Phytochemicals Flashcards
1
Q
What part of plants is more high in phytochemicals?
A
peel as it is a barrier
2
Q
Four classes of phytochemicals that we need to know
A
Phenolic compounds, terpenoids; organic acids, lipid and related compounds; nitrogen compounds
3
Q
Phenolic compounds subclasses
A
Flavonoid pigments including: anthocyanins, flavanols and flavones, tannins
4
Q
Terpenoids: subclasses
A
Essential oils, Carotenoids; triterpenoids and steroids
5
Q
Organic acids, lipid and related compounds: subclasses
A
Sulphur compounds
6
Q
Alkaloids subclass in what class it is included
A
Nitrogen compounds
7
Q
Phenolic compounds: solubility and where found
A
water-soluble and found in the vacuoles
8
Q
Phenolic compounds basic structure and what is the outcome
A
9
Q
How to recognize a flavonoid pigment?
A
10
Q
How flavonoids are usually present in plants?
A
Bound to a sugar as glycosides
11
Q
Flavonoid pigments: anthocyanins color
A
Scarlet, red, mauve and blue flower pigments
12
Q
Flavonols: color, where found
A
Mainly colourless co-pigments in flowers. Widespread in leaves
13
Q
Flavones: color, where found
A
Mainly colourless co-pigments in flowers. Widespread in leaves
14
Q
Flavanones: color, where found
A
Colourless, in leaves and fruit
15
Q
isoflavanones: pigment color, where found
A
Colourless, often in roots
16
Q
Isoflavones are common only in one family, which one
A
Only common in one family; the LEGUMINACEAE
17
Q
Substitution of one group on anthocyanin will result in___
A
Different color as different wavelength will be absorbed
18
Q
Flavonols occur most frequently in __ combiantions
A
Glycosidic
19
Q
KAEMPFEROL, QUERCETIN, MYRICETIN are three most common
A
Flavonols
20
Q
How flavonols differ from flavones and implication
A
differ in that they lack a 3-hydroxyl substitution. This affects their UV absorption.
21
Q
2 most common flavones
A
APIGENIN and LUTEOLIN
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
23
Q
What is it?
A
Flavonols
24
Q
Kaempferol, where found three, and 3 pharmacological activities
A
25
Common foods containing quesrcetin three
26
Quercetin is usually claimed to be anti-aging, are health claimed approved by USDA and HC?
No
27
what activity quesrcetin has
Quercetin glycosides have Estrogenic Activity. It’s roughly two to three orders of magnitude less potent than the endogenous estrogenic hormone 17β-estradiol
28
Three sources of myricetin
Abundant in Fruits, Vegetables, Nuts & Teas: Dock, Swiss Chard, Sweet Potato leaves, Rutabagas, Cranberries, Blueberries, Lemon, Blackberries, Garlic.
29
What properties myricetin has
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.**
30
Where apigenin found: 3 sources
•Abundant in many Fruits & Vegetables, but is particularly rich in: Parsley, Celery, Chamomile Tea.
31
Apigenin is one of the few phytochemicals to possess \_\_\_
•MONOAMINE TRANSPORT ACTIVITY.
32
Activity of apigenin
* 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.
33
Luteolin is the pronciple yellow pigment in
•*Reseda luteola*
## Footnote
(Dyer’s Rocket)
34
Luteolin is found in 3 names
Celery, Broccoli, Green Peppers, Parsley, Thyme, Dandelion, Chamomile Tea, Carrots, Olive Oil, Peppermint, Rosemary, Navel Oranges, and Oregano
35
Action of luteolin
* 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).
36
Where tannins are found
•Occur widely in plants – associated with woody tissue.
37
Where tannins are found in cells?
In plant cells, tannins are located separately from proteins and enzymes in the cytoplasm.
38
Tannins: how they react with protein and implications
* 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.**
39
Why herbivores avoid tannins
•Most herbivores avoid tannin-rich plants because of the astringent taste.
40
2 types of tannins
condensed adn hydrolysable
41
Condensed tannins: where occur and how it is formed
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
42
Two subtypes in hydrolysable tannins
Gallic tannins and ellagic tannins
43
Where hydrolysable tannins are found?
Limited to dicotyledon plants.
•Dicotyledon are flowing plants that are NOT grasses.
44
What is it?
1.**Gallic Tannins** – Glucose core surrounded by 5 or more galloyl ester groups
45
How gallotannins can be hydrolyzed
GALLOTANNINS release glucose and gallic acid by hydrolysis at low ambient pH.
46
What is it?
ELLAGITANNINS are made from ellagic acid glycosides
47
The difference in taste between hydrolysable and condensed tannins
•Condensed tannins have a reduced astringency when compared to hydrolysable tannins.
48
Where naturally condensed tannins are found
in the skins and seeds of grapes (*Vitis vinifera*)
49
What is it?
catechin← tannin
50
What class is it?
Coumarins
51
coumarins are classified as a part of what family
•benzopyrone family.
52
The most widespread coumarins in nature
Umbelliferone, esculetin and scopoletin
53
How coumarins look and flavor
•Odourless crystalline solid with a sweet odour resembling the scent of vanilla and a bitter taste.
54
How coumarins act as a defence mechanism
Serves as a chemical defense against predators by inhibiting synthesis of vitamin K.
•Potentially strong **photocontact sensitizers** but do not evoke phototoxic reactions.
55
Coumarin related anti-coagulant
56
What is it?
Isoprene monomer
57
Isoprene monomers are bases for what class? What is the general formula
Terpenoids
•(C5H8)n
58
What role terpenoids play in nature?
•Plays important roles in plant growth, metabolism, and ecology.
59
What is the difference between terpenes and terpenoids?
* **Terpenes** are hydrocarbons
* **Terpenoids** are compounds derived from terpenes but have an OXYGEN atom.
60
Functional groups and their name derivatives
61
Linalool and geraniol: give the class
Monoterpene alcohol
62
Is isoprene a terpenoid?
No, it is its own thing
63
Painful card: terpenoids classification, amount of isoprene units (n), # of carbons, name, example
64
The easiest way to recognize terpenes?
Count carbons, should be a derivative of (C5H8)
65
Terpenoids solubility
Oil
66
Where terpenoids are found
•Located in cytoplasm. Essential oils sometimes occur in glandular cells in leaf surface.
67
What types of stereochemistry terpenoids have
* Isomerism is common (geraniol vs. Nerol)
* Cyclohexane ring can be in “chair” or “boat” formation.
68
Carotenoids: color and function apart from antioxidant
•Carotenoids are accessory pigments in photosynthesis: Coloured pale yellow to bright orange to bright red.
69
Terpenoids that have smell and odors
Mono- and sequiterpenoids
70
Monoterpenes and sesquiterpenes: boiling point
1. **Monoterpenes** (C10) – boiling point 140-180 °C
2. **Sesquiterpenes** (C15) – boiling point \>200 °C
71
Monoterpenes and sesquiterpenes: subgroups
1. **Acyclic**
2. **Monocyclic**
3. **Bicyclic**
4. **Tricyclic**
5. **Polycyclic**
72
4 groups of triterpenoids
1. **True Triterpenoid**
2. **Steroids**
3. **Saponins**
4. **Cardiac Glycosides**
73
Where triterpenoids are found and use for what by plants
•Occur in waxy coating of leaves and fruit to protect from microbial attack.
74
Taste of tripterpenes and the example on the citrus fruit (give a name)
•Has bitter taste: **limonin** is the bitter principle in citrus fruits.
75
Steroids Hormones are synthesized from \_\_
Cholesterol
76
Why he skipped diterpenoids
Diterpenoids are mostly found in animals (retinol)
77
What is the precursor to all plant and animal sterols
Zero Rings: **SQUALENE** is a precursor for **ALL** plant and animal sterols, including CHOLESTEROL and STEROID HORMONES.
78
Why saponins are called like that?
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
what is it?
Terpenoids→Triterpene
80
What is it?
Terpenoids→Triterpene
81
What is it?
Terpenoids→Triterpene
82
What is it?
Terpenoids→Triterpene
83
Araloside A, Bacoside A, Ginsengoside, Withaferin A what class
Terpenoids→Triterpene
84
Why cardiac glycosides are called like that?
•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
What is it?
Cardiac glycoside (C30H48)
•Consists of a steroid molecule attached to a sugar (glycoside) and an R group.
86
What is it? from digoxin
cardiac glycoside
87
Carotenoid Lipid soluble pigment with 2 principle functions
1) Pigments in flowers & Fruits
2) Accessory pigments in photosynthesis
88
Two classes of carotenoids
Hydrocarbons and oxygenated derivatives
89
Hydrocarbons two subclasses, on what it is based?
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
Subclasses of oxygenated carotenoids and their examples
Monohydroxycarotenes: Lutein, Rubixanthin
Dihydroxycarotenes: Zeaxanthin
Dihydroxyepoxycarotenes: Violaxanthin
91
What disease results in too much eating beta carotene
You become orange and develop betacarotenemia
92
How much retinol you get from one beta carotene
2
93
what is the largest class of phytochemicals?
alkaloids
94
What is the color and taste of alkaloids?
•Usually colourless and have a bitter taste.
95
what is the general structure of alkaloids
•Alkaloids are a diverse class that contains one or more nitrogen atoms, usually as part of a cyclic system.
96
Alkaloids effect on humans
•Often toxic to humans and may have dramatic physiological activities.
97
Alakloids are generally absent in
•Alkaloids are generally absent in gymnosperms (conifers), ferns, and mosses.
98
3 groups of alkaloids
True akaloids
Protoalkaloids
Pseudoalkaloids
99
True alkaloids structure, originate from, examples
1)**True Alkaloids:** contain nitrogen in the heterocycle and originate from amino acids (atropine, nicotine, morphine)
100
What is it?
True alkaloid
101
Protoalkaloid: structure and example
2)Simple amine in which the amino acid N is not in a heterocyclic ring (Ephedrine)
102
What is it?
Protoalkaloid
103
Pseudoalkaloids: structure and examples
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
What is it?
Pseudoalkaloids
105
What type of true alkaloid is it?
Pyridine and piperidine
106
What type of true alkaloid is it?
Pyrrolizdine
107
What type of true alkaloid is it?
Tropane
108
What type of true alkaloid is it?
Quinoline
109
What type of true alkaloid is it?
Isoquinoline
110
What type of true alkaloid is it?
Indole
111
What type of true alkaloid is it?
Imidazole
112
What type of alkaloid is it?
Protoalkaloid→alkylamine
113
What type of alkaloid is it?
Pseudoalkaloid→purine
114
Classify this compound
true pyridine alkaliod
115
Classify this compound
True piperidine alkaloid
116
Classify this compound, what can you say from its structure
true pyrrolizidine alkaloid
Presence of reactive carbon→ hepato toxicity
117
Classify this compound
True tropane alkaloid
118
Classify this compound
True alkaloid quinoline
119
Classify this compound
true isoquinoline alkaloid
120
Classify morphin
True isoquinoline alkaloid
121
Classify this compound
Indole true alkaloid
122
Classify this compound
True alkaloid imidazole
123
Classify this compound
Alkylamine protoalkaloid
124
Classify this compound
Alkylamine protoalkaloid
125
Classify this compound
Purine pseudoalkaloid
