Lesson 4.2. Glycosides in Philippine Medicinal Plants

Cardiac Glycosides

contains CPPP nucleus (Sterol)

Adelfa and Kampanero

examples of Cardiac Glycosides

positive inotropic agent

Cardiac Glycosides have a a._______________________, so it is usually used for patients with b.________________________ such as c.___________.

a = ?

heart failure

Cardiac Glycosides have a a._______________________, so it is usually used for patients with b.________________________ such as c.___________.

b = ?

digoxin

Cardiac Glycosides have a a._______________________, so it is usually used for patients with b.________________________ such as c.___________.

c = ?

Anthraquinone Glycosides

anthracene derivative because it contains heteroatoms in its structure

Sabila and Akapulko

examples of Anthraquinone Glycosides

peristalsis and bowel movement

Anthraquinone Glycosides increases a.____________________ so it is usually used as a b.__________________

a = ?

laxative

Anthraquinone Glycosides increases a.____________________ so it is usually used as a b.__________________

b = ?

Saponin Glycosides

soap-like nature because it froths that contains CPPP nucleus

Gogo Bark, Maguey, and Patolang Bilog

examples of Saponin Glycosides

soap and shampoo

Saponin Glycosides are usually used as ________________

Cyanophore Glycosides

• contains cyanide

• considered as a phytotoxin which leads to hypoxia (decrease in blood oxygen), CNS depression, respiratory depression, cherry red blood, pale and blue skin (cyanosis due to arrest in the respiratory center)

Kamoteng Kahoy

example of Cyanophore Glycosides

Isothiocyanate Glycosides

• example of S-Glycosides

• has a sulfurous odor

Mustasa

example of Isothiocyanate

Flavonoid Glycosides

• polyphenolic compounds

• diphenylpropane derivatives (C6-C3-C6 nucleus)

• photosensitive (undergoes photooxidation) so it should be stored in amber bottles

Limon, Cajel, Bitter Orange, and Suha

examples of Flavonoid Glycosides

antioxidant

Flavonoids have a.__________ properties which means it also has a b._______ property

a = ?

reducing

Flavonoids have a.__________ properties which means it also has a b._______ property

b = ?

Libas

Alcohol Glycosides example

Lactone

• cyclic ester

yellow bell and kalatsutsi

examples of Lactone Glycosides

Nerium oleander Linn.

CARDIAC GLYCOSIDES:

Adelfa

Scientific Name: ?

Family:

Common Name:

Apocynaceae

CARDIAC GLYCOSIDES:

Adelfa

Scientific Name:

Family: ?

Common Name:

Constituents:

Ceylon Tree/Oleander

CARDIAC GLYCOSIDES:

Adelfa

Scientific Name:

Family:

Common Name: ?

Constituents:

Oleandrin and Digoxin

CARDIAC GLYCOSIDES:

Adelfa

Scientific Name:

Family:

Common Name:

Constituents: ?

digoxin

the only cardiac glycoside that humans can tolerate but it is very potent in nature, with a narrow therapeutic index

toxic

CARDIAC GLYCOSIDES:

Adelfa

• All parts of the plants are considered a.________________ as it can poison livestock and humans. Ingestion of the plant can cause b._________________________.

• The pharmacologic actions of c.___________________, resemble those of digitalis glucosides. In human beings, toxicity manifests as d.________________________________________________________ attributed to digitalis poisoning.

• Despite its toxicity, oleander can be used for e.________________________________________________________

a = ?

cardiac, gastrointestinal, and CNS effects

CARDIAC GLYCOSIDES:

Adelfa

• All parts of the plants are considered a.________________ as it can poison livestock and humans. Ingestion of the plant can cause b._________________________.

• The pharmacologic actions of c.___________________, resemble those of digitalis glucosides. In human beings, toxicity manifests as d.________________________________________________________ attributed to digitalis poisoning.

• Despite its toxicity, oleander can be used for e.________________________________________________________

b = ?

neriin and oleandrin

CARDIAC GLYCOSIDES:

Adelfa

• All parts of the plants are considered a.________________ as it can poison livestock and humans. Ingestion of the plant can cause b._________________________.

• The pharmacologic actions of c.___________________, resemble those of digitalis glucosides. In human beings, toxicity manifests as d.________________________________________________________ attributed to digitalis poisoning.

• Despite its toxicity, oleander can be used for e.________________________________________________________

c = ?

nausea, vomiting, colic, decreased appetite, dizziness, drowsiness, bradycardia, and irregular heartbeats, pupillary dilation, and unconsciousness

CARDIAC GLYCOSIDES:

Adelfa

• All parts of the plants are considered a.________________ as it can poison livestock and humans. Ingestion of the plant can cause b._________________________.

• The pharmacologic actions of c.___________________, resemble those of digitalis glucosides. In human beings, toxicity manifests as d.________________________________________________________ attributed to digitalis poisoning.

• Despite its toxicity, oleander can be used for e.________________________________________________________

d = ?

heart conditions, asthma, epilepsy, cancer, dysmenorrhea, leprosy, malaria, and ringworm

CARDIAC GLYCOSIDES:

Adelfa

• All parts of the plants are considered a.________________ as it can poison livestock and humans. Ingestion of the plant can cause b._________________________.

• The pharmacologic actions of c.___________________, resemble those of digitalis glucosides. In human beings, toxicity manifests as d.________________________________________________________ attributed to digitalis poisoning.

• Despite its toxicity, oleander can be used for e.________________________________________________________

e = ?

Cascabela thevetia

CARDIAC GLYCOSIDES:

Kampanero

Scientific Name: ?

Family:

Common Name:

Constituents:

Apocynaceae

CARDIAC GLYCOSIDES:

Kampanero

Scientific Name:

Family: ?

Common Name:

Constituents:

Yellow Bell/Campanero

CARDIAC GLYCOSIDES:

Kampanero

Scientific Name:

Family:

Common Name: ?

Constituents:

Thevetin

CARDIAC GLYCOSIDES:

Kampanero

Scientific Name:

Family:

Common Name:

Constituents: ?

Seeds

CARDIAC GLYCOSIDES:

Kampanero

• a._______ yield a toxic compounds, mostly cardiac glycosides and their free aglycones such as thevetin, theveridoside, theveside, cerberine, peruvoside, perusitin, and digitoxigenin.

• Thevetin has been classified with the digitaline group so it has activity on the b.__________________________________________. It can also cause c.____________________________________________.

• Experiments have shown that thevetin produces death by d._________________.

a = ?

heart muscle, blood pressure elevation, and heart irregularities

CARDIAC GLYCOSIDES:

Kampanero

• a._______ yield a toxic compounds, mostly cardiac glycosides and their free aglycones such as thevetin, theveridoside, theveside, cerberine, peruvoside, perusitin, and digitoxigenin.

• Thevetin has been classified with the digitaline group so it has activity on the b.__________________________________________. It can also cause c.____________________________________________.

• Experiments have shown that thevetin produces death by d._________________.

b = ?

increased intestinal peristalsis, increased salivation, and pupil contraction

CARDIAC GLYCOSIDES:

Kampanero

• a._______ yield a toxic compounds, mostly cardiac glycosides and their free aglycones such as thevetin, theveridoside, theveside, cerberine, peruvoside, perusitin, and digitoxigenin.

• Thevetin has been classified with the digitaline group so it has activity on the b.__________________________________________. It can also cause c.____________________________________________.

• Experiments have shown that thevetin produces death by d._________________.

c = ?

asphyxiation and cardiac paralysis

CARDIAC GLYCOSIDES:

Kampanero

• a._______ yield a toxic compounds, mostly cardiac glycosides and their free aglycones such as thevetin, theveridoside, theveside, cerberine, peruvoside, perusitin, and digitoxigenin.

• Thevetin has been classified with the digitaline group so it has activity on the b.__________________________________________. It can also cause c.____________________________________________.

• Experiments have shown that thevetin produces death by d._________________.

d = ?

Aloe vera Linn or Aloe barbadensis Mill

ANTHRAQUINONE GLYCOSIDES:

Sabila

Scientific Name: ?

Family:

Common Name:

Constituents:

Liliceae

ANTHRAQUINONE GLYCOSIDES:

Sabila

Scientific Name:

Family: ?

Common Name:

Constituents:

Aloe Vera

ANTHRAQUINONE GLYCOSIDES:

Sabila

Scientific Name:

Family:

Common Name: ?

Constituents:

Aloin A (Barbaloin), Aloin B (isobarbaloin) and Aloe-emodin

ANTHRAQUINONE GLYCOSIDES:

Sabila

Scientific Name:

Family:

Common Name:

Constituents: ?

dried latex

ANTHRAQUINONE GLYCOSIDES:

Sabila

• a._____________ from leaf taken by mouth as b._________ as it contains aloin

• Plant materials derived from c._________________ (flower extract, leaf, leaf extract, leaf juice, leaf polysaccharides, leaf waters) are included in cosmetics only at low concentrations and are used for d.______________________.

• other uses include e.________________________________

a = ?

laxative

ANTHRAQUINONE GLYCOSIDES:

Sabila

• a._____________ from leaf taken by mouth as b._________ as it contains aloin

• Plant materials derived from c._________________ (flower extract, leaf, leaf extract, leaf juice, leaf polysaccharides, leaf waters) are included in cosmetics only at low concentrations and are used for d.______________________.

• other uses include e.________________________________

b = ?

Aloe barbadensis

ANTHRAQUINONE GLYCOSIDES:

Sabila

• a._____________ from leaf taken by mouth as b._________ as it contains aloin

• Plant materials derived from c._________________ (flower extract, leaf, leaf extract, leaf juice, leaf polysaccharides, leaf waters) are included in cosmetics only at low concentrations and are used for d.______________________.

• other uses include e.________________________________

c = ?

skin conditioning purposes

ANTHRAQUINONE GLYCOSIDES:

Sabila

• a._____________ from leaf taken by mouth as b._________ as it contains aloin

• Plant materials derived from c._________________ (flower extract, leaf, leaf extract, leaf juice, leaf polysaccharides, leaf waters) are included in cosmetics only at low concentrations and are used for d.______________________.

• other uses include e.________________________________

d = ?

aromatic, astringent, aperient, purgative, emmenagogue, emollient, cholagogue, laxative, stomachic, tonic, vulnerary

ANTHRAQUINONE GLYCOSIDES:

Sabila

• a._____________ from leaf taken by mouth as b._________ as it contains aloin

• Plant materials derived from c._________________ (flower extract, leaf, leaf extract, leaf juice, leaf polysaccharides, leaf waters) are included in cosmetics only at low concentrations and are used for d.______________________.

• other uses include e.________________________________

e = ?

Cassia alata

ANTHRAQUINONE GLYCOSIDES:

Akapulko

Scientific Name: ?

Family:

Common Name:

Constituents:

Fabaceae

ANTHRAQUINONE GLYCOSIDES:

Akapulko

Scientific Name:

Family: ?

Common Name:

Constituents:

Ringworm Bush

ANTHRAQUINONE GLYCOSIDES:

Akapulko

Scientific Name:

Family:

Common Name: ?

Constituents:

Chrysophanic Acid

ANTHRAQUINONE GLYCOSIDES:

Akapulko

Scientific Name:

Family:

Common Name:

Constituents: ?

fungicide

ANTHRAQUINONE GLYCOSIDES:

Akapulko

• Its a.___________ property derives from chrysophanic acid.

• Plant is considered as: b.___________________________

a = ?

alterative, astringent, abortifacient, aperient, expectorant, purgative, sudorific, hydragogue, diuretic, vermifuge

ANTHRAQUINONE GLYCOSIDES:

Akapulko

• Its a.___________ property derives from chrysophanic acid.

• Plant is considered as: b.___________________________

b = ?

Entada phaseoloides Linn. (Merr.)

SAPONIN GLYCOSIDES:

Gogo

Scientific Name: ?

Family:

Common Name:

Constituents:

Fabaceae

SAPONIN GLYCOSIDES:

Gogo

Scientific Name:

Family: ?

Common Name:

Constituents:

St. Thomas Bean

SAPONIN GLYCOSIDES:

Gogo

Scientific Name:

Family:

Common Name: ?

Constituents:

Echinocystic Acid and Entagenic Acid

SAPONIN GLYCOSIDES:

Gogo

Scientific Name:

Family:

Common Name:

Constituents: ?

bark

SAPONIN GLYCOSIDES:

Gogo

• Study reported saponin to be abundant in the a.______, less so in the b.____, plentiful in the c.______, and absent from the d.______.

• The infusion of the e.__________________ of the gogo vines in water contains saponin which has an f._____________________ effect.

• Accidental contact with the eye may cause g.________________.

• In the Philippines, it is used to make h.________________.

a = ?

wood

SAPONIN GLYCOSIDES:

Gogo

• Study reported saponin to be abundant in the a.______, less so in the b.____, plentiful in the c.______, and absent from the d.______.

• The infusion of the e.__________________ of the gogo vines in water contains saponin which has an f._____________________ effect.

• Accidental contact with the eye may cause g.________________.

• In the Philippines, it is used to make h.________________.

b = ?

seeds

SAPONIN GLYCOSIDES:

Gogo

• Study reported saponin to be abundant in the a.______, less so in the b.____, plentiful in the c.______, and absent from the d.______.

• The infusion of the e.__________________ of the gogo vines in water contains saponin which has an f._____________________ effect.

• Accidental contact with the eye may cause g.________________.

• In the Philippines, it is used to make h.________________.

c = ?

leaves

SAPONIN GLYCOSIDES:

Gogo

• Study reported saponin to be abundant in the a.______, less so in the b.____, plentiful in the c.______, and absent from the d.______.

• The infusion of the e.__________________ of the gogo vines in water contains saponin which has an f._____________________ effect.

• Accidental contact with the eye may cause g.________________.

• In the Philippines, it is used to make h.________________.

d = ?

cortex (Bark)

SAPONIN GLYCOSIDES:

Gogo

• Study reported saponin to be abundant in the a.______, less so in the b.____, plentiful in the c.______, and absent from the d.______.

• The infusion of the e.__________________ of the gogo vines in water contains saponin which has an f._____________________ effect.

• Accidental contact with the eye may cause g.________________.

• In the Philippines, it is used to make h.________________.

e = ?

emetic and stimulant effect

SAPONIN GLYCOSIDES:

Gogo

• Study reported saponin to be abundant in the a.______, less so in the b.____, plentiful in the c.______, and absent from the d.______.

• The infusion of the e.__________________ of the gogo vines in water contains saponin which has an f._____________________ effect.

• Accidental contact with the eye may cause g.________________.

• In the Philippines, it is used to make h.________________.

f = ?

conjunctivitis (eye irritation)

SAPONIN GLYCOSIDES:

Gogo

• Study reported saponin to be abundant in the a.______, less so in the b.____, plentiful in the c.______, and absent from the d.______.

• The infusion of the e.__________________ of the gogo vines in water contains saponin which has an f._____________________ effect.

• Accidental contact with the eye may cause g.________________.

• In the Philippines, it is used to make h.________________.

g = ?

hair tonic and shampoo

SAPONIN GLYCOSIDES:

Gogo

• Study reported saponin to be abundant in the a.______, less so in the b.____, plentiful in the c.______, and absent from the d.______.

• The infusion of the e.__________________ of the gogo vines in water contains saponin which has an f._____________________ effect.

• Accidental contact with the eye may cause g.________________.

• In the Philippines, it is used to make h.________________.

h = ?

Agave americana Linn.

SAPONIN GLYCOSIDES:

Maguey

Scientific Name:

Family:

Common Name:

Constituents:

Agavaceae

SAPONIN GLYCOSIDES:

Maguey

Scientific Name:

Family: ?

Common Name:

Constituents:

American Agave

SAPONIN GLYCOSIDES:

Maguey

Scientific Name:

Family:

Common Name: ?

Constituents:

Agamenoside

SAPONIN GLYCOSIDES:

Maguey

Scientific Name:

Family:

Common Name:

Constituents: ?

antiseptic, depurative, diuretic, and laxative

SAPONIN GLYCOSIDES:

Maguey

• uses:

Luffa cylindirca (Linn.) M. Roem

SAPONIN GLYCOSIDES:

Patolang Bilog

Scientific Name: ?

Family:

Common Name:

Constituents:

Cucurbitaceae

SAPONIN GLYCOSIDES:

Patolang Bilog

Scientific Name:

Family: ?

Common Name:

Constituents:

Gourd Towel/Sponge Gourd

SAPONIN GLYCOSIDES:

Patolang Bilog

Scientific Name:

Family:

Common Name: ?

Constituents:

Arjunolic Acid, Maslinic Acid, Machaerinic Acid, and Quillaic Acid

SAPONIN GLYCOSIDES:

Patolang Bilog

Scientific Name:

Family:

Common Name:

Constituents: ?

17 compounds originating from 5 triterpene sapogenins

SAPONIN GLYCOSIDES:

Patolang Bilog

• As a rich source of saponins, a.___________________________ were identified. Saponins were previously reported in b._____ and revealed to exhibit biological actions as c._________________________________

• Its fruits is considered as d.____________________________

a = ?

luffa

SAPONIN GLYCOSIDES:

Patolang Bilog

• As a rich source of saponins, a.___________________________ were identified. Saponins were previously reported in b._____ and revealed to exhibit biological actions as c._________________________________

• Its fruits is considered as d.____________________________

b = ?

immunostimulatory, anti-inflammatory, and fibronolysis

SAPONIN GLYCOSIDES:

Patolang Bilog

• As a rich source of saponins, a.___________________________ were identified. Saponins were previously reported in b._____ and revealed to exhibit biological actions as c._________________________________

• Its fruits is considered as d.____________________________

c = ?

anthelmintic, carminative, laxative, depurative, emollient, expectorant, diuretic, and lactagogue

SAPONIN GLYCOSIDES:

Patolang Bilog

• As a rich source of saponins, a.___________________________ were identified. Saponins were previously reported in b._____ and revealed to exhibit biological actions as c._________________________________

• Its fruits is considered as d.____________________________

d = ?

Manihot esculenta Crantz

CYANOPHORE GLYCOSIDES:

Kamoteng Kahoy

Scientific Name: ?

Family:

Common Name:

Constituents:

Euphorbiaceae

CYANOPHORE GLYCOSIDES:

Kamoteng Kahoy

Scientific Name:

Family: ?

Common Name:

Constituents:

Cassava

CYANOPHORE GLYCOSIDES:

Kamoteng Kahoy

Scientific Name:

Family:

Common Name: ?

Constituents:

Linamarin and Prunasin

CYANOPHORE GLYCOSIDES:

Kamoteng Kahoy

Scientific Name:

Family:

Common Name:

Constituents: ?

hydrocyanic acid

CYANOPHORE GLYCOSIDES:

Kamoteng Kahoy

• Upon hydrolysis yields a.________________ which are located in the b.________________________ and is removed through peeling.

• The bitter, more robust and planted for its starch serves as the source of c.___________.

• The d._____________ containing HCN are considered poisonous but easily dissipated by heat (thru boiling)

• The root is e._________________________ but poisonous when stale so it must be peeled and boiled thoroughly.

• The f._________________ is grown for use as a vegetable

a = ?

cortical layers of the roots

CYANOPHORE GLYCOSIDES:

Kamoteng Kahoy

• Upon hydrolysis yields a.________________ which are located in the b.________________________ and is removed through peeling.

• The bitter, more robust and planted for its starch serves as the source of c.___________.

• The d._____________ containing HCN are considered poisonous but easily dissipated by heat (thru boiling)

• The root is e._________________________ but poisonous when stale so it must be peeled and boiled thoroughly.

• The f._________________ is grown for use as a vegetable

b = ?

tapioca

CYANOPHORE GLYCOSIDES:

Kamoteng Kahoy

• Upon hydrolysis yields a.________________ which are located in the b.________________________ and is removed through peeling.

• The bitter, more robust and planted for its starch serves as the source of c.___________.

• The d._____________ containing HCN are considered poisonous but easily dissipated by heat (thru boiling)

• The root is e._________________________ but poisonous when stale so it must be peeled and boiled thoroughly.

• The f._________________ is grown for use as a vegetable

c = ?

roots

CYANOPHORE GLYCOSIDES:

Kamoteng Kahoy

• Upon hydrolysis yields a.________________ which are located in the b.________________________ and is removed through peeling.

• The bitter, more robust and planted for its starch serves as the source of c.___________.

• The d._____________ containing HCN are considered poisonous but easily dissipated by heat (thru boiling)

• The root is e._________________________ but poisonous when stale so it must be peeled and boiled thoroughly.

• The f._________________ is grown for use as a vegetable

d = ?

harmless when fresh

CYANOPHORE GLYCOSIDES:

Kamoteng Kahoy

• Upon hydrolysis yields a.________________ which are located in the b.________________________ and is removed through peeling.

• The bitter, more robust and planted for its starch serves as the source of c.___________.

• The d._____________ containing HCN are considered poisonous but easily dissipated by heat (thru boiling)

• The root is e._________________________ but poisonous when stale so it must be peeled and boiled thoroughly.

• The f._________________ is grown for use as a vegetable

e = ?

sweet variety

CYANOPHORE GLYCOSIDES:

Kamoteng Kahoy

• Upon hydrolysis yields a.________________ which are located in the b.________________________ and is removed through peeling.

• The bitter, more robust and planted for its starch serves as the source of c.___________.

• The d._____________ containing HCN are considered poisonous but easily dissipated by heat (thru boiling)

• The root is e._________________________ but poisonous when stale so it must be peeled and boiled thoroughly.

• The f._________________ is grown for use as a vegetable

f = ?

Brassica integrifolia

ISOTHIOCYANATE GLYCOSIDES:

Mustasa

Scientific Name: ?

Family:

Common Name:

Constituents:

Brassicaceae

ISOTHIOCYANATE GLYCOSIDES:

Mustasa

Scientific Name:

Family: ?

Common Name:

Constituents:

Mustard

ISOTHIOCYANATE GLYCOSIDES:

Mustasa

Scientific Name:

Family:

Common Name: ?

Constituents:

Sinnigrin

ISOTHIOCYANATE GLYCOSIDES:

Mustasa

Scientific Name:

Family:

Common Name:

Constituents: ?

anticancer, anti-inflammatory, antibacterial, antifungal, antioxidant, wound healing, and biofumigation

ISOTHIOCYANATE GLYCOSIDES:

Mustasa

• Due to Sinigrin, it functions as an _____________________________

myrosin

ISOTHIOCYANATE GLYCOSIDES:

Mustasa

• When sinigrin undergoes enzymatic hydrolysis using a.______, it will be converted to b._______________________ which is an c.____________.

a = ?

allyl isothiocyanate (mustard oil)

ISOTHIOCYANATE GLYCOSIDES:

Mustasa

• When sinigrin undergoes enzymatic hydrolysis using a.______, it will be converted to b._______________________ which is an c.____________.

b = ?

ester volatile oil

ISOTHIOCYANATE GLYCOSIDES:

Mustasa

• When sinigrin undergoes enzymatic hydrolysis using a.______, it will be converted to b._______________________ which is an c.____________.

c = ?

fever

ISOTHIOCYANATE GLYCOSIDES:

Mustasa

• bark is used to treat __________