetic, racemic
o Flavorant, carminative, stimulant, mixture
counterirritant o Antipruritic, rubefacient, anti-infective
b. Coriander oil b. Spearmint
o Coriandum sativum o Mentha spicata
o Linalool o (-) carvone
c. Cardamom oil c. Caraway oil
o Elletaria cardamomum o Carum carvi
o Cinneole o (+) carvone
d. Rose oil d. Buchu oil
o Rosa gallica o Barosma betulina
o Geraniol, Citronella, Nerol o Diosphenol
e. Orange Flower or Neroli oil o For menstrual problems
o Citrus aurantium e. Wormwood oil or Absinthe oil oil
o Linalool o Artemisia absinthum
f. Juniper oil o (+) thujone
o Juniperus communis o Counterirritant
o Borneol f. Cedar leaf oil
o Flavorant, diuretic o Thuja occidentalis
g. Pine oil o (+) thujone, (-) fenchone
o Pinus palustris o Counterirritant
o α-terpineol, pinene
o Anti-eczema, disinfectant

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5. Phenol
a. Thyme oil
o Thymus vulgaris
o Thymol
o antiseptic
b. Clove oil
o Eugenia caryophyllus
o Eugenol (4-allyl-2 methoxyphenol)
o Component of toothache drops
c. Myricia oil or Bay oil
o Pimenta racemosa
o Eugenol
d. Creosole oil
o Fagus grandiflorus
o Creosol – disinfectant, guiacol

6. Phenol Ether
a. Nutmeg oil
o Myristica fragrans
o Myristicin, safrole
o Hallucinogen
o Toxicity – tachycardia, xerostomia,
flushing
b. Anise oil
o Aniseed (Pimpinella anisum)
o Trans-anethole, anisaldehyde
o Flavoring, condiment
c. Fennel oil
o Foeniculum vulgare
o Trans-anethole, fenchone
o Flavoring, condiment

7. Oxide
a. Eucalyptus oil
o Cajuput (E. globulus)
o Cineole (eucalyptol, cajuptol)
o Ingredient in Vicks Vaporub

8. Ester
a. Gaultheria oil
o Oil of wintergreen, Betula oil, sweet
birch oil
o Gaultheria procumbens
o Methylsalicylate – local irritant,
antiseptic, antirheumatic
b. Lavander oil
o Lavandula angustifolia, L. vera, L.
officinale
o (-) linalyl acetate
c. Pine Needle oil
o Pinus ugo
o Bornyl acetate
d. Mustard oil
o Brassica nigra – allyl isothiocyanate
o Brassica alba – acrinyl isothiocyanate
o Rubefacient in musterole

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RESINS AND RESIN COMBINATION

• Products of volatile oil oxidation (resinification e. Mastic

of terpenes) o Mastich, Mastiche (Pistachia lentiscus)
• Can be crystalline or amorphous o Contains α-resin (mastichic acid) and β-
• Mixture of resin acids, resin alcohols, resin (masticin)
resinotannols, esters and resenes o Dental varnish to seal cavities
• Found in schizongenous and schizolysigenous f. Kava-kava
ducts o Piper methysticum
Resin Combination Components o Contains styrypyrones: yangonin,
Oleoresin Homogenous combination of resin and kawain, methysticin and their
volatile oil derivatives
Oleogumresin Volatile oil, gum and resins o Tranquilizer, skeletal muscle relexant
Glycoresin Resin and carbohydrate (jalap, o Drug of abuse
podophyllum) g. Cannabis
Resin acids Oxyacids (carboxylic acids and o Indian hemp (Cannabis sativa)
phenols)
o Marijuana, MJ, grass, weed, pot, hashish
Resin alcohols Can be resinol or resinotannol (react
with FeCl3) o 1-9-Tetrahydrocannabinol (THC)
Balsams Resins and aromatic compounds (dronabinol), nabilone – psychoactive
(cinnamic and benzoic acids) constituent, causes euphoria
Pharmaceutical Obtained by:
Resins • Extracting alcohol and precipitating 2. Oleoresin
with water (jalap, podophyllum) a. Capsicum or Cayenne pepper
• Separating oil from oleoresin by o African chilies or Siling labuyo
distillation (turpentine, coapida) (Capsicum frutescens)
• Collecting exuded natural product o Louisiana long pepper or Siling haba (C.
(mastic)
anuum var. longum)
o Irish or Tobasco pepper (C anuum var
1. Resin
conoides)
• Brittle, amorphous solids that fuse readily o Capsaicin - counterirritant
when heated b. Ginger
• Leaves a varnish-like film upon evaporation o Zingiber officinale
a. Rosin or Colophony o Zingiberol, bisabolene – stomachic, for
o Shiny, sharp, angular fragments sore throat
o Translucent and amber in color o Flavorant, stimulant, carminative
o Pinus palustris c. Turpentine
o Contains abietic acid, silvic acid and o Gum thus
resene o Pinus palustris
o Stiffening agent for plasters and o Counterirritant
ointments, adulterants for other d. Copaida
resinous materials o Balsam of copaida (oleoresin)
b. Podophyllum (Copaifera sp.)
o American mandrake or mayapple o Copaivic and oxycopaivic acids
(Podophyllum peltatum) e. White pine
o Contains glycoresins Podophyllin – o Weymouth pine (Pinus strobus)
caustic agent for warts
o Peltatin – purgative 3. Oleogumresin
o Podophyllotoxins) Teneposide, a. Myrrh or Gum myrrh
Etoposide) – anticancer agents o Commiphora molmol, C. abyssinica
c. Eriodyction o Somali (African myrrh)
o Yerba santa (Eriodyction californicum) o Yemen (Arabian myrrh)
o Stimulant expectorant, flavorant o Ingredient in Astring-o-sol
d. Jalap o Embalming agent
o Root of Exoginium purge b. Asafetida
o Cathartic, hydragogue o Ferula foetida
o Jalapin, purganol – drastic purgative o Volatile oil: isobutylpropanylisulfide
o Asaresinotanol, ferulic acid
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4. Balsams
a. Storax
o Liquid storax, syrax (Liquidambar
orientalis)
o Levant’s storax (L. styraciflua) –
contains 50-50 α, β-storesin
o Storesin-contains cinnamic acid
▪ α – crystallizable with K
▪ β – not crystallizable with K
o Pharmaceutic aid for Compound
benzoin tincture (Storax, Tolu balsam,
Aloe, Benzoin)
b. Peru balsam
o Myroxylan pereirae
o Contains benzyl cinnamate
o Antiseptic and parasiticide
o Contains cinnamein, peruresintannol
c. Tolu balsam
o Myroxylan balsamum
o Contains toluresinotannol cinnamate
o Flavorant and expectorant
d. Benzoin
o Sumatra benzoin (Styrax benzoin, S.
paralleloneurus) – contains cinnamic
acid and benzoic acid,
sumaresinotannol, benzoresinol
o Siam benzoin (Styrax sp., Anthostyrax
sp.) – contains coniferyl benzoate,
siaresinotannol, benzoresinol
o Antiseptic, stimulant, expectorant
o Primary component of CBT – topical
protectant

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ALKALOIDS

• Basic nitrogenous plant constituents which are 1. Pyridine-Piperidine

physiologically active • From amino acid ornithine
• Bost of them ends in “-ine” a. Nicotiana
• Chemical forms: o Tobacco leaves (Nicotiana tabacum)
o Free base – sparingly soluble or insoluble o Nicotine – CNS stimulant and smoking
in water; soluble in ether, chloroform deterrent
o Alkaloidal salts – formed with acids, freely o Derivative of pyridine and pyrrolidine
soluble in water b. Areca
• Physical forms: o Dried ripe seed of Betel nut (Areca
o Solid alkaloids – most are crystalline, some catechu)
are amorphous o Stimulant masticatory chewed with
o Liquid alkaloids – lack oxygen in the lime and leaves of Piper betel
molecule o Arecoline – CNS stimulant and
1. Coniine – from poison hemlock anthelminthic
(Conium meculatum) – used to poison o Derivative on nicotinic acid
Socrates o Tannin content causes oropharyngeal
2. Arecoline – betel nut (Areca catechu); cancer (catechutannin)
mild parasympathomimetic stimulant, c. Lobelia
vermifuge (veterinary use) o Indian leaves (Lobelia inflata)
3. Nicotine – tobacco (Nicotiana o Lobeline – CNS stimulant and smoking
tobacum) deterrent
4. Sparteine - scotchbroom (Cysticus o Derivative of piperidine
coparius), lupin – Lupinus mutabilis;
antiarrhythmic 2. Tropane
• Chemical structure: • Dicyclic compounds from the amino caid
Heterocyclic Non-heterocyclic ornithine
Typical Atypical • Ester of 3-hydroxytropane (tropine) and (-)
Contains N atom within a ring Doesn’t contain a nitrogenous tropic acid
heteroatom ring a. Belladonna
Divided based on ring system Protoalkaloids or biologic o Deadly nightshade (Atropa belladonna)
amines o (-) Hyoscyamine, racemized to atropine
– parasympathetic depressant
• Alkaloidal reagents – used to detect alkaloids, o For functional digestive disorders such
forms colored precipitate with alkaloids as peptic ulcer and spasms
Reagent Content Result o Anticholinergic, mydriatic
Mayer’s Potassium mercuric iodide Cream ppt b. Hyoscyamus
Nessler’s Alkaline potassium Brown ppt
o Henbane (Hyoscyamus niger)
mercuric iodide
Wagner’s Iodine in potassium iodide Reddish-brown
o 0.04% alkaloid
ppt o Scoploamine and Hyoscyamine
Bouchard’s Iodine in Potassium iodide *Most sensitive c. Egyptian Hyoscyamus
Dragendorff’s Potassium bismuth iodide Reddish brown o Egyptian Henbane (Hyoscyamus
ppt muticus)
Valser’s Mercuric iodide o 1.5% alkaloid
Marme’s Potassium Cadmium White/Yellow o Scopolamine and hyoscyamine
iodide ppt d. Stramonium (Talumpunay)
Sonnecheim’s Phosphomolybdic acid o Jimsonweed (Datura stramonium)
Schiebler’s Phosphotungistic acid
o Scoploamine or Hyscine – CNS
Hager’s Saturated picric acid Yellow ppt.
depressant, for motion sickness,
Gold
compounds anesthetic with morphine
Tannic acid o Used for asthma and COPPD (burned
Ecolle’s Silicotungstic acid then vapors are obtained)
reagent e. Withania/Indian ginseng
o Withania somnifera
o Commercial source of atropine
f. Duboisia
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o Duboisia myoporoides o Ipecac syrup – emetic, used to induc
o Commercial source of atropine vomiting in cases of poisoning or
g. Pituri or Australian Tobacco overdose by acting on the CTZ in
o Duboisia howoodii medulla
o Nicotine and nornicotine o Ipecac fluidextract is 14x more potent
h. Mandragora o Ipecac + opium = Dover’s powder
o European mandrake or mayapple/ (diaphoretic)
Satan’s Apple (Mandragona o Paregoric (Camphorated opium
officinarum) tincture) - diarrhea
o Mandragorine - emetic o Laudanum (Deodorized opium
i. Coca tincture) – pain and cough suppressant
o Huanuco coca (Erythroxylin coca) b. Hydrastis
o Truxillo coca (E. truxillense) o Goldenseal (Hydrastis canadensis)
o Cocaine (methyl benzoylecgonine) o Hydrastine and berberine (bright
▪ “crack” or “coke” yellow crystals) - astringents
▪ Psychomotor stimulant, causes c. Sanguinaria
euphoria o Bloodroot (Sanguinaria canadensis)
▪ Local anesthetic o Sanguinarine (reddish nitrate and
▪ Ingredient in Brompton’s cocktail – sulfate salts) – stimulant expectorant,
analgesic for cancer pain, drug of emetic
abuse d. Curare
o Free-basing – inhalation of vapors of o South American Arrow poison
alkaloidal cocaine ▪ Strychnos castelnaui
▪ S. toxifera
3. Quinine ▪ Chondrodendron tomentosum
• From tryptophan o Types:
a. Cinchona ▪ Calabash – packaged in gourd
o Sources: Red cinchona bark (Cinchona ▪ Tube – packaged in bamboo
succirubra); Yellow cinchona bark (C. ▪ Pot – packaged in clay pot
calisaya) o Tubocurarine:
o Studied by Pelletier and Cavenotou ▪ Skeletal muscle relaxant (curariform
o Parent alkaloids are cinchonine and its effect) by blocking impulses in the
isomer cinchonidine NMJ – for surgical procedures
o Component of effervescent tonic water without deep anesthesia
o Toxicity: Cinchonism – temporary loss ▪ Standardized by head drop
of hearing, tinnitus, impaired sight crossover test in rabbits (least
o Quinine (6-methoxucinchonine) – amount of drug capable of producing
diastereomer of quinidine antimalarial, muscle relaxation so that head of
intercalates between Plasmodium DNA animal drops in a characteristic
bases manner)
o Quinidine – antimalarial, ▪ Anticonvulsant in strychnine
antiarrhythmic poisoning
o Test for Quinine - Thalleioquin test (fine ▪ SE: Anaphylactoid reaction –
blue fluorescence then green ppt) histamine release, not IgE mediated
b. Cuprea e. Opium alkaloids
o From bark of Remija pudieana and R. o Milky exudate of ripe poppy capsules
pendunculata (Papaver somniferum)
o Commercial source of quinidine o Only legal source is india
o Termed “stone of immortality”
4. Isoquinoline o Meconic acid – found only in opium,
• From tyrosine forms red color with FeCl3
a. Ipecac o Opioids – acts on opioid receptors (mu,
o Sources: Brazilian ipecac (Cephalis kappa, delta); analgesic, hypnotic,
ipecacuanha), Panama ipecac (C. narcotic
acuminata) ▪ Apomorphine – formed from
o Contains emetine, psychotrine and condensation of morphine with HCl;
cephaline emetic; administered SQ

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▪ Heroin, Diamorphine or ▪ Reversible inhibitor cholinesterase
Diacetylmorphine – acetylation ▪ As salicylate or sulfate salt
causes more pronounced effect than ▪ For glaucoma: miotic agent,
morphine increases outflow of aqueous humor,
▪ Hydromnorphone – more potent decreases IOP
narcotic analgesic, less frequent SE ▪ DOC for atropine or neostigmine
(constipation and habit forming) toxicity
▪ Hydrocodone – antitussive ▪ Toxicity: cholinergic crisis
o Preparations: e. Ergot
▪ Powdered Opium – 10-10.5% o Rye ergot or secale cornutum (Claviceps
morphine, used in making Dover’s purpurea, C. paspalis) found in rye
powder (Secale cereale)
▪ Paregoric o Decreases blood flow into the
▪ Laudanum extremities causing gangrenous
▪ Dover’s Powder ergotism (St. Anthony’s Fire)
▪ Poppy seed – maw seed o Found in sclerotium or resting bodies of
mycelia
5. Indole o Ergonovine or Ergometrine
• From tryptophan ▪ Oxytocic agent to assist in labor
a. Rauwolfia ▪ Partial agonist-antagonist at α-
o Rauwolfia serpentina adrenergic, serotonergic and
o Reserpine – hypotensive, tranquilizer, dopaminergic receptors
causes depression by depleting ▪ Methylergonovine – more potent
norepinephrine stores, treatment of and longer acting
snake bites ▪ Methysergide – serotonin antagonist
o Rescinnamine – hypotensive (ACEi) for prophylaxis of migraine
o Deserpidine – hypotensive, less o Ergotamine
incidence of SE ▪ Analgesic for migraine (with
o Alseroxylon fraction – basic powdered caffeine)
alkaloidal extract without toxicity in ▪ Decrease amplitude of pulsation of
long term use cranial arteries
b. Vinca alkaloids ▪ Vasoconstrictor – inhibits
o Catharantus or chichirika norepinephrine receptor uptake
(Catharanthus roseus formerly Vinca ▪ Dihyrdoergotamine – more potent
rosea) and longer acting
o Antineoplastic, arrest cell division at o Ergotoxine
metaphase ▪ As methylsulfonate mixture
o Vinblastine (Vincaleukoblastine) – for (ergoloid mexylates)
Hodgkin;s and other lymphoma ▪ Vasorelaxant, increases cerebral
o Vinleurosine (Leurosine) – blood flow to decrease systemic
lymphosarcoma, sarcomas, blastomas blood pressure
o Vinrosidine (Leurosidine o Lysergic acid diethylamide (LSD)
o Vincristine (Leurocristine) ▪ Serial synthesis from ergot
c. Nux vomica ▪ Strong sympathetic stimulation and
o Sources: Nux vomica (Strychnos nux slight depression
vomica); Ignatia or St. Ignatius Bean (S. ▪ Psychomimetic agent used in
ignatia)- commercial source experimental psychiatry
o Strychnine – CNS stimulant, vermin
killer, used in neuroanatomic research 6. Imidazole
o Brucine (dimethoxystrychnine) – • From histidine (has glyoxaline ring)
alcohol denaturant a. Pilocarpine
o Madelin’s test – spot test used to o Sources: Pernambuco jaborandi
identify alkaloids (violet) (Pilocapus jaborandi); Maranha,
d. Physostigma jaborandi (P. microphyllus); Paraguay
o Calabar, Esere or Ordeal bean jaborandi (P. pinatifolius)
(Physostigma venenosum) o Lactone of pilocarpic acid
o Physostigmie (Eserine)

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o Cholinergic for glaucoma – motic and 9. Purine
contracts ciliary muscles, improves • Methylated derivatives of xanthine
outflow of aqueous humor (methylxanthine)
• Derivatives of glycine, glutamine, aspartic
7. Steroidal fragments and carbon fragments from carbon
• Has cyclopentanoperhydrophenanthrene dioxide and tetrahydrofolate
(CPPP) • Do not precipitate with alkaloidal reagents
a. Green Hellebore • Inhibits phosphodiesterase, increases cAMP
o American hellebore (Veratrum viride) and epinephrine release
o Alkamines (jervine, veratramine) and o Relaxes smooth muscles in the bronchioles
their esters (germicide, germitrine) and (bronchodilator) and pulmonary blood
glucosides (veratrosine) vessels
o For HTN: hypotensive, cardiac o CNs stimulant
depressant, sedative o Diuretic
o Insecticide o Increase gastric acid secretion
b. White Hellebore o Inhibitor of uterine contractions
o European hellebore (V. album) o Weak positive chronotropic and inotropic
o Protoveratrine A&B a. Cola
o Hypotensive (not used), insecticide o Kola nuts (Cola nitida)
o Contains caffeine, theobromine and
8. Alkaloidal amines tannin kolacatechin
• No heterocyclic nitrogen atoms o CNS stimulant
• Derivatives of phenylethylamine (atypical b. Coffee
alkaloids) from phenylalanine or tyrosine) o Coffea arabica, C. robusta, C. libreica
a. Ephedra o Beans are roasted to acquire dark
o Ma Huang (Ephedra sinica) brown color and characteristic aroma
o Ephedrine (caused by the volatile oil containing
▪ Symptomatic acting on α and β caffeol)
receptors o Caffeine (1,3,7-trimethylxanthine),
▪ Vasoconstrictor – to combat Trigonelline (pyridine alkaloid) – CNS
hypotensive states in allergy, nasal stimulant, inotropic, chronotropic,
decongestant diuretic
▪ Cardiac stimulant o Caffeine is naturally bound chlorogenic
▪ Mydriatic acid (tannin) and released upon
▪ Diminishes hyperemia – for allergies roasting
▪ Bronchodilation – for bronchial o Decaffeinized coffee – less than 0.08%
asthma caffeine
b. Colchicum c. Guarana
o Colchicum autumnale o From the dried paste composed of the
o Colchicum – treatment of gout, by crushed seeds of Paullina cupana
inhibiting leukocyte migration and o Contains caffein and catechutannin
reduce lactic acid production, to o CNS stimulant and astringent
decrease deposition of uric acid d. Mate
c. Khat o Paraguay tea (Ilex paraguariensis)
o Abbysinian tea (Catha edulis) o Contains caffeine and tannins
o (-)-Cathinone – similar action with o Laxative, purgative, diuretic,
amphetamines, by increasing diaphoretic
catecholamine release from vesicles o CNs stimulant, astringent
d. Peyote e. Thea
o Mescal buttons (Lophophora williamsii) o Tea (Camelia sinensis)
o Mescaline – hallucinogen o Forms:
o Psilocybe ▪ Green tea – leaves are harvested
▪ Psilocybe Mexicana fresh, dried over mild heat (|China
▪ “shrooms” or “mushrooms” and Japan)
▪ Psilocybin – hallucinogen ▪ Black tea – elaves are harvested
after fermentation, dried over rapid
heat (India and Sri Lanka)

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o Theophylline (1,3-dimethylxanthine)
and thein
▪ Bronchodilator for bronchial asthma
and COPD, smooth muscle relaxant
in the bronchioles, tocolytic agent
▪ Diuretic
▪ Aminophylline – diethylamide
complex of theophylline
f. Theobroma
o Cacao (Theobroma cacao)
o Theobromine (3, 7-dimethylxanthine)
▪ CNS Stimulant
▪ Smooth muscle relaxant – for angina
pectoris
▪ Diuretic – for cardiac edema

COMMON NAME SCIENTIFIC NAME FAMILY USE

Bawang / Garlic Allium sativum Liliaceae Antihypertensive, controls
blood lipid levels
Akapulko/Ringworm Bush Cassia alata Fabaceae Antifungal, laxative
Bayabas (Guava) Psidium guajava Myrtaceae Astringent, antiseptic
Yerba Buena Mentha cardifolia/ Lamiaceae Analgesic, antipyretic
Clinopodium douglasii
Pansit-pansitan / Ulasimang-Bato Peperomia pellucida Piperaceae Lowers uric acid in gout
Lagundi Vitex negundo Lamiaceae Cough preparation
Ampalaya / Bitter gourd Momordica charantia Cucurbitaceae Anti DM supplement
Niyog-niyogan Quisqualis indica / Combretaceae Anthelminthic
Combretum indicum
Tsaang Gubat / Wild tea Carmona retusa / Ehretia Boraginaceae Stomachic
microphylla
Sambong Bluema balsamifera Asteraceae Diuretic, anti-urolithiasis

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