PHARMSEM PHARMACOGNOSY

SECOND SEMESTER | S.Y 2023-2024

Glycosides
● Yields sugar as one of the product of hydrolysis
● Always HYDROLYZABLE
○ Sugar: Glycine (b-D glucose)
○ Non-sugar: Aglycone/ Genin (Therapeutic activity)
● Sugar ethers
● Based on atoms involved glycosidic linkage: C,O,N,S-glycoside
● According to sugar moiety: GluRR- Glucosides, Ribosides, Rhamnosides

2 GLYCONES

CARD3NOLIDE BUF4DIENOLIDE

● 5 membered lactone @ place ● 6 membered lactone @ R (C24)

of R (C23) ● Chemical structure similar to BUFALIN- Toad
● Most cardiac glycosides skin toxic principle
belong to ● Ex: Scillaren from Squill

CARDIAC GLYCOSIDES
● Steroidal compound (has CPPP nucleus-
Cyclopentanoperhydrophenanthrene)
● Potently active in MYOCARDIUM
● MOA: inhibit Na/K ATPase (3 Na Out 2 K in)- a PUMP not
enzyme! (find another channel: Na/Ca exchanger –3 Na out 1
Ca in)
● Effect: Positive inotropic (inc. strength of myocardium)
● Clinical application: CHF, arrhythmia

Liebermann Burchard Test Most sensitive Blue green

Major test
Detects steroids
Test for cholesterol

Salkowski test Also detects steroid Red

Keller-Killiani test 2-deoxy sugar glycine Digitalis- Blue green

test (sugar of Squill- Red
cardenolides)
Differentiate
cardenolides and
befadienolides

Cardiac glycoside

1. Digitalis Digitalis lanata (Grecian

foxglove)- Digoxin
Digitalis purpurea
(Foxglove)-Digitoxin
PHARMSEM PHARMACOGNOSY
SECOND SEMESTER | S.Y 2023-2024

Desacetyl lanatoside Deslanoside Rapid Digitalization

Digitoxin Very lipophilic (absorb in

the body)
Very long half life -190 hrs

Digoxin Widely used- preferable DI: Quinidine, quinine,

pharmacokinetic profile electrolyte imbalance
Polar (Hypo Mg K, Hyper
Half life: 2-6 hours Ca)- increase toxicity

Toxicity: Antidote: Digoxin

GI disturbance immune Fab (Digifab,
Xanthopsia digibind)
Arrythmia

2. ConvaLLaria Lily of the valley Constituent:

Convallaria majalis Convallatoxin
(Liliacea) (Cardenolide),
Convallataxol,
Covalloside

3. Adonis Pheasant's eye Constituent:

Adonis Vernalis Adonitoxin
Cyamarin
K-strophanthin

4. ApoCYnum Black indian hemp/ Constituent:

Dogbane Cyamarin
Apocynum cannabinum (antiarrythmia,
Cardiotonic)

5. Cactus grandiflorus Night blooming cereus

Selenicereus grandiflorus

6. Black hellebore Christmas rose Black hellebore-

Helleborus niger BlyCosidal (cardiac
stimulant)
Green&White
Hellebore- Alkaloidal
(anti-HTN)

7. Strophantus Strophantus kombe, S. Constituent:

hispidus strophantosides

-k strophantin:
primary glycoside
-G strophantin: aka:
Ouabain): cardiac
stimulant IV)
PHARMSEM PHARMACOGNOSY
SECOND SEMESTER | S.Y 2023-2024

8. Squill White squill bulb/ Constituent:

Mediterranean squill Scillaren A
Urginea maritima (Buffadienolide)-
converted to
SCILLARENIN (active
form)
Red variety (Red
squill)- rat poison

ANTHRAQUINONE
● Related to anthracene
● Used as laxative or cathartic

Borntragers test Test for anthraquinone Pink, red, violet

glycosides

1. Cascara sagrada Sacred cascara/bark Cascarosides

Rhamnus purshiana A,B- optical isomer of
BARBALOIN
C,D-optical isomer of
Do not maintain laxative: CHRYSALOIN
cause laxative habits
Lanes pill-
casanthranol
(anthranols of cascara
sagrada)

2. FRangula Rhamnus frangula Constituents:

Frangulins A& B,
Preparation: Movicol- Glucofrangulin
Frangula + karaya gum -laxative activity

3. Rheum Chinese rhubarb Rhein anthrones-

Rheum palmaticum drastic cathartication

Oldest drug in china

4. Senna Alexandria- Cassia Sennosides A, B, C,

acutifolia D

Grow in riSE paddies

Component of slimming
teas

5. Aloe Aloe barbadensis Barbaloin,

(Curacao) aloe-emodin
PHARMSEM PHARMACOGNOSY
SECOND SEMESTER | S.Y 2023-2024

Uses:
Moisturizer
2% for burn preparation
Compound benzoin
tincture

6. Chrysarobin Mixture of natural principle Chysaloin- only

from GOA POWDER from non-cathartic
Andira araroba
Use:
keratolytic-eczema,
psoriasis, corns, and
warts

SAPONIN GLYCOSIDES
● AKA: Sapotoxin
● Most toxic plant principle (hemolysis)
● Used as fish poison
● 2 types: steroidal and triterpenoidal
● Saponin- Sternutatory- stimulant sneezing
● Aglycone: sapogenin

Froth test Honeycomb froth (>2cm) Stays 1-2 mins

Hemolysis test Blood agar plate- sheep's B- hemolytic: colorless

blood A-hemolytic: green
B- hemolytic- complete Y- hemolytic: remain
A-hemolytic: partial brown
Y- hemolytic: no hemolysis

Keller killiani test Steroidal saponins violet

-2 deoxysugar component

1. Glycyrrhiza Licorice Use to mask bitter

Glycyrrhiza glabra taste of quinine
50x sweeter than sucrose
(glycyrrhizin) Excessive intake:
Use in beer foaming sterility in male

CI: HTN & CHF- promotes

electrolyte and water
retention

2. Dioscorea Edible variety of yam Diosgenin- mexican

yam (dioscorea
floribunda)
- Anti-inflam for
arthritis,
muscle pain,
PHARMSEM PHARMACOGNOSY
SECOND SEMESTER | S.Y 2023-2024

and rawmat for

synthesis of
steroids

3. Ginseng Panax ginseng (asian Gensenosides,

ginseng) panoxide,
chickusetsusaponins
Uses: tonic,
adaptogen (relieves
stress), aphrodisiac
(sex stimulant)

4. Agave Agave cantalla Use:Molluscide-elimin

ate snails

5. Guava Psidium guajava Antimicrobial property

Cyanophore glycoside
● Glycoside that yield MANDELONITRITE and HCN derivative

1. Cherry Prunus serotina Sedative effect- due to

HCN derivative
Flavorant

2. Almond Prunus amygdalus

3. Apricot Prunus armeniaca

PRUNUS
Constituent:
● Amygdalin- primary glycoside
● Prunasin- product of hydrolysis of amygdalin
Note: Laetrile (Vit B17)-tx for sickle cell anemia
Glycoside + Emulsin (enzyme- amygdalase + prunase ) → mandelonitrite +HCN

4. Cassava Mannihot esculenta Mannihotoxin (skin)

ISOTHIOCYANATE GLYCOSIDE
● Sulfur containing
● Source out from mustard

1. Black mustard SN: Brassica nigra Sinigrin

Sinigrin + Myosin →
allyl isothiocyanate
(glycosidic volatile oil)

2. White mustard SN: Brassica alba Sinalbin

PHARMSEM PHARMACOGNOSY
SECOND SEMESTER | S.Y 2023-2024

Sinalbin+ Myosin
→Acrinyl
isothiocyanate

Flavanols
● AKA: flavonoids
● Plant pigment (yellow) -quercetin and rutin
● Bioflavonoids- antioxidants (hisperidin, hespentin, diosmin, naringenin)

Rutin + hisperidin Vitamin P (permeability Inc capillary rigidity

factor) -tx for capillary
bleeding 2nd to
capillary fragility

Vitamin F Essential fatty acid

-Linoleic acid- Omega 6
-Linolenic acid- omega 3
(heart)

Vitamin H Biotin

Milk thistle Silybium marianum Const: Silbinin,

silymarin

hepatoprotective

Ginkgo Ginkgo biloba Const: ginkgolides,

bilolabides (enough
dilation of blood
vessels in the brain)

Memory enhancer

Glutaphos-first
memory enhancer in
PH-peptide base

ALCOHOL GLYCOSIDES
Sapogenin: contains alcohol in the structure

Salicin Poplar and Willow (Salix Aglycone- saligenin

purpurea) Salicin-anti rheumatic
property/ anti
Family of salicylates inflammatory

Only alcohol glycoside

PHARMSEM PHARMACOGNOSY
SECOND SEMESTER | S.Y 2023-2024

ALDEHYDE GLYCOSIDES

Vanilla Mexican vera cruz vanilla Const: Glucovanillin

(Vanilla planifoloa) and Glucovanillic
alcohol

“Vanillin”-
aglygcone/genin
(flavor and aroma)

Ethylvanillin-
substitute for natural
vanilla

LACTONE GLYCOSIDES
-Exist as hydrocoumarins
- Aglycone- Lactone (ketone)

Horse Chestnut tree Const: Esculin

Japanese star anise Const: Skimmin

Coumadin Sweet cover leaf Const:

Dicumarol and
Bishydroxycoumadin-
Warfarin- used as warfarin (tonka
anticoagulant coumadins-Dipteryx
odorata (plant))
Dicoumarin- 1st oral
anticoagulant (dicumarol)

Psoralen Ammi majus (plant) Photosensitivity

furocoumarins

Methoxalen and Trioxalen Used for vitiligo

Note: (repigmentation)
Psoralen/ methoxalen/
trioxalen: contraindicated
w/ direct sunlight - causes
cancer (melanin)

Vitiligo- loss of color in the

skin

Cantharides Spanish/russian/ blistering Use: aphrodisiac,

fly cause priapism
(prolonged erection)
Cantharis vesicatoria
Release nitric
oxide-vasodilator
PHARMSEM PHARMACOGNOSY
SECOND SEMESTER | S.Y 2023-2024

INTRINSIC PATHWAY EXTRINSIC PATHWAY COMMON PATHWAY

-inside or loob -labas ng body Xa→ needs V,PL, Ca+ →

-there is interaction of blood -tissue damage (injury or Prothrombin → thrombin →
and collagen sugat) fibrinogen → fibrin → XIIIa
-factor cell death will be → stable fibrin clot
Factors involved: activated and used to activate
XII, XIIa, XI,XIa,IX, factor X
IXa (needs VIII,PL,Ca+), X
Factor involved: TF:VIIa
GOAL: activate Xa
(prothrombin activator)-work
on the common pathway

Slow blood clot formation Fast blood clot

Fibrin - aka blood clot; where anticoagulant will act on

Aspirin - will NOT act on FIBRIN; antiplatelet (platelet is involved in the

platelet surface contact)

TPA (Tissue - dissolve clots; degrade both fibrinogen and fibrin and inactivate
plasminogen activator) prothrombin, factor V and factor VIII

Hemophilia Bleeding disorder; kulang sa factor

Hemophilia A Kulang ng christmas factor IX (Tx: tranexamic acid)

PHARMSEM PHARMACOGNOSY
SECOND SEMESTER | S.Y 2023-2024

Phenol glycoside

Uva-ursi Arctostaphilus uva-ursi Const: Arbutin

CN: bearberry Uses:
astringent/diuretic

Astringent-close pores

Poison Ivy Rhus radicans

Poison oak Rhus toxidendron Urushiol-causes

delayed contact
dermatitis

Tannins
● Polyphenols that do NOT crystallize
● Characteristic:
○ Acidic, sharp puckering taste
○ Ppt alkaloids and proteins
○ Astringent and tx of burns

HYDROLYZABLE NON-HYDROLYZABLE/
CONDENSED

OTHER NAMES Pyrogallotanins Phlobatannins

Heated (pyrolysis) pyrogallol catechol

FeCl3 test HydrolyzaBLUE GREEN

Type of leather Bloom Tanner’s red

(phlobaphenes-red
complexes)

Bromine test No reaction/ No ppt w/ppt

Yield (hydrolyzed) Sugar + phenolic acid Catechin and

leucocyanidin

Hamamelis Witch hazel Const: Hamamelitannins

SN: Hamamelis virginiana
Distilled witch hazel
extract -contain volatile
oil of hamamelis &
tannins

Use: Astringent and Tx

for hemorrhoids

Nutgall Primary source of tannic acid Excresence: product of

(NOT a nut NEITHER a plant) insect boring on the plant
PHARMSEM PHARMACOGNOSY
SECOND SEMESTER | S.Y 2023-2024

Plant: Quercus infectoria

Insect: Cynips tinctoria

OTHER SOURCE Guava

Duhat
pineapple

Tannic acid Use: astringent and Component of tannic

component of universal acid:
antidote (ATM) ● Gallic acid
● Ellagic acid

STEROIDS
-contain CPPP nucleus

Sterol Solid sterols Cholesterol- animals;

most widely occurring
sterol, first discovered
B-sitosterol/
phytosterol-plant
Ergosterol-fungi
Stigmasterol- soybeans
(Glycine max)

Bile acids Cholic acid and Uses: emulsifying agent,

chenodesoxycholic acid- aid in intestinal
synthesized in the liver from absorption of fats
cholesterol, abundant in
humans Bile acid binding resin/
Bile acid sequestrants-
Deoxycholic acid and colestipol and
lithocholic acid- derived by cholestyramine (s/e:
microorganism steatorrhea)

Cardiac glycosides

Steroidal hormones Adrenocortical hormones- Sex hormones

cortex of adrenal medulla ● Estrogen-devt of
● Glucocorticoids- from female reproductive
diosgenin sys. & 2nd charac.
(hydrocortisone, cortisol, (estradiol, estriol,
cortisone, prednisone) estrone)
● Mineralocorticoids- ○ Used as
(Na+ and water OCP/LGBTQ/
retention)-aldosterone hormonal
imb/depression
○ Too
much=accumula
tion of fats
○ Inc risk of breast
cancer
● Progestin-progeste
rone (prepares
PHARMSEM PHARMACOGNOSY
SECOND SEMESTER | S.Y 2023-2024

body for pregnancy)

● Androgens- male
reproductive sys
and 2nd sexual
charac.

Anabolic steroids-
banned; copy male sex
hormone testosterone;
“performance and image
enhancing drugs”

PCOS- too much

testosterone

LIPIDS
-esters of long FA and alcohol
-NOT BIOPOLYMERS-no building blocks

FIXED OILS Unsaturated esters of FA + glycerol

● Unsaturated: less H; double/triple bond

FATS Saturated esters of FA + glycerol

● Saturated: lots of H; single bond

WAXES Esters of HMW alcohol + FA

PROSTAGLANDIN Lipid alcohols

● From arachidonic acid
● Produces COX enzyme

FIXED OILS

Castor oil CN: tangan tangan Const: Triricinolein →

SN: Ricinus communis ricinoleic acid (FA);
Ricin (toxic)
Undecylenic acid-
Use: cathartic; hair growing product of pyrolysis (
product through destructive
PHARMSEM PHARMACOGNOSY
SECOND SEMESTER | S.Y 2023-2024

distillatio-no solvent) as
antifungal

OFFICIAL OILS (CorCotPeSe) Corn-mais (Zea mays); Only oils APPROVED

fabaceae for use as vehicle in IV
preparation
Cottonseed-Gossypium
hirsutum (Malvaceae)
● Gossypol- male
contraceptive/ destroy
seminiferous ducts
(unable to produc
seminal fluid)
Peanut- Arachis hypogaea
(Arachis oil)
● Non-containing oil
(contains more
saturated FA
Sesame-
● CN: teel or Benne oil
● SN: Sesamum
indicum
● Const: sesamol

Olive oil CN: sweet oil, oil of europe Forms:

SN: Olea europa ● Virgin - low temp is
used (cold press)
● Tournant - fallen or
decomposing fruit
● Technical -
obtained using
boiling water
● Sulfur - used
carbon disulfide for
extraction
Adulterant: Tea tree oil/
Camelia oil (Camellia
sinensis) -means
pamparami

OTHER SOURCES Almond Oil (Prunus Safflower Oil

amygdalus) (Carthamus tinctorius)

Persic Oil (Apricot - Prunus Ethiodized Oil Injection

armeniaca) - product of
poppy seed (Papaver
Coconut Oil (Cocos nucifera) somniferum) oil
● Virgin Coconut Oil - (prepared by I2 or iodine
Lauric Acid addition)
(monolaurins) ● radiopaque
material - used for
Sunflower Oil (Helianthus imaging to have
anuus) clearer scans
PHARMSEM PHARMACOGNOSY
SECOND SEMESTER | S.Y 2023-2024

● uses: cosmetics for scar

removal,knees/elbow
discoloration corrector

Theobroma Oil “food of the gods” used as Suppository

SN: Theobroma cacao Base

TYPES OF
THEOBROMA OIL
● α - melts at RT
● β - melts at temp lower
than
body temp (solid at RT)
(this form is the one
used in suppository)

FATS
-generally solid at room temperature

THEOBROMA OIL OILS are generally liquid at RT except

COD LIVER OIL FATS are generally solid at RT except

LANOLIN obtained from sheep's wool ○ Lanolin (Hydrous

(Ovis aries) Wool Fat) -
20-25% moisture
○ Anhydrous Lanolin
(Wool Fat) -
0.25% moisture --
penetrates
faster on skin

HYDROGENATED SOLID due to addition of H oil that is solidified,

VEGETABLE OIL deodorized and
Decolorized
EX: margarine

COD LIVER OIL fat that is liquid at room has anti-sclerotic

temperature property
source: Godus morrhoa (anti-atherosclerosis)
● FATTY ACID: Na
marrhuate

WAXES
-ester of long FA and HMW alcohols

PLANT SOURCE Carnauba wax (Copernicia

prunifera)
Jojoba Oil - Liquid plant wax
○ SN: Simondsia chinensis
○ solidified form resembles
spermaceti
PHARMSEM PHARMACOGNOSY
SECOND SEMESTER | S.Y 2023-2024

ANIMAL SOURCES Spermaceti Wax - from brain

of a sperm whale (Physeter
macrocephalus)
○ Ambergis - crude material
○ Cetyl ester wax-Synthetic
wax substance

Bees Wax - from the

honeycomb of the
honey bee (Apis mellifera)
2 forms:
● White beeswax
(decolorized)
● Yellow beeswax
(TRUE BEES WAX)

VOLATILE OILS
● odoriferous plant principles
● insect repellant & insect attractant
● composed of terpenoids- isoprene unit
(5C) as building blocks (Chloroplast-non
mevalonate pathway)
● aka Ethereal oils or Essential Oils
● Storage Conditions: dark, cool place in a
full amber glass container
○ Reason: volatility, autooxidation,
photosensitivity
● STEAROPTENE - Solid portion
● ELEOPTENE - Liquid portion

1. DISTILLATION Water - vehicle; fresh sample, resistant to

high-temp (Ex:Turpentine Oil)

H2O & Steam - no active boiling, done on fresh or dried

samples (Ex: Cinnamon & Clove Oil)

No vehicle - Destructive Distillation

○ Disadvantage: formation of smoke-like/ burn-like odor
(empyreumatic odor)

2. EXPRESSION Ecuelle - using mechanical device w/ spikes designed to

puncture the oil glands
○ preferable for citrus

Enfleurage - involves the use of a fatty pomade which

absorbs the oil from the sample (lard)

3. EXTRACTION use of organic solvents

advantage: low BPs - the process can be done at a much
lower temp. w/o compromising the quality of the oil
disadvantage: cost of solvents; some are toxic (e.g.
PHARMSEM PHARMACOGNOSY
SECOND SEMESTER | S.Y 2023-2024

benzene)

4. ENZYMATIC HYDROLYSIS Ex: Glycosidic volatile oils

Sinalbin/ Sinigrin (Myosin) → Glycosidic volatile oils

I. HYDROCARBON VOLATILE OILS

Limonene, P-cymene, Pinene (most commonly found in plants)
Sabin & Myrcene

1. TURPENTINE OIL Contains pinene Forms/ Preparations:

Source: Pine Tree (Pinus Rectified Turpentine Oil:
palustris) - leaves of pine tree that
undergo distillation w/ an
aqueous solution of
NaOH (Water + NaOH)

Terpin Hydrate or
Terpineol
- formed by the reaction
of RTO
w/ HNO3 (nitric acid) in
the presence of alcohol
- RTO + nitric acid +
alcohol

both are used as

stimulant expectorant
(expel phlegm)

II. ALCOHOL VOLATILE OILS

Acyclic: Geraniol, Linalool & Citronellol (no ring, linear)
Monocyclic: Menthol, α-terpineol (1 ring)
Dicyclic: Borneol
Sesquiterpene: Zingiberol (3 isoprene units)

1. PEPPERMINT OIL SN: Mentha piperita source of menthol (will

be solidified by freezing
Japanese peppermint the oil)
SN: M. arvensis synthetic menthol
(racemic mixture-50%
dextro 50% levo; no
optical activity)
natural menthol
(levorotatory)

2. CARDAMOM OIL SN: Elettaria cardamom Chief Const: Cineole

Use: Spices
Ayurvedic medicine
use: Tx for UTI
● lower down
blood sugar
PHARMSEM PHARMACOGNOSY
SECOND SEMESTER | S.Y 2023-2024

3. CORIANDER OIL SN: Coriandrum sativum Const: Linalool

Use: Carminative
(anti-flatulence)

4. ROSE OIL CN: Otto of Rose Const: Geraniol, Nerol,

SN: Rosa gallica Citronellol

5. ORANGE FLOWER OIL CN: Neroli Oil Const: Linalool

SN: Citrus aurantium (ang
sour orange mismo)

6. JUNIPER OIL SN: Juniperus communis Const: Borneol

Use: OTC as diuretic
(Odrinyl®)

7. PINE OIL SN: Pinus palustris Const: α-terpineol

III. ALDEHYDE VOLATILE OILS

-Acyclic - Citral, Citronellol
-Aromatic - Cinnamaldehyde

1. CINNAMON Saigon - Cinnamomum Const.: cinnamaldehyde

laureini
Ceylon - C. zeylanicum
Cassia - C. cassia

Can be obtained from the

bark

2. LEMON SN: Citrus limon Const: Citral

(responsible for the odor)
- combination of Neral
& Geranial
Common problem:
Terebinthenate Odor
(attributed to the terpene
content)
High quality:
Terpeneless Oil (95% of
terpenes are removed)

3. ORANGE OIL (SWEET ORANGE) SN: Citrus sinensis Const: Decanal

Chief const: Limonene
(hydrocarbon content )

4. CITRONELLA OIL SN: Cymbopogon nandus Const: Citronellal -

CN: Tanglad mosquito repellant
action
Neem Tree - Azadiracta
indica
PHARMSEM PHARMACOGNOSY
SECOND SEMESTER | S.Y 2023-2024

5. HAMAMELIS Hamamelis virginiana Const: 2-hexen-1-al

Use: OTC or
hemorrhoids (astringent
property)

IV. KETONE
Monocyclic: Menthone, Carvone, Piperitone, Pulegone, Diosphenol
Dicyclic: Camphor, Fenchone, Thujone

1. CAMPHOR SN: Cinnamomum Const: Camphor

camphora (camphor is used for
liniments/ counter
irritants )
○ Natural: Dextro
○ Synthetic: Racemic

2. SPEARMINT SN: Mentha spicata Const: (-) Carvone

3. CARAWAY SN: Carum carvi Const: (+) Carvone

3. BUCHU SN: Barosma betulina Const: Diosphenol

Use: OTC for menstrual
period

5. WORMWOOD OIL SN: Artemisia absinthum Const: (+) Thujone

Use: Counterirritant

6. CEDAR LEAF OIL SN: Thuja occidentalis Const: (+) Thujone, (-)
Fenchone
Use: Vicks Vaporub®

IV. PHENOL
contains phenolic substances in their structures

1. THYME OIL SN: Thymus vulgaris Uses: Antifungal,

Antibacterial

2. CLOVE OIL SN: Eugenia caryophilus Const: Eugenol -

(Myrtaceae) analgesic property
Use: common ingredient
in dental
preparations
● Toothache drops

3. MYRCIA OIL CN: Bay Oil Const: Eugenol

SN: Pimenta racemosa

4. CREOSOTE CN: Beechwood creosote Const: Guaiacol cresol

SN: Fagus grandiflora Natural occurring
expectorant

5. JUNIPER TAR SN: Juniperus oxycedrus Use: OTC for eczema

CN: Cade Oil and psoriasis (Polytar®)
PHARMSEM PHARMACOGNOSY
SECOND SEMESTER | S.Y 2023-2024

6. PINE TAR Use: Anti-eczema and

psoriasis
Const: Phenol & Cresol

VI. PHENOLIC ETHER

Nutmeg "butter of nutmeg," Const: Myristicin,

myristica Saffrole
Uses: Flavoring agent,
Carminative (Anti
Note: Abused by prison Flatulence)
inmates. Nutmeg is a
hallucinogen. Const: Trans-anethole
○ Anise - Pimpinella
anisum
○ Fennel - Foeniculum
vulgare
○ Chinese Star Anise -
Illicum verum

VII. OXIDATIVE VOLATILE OILS

Eucalyptus SN: Eucalyptus globulus Const: Eucalyptol

(Cineole, Cajuptol,
Cajupot)
Use: Counterirritant

VIII. ESTER VOLATILE OIL

contains esters in their structure ( RCOOR′)

1. GAULTHERIA OIL CN: Wintergreen, Teaberry, Const: Methyl salicylate

Chuckerberry Name of Oil: Gaultheria
SN: Gaultheria procumbens Oil, Wintergreen
Oil, Betula Oil, Sweet
Birch Oil
Found in liniment oils
such as Efficascent oil

2. LAVANDER OIL SN: Lavandula augustifolia Const: Linalyl acetate -

from Linalool
Used as an aromatic
essential oil

3. PINE NEEDLE OIL SN: Pinus mugo Const: Bornyl acetate -

from borneol

4. MUSTARD OIL Allyl and acrinyl Allyl - black mustard

isothiocyanate Acrinyl -white mustard

Brassica alba (White) and

Brassicanigra (Black)

RESIN & RESIN COMBINATIONS

PHARMSEM PHARMACOGNOSY
SECOND SEMESTER | S.Y 2023-2024

RESINS
Produced from volatile oils
Sources: same as plants with volatile oils
Location: Lysogenous (example)

1. COLOPHONY aka: Rosin Uses: Adulterant of

Resin of pine tree oil (Pinus other resinous
palustris) material, stiffening agent
for plasters and cerates

2. PODOPHYLLUM aka: American mandrake, Const:

American mayapple Podophyllin - anti-wart
SN: Podophyllum peltatum property (HPV)
Peltatin: purgative
effects
Teniposide &
Etoposide-
antineoplastic activity
(microtubule inhibitor)

3. ERIODICTYON CN: Yerba Santa Use: Stimulant

SN: Eriodictyon californicum expectorant, flavorant
(used to mask the bitter
taste of beer),
also used as
antispasmodic (there
will be relaxation of the
smooth muscles).

4. JALAP SN: Exogonium purga Const: Ipurganol,

Jalapin
Use: purgative

5. MASTIC SN: Pistacia lentiscus Use: Dental varnish

6. KAVA-KAVA SN: Piper methysticum Use: skeletal muscle

relaxant (banned-
abused and caused
paralysis)

7. CANNABIS SN: Cannabis sativa Const: "Hashhish" -

concentrated form
of the resin containing
THC
(tetrahydrocannabinol)

OLEORESIN
Homogenous mixture of volatile oil and resin
2 groups: Pharmaceutical/Common or Ordinary

A. PHARMACEUTICAL OLEORESIN

1. CAPSIUCUM CN: Chile peppers Const: Capsaicin -

PHARMSEM PHARMACOGNOSY
SECOND SEMESTER | S.Y 2023-2024

SN: Capsicum frutescens concentrated in the

Seeds
Use: Counterirritant

2. GINGER SN: Zingiber officinale Const: Zingiberol,

Zingiberene, Bisabolene
(imparts the purgency)
Use: Stomachic (for
stomach ache)

3. COPAIBA SN: Copaifera spp.

CN: Balsam of Copaiba
(NOT a true balsam, it’s an
oleoresin)

4. TURPENTINE CN: Gum Turpentine or

Gum Thus

5. WHITE PINE SN: Pinus strobus

CN: Weymouth pine

B. OLEO-GUM RESIN
-homogenous mixture of gum and oleoresin
-oleo: volatile oils

1. MYRRH CN: Gum Myrrh Use: Astringent -

SN: Commiphora molmol Astring-O-Sol®
(mouthwash, used to
treat gingivitis);
embalming agent (very
large concentration)

2. ASAFETIDA SN: Ferula foetida

BALSAM
resinous material which are combined with aromatic substances such as
cinnamic acid and benzoic acid

1. STORAX SN: Liquidambar orientalis Const: Alpha &

CN: Levant Storax Beta-Storesin
Use: an ingredient in
Compound
Benzoin Tincture

2. PERUVIAN BALSAM SN: Myroxylon pereirae Const: Benzyl

cinnamate
Use: Local protectant,
disinfectant,
antiseptic, antibacterial

3. TOLU BALSAM SN: Myroxylon balsamum Const:

Toluresinotannol
cinnamate
PHARMSEM PHARMACOGNOSY
SECOND SEMESTER | S.Y 2023-2024

RESIN ALCOHOLS
Resinol - will not give a tannin reaction
Resinotannols - resin alcohol which reacts with FeCl3 like tannins do
● Use: Flavoring agent
● Example: Benzoin

1. BENZOIN SN: Styrax benzoin primary component in

the preparation of
Compound Benzoin
Tincture
○ Balsam Compound:
Benzoin, Tolu, Storax
○ Non-balsam: Aloe

ALKALOIDS

● physiologically active basic plant constituents; at least

one N-atom (nitrogen) forms a part of a cyclic system
● form ppts with alkaloidal reagents:
○ (CHON (protein)-contaminant→ false (+) result
due to N
● MOST ACTIVE pharmacologically among all
phytochemical constituents

I. PYRIDINE-PIPERIDINE

1. TOBACCO SN: Nicotiana tabacum Const: Nicotine

Use: potent CNS
stimulant; highly
addictive
● Varenicline
(Champix®):
smoking deterrent

2. INDIAN TOBACCO SN: Lobelia inflata Const: Lobeline

CN: Lobelia Use: CNS stimulant -
less addictive

3. ARECA NUT CN: Betel Nut Const: Arecoline

Local Name: Nganga Use: CNS stimulant,
SN: Areca catechu anthelmintic (can cause
esophageal cancer)
PHARMSEM PHARMACOGNOSY
SECOND SEMESTER | S.Y 2023-2024

4. WATER HEMLOCK SN: Cicuta macubra Const: Coniine

Aka: poison hemlock Use: sedative
(discontinued=death and
suffocation)

II. TROPANE ALKALOID

most members of the family Solanaceae

1. BELLADONNA SN: Atropa belladonna Const: Atropine, 1°

CN: Deadly nightshade Hyoscyamine
(racemic form)
Use: anticholinergic

2. HYOSCYAMUS CN: Henbane (Hyoscyamus Egyptian Henbane

niger) (Hyoscyamus muticus) -
commercial source of
Atropine, also source of
Scopolamine
(anti-motion sickness)

3. STRAMONIUM SN: Datura stramonium Const: Scopolamine or

CN: Jimson or Jamestown Hyoscine
weed
Local: Talumpunay (Datura
metel)

4. WITHIANA & DUBOISIA other/commercial

sources of Atropine

5. MANDRAGORA CN: European mandrake Const: Mandragorine

SN: Mandragora
officinarum

6. COCA PLANT CN: Huanoco coca Const: Cocaine

(Erythroxylon coca), Use/s: 1st ester local
Truxillo coca (E. truxillense) anesthetic agent, for
terminal cancer patient
Cocaine-drug of abuse suffering from pain;
MOA: inhibit NET potent analgesic,
(Norepinephrine Transporter) Brompton's Cocktail (has
cocaine content)

III. QUINOLINE
● discovered by Caventou
● parent compound: "Cinchonine"
○ Cinchonidine
○ Quinine
○ Quinidine

1. CINCHONA BARK Red cinchona - Cinchona Use/s: Anti-malarial

succirubra ○ Quinine: Black Water
Yellow cinchona - C. Fever (hemolysis)
calisaya (anti-malaria)
PHARMSEM PHARMACOGNOSY
SECOND SEMESTER | S.Y 2023-2024

○ Quinidine:
prolongation of QT
interval (anti-arrhythmia)

2. CUPREA BARK SN: Remijia purdieana

IV. ISOQUINOLINE ALKALOIDS

1. IPECAC CN: Rio or Brazilian Const: Emetine (primary

(Cephaelis ipecacuanha) alkaloid), Cephaelin,
Psychotin
Nicaragua or Panama
(C. acuminata) Use: Emesis

2. HYDRASTIS CN: Golden Seal Const: Hydrastine,

SN: Hydrastis canadensis Berberine, Canadine
Use: Astringent

3. SANGUINARIA CN: Blood Root Const: Sanguinarine

SN: Sanguinaria canadensis (acrid emetic)

4. TUBOCURARE CN: Arrow Head Poison Const: Tubocurarine

SN: Strychnos toxifera, S. Use: Skeletal Muscle
castelanei, Relaxant
Chondodendrum spp.

5. OPIUM CN: Poppy plant Const:

SN: Papaver somniferum ○ Morphine: most
OPIUM DERIVATIVES important (unripe seeds
● Dover's Powder - ipecac with opium of opium poppy)
Note: DON’T REACT in ○ Codeine: converted to
● Laudanum - opium tincture
alkaloidal tests. Thus, it has methyl morphine
● Paregoric - camphorated opium its own test (Ferric Chloride ○ Papaverine
tincture Test). ○ Noscapine/Narcotine:
non-narcotic

FERRIC CHLORIDE TEST

● identification test for opium
● positive result: red color
○ due to meconic acid component of opium alkaloid

V. INDOLE ALKALOIDS
PHARMSEM PHARMACOGNOSY
SECOND SEMESTER | S.Y 2023-2024

1. CHICHIRIKA CN: Vinca, Periwinkle Const: Vinblastine,

SN: Catharantus roseus Vincristine
○ antineoplastic

2. RAUWOLFIA SN: Rauwolfia serpentina Const: Reserpine

Use: Anti-HTNsive
(depletion of NE stores)
MOA: inhibits PMAT,
stop storing dopamine
and epinephrine

4. PHYSOSTIGMINE CN: Ordeal (brand) or Const: Physostigmine or

Calabar Bean Eserine
SN: P. venenosum Use/s: Antidote for
Atropine toxicity;
Management of
glaucoma and
myasthenia gravis

It is a cholinergic
agonist. An indirect
agonist that inhibits
the
acetylcholinesterase
(inc ACh =
DUMBELSS)

5. ERGOT CN: Spurred Rye Const:

SN: (Fungus) Claviceps ○ Ergotamine: migraine
purpurea ○ Ergonovine: oxytocic
(uterine stimulant)
Ergotism - St. Anthony's Fire ○ Ergotoxin: anti-HTN
(Gangrenous form)
● Gangrene–lysis of
tissues; will blacken