HYDROCARBONS AND DERIVATIVES
- Esterified long-chain alcohols
HYDROCARBONS
- Contain carbon and hydrogen atoms and
additional functional groups; interaction of
natural compounds
- Odd-numbered long chain alkanes within
the range of 25-35 no. of carbons usually
formed by decarboxylation processes
MONOBASIC ACIDS
- Possess one or more carboxyl groups
- Participate in essential metabolism
- Ex. fatty acids, amino acids, aromatic
acids
FATTY ACIDS
- Important components of plant oils (acyl
lipids) in which they occur as esters with
the trihydric alcohol glycerol
- Ricinoleic acid (hydroxyoleic acid)- has
both a hydroxyl group and an unsaturated
double bond (acetylenic fatty acid)
AROMATIC ACIDS
- Compounds that contain COOH group
bonded to an aromatic ring
- Two common aromatic acids: Benzoic
acid and Cinnamic acid- occur as free
acids and combined in plant products
such as balsams
- Truxillic acid- polymer of cinnamic acid
that occurs in coca leaves
- Gallic acid (3,4,5-trihydroxybenzoic acid)
- Quinic acid - acid that has an alcohol
group; high amounts in Cinchona bark
- Shikimic acid - important intermediate
metabolite; modern application-
semisynthesis of Oseltamivir
DIBASIC AND TRIBASIC ACIDS
- 2 carbon atoms attached with COOH
groups; 3 carbon atoms attached with
COOH group
- Dibasic acid: forms the first series of acids
like Malonic acid and Sulfuric acid
- Tribasic acids: Citric, Isocitric and Aconitic
acids
ALCOHOLS
- Possess one or more hydroxyl groups and
exist naturally in either the free state or
combined as esters
- Classified as: monohydric, dihydric,
trihydric and polyhydric
MONOHYDRIC ALIPHATIC ALCOHOLS
- Pharmaceutical animal eaxes
- Ex. Cetyl alcohol, Cetyl alcohol and
Myricyl alcohol
MONOHYDRIC TERPENE ALCOHOLS
- Associated with that large group of
compounds which arise from mevalonic
acid and have isoprene as a fundamental
functional unit
- Ex: Menthol - oil of peppermint
MONOHYDRIC AROMATIC ALCOHOLS
- Benzyl alcohol and Cinnamyl alcohol-
occur both free and as esters of benzoic
acid and cinnamic acid in balsams
DIHYDRIC ALCOHOLS
- Compounds containing two hydroxyl
groups; found naturally in many structural
classes of compounds
- “Glycols”
- Ex. Panaxadiol- component of some
ginseng compounds
TRIHYDRIC ALCOHOLS
- Occur in a range of structural types
- Ex. Glycerol (propan-1,2,3-triol)- essential
component of fixed oils and fats
ESTERS
- Arise from the union of an alcohol and an
acid with a loss of water
- Reaction is reversible and in plant
esterase enzymes control the reaction
- Ex: Lecithins - esters of glycerophosphoric
acid
DRUGS CONTAINING ACID, ALCOHOLS AND
ESTERS
1. ROSELLE
- Hibiscus sabdariffa (Malvaceae)
- Leaves, stems and seeds
- Constituents; citric acid, tartaric
acid and lactone hydroxycitric acid
- Use: colourant and flavorant;
astringent, cooling and diuretic
- Reports: polysaccharides-
stimulation of proliferation
2. TAMARIND PULP
- Tamarindus indica (Leguminosae)
 - Fruit (contains pulp)
- Occurs as reddish brown, moist,
sticky mass
- Constituents: tartaric acid, citric
acid, malic acid, and nicotinic acid;
potassium hydrogen tartrate
- Use: mild laxative and a confection
of senna
3. MANNA
- Biblical name- Lecanora esculenta
(Lichen)
Commercial manna (ash manna)-
Fraxinus ornus (Oleaceae)
- Constituents: 55% Mannitol (hexahydric
alcohol)
- Use: mild laxative action
4. BENZOINS
- Two commercial varieties: Sumatra
benzoin and Siam benzoin
- SUMATRA BENZOIN
- Gum Benjamin
- Styrax benzoin
- Parts used: incised stem; occurs in brittle
masses, opaque, whitish or reddish
material
- Does not give + result in alcoholic ferric
chloride test
- Constituents: cinnamic and benzoic acids;
siaresinolic acid (19-hydroxyoleanolic
acid) and sumaresinolic acod (6-
hydroxyoleanolic acid)
- Allied drug: Palembang benzoin- reddish
brown; source of natural benzoic acid
- Uses: expectorant and antiseptic;
ingredient of friars balsam and component
of incense
- SIAM BENZOIN
- Styrax tonkinensis
- Obtained from incision of the trunk
- Constituents: coniferyl benzoate and
coniferyl cinnamate
- Test: gives green color with ferric chloride
- Uses: same with sumatra benzoin
5. ASH LEAF
- Fraxinus oxyphylla (Oleaceae)
- Parts used: leaves
- Constituents: hydroxycinnamic acid
derivatives (chlorogenic acid), tannins and
sugar alcohol mannite
- Use: mild laxative and diuretic action
6. ARTICHOKE LEAF
- Cynara scolymus (Asteraceae)
- Parts use: leaves (greyish-green to brown-
epidermis)
- Constituents: chlorogenic acid, caffeine
acid and cynarin
- Uses: treatment of indigestion and
dyspepsia
7. NETTLE LEAF
- Urtica dioica L. (Stinging nettle) and Urtica
urens (small nettle)
- Green powdered drug - slight odor and
bitter taste
- Constituents: chlorogenic acid,
caffeoylmalic, caffeic, malic and fumaric
acids
- Uses: tx of rheumatic conditions and
assist micturition in benign prostatic
hyperplasia
8. ECHINACEA SPP.
- Coneflowers; perennial herbs of
Compositae/ Asteraceae
- E. augustifolia (narrow-leaved coneflower)
and E. purpurpea (purple coneflower)
- Constituents: Echinacoside (caffeic acid
derivative) and Cynarin (quinic acid
derivative); Esters of tartaric acid, caftaric
acid and cichoric acid
- Uses: immunostimulant, prevention and
treatment of common colds and other
respiratory complaints; anti-inflammatory
and antibacterial
9. PYGEUM BARK
- Prunus africana (Rosaceae)
- Parts used: stems and branches
- Dark to reddish-brown pieces
- Constituents: ferulic acid esters,
phytosterols, triterpenoid pentacyclic acids
- Uses: symptomatic relief of benign
prostatic hyperplasia
10. PERU BALSAM
- Myroxylon balsamum (Leguminosae)
- Parts used: bark
- Viscid liquid and oily; insoluble in water
and soluble in one volume of alcohol
- Constituents: benzyl cinnamate, benzyl
benzoate and cinnamyl cinnamate
- Uses: antiseptic and parasiticide; tx of
catarrh and diarrhoea (allergic reactions)
11. PREPARED STORAX
- Liquidambar orientalis
(Hamamelidaceae)= levant storax
- Part used: trunk
 - Crude- greyish, viscous with pleasant odor
and bitter taste; purified storax- brown,
viscous, semisolid mass, characteristic
balsamic odor and taste
- Constituents: cinnamic acid; after
purification-30-4% total balsamic acids;
distilled storax-styrene, cinnamic esters,
vanillin and free cinnamic acid
- Allied drug- american storax obtained from
Liquidambar styraciflua - rich source of
shikimic acid
- Uses: preparation of friars balsam and
benzoin inhalation
12. TOLU BALSAM
- Myroxylon balsamum (Leguminosae)
- Part used: trunk
- Soft yellow, semisolid that turns brown,
brittle solid; solute in alcohol
- Constituents: resin alcohols combined
with cinnamic and benzoic acids, benzyl
benzoate, benzyl cinnamate, and vanillin
- Uses: antiseptic and flavouring properties;
added to cough mixtures (in syrup or
tinctures)
FATS AND FIXED OILS
Fats- triglyceride compounds that contains
unsaturated and saturated acids
Fixed oils- contains fatty acids; obtained from fruit
pericarps
EXTRACTION PROCESS
- Derived from seeds or fruits
- Solvent extraction, expression
QUANTITATIVE TEST
1. Acid value
- Refers to the number of mg potassium
hydroxide required to neutralize the free
acids in 1 g of oil
- High acid values - rancified oils
- Low acid values - used in parenteral
preparations
2. Saponification value
- Hydrolysis reaction of lipids
- Number of mg potassium hydroxide
required to neutralize the free acids and to
hydrolyse the esters in 1 g of substance
3. Ester value
- Difference between the saponification
value and acid value
4. Iodine value
- Gives a measure of the unsaturation of
the oil
5. Acetyl value
- Number of mg potassium hydroxide
required to neutralize the acetic acid freed
by hydrolysis of the acetylated fat or other
substance
6. Hydroxyl value
- Depends on the number of free hydroxyl
groups present
- Expressed as the number of mg of
potassium hydroxide required to neutralise
the acid combined by acetylation of the
sample.
7. Peroxide value
PHARMACEUTICAL FIXED OILS AND FATS
1. ALMOND OIL
- Prunus dulcis var. Dulcis and var. Amora
(Rosaceae)
- Seeds; expression
- Constituents: amygdalin; colorless and
crystalline
- Refined almond oil - pale yellow liquid with
slight odor
- Uses: mild laxative; vehicle for oily
injections
2. ARACHIS OIL
- Arachis hypogaea (Leguminosae(;
earthnut, ground nut
- Seeds; expression; world's fourth largest
source of fixed oils
- Constituents: glycerides of oleic, linoleic,
palmitic, arachidic, stearic and lignoceric
acids.
- Uses: ingredient of camphorated oil;
mainly used in the production of
margarine
3. COTTONSEED OIL
- Gossypium soo. (Malvaceae)
- Seeds; hot expression
- Semidrying oil; high iodine value
4. COCONUT OIL
- Cocos nucifera (Palmae) - dried solid part
of the endosperm; expression
- Constituents: caprice, caprylic, oleic,
palmitic and stearic acids
5. LINSEED OIL
- Linum usitatissimum (Linaceae)
- Seeds; hot expression; yellowish-brown
drying oil
- Constituents: linolenic acids, linoleic acid,
oleic acid, myristic acid, stearic and
palmitic acids
- Uses: making demulcent preparation,
antibacterial
6. OLIVE OIL
- Salad oil, sweet oil
- Olea europaea (Oleaceae); ripe fruits-
expression
- 6th in the world’s production of vegetable
oil
- Pale yellow liquid
- Constituents: oleic acid, linoleic acid,
palmitic acid and stearic acid
- Uses: preparation soaps and plaster
7. PALM OIL AND PALM KERNEL OIL
- Elaeis guineensis (Palmae); steaming and
expression of the mesocarp of the fruits
- Constitutes: triglycerides of lauric acid
8. SAFFLOWER OIL
- Carthamus tinctorius (Compositae);
expression or extraction from seeds
- Constituents: palmitic acid, oleic acid,
stearic acid and linoleic acid
9. SESAME OIL
- Gingelly oil, Teel oil
- Sesamum indicum (Pediaceae)
- Pale yellow, bland oil
- Constituents: sesamin, sesamolinol and
seamolin
10. SOYA OIL
- Glycine soja- seeds
- Constituents: linoleic acid, oleic acid,
linoleic acid and stearic acids
- Refined soya oils
- Hydrogenated soya oil - palmitic and
stearic acids
11. SUNFLOWER OIL
- Helianthus annuus - seeds mechanical
expression or extraction
- Linoleic acid, oleic acid, palmitic acid and
stearic acid
12. THEOBROMA OIL
- Oil of theobroma; cocoa butter
- Theobroma cacao (Sterculiaceae) - hot
expression seed kernels
- Constituents: glycerides of stearic,
palmitic, arachidic, oleic acids
- Uses: suppository base
13. WHEAT GERM OIL
- Triticum aestivum - wheat grain; cold
expression
- Constituents: linoleic, palmitic, oleic,
linolenic acids
14. CASTOR OIL (VIRGIN CASTOR OIL)
- Ricinus communis (Euphorbiaceae) -
seeds
- Medicinal castor oil - colorless or pale
yellow liquid with slight odor; extremely
high viscosity
- Constituents: 46-53% fixed oils,
glycosides of ricinoleic, isoricinoleic,
stearic and dihydroxystearic acids
- Use: laxative
15. EVENING PRIMROSE OIL
- Oenothera app. (Onagraceae)- seeds;
expression
- Constituent: gamma linolenic acid
- Uses: dietary supplement; treatment of
atopic eczema
16. BORAGE OIL
- Brag officinalis (Boraginaceae) -
starflower;
- Seeds; expression
- Constituents: linoleic, gamma linolenic,
oleic, palmitic acid
- Use: same with evening primrose oil
17. SAW PALMETTO
- Serena repens (Arecaceae) - bartram;
endosperm
- Constituents: oleic, lauric, myristic and
palmitic acid
- Use: symptomatic relief of benign prostatic
hyperplasia
18. HYDNOCARPUS OIL
- Hydnocarpus wightiana, H. anthelmintica,
H. heterophylla and Taraktogenos kurzii;
ripe seeds; cold expression
- Constituents: hydnocarpic acid, golric PHENOLS AND PHENOLIC GLYCOSIDES
acid, and chaulmoogric acid
- Phenols or polyphenolic compounds - comprised
19. WOOL FAT to different classifications; substituents to some
- Anhydrous lanolin; purified fat-like plant metabolites
substance
- Ovis aries; wool of the sheep Glycosidic compound - attached with a phenol-
- Pale yellow, tenacious substance with a related moiety or substituents; considered to be
faint but characteristic odor plant metabolites; has different classes or types
- Constituents: cholesterol and
isocholesterol, unsaturated monohydric Type of glycosides (related to polyphenols)
alcohols, lanoceric, lanopalmitic,
carnaubic, aliphatic alcohols (cetyl, cereal Glycosides also called as sugar ethers
and carnaubyl alcohols)
Two important concepts:
- Use: emollient base for creams and
ointments glycone (genin) or sugar moiety

20. LARD Aglycone - non sugar

- Purified internal fat of Sus scruff (flare-
abdominal fat) Cathecol -
- Soft, white fat with a non rancid odor
- Constituents: myristin, stearin, palmitin nd Eugenol - came from sweet clove oil; used as
olein dental analgesic

Vanilin - occurs in the pods of vanilla

21. BEESWAX
- Apis mellifera (honeycomb)
- Yellowish-brown or yellowish-white solid
- Constituents: myricyl palmitate and
myricyl stearate
- Uses; preparation of plasters, ointments
and polishes

22. CARNAUBA WAX

- Copernicus cerifera (Palmae); leaves
- Hard light brown to pale yellow in color
and moderate coarse powder
- Use: tablet coating agent
 Phenols and Phenolic
Glycosides, and their Derivatives
Phenols or polyphenolic compounds - comprised to
different classifications; substituents to some plant
metabolites
Glycosidic compound - attached with a phenol-
related moiety or substituents; considered to be
plant metabolites; has different classes or types of
glycosides (related to polyphenols) glycosides also
called as sugar ethers two important concepts:
glycone (genin) or sugar moiety and Aglycone - non
sugar
Phenols
- Probably constitute the largest group of
plant secondary metabolites
- Simple phenolic compounds
- Tannins
- Coumarins and their glycosides
- Anthraquinones and their glycosides
Simple phenolic compounds
- Catechol (0-dihydroxybenzene) occurs in
kola seeds and in the leaves of Gaultheria
spp.
- Resorcinol
- Eugenol
- Vanillin
**cathecol resorcinol eugenol -came from sweet
clove oil; used as dental analgesic vanilin - occurs in
the pods of vanilla ___
MEADOWSWEET
- it contains vanillin
- Filipendula ulmaria (Rosaceae)
- Occurs as clumps of broken leaflets
- Constituents: 70% salicylaldehyde, methyl
salicylate, benzaldehyde, benzyl alcohol and
vanillin
- Uses: diuretic and anti-inflammatory
OIL OF WINTERGREEN
- gaultheria plant spp contains the ester
methyl salicylate methyl salicylate - used to
sensitize salicylic acid aside from gautheria
oil it contains phenolic compound Catechol
- Gaultheria procumbens (Eriaceae) – leaves
- Betula lenta (Betulaceae)
- Gaultheria oil – 98% esters= methyl
salicylate
WILLOW BARK
- Salix purpurea (Purple willow); S.
daphnoides; S. fragilis (crack willow)
- Constitunets: salicin; other salicortin and
fragilin
- Uses: anti-inflammatory, tx of rheumatism,
arthritis and muscular pains
- Salicin - phenolic glycoside; attain from
purple willow or salix purpurea salicin -
natural aspirin because salicin also possess
the 4 As of therapeutic classes of aspirin
(Analgesic, Antipyretic, Anti-inflamatory,
Anti-thromobotic) widely used as a drug
product sa synthetic salaici high toxicity and
short halflife di madaling ma-excrete upon
ingestion
- therapeutic effects same lang
TAR (PIX LIQUIDA)
- source of tar wood tar, pine tar, creosote
guaiacol - parent compound of drug
compound called Guaiafenesin (sold as
expectorant)
- Wood tar- Stockholm tar
- Constituents: phenols, cresols, methyl
cresols, guaiacol
- Pine tar- guaiacol
- Creosote- from wood tar
- Use: antiseptic
BLACK HAW BARK
- Viburnum pruniform (Caprifoliceae)
- Contains 0.2% salicin, isovaleric acid and
tannins
HOPS
- Humulus lupulus (Cannabinaceae) –
strobiles
- Constituents: Xanthohumol and
acylpholoroglucinol –glucopyranosides
- Mild sedative propertys
KAMALA
- Mallotus philippinensis (Euphorbiaceae)-
trochomes/fruits
- Use: tx of tapeworm infestation
VANILLA
- once that they would undergo ___ process
it would produce vanillin flavoring agents,
confectionaries, food products, also
cosmetics and making perfumes
- vanilla planifolia (Orichidaceae) – unripe
fruits
- constituents: Glucovanillin, glucovanillic
acid
- used in cinfectionary and in perfumery
BEARBERRY LEAVES (UVA URSI)
- arbutin - very important phenolic glycoside;
used as powders comsmetiotical - cosmetic
product that possess biological effects that
it can alter integumentary system
- arctostaphylos uwa-ursi (Ericaceae)- leaves
- constituents: arbutin, methylarbuttin and 6-
7% tannins, catechol, ursine, and flavones
- use: diuretic and astringent
CAPSICUM
- capsicum annuum (Chillies/Red peppers)
- constituent: capsaicin
- Capsaicin - an alkaloid because it possesses
characteristics of glycosides and alkaloids;
nowadays, utilized in liniments due to its
 counterirritant property counterirritant for
arthritic pain – ointments
- Uses: condiment, rx of atomic dyspepsia
and flatulence (in creams for relief of pain
in osteoarthritis)
TANNINS
- tannins are widely utilized as an astringent
and hemostatic agents (pampatigil ng
blood)
- hydrolysable tannins
- condensed tannins
- pseudotannins
- greatest quantity in dead or dying cells
PSEUDOTANNINS
- Gallic acid
- catechize
- chlorogenic acid
- ipecuanhic acid
OAK BARK
- Quercus robur (Fagaceae) – young branches
– common oak
- Constituents: phlobatannins, ellagitannins,
and gallic acid; 3% pyrogallos
- Use: astringent
GALLS
- Turkish galls/turkey galls
- Quercus infectoria (Fagaceae)- young twigs
- Constituents: 50-70% gallotannic acid; gallic
acid, ellagic acid and sitosterol
- Use: source of tannic acids; astringent and
styptic
- Gallic acid - pseotannin
HAMAMELIS LEAF
- Witch hazel leaves
- Hamamelis virginiana (Hamamelidaceae)
- Constituents: hamamelitannin, gallitannins,
ellagitannins
- Use: astringent and hemostatic
TORMENTIL
- Potentilla spp. – dried rhizomes
- Contains hydrolysable tannins and
condensed tannins
- Use: astringent and antidiarrheal
HAWTHORN
hawthorn - chinese stimulates or regulates heart
muscles
- Crataegus monogyne and C. laevigata
(Rosaceae) – fruits
- Constituents: 1-3% oligomeric procyanidins
- Use: mild cardia tonic
AGRIMONY
- Agrimonia eupatoria (Rosaceae)
- Constituents: pyrogallol and tannins
- Use: mild astringent and anti-inflammatory
ALCHEMILLA
tannins - good for diarrhea due to its antibacterial
property hot tea - high in tannins kaya mao gina
inom
- Alchemilla xanthoclora (Rosaceae) –
floweing parts
- Constituents: ellagitannin (pedunculagin
and alchemillin)
- Use: astringent against bleeding and
diarrhoea
RHATANY
- Krameria triandra (Krameriaceae) – roots
- Constituents: Ratanhiaphenols I and II
- Use: antimicrobial
CATECHU
- Gambir or pale catechu
- Uncaria gambir (Rubiaceae) – young twigs
- Constituents: 7.33% catechins, 20-50%
catechuic acid, catechu red, quercetin and
fluorescin
- Use: astringent
COUMARINS AND GLYCOSIDES
coumarins and flavonoids have benzopyrene
nucleus, pero ang difference lang nila kay ang
conformation nila coumarins – derivatives of benzi-
alpha-pyrone
- benzene-alpha-pyrone flavonoids -
benzene-gamma-pyrone
ANGELICA ROOT
- angelica officinalis (Umbelliferae)
- constituents: furanocoumarins, bergapten,
angelicin, archangelic and apterin
- use: tx of bronchitis and dyspeptic
conditions
- potential- vasodilator
MELILOT
- mellitus officinalis (Leguminosae) –
flowering tops
- constituents: melitoside, dihydrocoumaric
acid (melitolic acid) and caffeic acid
ANTHRAQUINONES AND GLYCOSIDES
if tannins are used as astringent, anthraquinone
are used as cathartics or laxatives
- anthraquinones
- anthranols
- oxanthrones
- dianthrones
- aloin-type/C-glycosides
SENNA LEAD ANF FRUIT
increase the smooth muscle tone of the wall of the
colon, once the wall of the colon has been
affected, eventually, it would stimulate the
secretion of water and electrolytes or minerals in
the large intestine, thereby causing cathartics.
Increase the smooth muscle tone of the wall of the
colon
—> stimulate the secretion of water and
electrolytes/minerals in the large intestine cassia
acutifolia - also called as Alexandra sena cassia
anguvstifolia - also called as Tinevelly senna;
commercial source of sena senocot tablet used to
induce cathartic
- cassia senna; Cassia acutifolia; Cassia
anguvstifolia
- tinnevelly senna
- constituents: sennosides A and B, aloe-
emodin and rhein
- use: cathartic
CASCARA BARK
Cascara sagrada –
- Sacred bark;chittern bark
- Rhamnus purshianus /Frangula purshiana
- Constituents: 6-9% anthracene derivatives,
Cascarosides A,B,C, and D; aloins
Cascarosides A and B - optical polymers of
Barbaloin
Cascarosides C and D - optical isomers of Chysaloin
Lanes pill antiparasitic property
- Uses: purgative and cathartic
FRANGULA BARK (BUCKTHORN)
frangula is one of the components of the drug
called movicol (a laxative agent)
- Alder buckthorn
- Frangula alnus/ Rhomvus frangula
(Rhamnaceae)
- Constituents: 7.0% glucofrangulins (A and
B); frangulins A nad B; Rhamnoside
franguloside; Rhamnoglucosides
RHUBARB (CHINESE RHUBARB)
Rheum - contains anthrones such as chrysophanol
Anthrones – chrysaphanol
- Rheum palmatum and Rheum officnale
(Polygonaceae)
- Constituents: chrysophanol, aloe-emodin,
rhein, emodin and physicon
- Use: tx of diarrhea, purgative, and
astringent
ALOES
same genus and family of aloe vera
Aloe barbadensis and Aloe spicata are very rich in C
glycosides
Aloes - C-glycosides
Aloin A - Barbaloin Aloin b - Isobarbaloin it contains
anthrones as well
- Aloe spp. (Liliaceae)
- Constituents: C-glycosides and resins
- Chrysarobin and Madder
HYPERICUM
- St. John's wort- it contains hypericin it
contains anthraquinone ___ which is
hypericin di ginagamit as laxative, it is used
as antidepressant
- Hypericum perforatum (Clusiaceae)
- Constituents: anthraquinone (hypericin)
and prenylated phloroglucinol derivatives
- Use: tx of mild to moderate depression
NAPTHOQUINONES AND GLYCOSIDES
- Commonly occur in reduced and glycosidic
forms
- Fungicidal, antibacterial, insecticidal,
phytotoxic and anticarcinogenic
HENNA
- Lawsonia inermis (Lythraceae)- dried leaves
- Lawsone – coloring matter
(hydroxynapthoquinons)
- Stem bark – tx of liver problems (jaundice)
and enlargement of the liver and spleen
LITHOSPERMUS
- L. officinale (Boraginaceae)- gromwell;seeds
- Constituents: shikonin, scyllitol, caffeic,
chlorogenic, and ellagic acids
- Tx. Of burns, inflammations, wounds, and
ulcers
ALKANNA ROOT
- Alkanna tinctoria (Boraginaceae)- alkanet or
anchusae radix
- Constituents: alkannin, alkannan, and
shikonin
CHROMONES AND XANTHONES
- Structural derivatives of benzo-gamma
pyrone
- Chromosomes- isomeric with coumarins
- Xanthones- gentianaceae, guttiferae,
moraceae, and polygonaceae
- Gentian root – gentisin (yellow)
- Marila laxiflora – antifungal
- Mangiferin - anti-inflammatory,
antihepatotoxic and antiviral; hypericum
and chiretta
- Mycotoxin – claviceps purpurea (secalonic
acids)
FLAVONE AND RELATED FLAVONE GLYCOSIDES
- Flavonoids – occur as free state; largest
group of naturally occuring phenols
- Isoflavonoids – heartwood species of
Prunus and Iris
- Biflavonoids – Gintein and amentoflavone
AGNUS CASTUS FRUIT
- Vitex agnus (Verbanaceae) – chaste tree,
chaste berry and monk’s pepper
- Constituents: vitexin, penduletin and
kaempferol
BIRCH LEAF
- Betula pendula and Betula pubescens
(Betulaceae); leaves
 - Constituents: Quercetin and Avicularin
- Betulinic acid- anticancer agent

CALENDULA FLOWER
- Calendula officinalis (Compositae)
- Constituents: flavonoids, triterpenoids and
polysaccharides
- Uses: management of GIT disorders

SPINY RESTHARROW ROOT

- Ononis spinosa (Leguminosae) –
restharrow, cammock and stayplough
- Constituents: medicarpin (isoflavone)
- Uses: diuretic and anti-inflammatory; renal
diseases (kidney and bladder stones)

ANTHOCYANIDINS AND GLYCOSIDES

- Structurally related to flavones
- Constitutes the monomers of the polymeric
condensed tannins

STILBENES
- Biosynthesized from hydroxycinnamic acis
and acetate
- Rhaponticin and reservatrol
- Glycosidal constituent if rhubarb
- Reservatol0 archis, cassia, eucalyptus,
polygonum, and veratrum
- Pinosylvin – heartwood of pinus

LIGNANS AND LIGNIN

Lignans- dimeric compounds formed by the union
of two molecules of phenylpropene derivatives
Lignin – polymeric substance, component of woody
tissues and fibers
SAPONINS, CARDIOACTIVE DRUGS & OTHER STEROIDS
OCTOBER 26, 2021
Subject: Pharmacognosy with Plant and Medicine Chemistry (LECTURE)
PROFESSOR: JOSEPH MARI QUEREQUINCIA
➔ Plants that are containing saponin glycosides.
Saponins
- TRITERPENE GLYCOSIDES
- High MW and high polarity plants compounds -
that is why very miscible with aqueous
solvents
- Can easily be hydrolysed to aglycones and
sugars
- GLYCONE & AGLYCONE - the common
products when undergone hydrolysis.
- Easily undergoes hydrolysis
- 2 types:
1. Steroidal (tetracyclic
triterpenoids)
➔ Contain more than 5 cyclic
rings
➔ Related to sex hormones,
cortisone, diuretic steroids,
vitamin D and cardiac
glycosides
➔ Ex. Sarsaponin, Digitonin,
Gitonin, and Dioscin
I. DIOSCOREA SPECIES
➢ Dioscoreas-yams-starch
➢ Dioscorea floribunda
➢ Constituent: Diosgenin
➢ Use: anti-inflammatory
II. SISAL
➢ Agave sisalana (Agavaceae) - leaves
➢ Constituent: Hecogenin
➢ Use: anti-inflammatory
III. FENUGREEK
➢ Trigonella foenum-graceum
(Leguminosae) - seeds
➢ Constituent: trigonelline (- a unique
saponin), diosgenin, trigoneosides
➢ Use: antidiabetic,
cholesterol-lowering,
anti-inflammatory, antipyretic,
antiulcer and anti cancer
IV. SARSAPARILLA ROOT
➢ Smilax spp (Liliaceae)
➢ Smilax aristolochiaefolia (Liliaceae)
➢ Constituent: Parillin (a saponin
glycoside made up by aglycone,
Sarsaponin and glycone,
sarsamonoside, sarsasaponoside) and
Sarsaparilloside
➢ Use: treatment of syphilis,
rheumatism and certain skin diseases
V. BLACK COHOSH
➢ Actea racemosa (Ranunculaceae) -
rhizomes
➢ Constituent: Deoxyactein,
Cimiracemoside, Cimifugin
VI. BUTCHER’S BROOM
➢ Rusus aculeatus (Liliaceae)
➢ Constituents: sapogenin
(1B-hydroxydiosgenin/Ruscogenin)
➢ Use: anti-inflammatory
VII. ELEUTHEROCOCCUS
➢ Siberian Ginseng
➢ Eleutherococcus senticosus (Araliaceae) -
rhizomes
➢ Constituents: Eleutheroside B (Syringin);
coumarins
1
➢ Use: tx of rheumatoid conditions and
2. Pentacyclic triterpenoids
adaptogenic

➔ Contain at least 5 ring

VIII. GINSENG
moieties in its structure.
➢ Panax ginseng (Araliaceae) - roots
➢ Constituents: panaxosides, ginsenosides,
X. LIQUORICE ROOT
protopanaxatriol and protopanaxadiol;
➢ Example of plant that contains pentacyclic
Panaxans and chiketsusaponins are the most
➢ Glyrrhiza glabra var. Typica, glandulifera and
active compounds present in ginseng.
violacea - roots and stolons
➢ Use: tx of anemia, diabetes, gastritis, sexual
➢ Constituents: glycyrrhizin - a saponin
impotence and anti-aging, adaptogenic - a
glycoside, 50x sweeter than the table sugar,
stress releasing agent
glycyrrhizic acid, liquiritin - responsible for
➢ Korean ginseng - most expensive variety of
the yellow color and polysaccharides
ginseng
➢ Use: flavoring agent, demulcent and mild
➢ Panax notoginseng - a specie of ginseng in
expectorant; tx of inflammatory disease
south china.
➢ Caution must be observed as it can cause
➢ American ginseng - Panax quiqefolium
sodium and water retention. Not for patients
➢ Constituents: Quinquenosides
with hypertension and congestive heart
➢ Panax vietnamensis - vietnamese ginseng
failure.

IX. PENTACYCLIC TRITERPENOID

XI. PRIMULA ROOT
SAPONINS
➢ Primula veris (Primulaceae)- cowslip
➢ Abundant in dicotyledons
➢ Constituents: triterpenoid saponins
➢ Pentacyclic triterpenes - has expectorant
➢ Use: expectorant
properties
➢ Contains a lot of pentacyclic saponins
➢ 80 plant families
➢ Caryophyllaceae, sapindaceae, polygalaceae,
XII. QUILLAIA BARK
sapotaceae, theaceae
➢ Soap bark, panama wood, Quillaia
➢ Quillaja saponaria
➢ Constituents: hydroxygypsogenin (quillaic
acid) and gypsogenin
➢ Use: emulsifying agent

XIII. SENEGA ROOT

➢ Polygala senega (Polygalaceae) - roots
➢ Constituents: Senegin, seneginin
➢ Use: expectorant

XIV. GOLDENROD
➢ Solidagp gigantea ; Solidago canadensis
(Compositae)
➢ Constituents: bayogenin - unique type of
pentacyclic saponin

2
 ➢ Uses: tx of urolithiasis - (a condition related
to formation of crystals that occur in kidneys
or kidney stones, the oxalate crystals that
forms in the kidneys), hypertension,
rheumatism, cystitis - (inflammatory condition
in the urinary bladder).
XV. CENTELLA
➢ Indian pennywort, gotu kola, indian water
navelwort and tiger grass
➢ Centella asiatica (Umbelliferae) - aerial
parts
➢ Constituents: centelloside and medecasside -
2 saponin glycoside
➢ Use: mild diuretic antirheumatic and anti
hypertensive property as a vasodilator.
CARDIOACTIVE GLYCOSIDES
➔ Termed as “cardiac glycosides”
➔ Have highly specific actions in cardiac/heart
muscles.
➔ The phenanthrene rings from steroids are
both possessed by cardenolides and
bufadienolides.
➔ Differs in the ring moiety attached in the last
cyclic ring of the nucleus.
➔ 2 classes:
➢ CARDENOLIDES
- Most important and prevalent
- Has medical potential
- Contains a 5 carbon lactone ring
- Commercially available used to treat
cardiac conditions - the compound
digoxin.
- Plants that have cardenolides:
1. DIGITALIS
● Called purple foxglove - DIGITALIS
PURPUREA (Sacrophulariaceae) - dried leaves
- Constituents: Digitoxigenin and
Gitoxigenin
➔ Digitoxigenin
- Lipophilic and
reabsorbs easily.
- Action: cardiac muscle stimulant
● Gracian foxglove - DIGITALIS LANATA
(Sacrophulariaceae) - leaves
- Constituents: Digoxin and Lanatosides
- Uses: treatment of congestive heart
failure
➔ Digoxin - trade name: lanoxin
- The one used in medicine:
For congestive heart
failure/atrial fibrillation.
- Very polar/water soluble that
is why it used for medicinal
purposes.
- Can be excreted easily
- Available in tablets and elixir
forms.
● Both contains digitoxin, digoxin, and
deslanoside (an example of lanatoside
compound)
● Note: ang pagka toxic sa drug kay ga occur
because of the fact that the drug easily
reabsorbs ang isang active compound/drug
that is why it exhibits adverse effects. Kay
dapat ang design sa isa ka drug, it must be
excreted easily. Digoxin fits this standard
2. STROPHANTUS
- Strophantus kombe (Apocynaceae) -
seeds
- Constituents: K-strophantoside,
K-strophantidin
- Strophantus gratus - seeds; Ouabain
(G-Strophantin)
3
 ➔ More potent than digitalis
compound as a cardiac muscle
stimulant. Not used as drug
product because it is potent,
it can cause toxicity.
3. CONVALLARIA
- Lily of the valley - has a very toxic
compound called convollatoxin.
- Convallaria majalis (Convulvulaceae) -
rhizomes and roots
- Constituents: Convollatoxin,
Convalloside and Convallamaroside
- Other constituent: Convallaria keiskei
(Japanese lily of the valley) -
convallagenin
➢ BUFADIENOLIDES
- Toxic in nature
- Contains 6 membered lactone ring
- Plants - Liliaceae and Ranunculaceae
➔ Both are rich in bufadienolides.
- Toad venoms also contain bufadienolides
Other steroidal compounds:
1. WITHANOLIDES
- An example of steroidal lactones
➔ Present in the plant withania
somnifera (Solanaceae) -
hypnotics, antiseptic and
antimitotic
➔ Proven to be a hypnotic agent.
2. DESLANOSIDE
- A lanatoside
- Used in digitalisation process -
Deslanoside first, and if the pt does
not have adverse effects or
hypersensitivity reactions, saka
hatagan ug digoxin.
- Starting dose for patient prescribed
with digoxin. Used to check the
patient is compatible with the drug.
NOTE: SAPONINS in general, are
ANTI-INFLAMMATORY.

1. URGINEA MARITIMA (SQUILL)

- Drimia maritima (Liliaceae) or
Uruginea maritima - bulbs - studied to
have an expectorant property.
However, di siya magamit as drug
product as it can cause gastric
irritation.
- Constituents: Scillaren A snd Scillaren
B; glucoscillaren A
- Action: promotes mild gastric
irritation; expectorant
- Indian squill - Drimia indica or Urginea
indic
2. BLACK HELLEBORE
- Hellebrous niger (Ranunculaceae) - rhizomes
- Constituents: helleborin, helleborein, and
hellebrin; hellebrigenin
- Action: abortifacient; cardiotonic