Biologically active compounds 2015

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1

BIOLOGICALLY ACTIVE COMPOUNDS

IN PLANT RAW MATERIALS

PRIMARY METABOLITES:
carbohydrates
amino acids, peptides, proteins

lipids
nucleic acids
chlorophyll
SECONDARY METABOLITES:
glycosides
alkaloids
essential oils
tannins
bitter compounds
etc.

PRIMARY METABOLITES:

CARBOHYDRATES

Monosaccharides

Glucose, fructose, rhamnose, arabinose – constituents of numerous glycosides and polysaccharides

Digitoxose (deoxyrhamnose) – component of cardiac glycosides of foxglove (Digitalis sp.)

Oligosaccharides – consist of 2-10 monosaccharides

Rutinose (rhamnose + glucose) – component of rutin=rutoside (quercetin-3-rutinoside)

obtained from buckwheat (Fagopyrum esculentum) herb

Polysaccharides – consist of ≥ 10 monosaccharides

Starch

Celulose

Inulin – storage polysaccharide in the roots of plants from the family Asteraceae,

e.g. elecampane (Inula helenium), Jerusalem artichoke (Helianthus tuberosus),
common dandelion (Taraxacum officinale);
– sweetener for diabetes
– prebiotic

– source of fructose

Polysaccharides with immunomodulatory activity
– e.g. in purple coneflower (Echinacea purpurea) herb, aloe (e.g. Aloë arborescens) leaf,
European goldenrod (Solidago virgaurea) herb, common dandelion (Taraxacum officinale) flowers

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Mucilages – mixtures of polysaccharides

- occur in special cells or reservoirs
- in water form slippery colloidal dispersions
- activity: coating, protecting, demulcent, soothing, mildly laxative
- internally used – in irritation and inflammations of mucous membranes

of gastrointestinal tract (they are not absorbed and act locally)
and respiratory tract (dry irritating cough)

- externally used – to alleviate skin irritation

Mucilage-containing raw materials: flax (Linum usitatissimum) seed,
fenugreek (Trigonella foenum-graecum) seed, marshmallow (Althaea officinalis) root,
black hollyhock (Althaea rosea var. nigra) flower, wool mullein (Verbascum densiflorum) flower,
ribwort plantain (Plantago lanceolata) leaf, psyllium (e.g. Plantago ovata, P. arenaria) seed,
coltsfoot (Tussilago farfara) leaf


PEPTIDES


R

CH

CO

NH

2

NH

CH

COOH

R

1

• dipeptides: consist of 2 amino acids

• oligopeptides: consist of 3-10 amino acids

• polypeptides: consist of > 10 amino acids


viscotoxins – in mistletoe (Viscum album) herb;

- injected subcutaneously cause necrosis of skin tumours


in shepherd’s purse (Capsella bursa-pastoris) herb – peptides with hemostyptic action

PROTEINS – polypeptides with molecular weight > 10 000

Simple proteins (composed of amino acids only)

Complex proteins, e.g.:

glycoproteins = proteins + carbohydrates

• glycoproteins with immunostimulatory activity – in purple coneflower (Echinacea

purpurea) herb, aloe (Aloë vera, A. arborescens) leaf

• lectins – in herb of mistletoe (Viscum album);

- agglutinate red blood cells
- agglutinate cancer cells

chromoproteins – proteins + pigments/metal ions


e.g. chlorophyll – obtained from stinging nettle (Urtica dioica L.) herb

peptide bond

by binding sugars in cell membranes

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LIPIDS
Simple lipids, e.g. fats (composed of triglycerides = esters of glycerol and fatty acids)

Complex lipids – e.g. phosphoglycerides (e.g. lecithin in soy seeds)

Plant fats (oils) contain mainly unsaturated fatty acids and have a liquid form.

PUFA – polyunsaturated fatty acids
EFA – essential fatty acids

Essential fatty acids:






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Biological activity of essential fatty acids:

constituents of cell membranes

take part in biosynthesis of prostaglandins, prostacyclins, thromboxanes, leukotrienes

take part in cholesterol transport

affect body immune resistance

important in prophylaxis of atherosclerosis

used in chronic skin diseases, allergic diseases, rheumatoid arthritis, disorders of central

nervous system (e.g. in supportive therapy of multiple sclerosis)


Plant oils rich in γ-linolenic acid:

evening primrose (Oenothera paradoxa, O. biennis) seed oil

borage (Borago officinalis) seed oil

black currant (Ribes nigrum) seed oil

H

3

C

COOH

H

3

C

COOH

H

3

C

COOH

linoleic acid
18:2, n-6

α-linolenic acid
18:3, n-3

γ-linolenic acid
18:3, n-6

soy oil,
sunflower oil,
evening primrose seed oil

flax seed oil

evening primrose seed oil,
borage seed oil,
black currant seed oil

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SECONDARY METABOLITES:

GLYCOSIDES

– consist of glycone (sugar moiety) and aglycone

Classification of glycosides in regard to the type of bond between glycone and aglycone:
O-glycosides
C-glycosides
S-glycosides
N-glycosides

Classification of glycosides in regard to aglycone:

flavonoid glycosides

anthocyanosides

saponosides

cardiac glycosides – cardenolide and bufadienolide glycosides

anthraglycosides

coumarin glycosides

phenolic glycosides

iridoid glycosides

sterol glycosides

glucosinolates


FLAVONOIDS

yellow pigments, occurring in vacuoles, esp. in aerial parts of plants (flowers, leaves)

occur as free compounds or as O-, rarely C-glycosides

Flavones – e.g. apigenin, luteolin

Flavone glycosides – e.g. vitexin (apigenin-8-C-glucoside) – in hawthorn (e.g. Crataegus
monogyna
) inflorescence – improves coronary flow

Flavonols

e.g. quercetin, kaempferol, myricetin


Flavonol glycosides

e.g.
rutin (quercetin-3-rutinoside) – in buckwheat (Fagopyrum esculentum) herb,
rue (Ruta graveolens) herb, heartsease (Viola tricolor) herb,
black elder (Sambucus nigra) flower

- decreases capillary permeability
- antioxidant (e.g. prevents the oxidation of ascorbic acid)


hyperoside (quercetin-3-galactoside) – e.g. in St. John’s wort (Hypericum perforatum) herb,
birch (Betula pendula, B. pubescens) leaf

quercetin

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Isoflavones

genistein, daidzein – in soy seeds

– phytoestrogens; anti-cancer activity


Biflavonoids

bilobetin, ginkgetin – in maidenhair tree (Ginkgo biloba) leaf

– enhance coronary and brain flow


Flavonolignans

Silymarin (main compound – silybin) – in milk thistle (Silybum marianum) fruit

– anti-hepatotoxic, regenerating liver cells, anti-inflammatory action


Biological activity of flavonoids:

reducing blood vessel permeability and fragility

prevent bleeding, ecchymosis, varicose

veins, atherosclerosis

anti-aggregatory (inhibiting platelet aggregation)

antioxidant

diuretic

spasmolytic

anti-inflammatory

detoxifying – they chelate metal ions, e.g. Cu

UV-protecting

antiviral


Flavonoid-containing raw materials: field horsetail (Equisetum arvense) herb,
common knotgrass/knotweed (Polygonum aviculare) herb, birch (Betula pendula) leaf,
heartsease (Viola tricolor) herb, European goldenrod (Solidago virgaurea) herb,
lime (Tilia cordata, T. platyphyllos) inflorescence, black elder (Sambucus nigra) flower,
hawthorn (Crataegus monogyna ) inflorescence,
sandy everlasting (Helichrysum arenarium) inflorescence,
St. John’s wort (Hypericum perforatum) herb, chamomile (Matricaria chamomilla) flower head

O

OH

O

OH

O

H

genistein

amenthoflavone
bilobetin
ginkgetin

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ANTHOCYANINS

• plant pigments: pink-red-blue-violet

• usually occur as O-glycosides – anthocyanosides;

aglycone – anthocyanidin:


Biological activity of anthocyanins:

reducing capillary permeability and fragility

slightly diuretic

anti-inflammatory

anti-aggregatory

UV-protecting

antiviral

antioxidant

improving microcirculation in eye

improving visual acuity


Anthocyanin-containing raw materials:
bilberry (Vaccinium myrtillus) fruit, black elder (Sambucus nigra) fruit,
bluebottle (Centaurea cyanus) flower, black hollyhock (Althaea rosea var. nigra) flower

SAPONINS

triterpene saponins

steroid saponins

Biological activity of saponins:

they lower the surface tension of water solutions (

foaming)

facilitate dissolving and absorption of other active substances

haemolytic

lowering blood cholesterol level

expectorant (by irritating stomach mucous membrane)

diuretic

anti-inflammatory

antifungal

psychostimulant

immunomodulatory

chemopreventive

antioxidant

toxic for fish and other cold-blooded animals;

for mammals – when given parenterally;
some of them (e.g. saponins of Agrostemma githago, Cyclamen) – also after ingestion

Raw materials containing triterpene saponins: soapwort (Saponaria officinalis) root, cowslip
(Primula veris) root [e.g. primulasaponin A], liquorice (Glycyrrhiza glabra) root [e.g. glycyrrhizin],
horse chestnut (Aesculus hippocastanum) seed [escin – decreases capillary permeability],
pot marigold (Calendula officinalis) flower, ginseng (Panax ginseng) root [ginsenosides]

Raw materials containing steroid saponins: yam (e.g. Dioscorea zingiberensis) tuber, fenugreek
(Trigonella foenum-graecum) seed [diosgenin]

pelargonidin
cyanidin
delphinidin
malvidin
peonidin
petunidin

e.g. ginsenosides

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CARDIAC GLYCOSIDES

cardenolide type

bufadienolide type


e.g.

digoxigenin

e.g.

scillarenin


Glycone: 1-4 sugars at C-3

primary glycosides

secondary glycosides

e.g.:

lanatoside C (digoxigenin-digitoxose-digitoxose-acetylodigitoxose-glucose)

digoxin (digoxigenin-digitoxose-digitoxose-digitoxose)


Biological activity of cardiac glycosides:

increase the force of contraction of the heart muscle (positive inotropic effect)

decrease the rate of contractions (negative chronotropic effect)

increase cardiac output

indirect diuretic effect; reduction of swellings

indications: systolic heart failure, arrhythmia: atrial flutter, atrial fibrillation


Aglycone is responsible for the direction of activity.

Sugar moiety affects the solubility, absorption, strength and time of action,
ability to bind blood plasma proteins.

Strength of activity: aglycones < primary glycosides < secondary glycosides

Raw materials containing cardenolide glycosides: Grecian foxglove (Digitalis lanata) leaf [used
only for isolation of cardiac glycosides], lily of the valley (Convallaria majalis) herb,
spring adonis (Adonis vernalis) herb

Raw materials containing bufadienolide glycosides: sea squill (Drimia maritima) bulb

Aglycone:

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ANTHRAGLYCOSIDES
Aglycone: anthrone, dianthrone, anthranol or anthraquinone
Glycone: 1-3 sugars, mainly glucose and rhamnose
Type of glycoside bond: O- or C-



Biological activity of anthraglycosides:

laxative

 reduce water absorption from the large intestine
 irritate colon walls

stimulate peristalsis

accelerate colonic transfer

The most active compounds are dianthrones and anthrones.
Anthraglycosides are hydrolysed by colon microflora to aglycons and reduced to anthrones.
More sugar moieties in a glycoside and C-glycoside bond

stronger laxative activity.

cholagogue

enhancing gastric juice secretion

long-term use

irritation of gastrointestinal tract

vomiting, bloody diarrhoea

contraindications: pregnancy, lactation, acute intestinal inflammation, e.g. colitis ulcerosa

Raw materials containing anthraglycosides: alder buckthorn (Frangula alnus) bark,
senna (Senna alexandrina) leaf, rhubarb (Rheum palmatum) root, aloe (Aloë ferrox) leaf juice

Naphthodianthrones

anthraquinone

anthrone

anthranol

dianthrone

hypericin R=H
pseudohypericin R=OH

Biological activity of hypericin:

- photosensitising
- antidepressant
- anti-inflammatory
- antiviral (e.g. against HIV-1)
- anticancer

in St. John’s wort (Hypericum perforatum) herb

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COUMARINS



Coumarin is a product of hydrolysis of glycosides of coumaric acid (e.g. melilotoside) during
drying of raw material → specific smell
Hydroxycoumarins – occur in plants as free compounds or aglycones of glycosides (e.g. esculin=
esculetin glycoside).

Biological activity of coumarins:

UV-protecting, e.g. esculin, umbelliferone

sedative, e.g. coumarin

spasmolytic, e.g. coumarin

hypotensive, e.g. scopoletin

anticoagulant, e.g. dicoumarol, coumarin

cholagogue, e.g. fraxidin, isofraxidin

antioxidant

hepatotoxic, e.g. coumarin

Raw materials containing coumarins:
coumarin: yellow melilot (Melilotus officinalis) herb, sweet woodruff (Galium odoratum) herb,
Southern sweetgrass (Hierochloë australis) herb
hydroxycoumarins: chamomile (Matricaria chamomilla) flower head [umbelliferone],
common ash (Fraxinus excelsior) bark [isofraxidin], southernwood (Artemisia abrotanum) herb,
horse chestnut (Aesculus hippocastanum) bark [esculin],
raw materials obtained from plants from the family Apiaceae, e.g. lovage (Levisticum officinale)
root, garden angelica (Angelica archangelica) root









Biological activity of furanocoumarins:

photosensitising, e.g. psoralene, bergaptene, xanthotoxin (but not angelicin)

used for the treatment of vitiligo and psoriasis

spasmolytic, e.g. angelicin

vasorelaxant

blocking Ca

2+

channels in heart, e.g. imperatorin

cns depressant, e.g. angelicin

Raw materials containing furanocoumarins: rue (Ruta graveolens) herb, garden angelica (Angelica
archangelica
) root and fruit, parsnip (Pastinaca sativa) fruit
hogweed (Heracleum sp.)

COOH

O

Glu

Coumarins

Furanocoumarins

COOH

OH

O

O

melilotoside

coumarinic acid

coumarin

O

O

O

O

O

O

psoralene-type

angelicin-type

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PHENOLIC GLYCOSIDES
Aglycone: phenol or its derivative


















Phenolic acids

- occur in plants as free compounds, depsides (e.g. chlorogenic acid)

or aglycones of glycosides

- some of them are precursors of tannins



Biological activity of phenolic acids:

choleretic and cholagogue

antiviral

immunotropic

anti-inflammatory

detoxifying

antioxidant


Raw materials rich in phenolic acids:
knotweed (Polygonum aviculare) herb,
oregano (Origanum vulgare) herb,
lemon balm (Melissa officinalis) leaf,
purple coneflower (Echinacea purpurea) herb,
poplar (Populus nigra) buds

O

O

O

CH

3

O

Glu

OH

O

Glu

OH

O

Glu

arbutin – hydroquinone glucoside

bearberry (Arctostaphylos uva-ursi) leaf
lingonberry (Vaccinium vitis-idaea) leaf

Hydroquinone (product of hydrolysis of arbutin in urinary tract):

- disinfects urinary tract
- potent mutagenic activity

salicin – glucoside of salicylic alcohol (saligenin)

willow (Salix alba, S. purpurea) bark

poplar (Populus nigra) buds

Activity: antipyretic, anti-inflammatory

esp. in rheumatic disorders

O

Glu

HOH

2

C

leiocarposide

European goldenrod (Solidago virgaurea) herb

Activity: diuretic

O

H

O

H

CH

CH

COO

Glu

Glu

Rmn

O

CH

2

CH

2

OH

OH

echinacoside – phenylpropane derivative

narrow-leaf purple coneflower (Echinacea angustifolia) root

Activity: immunostimulant, antiviral

OH

OH

O

O

H

O

H

O

OH

O

OH

O

H

O

H

OH

O

O

OH

OH

salicylic acid

caffeic acid

chlorogenic acid

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IRIDOID GLYCOSIDES

Raw materials: eyebright (Euphrasia rostkoviana) herb,

wool mullein (Verbascum densiflorum) flower, ribwort plantain (Plantago lanceolata) leaf,
common plantain (Plantago major) leaf

harpagoside – in devil’s claw (Harpagophytum procumbens) root

– analgesic (in arthritic pains)
– anti-inflammatory




STEROLS


Occur in plants as free sterols (e.g. β-sitosterol, stigmasterol, campesterol), sterol glycosides or
sterol esters.

Biological activity of sterols:

lowering blood cholesterol level

antioxidant

anticoagulant

preventing prostatic hyperplasia

anti-inflammatory

preventing colon cancer

immunostimulatory

anti-ulcer


Raw materials with high sterol content:
stinging nettle (Urtica dioica) root, fireweed (Chamerion angustifolium) herb,
pumpkin (Cucurbita pepo) seed,
red stinkwood (Prunus africana) bark, saw palmetto (Serenoa repens) fruit

O

H

CH

3

CH

3

CH

3

CH

3

H

H

H

H

H

H

C

H

3

O

O

Glu

CH

2

OH

OH

aucubin (aucuboside)

- bacteriostatic
- anti-inflammatory
- hepatoprotective

β-sitosterol

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TANNINS

- large-molecule polyphenolic substances capable of binding proteins

hydrolysable tannins: gallotannins (esters of gallic acid),

ellagitannins (esters of ellagic acid)

condensed tannins (composed of numerous catechin molecules)


Biological activity of tannins:

astringent (protein coagulating)

wound healing

reduce bleeding from gastrointestinal tract

anti-inflammatory

anti-diarrhoea

antibacterial

antiviral

detoxifying (e.g. they bind alkaloids)

antioxidant

used for a long time in larger doses – decrease absorption of vitamins and minerals


Raw materials with high tannin content: oak (Quercus robur, Q. petraea) bark,
bistort/snakeweed (Bistorta officinalis) rhizome, tormentil (Potentilla erecta) rhizome,
common avens (Geum urbanum) herb and rhizome, great burnet (Sanguisorba officinalis) herb,
silverweed (Potentilla anserina) herb, bilberry (Vaccinium myrtillus) fruit,
willow (Salix alba, S. purpurea) bark, lingonberry (Vaccinium vitis-idaea) leaf,
sage (Salvia officinalis) leaf


BITTER COMPOUNDS

- bitter taste
- varied chemical structures, most often:

 sesquiterpene lactones, e.g. absinthin in wormwood (Artemisia absinthium) herb
 secoiridoids:

e.g. gentiopicroside – in yellow gentian (Gentiana lutea) root

amarogentin

sweroside

loganin

Activity:

increase the secretion of saliva and gastric juice

improve appetite and digestion

improve intestinal absorption

in bogbean (Menyanthes trifoliata) leaf

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ESSENTIAL OILS

obtained mainly by steam distillation of plant raw materials

in plants they occur in special cells or reservoirs:

 exogenous:

- glandular trichomes:

• simple, e.g. capitate trichomes

• multicellular (e.g. asteraceous glandular trichomes – in the family Asteraceae,

peltate glandular trichomes – in the family Lamiaceae)

 endogenous:

- essential oil cells
- secretory reservoirs
- secretory ducts (e.g. in caraway fruit, anise fruit, angelica root)
- resin canals (e.g. in pine needles)

physical traits of essential oils:

- usually liquid consistence
- usually colourless or yellowish; also brownish, blue or green
- readily volatile
- intensive smell
- insoluble in water
- usually of lower density in comparison with water

mixtures of volatile compounds of different chemical nature, mainly:

- terpenes (mono- and sesquiterpenes)

monoterpenes: e.g. menthol (peppermint essential oil), carvone (caraway essential oil),
thujone (wormwood e.o., tansy e.o.)
sesquiterpenes: e.g. α-bisabolol, chamazulene (chamomile e.o.)

- phenols and their derivatives

phenols: e.g. thymol (thyme e.o.), anethol (anise e.o., fennel e.o.)

- heterocyclic derivatives of aromatic compounds: phthalides (lovage e.o.)
- esters of organic acids
- coumarins

Biological activity of essential oils:

skin irritating, hyperemic (e.g. rosemary, pine, eucalyptus)

diuretic (e.g. juniper)

expectorant (e.g. anise, fennel, thyme, eucalyptus)

antiphlogistic (e.g. chamomile)

antiseptic (e.g. thyme, clove, marjoram)

choleretic, cholagogue (e.g. peppermint, pine)

anti-spasmodic, carminative (e.g. chamomile, caraway, fennel, dill, coriander, peppermint)

antineuralgic (e.g. pine, juniper)

sedative (e.g. valerian, lemon balm)

anthelmintic (e.g. wormwood, tansy, rosemary)

Essential oil-containing raw materials:

- obtained from plants from the family Lamiaceae: peppermint (Mentha x piperita) leaf,

lemon balm (Melissa officinalis) leaf, sage (Salvia officinalis) leaf,
rosemary (Rosmarinus officinalis) leaf, thyme (Thymus vulgaris) herb,
marjoram (Origanum majorana) herb, lavender (Lavandula angustifolia) flower

- obtained from plants from the family Apiaceae: caraway (Carum carvi) fruit,

fennel (Foeniculum vulgare) fruit, dill (Anethum graveolens) fruit,
coriander (Coriandrum sativum) fruit, anise (Pimpinella anisum) fruit,
garden angelica (Angelica archangelica) root, lovage (Levisticum officinale) root and leaf

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- obtained from plants from the family Asteraceae: chamomile (Matricaria chamomilla)

flower head, yarrow (Achillea millefolium) herb, wormwood (Artemisia absinthium) herb,
tansy (Tanacetum vulgare) herb

- obtained from other plants: hop (Humulus lupulus) strobile, pine (Pinus sylvestris) buds,

juniper (Juniperus communis) cone berry, calamus/sweet flag (Acorum calamus) rhizome


Some plants contain scentless, non-volatile precursors of volatile compounds. These plants also
contain specific enzymes catalysing the conversion of these precursors to volatile forms. The
precursors and the enzymes are stored in separate compartments of the cell. Releasing of volatile
compounds is only possible after plant injury (e.g. during chopping or crushing).

GLUCOSINOLATES –
S-glycosides commonly occurring in the family Brassicaceae,
e.g. sinigrin – in black mustard (Brassica nigra) seed, horseradish (Armoracia rusticana) root














SULPHUR COMPOUNDS IN ALLIUM
SP. (e.g. in garlic)


sinigrin

myrosinase

N

C

S

allyl isothiocyanate

H

2

O

highly volatile

irritates skin and mucous membranes

pungent taste

enhances gastric juice and bile secretion

non-volatile

non-volatile

volatile

burning taste, intensive smell

antibacterial, antifungal,

anti-aggregatory activity

other sulphur compounds

allicin

alliinase

alliin

x 2

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ALKALOIDS

True alkaloids

• derivatives of amino acids containing nitrogen in a heterocyclic ring

- tropane alkaloids

e.g.

atropine, scopolamine

Raw materials: downy thorn-apple (Datura inoxia) leaf,

Jimsonweed (Datura stramonium) leaf, deadly nightshade (Atropa belladonna) root

- isoquinoline alkaloids

e.g.

morphine, codeine – in opium poppy (Papaver somniferum)

papaverine – in opium poppy (Papaver somniferum)

chelidonine – in celandine (Chelidonium majus) root

- indole alkaloids

e.g.

ergometrine, ergotamine, ergotoxine – in ergot (Claviceps purpurea)

vinblastine, vincristine – in Catharanthus roseus leaf

- quinoline alkaloids

e.g.

quinine, quinidine – in Cinchona officinalis bark

- quinolizidine alkaloids

e.g.

sparteine – in Scotch broom (Sarothamnus scoparius) herb

- pyrrolizidine alkaloids

e.g. in borage (Borago officinalis), comfrey (Symphytum officinale),

coltsfoot (Tussilago farfara) → hepatotoxic, carcinogenic

- pyridine alkaloids

e.g. nicotine – in tobacco (Nicotiana tabacum)

Pseudoalkaloids

• nitrogen-containing compounds biogenetically not related to amino acids;

derivatives of terpenes, steroids, purines

e.g. purine alkaloids: caffeine, theobromine, theophylline

Protoalkaloids

• derivatives of amino acids,

but nitrogen in their molecules is not included in a heterocyclic ring

e.g. capsaicin – in red pepper (Capsicum annuum) fruit

ephedrine – in Chinese ephedra (Ephedra sinica)


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