2019-09-15

Bioactive compounds in food

Viktoriia Burkina

Department of Molecular Sciences, SLU

viktoriia.burkina@slu.se

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At the end of this lecture you should be able to:

• Define bioactive compounds
• Explain molecular background for bioactivity
• Describe major classes of bioactive compounds in plants
• Give examples of important areas where bioactive compounds are
involved

-Anonymous

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Use of medicinal plants in prehistoric times

• From this region one has found old clay plates from

around 4000 B.C. containing drawings and scripts

showing that the culture already knew about the use
of medical plants also known today as opium, thyme
and liquorice

Use of medicinal plants in prehistoric times - Egypt

The Ebers Papyrus is the most famous plant - medicine "encyclopedia". It is a

110 page scroll which rolls out to be about 20 meters long.

The documents contained at least 800 recipes

and around 700 medicinal plants of both
local and foreign origin which were also known
among the Babylonians

Amongst those mentioned are aloe,

peppermint, Indian hemp (cannabis) as well as
garlic, opium poppy, cumin

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Remedies from the ancient Ebers Papyrus scrolls:

• Aloe vera was used to alleviate burns, ulcers, skin diseases and allergies
• Basil was written up as heart medicine
• Dill was recognized for laxative and diuretic properties
• Garlic was given to the Hebrew slaves daily to give them strength for building the pyramids
• Onion was taken to prevent colds and to address cardiovascular problems (How did they know?)
• Parsley was prescribed as a diuretic
• Thyme was given as a pain reliever
• Poppy was used to relieve insomnia, as an anesthetic
• Persian henna was used against hair loss

From: http://www.messagetoeagle.com/egyptians-mastered-medicine-thousands-of-years-ago/#ixzz4hEPRKV00

Scurvy

The first clinical trial

• Scurvy affected sailors deprived of fresh foods
• James Lind of the Royal Navy – 1747
• 12 scorbutic sailors divided into 6 groups
• Same diet plus:
1. A quart of cider daily
2. 25 drops of elixir of vitriol (sulphuric acid)
3. 6 spoons of vinegar
4. Half a pint of seawater
5. Two oranges and lemon
6. A spicy paste plus a drink of barley
• Follow up with bottled juice didn’t work

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From plants to pure bioactive compound

Friedrich Sertürner isolated morphine from
Papaver somniferum in 1806

Morphine

Quinine Strychnine Caffeine

Cínchona Strychnos nux-vomica Coffea

Bioactive compounds

• Extranutritional constituents that typically occur in small quantities in food

and feed

• Bioactive compounds are also referred to as nutraceuticals, a term

invented by Stephan DeFelice

• Bioactive compounds have actions in the body that may promote good
health
• (with anticipated health promoting/beneficial effects, and/or toxic effects, when
ingested)

The ingested dose of bioactive compounds is often decisive for whether the effect
positive or adverse

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Bioactive compounds in plants

• = Secondary metabolites

• Have no direct implication on the growth and development of plants

• Are often accumulated in high concentrations (1–3%) fresh weight

• Have a distribution which is sometimes confined to a genus or species

• May have a marked biological effect on other organisms

• May show high toxicity

Classification

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Terpenes and Terpenoids

• Terpenes - class of compounds containing carbon atoms in multiples of five

• Terpenoids - oxygen-containing terpenes (alcohols, ketones, aldehydes)

Terpenes and terpenoids are the primary constituents of the essential oils of many types
of plants and flowers

C5 Isoprene

C10 monoterpene used as fragrances for making perfumes and in other cosmetics

C15 sesquiterpenes latex in latex-producing plants contain sesquiterpene

roots and leaves of different plants

C20 diterpenes

naturally present in the fungus, marine organism, insects,

C25 sesterpenes sponges, lichens, and protective waxes of insects.

Triterpenes have many active sites for the glycosylation which

C30 triterpenes converts it into another big class of compounds, namely,
C40 tetraterpene saponins
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Terpenes in plants

Terpenes are distributed in families like Myrtaceae, Lauraceae, Rutaceae, Lamiaceae,

Asteraceae, Umbelliferae, Verbenaceae and Piperaceae

Apiaceae Lamiaceae Asteraceae

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Variations – stage of development

Chamazulene
Achillea millefolium

Terpenes in human health

• Anti-inflammatory effects by inhibiting various proinflammatory pathways

in ear edema, bronchitis, chronic obstructive pulmonary disease, skin
inflammation, and osteoarthritis (α-Pinene)

• Treatment with linalool, a natural compound found in essential oils of

aromatic plants, inhibited cigarette smoke-induced acute lung
inflammation by inhibiting infiltration of inflammatory cells and production of
TNF-α, IL-6, IL-1β, IL-8

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Other use of terpenes

• Many terpenes (menthol, camphor) have medicinal values

• Preparation of perfumes

• Insect repellants

• Air fresheners

• Varnish (coating)

• Adverse/ Toxic effects: include depressive effects on Central Nervous

System (CNS) and respiratory disorders in case of aspiration of increased
quantities

Terpenoids

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Cyanogenic glycosides

Hydrogen cyanide is released from the cyanogenic glycosides

Poisonous

• Human oral lethal dose is 0.7 - 3.5 mg/kg body weight

• Sheep 2.0 - 2.4 mg/kg live weight
• Cattle with body condition score 3 or more are more resistant to HNC than slimmer animals

Alkaloids
• Alkaloids are defined as basic compounds synthesized by living organisms
containing one or more heterocyclic nitrogen atoms, derived from amino acids
(with some exceptions) and pharmacologically active
• Usually with potent activity and bitter taste

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Alkaloids

Luckily
• glycoalkaloids are poorly absorbed by the
gastrointestinal tract of mammals
• an appreciable amount of solanum-type glycoalkaloids is
hydrolyzed in the gut of mammals to the less toxic
aglycones
Solanum • these metabolites are rapidly excreted

Pyrrolizidine alkaloids
• Biosynthetically derived from amino acid ornithine. The nitrogen atom
located in a pyrrolizidine structure, called necic base, which is esterified
with structurally complex acids
• Can cause major problems in grazing animals, particularly in regions with
extensive livestock management
• The main toxic components of Senecio spp. (Family: Asteraceae)

From the Latin senex meaning ‘old man’ because of

the woolly, hairy seed of the plants

Ragwort

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Phenolic compounds

Phenols are compounds with an –OH group attached

to an aromatic carbon. Although they share the same
functional group with alcohols, where the –OH group
is attached to an aliphatic carbon, the chemistry of
phenols is very different from that of alcohols

Structure of major polyphenols

Flavonoid Stilbene

Coumestans

Resveratrol

Apigenin

Phenolic acid Lignan Coumestrol

Gallic acid
Enterodiol

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Flavonoids

anthocyanidins
flavan-3-ols flavonols

flavones flavanones isoflavones

phenolic compounds, which contain in their main structure 15 carbon atoms that
form a characteristic carbon skeleton composed of two aromatic rings connected by
either tri-carbon bridge or heterocyclic ring

Glycosides vs aglycones

Glycosides is any of the class of compounds that yield a sugar and an aglycon upon hydrolysis

Aglycone is nonsugar component of a glycoside that results from hydrolysis of the glycoside

Glycosides are predominant form of flavonoids in plants

Quercetin-3-glycoside or rutin Quercetin aglycone

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Absorption and metabolism of plant polyphenols

Metabolism

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Resveratrol

Trans-resveratrol – active form

1.9±1.7 mg trans-resveratrol/L

Produced in grapes as a defense against toxins, and is contained in the skins

Tannins

• Tannins are secondary metabolites of plants,

non-nitrogenous, phenolic in nature

• Tannins have a property to tan animal skin to

convert to leather or hide
Tannic acid

Tannins can complex with:

• Proteins
Harmful, harmless or beneficial - type
• Starch
and chemical structure, species, the
• Cellulose amount ingested and the animal
• Minerals

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Hydrolyzable tannins

Gallotannins
hydrolysable tannin
Gallic acid
(gallotannin)
composed of esters
of gallic acid linked
to a sugar core

Ellagitannins

Condensed tannins (Proanthocyanidins)

Flavan-3,4-diols

Proanthocyanidins Anthocyanidins

Acid

Heat

A characteristic of PAs is that they yield anthocyanins upon heating in acidic media

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Despite the previous, several animal species including ruminants, and

rhinoceros species and primates seem to tolerate (or even prefer)
considerable amounts of tannins (<50 g condensed tannin (CT)/kg dry matter)
in their diets!

Effect of tannins

•
☺
reduction in internal parasite load •

astringency, reduced voluntary

• prevention of frothy bloat when feed intake in the short term

animals consume pastures that • reduces the amount of nutrients

are rich in soluble proteins absorbed from the digestive tract

• improved nitrogen utilization • toxicity

efficiency
• erosion of gastrointestinal tract
• reduced enteric methanogenesis
• animal deaths
• reduced nitrogen pollution through
animal waste

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Phenolic compounds in wild mushrooms

Bioactivity

Ana Rodriguez-Mateos et al., 2014

• Specific effect on, or a

reaction in, living animal or
plant tissue upon exposure
to a substance

• Bioactive compounds
interact with many different
molecular and cellular
targets

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Bioactive compounds with hormone-like activity

Steroid and nonsteroid hormones affect target cells through different mechanisms

Phytoestrogens

Woclawek-Potocka et al., 2013

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Phytoestrogens

Genistein exerts mild

estrogenic activity (around
35% of 17β-estradiol)
S-equol has a higher overall
affinity than genistein.
Therefore, efficacy as well as
bioavailability of isoflavones is
influenced by digestive health
and the intestinal microflora.

Compounds with enzyme-modulating action

• ACE inhibitory bioactive peptides (blood pressure)

• Modulation of detoxification enzymes (various flavonoids)

• Modulation of steroid hormone metabolising-enzymes (indole-3-carbinol)

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Angiotensin-Converting Enzyme

ACE is a key part in the regulation of blood pressure

1. Blood pressure dropped

The goal of renin-angiotensin-aldosterone
system (RAAS) is to create angiotensin II
(major Vasoconstrictor)
2. Kidney release Renin
3. Presence of renin in circulation causes
Angiotensinogen (protein created and
produced in liver)
4. Angiotensinogen create Angiotensin I
5. ACE convert angiotensin I to
Angiotensin II

= Vasoconstriction: it is trigger release of aldosterone, which will going to help to

increase blood volume in the body = increasing of blood pressure

wheat, peas, mushrooms, soybeans, walnuts, date seed flour, bitter melon seeds and
spinach

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Food processing and bioactive compounds

Phenol compounds in Raw Boiled Microwaved Basket Oven steamed

Broccoli (mg/100 g) steamed

Caffeic acid 6.6 2.2 2.9 4.0 9.1

Coumaric acid 11.2 3.1 1.5 3.7 12.5
Chlorogenic acid 20.2 88.9 5.7 19.1 135.2
Ferulic acid 4.3 0.8 1.2 1.8 4.6
Total phenol compounds 111.4 128 36.7 74.6 263.3

Potential for the use of plant bioactives in agriculture

Bioactive components

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Bioactive compounds through food, nutraceuticals or

pills?

• moderate amounts of e.g. food antioxidants protect against disease, but more
is not necessarily better

• promising results in the laboratory are not necessarily relevant for humans

Without a balanced diet as a basis, nutraceuticals, functional foods

and supplements will have marginal impact on public health

Helle Margrete Meltzer, Norwegian Institute of Public Health, Oslo, Norway

Conclusion

• Plants, including most food and feed plants, produce a broad range of bioactive
chemical compounds
• Boactive compounds may elicit a long range of different effects in man and
animals eating the plants dependent on plant species and amount eaten
• Plants with potent bioactive compounds are often characterised as both poisonous
and medicinal
• Beneficial or an adverse effects depend on the amount eaten
• For typical food and feed plants with bioactive compounds with less pronounced
effects, the intakes are usually regarded as beneficial.

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Without a balanced diet as a basis,

nutraceuticals, functional foods and
supplements will have marginal
impact on public health

Helle Margrete Meltzer

Norwegian Institute of Public Health, Oslo, Norway

Opportunities and challenges

https://www.ncbi.nlm.nih.gov/pubmed/19719126

Topic for discussion

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Thank you!

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