[3] GLYCOSIDES: SHIKIMIC ACID PATHWAY

Type of Anthraquinone: carminic acid

Anthraquinone

Type of Anthraquinone: Cascara sagrada (bitter bark) or Rhamnus purshianus (sacred bark)

Oxanthrone

Type of Anthraquinone: Andira araroba (Chrysarobin)

Anthranol

Type of Anthraquinone: Cassia, Sena leaves, Rhubarb

Dianthrone

Most water soluble anthraquinone aglycone due to its carboxylic acid group

Rhein

Anthraquinone qualitative tests: Antrhaquinones are soluble in?

dilute alcohol and boiling/hot water

Anthraquinone qualitative tests: Give a _________ color with a base (ex. NH₃/ NaOH)

red, violet, or green

Anthraquinone qualitative tests: has a characteristic ______ action except for chrysarobin (Andira araroba)

cathartic/laxative

Anthraquinone qualitative tests: A test that involves the extraction using an organic solvent followed by the addition of a base.

Borntrager’s Test

Anthraquinone qualitative tests: In Borntrager’s Test, the sample is positive if there is a presence of _____ on the lower alkaline layer.

red color

Anthraquinone qualitative tests: If the sample is negative in the Borntrager’s Test, it indicates that the anthraquinone is _________, hence need to proceed to the modified Borntrager’s Test.

very stable

Anthraquinone qualitative tests: In the Modified Borntrager’s Test, the test is positive is there is the presence of _______ color in the alkaline layer

pink or red color

Anthraquinone qualitative tests: In Modified Borntrager’s Test, the addition of _________ force oxidative hydrolysis to release the aglycone unit.

ferric chloride or peroxide

Anthraquinone qualitative tests: If the anthraquinone is too stable, the reaction/s ________ must occur

hydrolysation and oxidation

Constituents of Sacred Bark

Barbaloin (cascarosides A and B), and Chrysaloin (C and D)

Used as a cathartic for habitual constipation, which restores the natural tone of the colon.

Sacred Bark

_______ is a purified mixture of anthranol glycosides.

Casanthranol

Casanthranol should be aged for at least _______ prior to use to oxidize it to an anthraquinone and lessen its toxicity

1 year

To reduce the bitter taste of bitter bark, curing using ___________ is done

MgO or alkaline earth metals

Chronic use of Casanthranol (Sacred bark) can cause ________, which causes the discoloration of the colon.

Melanosis coli

Scientific name of Sacred bark

Rhamnus purshianus

Scientific name of Frangula, also called Alder buckthorn

Rhamnus frangula

Used as cathartic or a bulk laxative together with karaya (Movicol^®) but is not commonly used in the local setting

Frangula

Scientific name of Curacao aloe

Aloe barbadensis

Scientific name of Cape aloe

Aloe ferox / Aloe spicata

Scientific name of Zanzipar/Socotrine aloe

Aloe perryi

Family of Aloe

Liliaceae or Asphodelaceae

Constituents of Aloe

Barbaloin and emodin

Used as a cathartic in benzoin tincture.

Aloe

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

Aloe vera Gel

Stabilized aloe is used for _____ production.

lotion or yogurt

False rhubarb (no cathartic activity)

Rheum raponticum

Family of Rhubarb

Polygonaceae

Considered a Rhein anthrones (at 2.2%), glucorhein, glucogallic acid due to its carboxylic acid attached at the anthracene.

Rhubarb

Rhubarb type: High-grade

Chinghai, Shensi-type

Rhubarb type: Medium grade

Canton-type

A Rhubarb derivative used as adulterant from rhapontic rhubarb, which shows a blue fluorescence

Rhanponticin

Rhubarb with cathartic activity

Rheum officinale and Rheum palmatum

Used for jaundice and kidney stones

Rhubarb

Dried leaflets of Cassia species used as a very potent cathartic (more so than Cascara sagrada). It is used only for a week as it can cause too much water loss.

Sennas / Slimming Tea

Family of Senna / Slimming tea

Fabaceae

Alexandria Sennas leaves found in Egypt that is _____ with MgOAc in daylight, and ________ in filtered uv

pink; green-orange

Tinnevelly Sennas leaves found in India that is _____ with MgOAc in daylight, and ________ in filtered uv

orange; yellow-green

Senna leaves found in Egypt

Cassia acutifolia (Alexandria senna)

Sennas leaves found in India

Cassia angustifolia (Tinnevelly senna)

Constituents of Sennas leaves

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

Sennas leaves is adulterated with _______ due to its similar composition

Argel leaves (Solenostemma arghel)

Blue green Sennas leaves: ________ quality

Yellow Sennas leaves: ______ quality

best; poorest

Sennas leaves contain a _______ anthraquinone

Dianthrone

Scientific name of Goa Powder

Andira araroba

Family of Goa Powder

Fabaceaea

The anthranol constituent of Goa powder

Chrysarobin

Only anthraquinone used as a topical or keratolytic agents (e.g., in shampoo), to treat psoriasis, trichophytosis, eczema

Goa powder

Chrysarobin is extracted by _______

hot benzene

______ has replaced the use of chrysarobin (a synthetic derivative) because of its kidney toxicity and tumor promoting activities

Anthralin

Scientific name of St. John’s Wort (SJW)

Hypericum perforatum

Family of St. John’s Wort (SJW)

Hypericaceae

Constituents of St. John’s Wort (SJW)

Hyperforin and Hypericin

_______ is a prenylated ring, whcih acts as reuptake inhibitor → increase neurotransmitters in the synapse.

Hyperforin

Was one dubbed as “Nature’s Prozac” (Fluoxetine), an selective serotonin reuptake inhibitor (SSRI) used to treat depression

St. John’s Wort (SJW)

SJW is a well-known enzyme inducer, specifically ______ enzymes

CYP450

SJW is contraindicated for patients

taking contraceptives and warfarin

Enzyme inducers (like hyperforin) increase drug metabolism and can potentially _____ drug DoA and/or efficacy

lower

The one treating depression. If you notice in its structure, it has lipid groups as its “tail” (ung mukhang elisi), which is non-soluble and thus, can cross the BBB.

Hyperforin

Structure of Danthrone

Chrysazin/1,8-dihydroxyanthraquinone

Anthraquinones as pigments: Used for production of anthralin and indantherene dyestuffs but also as a cathartic

Danthrone

Anthraquinones as pigments: used as a colorant in lipstick (carminic acid)

Cochineal

Cochineal is from a dried female insect of ________ often found in cacti (mexico)

Dactylopius coccus

Compounds like salicylic acid and phenolic compounds give a positive result to this test.

Millon’s Test

What are the qualitative tests to detect aldehydes

Fehling’s, Nessler’s Tollen’s, and Schiff’s

All phenols are positive in millions test

False

In the MIllon’s test detecting phenolic groups, a positive result is a _____ colored Hg complex of nitrophenyl derivative

peach/salmon/pink

Most tannins and flavonoids are also phenol glycosides by technicality (their structure are intrinsically phenolic too)

True

What branch of the shikimic acid pathway are phenol glycosides derived from?

chorismate branch

A phenolic glycoside used as a diuretic, astringent and antiseptic but also has skin-lightening potential

Bearberry/Rockberry

Family of Bearberry/Rockberry

Ericaceae

Scientific name of Bearberry/Rockberry

Arctostaphylos uva-ursi

Constituents of of Bearberry/Rockberry

Arbutin and ericolin

______ has some tyrosinase-inhibiting effect. Since, tyrosinase is the precursor for melanin, if inhibited, melanin-production is halted, which causes skin-lightening potential

Arbutin

An aglycone dominated by the salicylates and is detected by ester formation.

Alcohol glycosides

What branch of the shikimic acid pathway are alcohol glycosides (like salicylates) derived from?

chorismate branch

Scientific name of Willow

Salix purpurea and Salix fragilis

Family of Willow

Salicaceae

Salicin is hydrolyzed by emulsin to yield ______

Salicylalcohol

Salicylalcohol can be oxidized in the lab to yield ________

Salicylic acid

Used as antirheumatic and anti-inflammatory once its major constituent is acetylated

Willow

Constituent of Willow

Salicin

Scientific name of Poplar

Populus tremuloides

Family of Poplar

Salicaceae

Constituent of Poplar

Populin (benzoylsalicin)

Can be used as a quinine substitute (anti-malarial), expectorant, antipyretic, and analgesic

Poplar

Common ingredient of herbal cough mixtures (expectorant)

Poplar

Which of the following is not true about an aldehyde glycoside

Synthesized under the chorismic branch

A hydrocarbon bearing the formyl group CHO

Aldehyde glycosides

Aldehyde glycosides are synthesized under ______

prephenate branch

Aldehyde glycosides are represented by ______

Vanillin

IUPAC name of Glucovanillin

4-hydroxyl-3-methoxy benzaldehyde

The non-aromatic, water-soluble, glycosylated form of vanillin

Vanillin-O-glucoside or Glucovanillin

Glucovanillin has to undergo ________, a curing process to hydrolyze/release vanillin and glucose—the final aroma and flavor of vanilla

sweating

Prephenate is converted to _______ then to _______ then ______ to form Vanillin

Prephenate → Coumaric acid → Caffeic acid → Ferulic acid → Vanillin