4- chemical classes of plants and natural products

Major groups of natural products

isoprenoids, phenolics, alkaloids

How many natural products may be found in a botanical?

thousands

Natural product=

secondary metabolite

What is considered a natural product

small compounds weighing less than 2,000 DA often nonpolar, soluble with organic solvent

examples of primary metabolites

amino acids, sugars, nucleic acids

how are primary metabolites different than secondary

secondary do not have role in primary metabolism of producing organism

What kind of role to plant secondary metabolites have

ecologicol

What is a simple isoprenoid (terpenoid)

made on isopren, with monoterpenes and sesquiterpenes

Voltatile oilds role in herbal teas

add flavor

do volitile oils have solublity in water

some solubility

what is a volatile oil

give off an odor and are used in perfumery and medicinally

what are volatile oilds made of

isoprenoids and phenylpropanoids

isoprene forumla

C5H8

monoterpene formula

C10H16

sesquitterpene formula

C15H24

How are isoprene units attached

head to tail

what is a triterpene

six isoprene unit skeleton

What drug approved by the FDA is composed of triterpenes

filsuvez

filsuevez use

gel for wounding of skin from dystrophic and junctional epidermolysis bullosa

Common isoprenoids

geraniol, cadinene, menthol

What is a phenylpropanoid

simple aromatic compound with C3 side chain and happen with simple terpenoids in plant volatile oils

three common phenylpropanoids

eugenol

cinnamaldehyde

methyl salicylate

How do the flavonoids of green tea occur?

as esters of ()-epicatechin

are the flavonoids of green tea water soluble?

yes because large amt of OH present

What does green tea contain a mixture of

flavonoid subtype called catechin

What is epigallocatechin gallate

major flavonoid of green tea

Function of epigallocatechin gallate

antioxidant that is highly studyed

What is veregen

polyephenon E= sinecatchins

What is veregen used for

venereal and perineal warts

What is a flavonoid structure

C6-C3-C6

what are flavonoids

common plant phenol in plant or as free form

what is the free form of flavanoid

aglycones

what is the more water soluble form of flavanoids

glycosides

example of glycoside

ginkgo

Common flavanoids

quercetin, flavonoid glycoside

what is quercetin sub class

flavone

What is crofelmer

complex mixture of proanthocyanidins with thousands of compounds

What is crofelemer now known as

mytesi

what is mytesi used for/ canalelevia CA1

anti diarrhea for humans and dogs

What do alkaloids names end in

ine

How are alkaloids made

biosynthesized in plant of origin from amino acid precuroser

how are alkaloids classified

according to the type of nitrogen containing heterocyclic ring system present

what kind of alkaloid is atropine

tropane

why are alkaloids water soluble

because they are salts complexed with small organic acids

example of small organic acids for alkaloids

citrate malate tartrate

Physical look of alkaloids

colorless, crystalline, and sharp melting point

how can solubility of alkaloids be manipulated

during extraction process according to the pH of solvents used

In what PH are alkaloid free bases soluble in

organic solvents like CHCL3 @ high pH like 8.5

In what conditions are alkaloid salts soluble

in water at low pH values 3.5

Atropa belladonna

deadly nightshade

What alkaloid is found inside of deadly nightshade?

atropine, a tropane alkaloid

What is atropine classified as

a true alkaloid because it has a heterocyclic tertiary nitrogen atom

wha kind of compound is atropine chemically

an ester, made of amino alcohol and organic acid

what kind of use does atropine have

anticholinergic use, but it is toxic

What kind of alkaloid is berberine?

a quaternary alkaloid

What kind of nitrogen is in berberine

a quaternary protonated nitrogen

is berberine soluble in water

yes

is berberine soluble in organic solvents

less than it is in water

What kind of activity does berberine have

antibacterial, anti inflammatory, antiamebic

What remedy is berberine a part of

goldenseal

what has berberine recently been discovered for

weightloss induction

Can a safe level of berberine be established for goldenseal

no

restriction to berberine

10 mg a day in belgium

side effects of berberine

upset stomach and diarrhea

what is proanthocyanidiin

condensed tannin

When is caffeine more soluble

in boiling water

what has pure powdered caffeine been found to do

cause death, 1 tsp is 25 cups of coffee

Example of protoalkaloid

mescaline

example of pseudoalkaloid

caffeine

ephedrine use

bronchodialator

pseudoephedrine used

decongestant

what plant source is used for ephedrine and pseduoephedrine

ma huang - ephedra

what kind of molecules are ephedrine and pseudoephedrine?

protoalkaloids

what was ephedra used for

weight loss, but was banned due to toxicity

what is a plant glycoside

acetals in which an -OH of the glycone sugar is condensed with OH of non sugar moiety (aglycone or genin)

what kind of glycosides are common in plants

beta glycosides

most common beta glycoside

beta d glucose

What does acid hydrolysis of a glycoside produce?

one or more sugars among products of acid hydrolysis as well as an aglycone (genin)

what splits plant glycosides

acid hydrolysis

What are anthraquinone glycosides

a group of glycosides used medicinally

what compounds can anthraquinone glycosides be found as?

laxatives and botanical dietary supplements

anthraquinone glycosides overall sahpe

3 rings together with ketones coming out of middle

What are 2 forms of anthraquinones that occur

O-glycoside, C-glycoside

O-glycoside

sugar linkage through an acetal group

C-glycolside

sugar directly attached to C of aglycone

example of anthraquinone glycosides

rhein (aglycone)

rhein 8 glucoside (o- glycoside)

are anthraquinone glycols safe

not when taken on daily basis

What secondary metabolites can be found in an herbal tea

glycosylated flavonoid

other types of plant glycosides

simple phenol (phenylpropanoids)

simple isoprenoid

What might phenylpropanoids have an effect of

flavoring effect, with sugar could be sweetiening

How would alkaloid salts be extracted

into hot water

What is important fact about alkaloid?

TOXIC TO CNS

do a lot of supplements have alkaloids

NO

What is a protoalkaloid STRUCTURE

An alkaloid with its nitrogen atom in a side chain, NOT inside a ring.

What is a pseudoalkaloid? STRUTCURE

An alkaloid that is NOT biosynthesized from an amino acid precursor.

What is a quaternary alkaloid? STRUCTURE

An alkaloid with a quaternary (positively charged) nitrogen atom.

What type of plant compound is quercetin?

flavonoid, has C6-C3-C6 ring

structure of methyl salicylate

has a degraded side chain, only two c

what kind of molecule is caffeine

pseudoalkaloid

what kind of molecule is mescaline

protoalkaloid

active principle of filsueves

triterpenes