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Questions and Answers
What is the primary advantage of alpha-arbutin over beta-arbutin?
What major component is produced when gaultherin undergoes hydrolysis?
Which of the following is a common use of salicin?
What is a potential side effect of high doses of salicin?
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From which plant is gaultherin sourced?
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What is the product of acid hydrolysis of Salicin?
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Which reagent produces a violet color when tested with Salicin?
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Which of the following is a source of populin?
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What is the byproduct of alkali hydrolysis of populin?
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Which chemical test results in a red color that disappears upon addition of water?
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Study Notes
Arbutin
- Alpha-arbutin, a synthetic form, is more stable and potent than the natural form, beta-arbutin.
- Alpha-arbutin is commonly used in high-performance skincare products due to its effectiveness.
Phenolic Ester Glycosides
- Gaultherin is a phenolic ester glycoside found in Wintergreen (Gaultheria procumbens).
- It is used as an analgesic, antipyretic, and anti-rheumatic.
- Upon hydrolysis (by acid or the enzyme gaultherase), it yields methyl salicylate, xylose, and β-D-glucose.
Phenolic Alcohol Glycosides
Salicin
- O-Hydroxybenzyl glucoside, found in willow barks (e.g., Salix fragilis).
- Used as an analgesic, antipyretic, and anti-rheumatic.
- Topical application can help treat skin conditions such as acne, psoriasis, and eczema.
- High doses can cause side effects similar to aspirin (e.g., stomach ulcers, bleeding, allergic reactions).
Populin
- A 6’- benzoyl salicin, found in Populus species.
- Hydrolysis by alkali yields benzoic acid and slicin.
- Acid hydrolysis yields benzoic acid, glucose, and saligenin.
Thioglycosides (Glucosinolates)
- Thioglycosides are S-glycosides, containing glucose.
- They are anions.
- Rich sources include oil seeds (rapeseed), condiments (mustard), and vegetables (broccoli, cabbage, and turnips).
Black Mustard
- Black mustard acts as a local irritant and emetic.
- Used externally as a rubefacient and commercially as a condiment.
- Possesses anticarcinogenic properties.
Sinigrin
- Found in the seeds of Brassica nigra (black mustard).
- Hydrolysis yields glucose, sulfate, and allyl isothiocyanate.
Sinalbin
- Found in the seeds of Brassica alba (white mustard).
- Hydrolysis by the myrosinase enzyme yields p-hydroxybenzyl isothiocyanate, sinapine acid, sulfate, and glucose.
Isoflavonoid Glycosides
- Diadizin and genistin are isoflavonoid glycosides.
- Diadizin occurs in soya beans (Glycine max) and genistin in Genista lupines and Prunus spp.
- Both yield their respective aglycones (diadzein and genistein) and glucose upon hydrolysis.
- Isoflavones are considered dietary phytoestrogens and cancer protective compounds.
- Diadzin is used as an antioxidant.
Biflavones Glycoside
- Amentoflavone is a biflavones glycoside, found in Ginkgo biloba, formed by the linkage of two Apigenin molecules.
- It is used as a uterine antispasmodic, and helps delay diabetic cataract and diabetic neuropathies.
- It also acts as a cardiotonic.
Flavanolignans
- Silymarin is a mixture of various flavanonol or flavanol derivatives, found in the fruits of Silybum marianum.
- It consists of three principle components: silybin, silychristin, and silydianin.
- Silymarin has hepatoprotective properties, protecting the liver from damage caused by metabolic toxins.
- It is used in liver dysfunction and after hepatitis treatment.
- It also has antioxidant activity.
Cyanogenic Glycosides
- Linamarin is a cyanogenic glycoside, found in flax (Linum usitatissimum).
- Hydrolysis yields glucose and acetone cyanohydrin.
- Further hydrolysis yields glucose, acetone, and hydrocyanic acid.
Amygdalin
- Found in bitter almond seeds (Prunus amygdalus) and kernels of apricots (Prunus armeniaca), peaches, and plums.
- Used in the preparation of benzaldehyde, a volatile oil of bitter almond, which acts as a bactericidal, antispasmodic, and sedative.
- Hydrolysis by a mixture of three enzymes (amygdalin hydrolase, prunasin hydrolase, and mandelonitrile lyase) yields benzaldehyde, HCN, and two molecules of glucose.
Method of Isolating Amygdalin
- The fruits are cracked to obtain the kernels, which are dried in the sun or in ovens.
- The kernels are boiled in ethanol.
- Evaporation of the solution and the addition of diethyl ether precipitates amygdalin as white crystals.
Rutinose
- A sugar moiety formed from rhamnose and glucose.
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Description
Explore the roles of alpha-arbutin, salicin, and gaultherin in skin care and medicinal applications. This quiz covers their properties, uses, and potential side effects. Test your knowledge on these phenolic compounds and their benefits.
