PHA6117: Glycosides

inactive

inactive

glycone: ______ (active/inactive) sugars

active

aglycone/genin: non-sugar ____ (active/inactive) portion

Beta form

What form of glycosides occur in plants?

Myrosin
Emulsin

enzymes that can hydrolyze glycosides?

Emulsin

What enzyme can only target the beta forms of glycosides?

Tannins

special polyphenolic glycosides with many distinct properties

Aglycones

too different to be generalized

Mevalonate Pathway
Shikimic Acid Pathway

Important pathways

Glycone

from photosynthesis

Tannins

also from the shikimic acid pathway

Shikimic Acid Pathway

Gives rise to aromatic amino acids

prephenic acid branch

What branch of shikimic acid pathway give rise to the phenylpropanoids (shortcut: C6-C3's)>

glycosides and volatile oils

Many _____ and _____ are classified as phenylpropanoids

phenylpropanoids

Many glycosides and volatile oils are classified as ________

LIGNANS

Union of two phenylpropanoid molecules

Lignin

polymeric substance that assists cellulose in
strengthening cell walls

- Silymarin derivatives
- Podophyllotoxin

Important lignans

A) Anthraquinone
B) Phenol
C) Alcohol

Glycosides related to the Shikimic Acid Pathway: From chorismate

D) Aldehyde
E) Flavonoid
F) Lactone

Glycosides related to the Shikimic Acid Pathway: From prephenate

F) Saponins
G) Cardiac glycosides

Glycosides related to the Mevalonic Acid Pathway

H) Cyanophores
I) Glucosinolates
J) Miscellanous

Other Glycosides

oxidized forms of anthracene

ANTHRAQUINONE GLYCOSIDES: Aglycones are ______ forms of _______

- Anthraquinones
- Oxanthrones
- Anthranols
- Anthrones
- Dianthrones

ANTHRAQUINONE GLYCOSIDES Can be classified as

- Orange-red colored compounds
- Soluble in dilute alcohol and boiling/hot water
- Give a red, violet, or green color with a base
- Cathartic action (except chrysarobin)

ANTHRAQUINONE GLYCOSIDES: Characteristics

chrysarobin

Characteristic of their cathartic action, except for __________, which is too irritating to the GIT

red color on the lower alkaline layer

Positive result of borntrager's test

very stable form of anthraquinone especially the reduced types of anthranol

Negative result on the Borntrager's test indicates what?

ferric chloride/peroxide

What is the modification added to the MODIFIED BORNTRAGER'S TEST so it can force oxidative hydrolysis?

(+) pink or red color in the alkaline layer

MODIFIED BORNTRAGER'S TEST: Positive Result

presence of a very stable type of anthraquinone

Positive result on the modified borntrager's test indicates what ?

SACRED BARK
Cascara sagrada

Rhamnus purshianus common name

Rhamnus purshianus

SACRED BARK; Cascara sagrada Scientific Names

Rhamnaceae

SACRED BARK; Cascara sagrada (Rhamnus purshianus): Family

Barbaloin (Cascarosides A and B), chrysaloin(Cascarosides C and D)

SACRED BARK; Cascara sagrada (Rhamnus purshianus): Constituents

Cascarosides A and B

Barbaloin →

Cascarosides C and D

chrysaloin →

Cathartic for habitual constipation

SACRED BARK; Cascara sagrada (Rhamnus purshianus): Uses

Casanthranol

purified mixture of the anthranol glycosides, and is combined with surfactants or hydrocolloids

1 year

How long should sacred bark be stored prior to use?

cure with MgO or alkaline earths

What is done to reduce the bitter taste of sacred bark?

FRANGULA
Alder buckthorn

Rhamnus frangula Common names

Rhamnus frangula

FRANGULA; Alder buckthorn: Scientific Name

Rhamnaceae

FRANGULA; Alder buckthorn (Rhamnus frangula): Family

Frangulin, glucofrangulin

FRANGULA; Alder buckthorn (Rhamnus frangula): Constituents

Cathartic

FRANGULA; Alder buckthorn (Rhamnus frangula): Use

frangula + karaya

"Movicol" = _____ + _____

Sabila

ALOE Synonym

Aloe barbadensis

Curacao aloe SN

Aloe ferox/ Aloe spicata

Cape aloe SN

Aloe perryi

Zanzibar/Socotrine aloe SN

Liliaceae

Aloe: Family

Barbaloin, emodin, aloe emodin

Aloe: Constituents

Cathartic, used for compound benzoin tincture

Aloe: Uses

treatment of burns, abrasions, skin irritations,
purgative, alopecia

Aloe vera Gel: uses

lotion or yogurt production

Stabilized aloe is used for

Rheum officinale, R. palmatum, R. raponticum

RHUBARB SN

RHUBARB

Rheum officinale, R. palmatum, R. raponticum Common name

Polygonaceae

RHUBARB (Rheum officinale, R. palmatum, R. raponticum): Family

- Rhein anthrones (at 2.2%)
- glucorhein
- glucogallic acid

RHUBARB (Rheum officinale, R. palmatum, R. raponticum): Constituents

Rhanponticin

adulterant from rhapontic rhubarb - blue fluorescence

For jaundice, kidney stones

RHUBARB (Rheum officinale, R. palmatum, R. raponticum): Use

Chinghai, Shensi-type

High-grade Rhubarb

• High-grade (Chinghai, Shensi-type)
• Medium grade (Canton-type)
• Third grade

Types of Rhubarb

Canton-type

Medium grade

Dried leaflets of
• Cassia angustifolia (Tinnevelly senna)
• C. acutifolia (Alexandria senna)

Family: Fabaceae

SENNAS/ SLIMMING TEA: Source; Family

C. acutifolia (Alexandria senna)

pink w/ MgOAc in daylight, green-orange in filtered uv

Cassia angustifolia (Tinnevelly senna)

orange w/MgOAc in daylight, yellow-green in filtered uv

Sennosides A and B (major),
sennosides C and D (minor)

SENNAS/ SLIMMING TEA Constituents

Very potent cathartic (more so than cascara sagrada)

SENNAS/ SLIMMING TEA Use

SENNAS/ SLIMMING TEA

Cultivated on wet lands resembling rice paddies; as successor to rice

Argel leaves (Solenostemma arghel)

SENNAS/ SLIMMING TEA are Adulterated with _____

Blue-green leaves

What leaves of Senna are the best quality?

White-yellow leaves

What leaves of Senna are the poorest quality?

Scientific Name: Andira araroba
Family: Fabaceae
Constituents: Chrysarobin (anthranol-type)
Use: Keratolytic agent, for psoriasis, trichophytosis, eczema

GOA POWDER
- SN
- Family
- Constituents
- Use

by hot benzene

How is Chrysarobin extracted?

Chrysarobin

only anthraquinone glycoside too irritating for oral use

Anthralin

replaced the use of chrysarobin

Scientific Name: Hypericum perforatum
Family: Hypericaceae
Constituents: Hyperforin, hypericin
Use: enzyme inducer, "nature's Prozac"

ST. JOHN'S WORT (SJW)
- SN
- Family
- Constituents
- Use

Hyperforin

prenylated ring -acts as reuptake inhibitor -> increase neurotransmitters

ST. JOHN'S WORT (SJW)

Was once dubbed as "Nature's Prozac"; Claims to treat depression; well-known enzyme inducer

Enzyme inducers

increase drug metabolism and can potentially lower drug DoA and/or efficacy

Hyperforin

well-known natural product that induces CYP enzymes

Danthron
Cochineal

ANTHRAQUINONES AS PIGMENTS

Chrysazin/ 1,8-dihydroxyanthraquinone

Danthron

Danthron

• Cathartic
• For production of anthralin and indanthrene dyestuffs

• Dried female insect of Dactylopius coccus
• Carminic acid
• Colorant

Cochineal Source, constituent, use

phenolic group

PHENOL GLYCOSIDES aglycone

Millon's Test

PHENOL GLYCOSIDES is detected by

peach/salmon/pink-colored Hg complex of nitrophenyl derivative

Millon's Test positive result

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

BEARBERRY
- Synonyms
- SN
- Family
- Constituents
- Use

hydroquinone

Hydrolysis of arbutin yields

tyrosinase-inhibiting

Arbutin has some _______ effect causing the skin-lightening potential

hydrocarbon bearing an alcohol moiety

ALCOHOL GLYCOSIDES: Aglycone

salicylates

ALCOHOL GLYCOSIDES are dominated by

Ester Formation

ALCOHOL GLYCOSIDES are detected by:

Scientific Name: Salix purpurea and S. fragilis
Family: Salicaceae
Constituents: Salicin
Use: Antirheumatic, anti-inflammatory

WILLOW
- SN
- Family
- Constituents
- Use

salicyl alcohol by emulsin

Salicin is hydrolyzed to yield _______ by ______

oxidized; salicylic acid

Salicyl alcohol can be _______ in the lab to yield ______

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

POPLAR
- SN
- Family
- Constituents
- Use

Part Used: bark
SN: Viburnum prunifolium
Family: Caprifoliaceae
Constituents: Has 0.2% salicin, isovaleric acid
Use: Dysmenorrhea, bleeding, asthma

BLACK HAW
- Part Used
- SN
- Family
- Constituents
- Use