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Herbs and phytochemicals > Phytochemicals > Flashcards

Phytochemicals Flashcards

1
Q

What part of plants is more high in phytochemicals?

A

peel as it is a barrier

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2
Q

Four classes of phytochemicals that we need to know

A

Phenolic compounds, terpenoids; organic acids, lipid and related compounds; nitrogen compounds

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3
Q

Phenolic compounds subclasses

A

Flavonoid pigments including: anthocyanins, flavanols and flavones, tannins

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4
Q

Terpenoids: subclasses

A

Essential oils, Carotenoids; triterpenoids and steroids

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5
Q

Organic acids, lipid and related compounds: subclasses

A

Sulphur compounds

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6
Q

Alkaloids subclass in what class it is included

A

Nitrogen compounds

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7
Q

Phenolic compounds: solubility and where found

A

water-soluble and found in the vacuoles

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8
Q

Phenolic compounds basic structure and what is the outcome

A
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9
Q

How to recognize a flavonoid pigment?

A
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10
Q

How flavonoids are usually present in plants?

A

Bound to a sugar as glycosides

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11
Q

Flavonoid pigments: anthocyanins color

A

Scarlet, red, mauve and blue flower pigments

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12
Q

Flavonols: color, where found

A

Mainly colourless co-pigments in flowers. Widespread in leaves

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13
Q

Flavones: color, where found

A

Mainly colourless co-pigments in flowers. Widespread in leaves

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14
Q

Flavanones: color, where found

A

Colourless, in leaves and fruit

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15
Q

isoflavanones: pigment color, where found

A

Colourless, often in roots

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16
Q

Isoflavones are common only in one family, which one

A

Only common in one family; the LEGUMINACEAE

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17
Q

Substitution of one group on anthocyanin will result in___

A

Different color as different wavelength will be absorbed

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18
Q

Flavonols occur most frequently in __ combiantions

A

Glycosidic

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19
Q

KAEMPFEROL, QUERCETIN, MYRICETIN are three most common

A

Flavonols

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20
Q

How flavonols differ from flavones and implication

A

differ in that they lack a 3-hydroxyl substitution. This affects their UV absorption.

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21
Q

2 most common flavones

A

APIGENIN and LUTEOLIN

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22
Q

Who is the cousin to apigenin; luteolin and why?

A

Kaempferol to apigenin
Quercitin to luteolin because they only differ by one hydroxyl group

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23
Q

What is it?

A

Flavonols

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24
Q

Kaempferol, where found three, and 3 pharmacological activities

A
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25
Q

Common foods containing quesrcetin three

A
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26
Q

Quercetin is usually claimed to be anti-aging, are health claimed approved by USDA and HC?

A

No

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27
Q

what activity quesrcetin has

A

Quercetin glycosides have Estrogenic Activity. It’s roughly two to three orders of magnitude less potent than the endogenous estrogenic hormone 17β-estradiol

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28
Q

Three sources of myricetin

A

Abundant in Fruits, Vegetables, Nuts & Teas: Dock, Swiss Chard, Sweet Potato leaves, Rutabagas, Cranberries, Blueberries, Lemon, Blackberries, Garlic.

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29
Q

What properties myricetin has

A

Myricetin glycosides have Antioxidant / Pro- oxidant Activity. It can undergo autoxidation depending on its environment.

May have Anticancer Activity: It inhibits cell- growth in leukemia, bladder cancer, prostate cancer, and lung cancer.

It is Anti-inflammatory, Anti-hypertensive, and may be anti-HIV.

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30
Q

Where apigenin found: 3 sources

A

•Abundant in many Fruits & Vegetables, but is particularly rich in: Parsley, Celery, Chamomile Tea.

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31
Q

Apigenin is one of the few phytochemicals to possess ___

A

•MONOAMINE TRANSPORT ACTIVITY.

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32
Q

Activity of apigenin

A
  • It’s a weak ligand for Benzodiazepine receptors and has anxiolytic and sedative properties.
  • It’s a Positive Allosteric Modulator (PAM) on GABAA receptors.
  • It’s an acute antagonist of NMDA receptors.
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33
Q

Luteolin is the pronciple yellow pigment in

A

•Reseda luteola

(Dyer’s Rocket)

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34
Q

Luteolin is found in 3 names

A

Celery, Broccoli, Green Peppers, Parsley, Thyme, Dandelion, Chamomile Tea, Carrots, Olive Oil, Peppermint, Rosemary, Navel Oranges, and Oregano

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35
Q

Action of luteolin

A
  • Luteolin is a natural PDE4 inhibitor in the brain. Excess PDE4 degrades cAMP. cAMP is important for neural signaling within brain cells.
  • cAMP produces proteins needed for neuron and synapse growth. This process is called Long-Term Potentiation (LTP).
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36
Q

Where tannins are found

A

•Occur widely in plants – associated with woody tissue.

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37
Q

Where tannins are found in cells?

A

In plant cells, tannins are located separately from proteins and enzymes in the cytoplasm.

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38
Q

Tannins: how they react with protein and implications

A
  • Tannins have the ability to react with protein, forming stable water-insoluble co-polymers.
  • Have the ability to cross-link with protein. Transforms raw animal skin into leather.
  • When tissue is damaged (herbivory), tannins react with protein and make them less accessible to digestive proteases.
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39
Q

Why herbivores avoid tannins

A

•Most herbivores avoid tannin-rich plants because of the astringent taste.

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40
Q

2 types of tannins

A

condensed adn hydrolysable

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41
Q

Condensed tannins: where occur and how it is formed

A

Occurs in ferns and conifers. Widespread in woody flowering plants.

•Formed by the condensation of single catechin or gallocatechin to form dimers and higher oligomers

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42
Q

Two subtypes in hydrolysable tannins

A

Gallic tannins and ellagic tannins

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43
Q

Where hydrolysable tannins are found?

A

Limited to dicotyledon plants.

•Dicotyledon are flowing plants that are NOT grasses.

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44
Q

What is it?

A

1.Gallic Tannins – Glucose core surrounded by 5 or more galloyl ester groups

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45
Q

How gallotannins can be hydrolyzed

A

GALLOTANNINS release glucose and gallic acid by hydrolysis at low ambient pH.

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46
Q

What is it?

A

ELLAGITANNINS are made from ellagic acid glycosides

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47
Q

The difference in taste between hydrolysable and condensed tannins

A

•Condensed tannins have a reduced astringency when compared to hydrolysable tannins.

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48
Q

Where naturally condensed tannins are found

A

in the skins and seeds of grapes (Vitis vinifera)

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49
Q

What is it?

A

catechin← tannin

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50
Q

What class is it?

A

Coumarins

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51
Q

coumarins are classified as a part of what family

A

•benzopyrone family.

52
Q

The most widespread coumarins in nature

A

Umbelliferone, esculetin and scopoletin

53
Q

How coumarins look and flavor

A

•Odourless crystalline solid with a sweet odour resembling the scent of vanilla and a bitter taste.

54
Q

How coumarins act as a defence mechanism

A

Serves as a chemical defense against predators by inhibiting synthesis of vitamin K.

•Potentially strong photocontact sensitizers but do not evoke phototoxic reactions.

55
Q

Coumarin related anti-coagulant

A
56
Q

What is it?

A

Isoprene monomer

57
Q

Isoprene monomers are bases for what class? What is the general formula

A

Terpenoids

•(C5H8)n

58
Q

What role terpenoids play in nature?

A

•Plays important roles in plant growth, metabolism, and ecology.

59
Q

What is the difference between terpenes and terpenoids?

A
  • Terpenes are hydrocarbons
  • Terpenoids are compounds derived from terpenes but have an OXYGEN atom.
60
Q

Functional groups and their name derivatives

A
61
Q

Linalool and geraniol: give the class

A

Monoterpene alcohol

62
Q

Is isoprene a terpenoid?

A

No, it is its own thing

63
Q

Painful card: terpenoids classification, amount of isoprene units (n), # of carbons, name, example

A
64
Q

The easiest way to recognize terpenes?

A

Count carbons, should be a derivative of (C5H8)

65
Q

Terpenoids solubility

A

Oil

66
Q

Where terpenoids are found

A

•Located in cytoplasm. Essential oils sometimes occur in glandular cells in leaf surface.

67
Q

What types of stereochemistry terpenoids have

A
  • Isomerism is common (geraniol vs. Nerol)
  • Cyclohexane ring can be in “chair” or “boat” formation.
68
Q

Carotenoids: color and function apart from antioxidant

A

•Carotenoids are accessory pigments in photosynthesis: Coloured pale yellow to bright orange to bright red.

69
Q

Terpenoids that have smell and odors

A

Mono- and sequiterpenoids

70
Q

Monoterpenes and sesquiterpenes: boiling point

A
  1. Monoterpenes (C10) – boiling point 140-180 °C
  2. Sesquiterpenes (C15) – boiling point >200 °C
71
Q

Monoterpenes and sesquiterpenes: subgroups

A
  1. Acyclic
  2. Monocyclic
  3. Bicyclic
  4. Tricyclic
  5. Polycyclic
72
Q

4 groups of triterpenoids

A
  1. True Triterpenoid
  2. Steroids
  3. Saponins
  4. Cardiac Glycosides
73
Q

Where triterpenoids are found and use for what by plants

A

•Occur in waxy coating of leaves and fruit to protect from microbial attack.

74
Q

Taste of tripterpenes and the example on the citrus fruit (give a name)

A

•Has bitter taste: limonin is the bitter principle in citrus fruits.

75
Q

Steroids Hormones are synthesized from __

A

Cholesterol

76
Q

Why he skipped diterpenoids

A

Diterpenoids are mostly found in animals (retinol)

77
Q

What is the precursor to all plant and animal sterols

A

Zero Rings: SQUALENE is a precursor for ALL plant and animal sterols, including CHOLESTEROL and STEROID HORMONES.

78
Q

Why saponins are called like that?

A

oSaponins are amphipathic glycosides grouped by the soap-like foam they produce when shaken in the water, and structurally by having one or more hydrophilic glycoside moieties combined with a lipophilic triterpene or steroid derivative.

oSaponin glycosides reduce the surface tension of water with foaming and will break down lipids.

79
Q

what is it?

A

Terpenoids→Triterpene

80
Q

What is it?

A

Terpenoids→Triterpene

81
Q

What is it?

A

Terpenoids→Triterpene

82
Q

What is it?

A

Terpenoids→Triterpene

83
Q

Araloside A, Bacoside A, Ginsengoside, Withaferin A what class

A

Terpenoids→Triterpene

84
Q

Why cardiac glycosides are called like that?

A

•Class of organic compounds that increase the output force of the heart and increase its rate of contractions by acting on the cellular sodium- potassium ATPase pump.

85
Q

What is it?

A

Cardiac glycoside (C30H48)

•Consists of a steroid molecule attached to a sugar (glycoside) and an R group.

86
Q

What is it? from digoxin

A

cardiac glycoside

87
Q

Carotenoid Lipid soluble pigment with 2 principle functions

A

1) Pigments in flowers & Fruits
2) Accessory pigments in photosynthesis

88
Q

Two classes of carotenoids

A

Hydrocarbons and oxygenated derivatives

89
Q

Hydrocarbons two subclasses, on what it is based?

A

Based on lycopene (8 isoprene units)

Cyclization of lycopene at one end gives γ-carotene Cyclization of lycopene at both ends give β-carotene

90
Q

Subclasses of oxygenated carotenoids and their examples

A

Monohydroxycarotenes: Lutein, Rubixanthin

Dihydroxycarotenes: Zeaxanthin

Dihydroxyepoxycarotenes: Violaxanthin

91
Q

What disease results in too much eating beta carotene

A

You become orange and develop betacarotenemia

92
Q

How much retinol you get from one beta carotene

A

2

93
Q

what is the largest class of phytochemicals?

A

alkaloids

94
Q

What is the color and taste of alkaloids?

A

•Usually colourless and have a bitter taste.

95
Q

what is the general structure of alkaloids

A

•Alkaloids are a diverse class that contains one or more nitrogen atoms, usually as part of a cyclic system.

96
Q

Alkaloids effect on humans

A

•Often toxic to humans and may have dramatic physiological activities.

97
Q

Alakloids are generally absent in

A

•Alkaloids are generally absent in gymnosperms (conifers), ferns, and mosses.

98
Q

3 groups of alkaloids

A

True akaloids

Protoalkaloids

Pseudoalkaloids

99
Q

True alkaloids structure, originate from, examples

A

1)True Alkaloids: contain nitrogen in the heterocycle and originate from amino acids (atropine, nicotine, morphine)

100
Q

What is it?

A

True alkaloid

101
Q

Protoalkaloid: structure and example

A

2)Simple amine in which the amino acid N is not in a heterocyclic ring (Ephedrine)

102
Q

What is it?

A

Protoalkaloid

103
Q

Pseudoalkaloids: structure and examples

A

Alkaloid-like compounds that do not originate from amino acids. Includes terpene-like and steroid-like alkaloids, as well as purine-like alkaloids (Caffeine, Theobromine, and Theophyline)

104
Q

What is it?

A

Pseudoalkaloids

105
Q

What type of true alkaloid is it?

A

Pyridine and piperidine

106
Q

What type of true alkaloid is it?

A

Pyrrolizdine

107
Q

What type of true alkaloid is it?

A

Tropane

108
Q

What type of true alkaloid is it?

A

Quinoline

109
Q

What type of true alkaloid is it?

A

Isoquinoline

110
Q

What type of true alkaloid is it?

A

Indole

111
Q

What type of true alkaloid is it?

A

Imidazole

112
Q

What type of alkaloid is it?

A

Protoalkaloid→alkylamine

113
Q

What type of alkaloid is it?

A

Pseudoalkaloid→purine

114
Q

Classify this compound

A

true pyridine alkaliod

115
Q

Classify this compound

A

True piperidine alkaloid

116
Q

Classify this compound, what can you say from its structure

A

true pyrrolizidine alkaloid

Presence of reactive carbon→ hepato toxicity

117
Q

Classify this compound

A

True tropane alkaloid

118
Q

Classify this compound

A

True alkaloid quinoline

119
Q

Classify this compound

A

true isoquinoline alkaloid

120
Q

Classify morphin

A

True isoquinoline alkaloid

121
Q

Classify this compound

A

Indole true alkaloid

122
Q

Classify this compound

A

True alkaloid imidazole

123
Q

Classify this compound

A

Alkylamine protoalkaloid

124
Q

Classify this compound

A

Alkylamine protoalkaloid

125
Q

Classify this compound

A

Purine pseudoalkaloid

Herbs and phytochemicals (10 decks)

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