Session 4- Chemical Classes of Natural Products found in botanical DS

How many different natural product molecules may be present in a given botanical DS extract?

thousands

What are the major groups of natural products that may be found in botanical DS?

isoprenoids, phenolics, and alkaloids

What is the molecular weight of small organic compounds that are so called natural products (secondary metabolites)?

less than 2,000 daltons

How do secondary metabolites differ from primary metabolites?

secondary metabolites don’t have a role in the primary metabolism of the producing organism

plant secondary metabolites have an ecological role and exist in the correct chiral form to exhibit biological activity

What are volatile oils?

complex mixtures of isoprenoids and phenylpropanoids

Isoprenoids are based on the isoprene unit. What is this unit?

C5H8

How many isoprene units are in monoterpenes?

2

How many isoprene units are in sesquiterpenes?

3

How many isoprene units are in triterpenes?

6

What is the indication of Filsuvez?

applied as a gel for wounding of the skin associated with dystrophic and junctional epidermolysis bullosa

What is Filsuvez composed of?

triterpenes

What are phenylpropanoids?

simple aromatic compounds with a propyl side chain (C3) and occur along with simple terpenoids in plant volatile oils

What is the chemical formula for flavonoids?

C6-C3-C6

What do Ginkgo leaves consist of?

flavonoid glycosides

What is the major flavonoid ester in green tea?

EGCG

What does green tea contain?

mixtures of a flavonoid subtype known as catechins

What was Crofelemer approved for?

antidiarrheal agent for humans

What is found in Deadly nightshade?

atropine

What type of alkaloid is atropine?

tropane

What is a tropane alkaloid?

contains a heterocyclic tertiary nitrogen atom

What type of alkaloid is berberine?

quaternary

What is berberine found in?

the plant goldenseal

What activities does berberine have?

antiamebic, antibacterial, anti-inflammatory

What are the general properties of true alkaloids?

alkaloid common names end in “ine”. Named after the plant genus or pharmacological effect

biosynthesized in their plant of origin from amino acid precursors

classified according to the type of nitrogen-containing heterocyclic ring system present

tend to be water soluble because they occur in the plant in the form of salts complexed with small organic acids

How do protoalkaloids differ from true alkaloids?

do not contain a heterocyclic nitrogen ring

How do pseudoalkaloids differ from true alkaloids?

not biosynthesized from an amino acid

Mescaline is an example of which type of alkaloid?

protoalkaloid

Caffeine is an example of what type of alkaloid?

pseudoalkaloid

What is ephedrine used for?

bronchodilator

What type of alkaloid are ephedrine and pseudoephedrine?

protoalkaloid

What are anthraquinone glycosides used for?

laxatives

Why are alkaloids not generally found in botanical dietary supplements?

due to their general CNS toxicity