Secondary Metabolites (Phenolic Compounds)

[Phenolic Compounds] Large __ group

heterogenous

[Phenolic Compounds] Also claimed to be the __ class of secondary metabolites

largest

[Phenolic Compounds] Classify

Coumaric Acid, Caffeic Acid, Ferulic Acid

Phenolic Acids; Hydroxy Cinnamic Acids

[Phenolic Compounds] Classify

Salicylic Acid

Phenolic Acids; Hydroxy Benzoic Acids

[Phenolic Compounds] Classify

Cyanidin, Delphinidin, Malvidin, Pelargonin, Peonidin, Petunidin

Flavonoids; Anthocyanins

[Phenolic Compounds] Classify

Kaempferol, Myrcetin, Quercitin

Flavonoids; Flavonols

[Phenolic Compounds] Classify

Catechin, Epicatechin, Epigallocatechin, Proanthocyanidins, Theaflavins, Thearubigins

Flavonoids; Flavanols

[Phenolic Compounds] Classify

Apigenin, Luteolin, Baicalein, Chrysin

Flavonoids; Flavones

[Phenolic Compounds] Classify

Eriodictyol, Hesperetin, Naringenin

Flavonoids; Flavanones

[Phenolic Compounds] Classify

Daidzein, Genistein, Glycitein, Formonetin

Flavonoids; Isoflavones

[Phenolic Compounds] Classify

Resveratrol

Stilbenes

[Phenolic Compounds] Classify

Secoisolariciresinol

Lignans

[Phenolic Compounds] In higher plants, most phenolics are derived at least in part from _, a product of the shikimic acid pathway

phenylalanine

[Phenolic Compounds] What is the structure of Simple phenylpropanoids

C6-C3

[Phenolic Compounds] What is the structure of Benzoic acid derivatives

C6-C1

[Phenolic Compounds] Coumarins are considered as

Simple phenylpropanoids

[Phenolic Compounds] Classify: Caffeic acid

Simple phenylpropanoids

[Phenolic Compounds] Classify: Ferulic acid

Simple phenylpropanoids

[Phenolic Compounds] Differentiate the structures of Caffeic and Ferulic Acid

Caffeic acid has a hydroxyl group while ferulic acid has a methoxy group

[Phenolic Compounds] Classify: Umbelliferone

Simple phenylpropanoids, Coumarin

[Phenolic Compounds] Classify: Psoralen

Simple phenylpropanoids, Coumarin

[Phenolic Compounds] Differentiate Umbelliferone and Psoralen

Psoralen has a furan ring on the left

[Phenolic Compounds] Classify: Vanillin

Benzoic acid derivatives

[Phenolic Compounds] Classify: Salicylic Acid

Benzoic acid derivatives

[Phenolic Compounds] Differentiate vanillin and Salicylic acid

Vanillin has 3 feet

[Phenolic Compounds] Can inhibit the growth of neighboring plants when released into the soil (allelopathy)

Simple phenylpropanoids

[Phenolic Compounds] Exhibits phototoxicity to insect herbivores

Coumarins

[Phenolic Compounds] plant hormone that is also involved in systemic resistance to plant pathogens

Salicylic Acid

[Phenolic Compounds] at high concentration can be toxic to living cells

Vanillin

[Phenolic Compounds] Lignins Lignin’s complex structure:

highly branched polymer of the phenylpropanoid groups

[Phenolic Compounds] Lignins Lignin is the most abundant __ (after cellulose)

organic substance

[Phenolic Compounds] Lignins Lignin is the most abundant organic substance (after _)

cellulose

[Phenolic Compounds] Lignins Lignin is Found in ___ and make up supporting (for mechanical rigidity) and conducting tissues (for water transport)

cell walls

[Phenolic Compounds] Lignins Lignin is Found in cell walls and make up __

supporting (for mechanical rigidity) and conducting tissues (for water transport)

[Phenolic Compounds] Lignins Lignin block the growth of _

pathogens

[Phenolic Compounds] Lignins Lignin are Relatively __ herbivores

indigestible and deters

[Phenolic Compounds] Flavonoids What is the basic structure of flavonoids

C6-C3-C6

[Phenolic Compounds] Flavonoids The green C3 (bridge)-C6 (ring) is derived from

Shikimic acid pathway via phenylalanine

[Phenolic Compounds] Flavonoids The yellowC6 (ring) is derived from

Malonic acid pathway

[Phenolic Compounds] Flavonoids What sub group are glycosides; pigment responsible for the red, pink, purple and blue colors in flowers and fruits – this functions to attract pollinators and seed disperser

Anthocyanins

[Phenolic Compounds] Flavonoids Anthocyanins contain

sugar

[Phenolic Compounds] Flavonoids Correlate the pigments: Chlorphyll, Anthocyanin, Carotene

Green, Red, Yellow

[Phenolic Compounds] Flavonoids absorb light at shorter wavelengths only visible to insects

Flavones and flavonols

[Phenolic Compounds] Differentiate Flavones from Flavonols

[Phenolic Compounds] Flavonoids Flavones and flavonols protect cells from __ while they accumulate on leaves and stems

excessive UV radiation

[Phenolic Compounds] Flavonoids Flavones and flavonols can also be secreted into the soil by the roots of legumes to mediate in the __

interaction between legumes and rhizobacteria

[Phenolic Compounds] Tannins General toxins that can __

reduce the growth and survival of herbivores

[Phenolic Compounds] Tannins Act as feeding __

repellents to a great variety of animals (cattle, deer, apes)

[Phenolic Compounds] Tannins Classify the Tanin class: Formed from flavonoid polymerization

Condensed tannin

[Phenolic Compounds] Tannins Classify the Tanin class: Pro-anthocyanidins

Condensed tannin

[Phenolic Compounds] Tannins Classify the Tanin class: Common constituents of woody plants

Condensed tannin

[Phenolic Compounds] Tannins Classify the Tanin class: Heterogenous polymers containing phenolic acids like gallic acids and sugars

Hydrolyzable tannins

[SHIKIMIC ACID PATHWAY] Shikimic acid is a key intermediate in biosynthesis of

aromatic amino acids

[SHIKIMIC ACID PATHWAY] aromatic amino acids

tyrosine, tryptophan and phenylalanine

[SHIKIMIC ACID PATHWAY] aromatic amino acids are precursors of secondary metabolites like __

alkaloids and flavonoids

[SHIKIMIC ACID PATHWAY] How many steps are there in the formation of chorismate?

7 + Chorismate formation

[SHIKIMIC ACID PATHWAY] What is the mnemonic for Shikimic Acid pathway

PPE 2K DUDS SS5 3EPS C 2K PPE ARE DUDS SSS PEP COSTS 3 Epsilon

[SHIKIMIC ACID PATHWAY] What is the Step 1 in Shikimic Acid Pathway

Phosphoenol Pyruvate + Erythrose-4-P + H2O

[SHIKIMIC ACID PATHWAY] What is the Step 2 in Shikimic Acid Pathway

2-Keto-3-Deoxy-Darabinoheptulosonate-7- Phosphate

[SHIKIMIC ACID PATHWAY] What is the Step 3 in Shikimic Acid Pathway

5-Dehydroquinate

[SHIKIMIC ACID PATHWAY] What is the Step 4 in Shikimic Acid Pathway

5-Dehydroshikimate + NADPH + H+

[SHIKIMIC ACID PATHWAY] What is the Step 5 in Shikimic Acid Pathway

Shikimate

[SHIKIMIC ACID PATHWAY] What is the Step 6 in Shikimic Acid Pathway

Shikimate-5-P + PEP

[SHIKIMIC ACID PATHWAY] What is the Step 7 in Shikimic Acid Pathway

3-Enolpyruvylshikimate-5-P

[SHIKIMIC ACID PATHWAY] What is the Step 8 in Shikimic Acid Pathway

Chorismate

[SHIKIMIC ACID PATHWAY] In tryptophan biosynthesis (Short version) what are the intermediates

Chorismate > Anthranilic Acid > Tryptophan

[SHIKIMIC ACID PATHWAY] In tryptophan biosynthesis (Long version) what are the intermediates 5+1

Chorismate + Glutamine > Anthranilic Acid + PRPP > N-(5’-Phosphoribosyl)- Anthranilate > enol-1-O-Carboxyphenylamino-1- Deoxyribulose Phosphate > Indole-3-Glycerol-P > Tryptophan

[SHIKIMIC ACID PATHWAY] In tryptophan biosynthesis (Long version) what are the intermediates of step 1

Chorismate + Glutamine

[SHIKIMIC ACID PATHWAY] In tryptophan biosynthesis (Long version) what are the intermediates of step 2

Anthranilate + Prpp

[SHIKIMIC ACID PATHWAY] In tryptophan biosynthesis (Long version) what are the intermediates of step 3

N-(5’-Phosphoribosyl)- Anthranilate

[SHIKIMIC ACID PATHWAY] In tryptophan biosynthesis (Long version) what are the intermediates of step 4

Enol-1-O-Carboxyphenylamino-1- Deoxyribulose Phosphate

[SHIKIMIC ACID PATHWAY] In tryptophan biosynthesis (Long version) what are the intermediates of step 5

Indole-3-Glycerol-P + Serine

[SHIKIMIC ACID PATHWAY] In tryptophan biosynthesis (Long version) what are the product of step 6

Tryptophan

[SHIKIMIC ACID PATHWAY] In phenylalanine biosynthesis what are the intermediates

Chorismate > Prephenic acid > Phenylalanine

[SHIKIMIC ACID PATHWAY] In Salicylic Acid biosynthesis what are the intermediates

Chorismate > Isochorismate > Salicylic Acid

[Phenolic Compounds] biopolymer derived from wood

lignins

[Phenolic Compounds] lignins are derived from what amino acid

phenylalanine (and tyrosine in some cases)

[Phenolic Compounds] Lignins What intermediate of sinapic acid is being described Step 2: from oil of cinnamon

cinnamic acid

[Phenolic Compounds] Lignins What intermediate of sinapic acid is being described Step 3

p-coumaric acid

[Phenolic Compounds] Lignins What intermediate of sinapic acid is being described Step 4 carcinogenic inhibitor; antioxidant

caffeic acid

[Phenolic Compounds] Lignins What intermediate of sinapic acid is being described Step 5 phytochemical; found in plant cell wall

ferulic acid

[Phenolic Compounds] Lignins Rosmarinic Acid is derived from what 2 amino acids

Phe and Tyr

[Phenolic Compounds] Lignins antioxidant; commonly found in herbs like rosemary, oregano, sage, thyme, peppermint (Mentha species)

rosmarinic acid

[Phenolic Compounds] Lignins podophyllotoxin, a tumour-inhibitory lignan is derived from what intermediate of sinapic acid

ferulic acid (2 units)

[Phenolic Compounds] Lignins podophyllotoxin pathway is composed of 3 intermediates

ferulic acid (2 units), matairesinol, and yatein

[Phenolic Compounds] allylphenols are derived from

phenylalanine

[Phenolic Compounds] allylphenols used in perfumery, flavoring; antiseptic and anesthetic; main component of clove oil

eugenol

[Phenolic Compounds] allylphenols active constituent of fresh ginger

gingerol

[Phenolic Compounds] allylphenols found in red grapes; constituent of red wine phytoalexin (antibiotic produced by plants when under attack)

resveratrol

[Phenolic Compounds] What is the classification of eugenol

allylphenols

[Phenolic Compounds] What is the classification of gingerol

allylphenols

[Phenolic Compounds] What is the classification of this compound

allylphenols; psilotin

[Phenolic Compounds] What is the classification of this compound

allylphenols; resveratrol

[Phenolic Compounds] What is the classification of this

allylphenols; lunaric acid

[Phenolic Compounds] What is the classification of this

allylphenols; hircinol

[Phenolic Compounds] What is the classification of this

allylphenols; magniferin (a xanthone)

[Phenolic Compounds] What is the classification of this

allylphenols; bakuchiol

[Phenolic Compounds] What is the classification of this

allylphenols; isobatatasin I

[Phenolic Compounds] What is the classification of this

quinones; benzoquinone

[Phenolic Compounds] What is the classification of;

quinones; naphthoquinone