Course Plan We will study effects of soil and stresses on plant secondary products and see where it leads us Learn more about plant secondary products Why do they make them? When do they make them? Where do they make them?

Pick some plants to study Capsicum (Chiles) = capsaicin Nicotiana (Tobacco) = nicotine Onions (Allium cepa)?= syn-Propanethial-S-oxide Garlic (Allium sativum)?= Alliin Radishes (Raphanus sativus) = glucosinolates Mustard (Brassica juncea) = glucosinolates Peppermint (Mentha × piperita) = menthol + many Catnip (Nepeta cataria) = nepetalactone Stresses Water Nitrogen Sulfur Herbivory Shaking

On Friday Present a plant stressor, what is known about it, and why it might affect plant 2˚ compounds in an ~ 10 minute presentation. Alternative: presenting another good plant/stressor response to study and why we should choose it over the ones already chosen.

Secondary Metabolites 1˚ metabolites are essential for growth & development therefore present in all plants 2˚ metabolites “not” required for growth & development therefore not present in all plants

1˚ metabolites are essential for growth & development Natural Products 1˚ metabolites are essential for growth & development therefore present in all plants 2˚ metabolites “not” required for growth & development therefore not present in all plants Often only found in one or a few spp. capsaicin Nepetalactone, menthol Nepetalactone Menthol

Natural Products 1˚ metabolites are essential for growth & development therefore present in all plants 2˚ metabolites “not” required for growth & development therefore not present in all plants Often only found in one or a few spp. Derived from 1˚ metabs

Natural Products 2˚ metabolites “not” required for growth & development therefore not present in all plants Often only found in one or a few spp. Derived from 1˚ metabs, can be hard to draw line

Natural Products 2˚ metabolites “not” required for growth & development therefore not present in all plants Often only found in one or a few spp. Derived from 1˚ metabs, can be hard to draw line

Natural Products 2˚ metabolites not present in all plants Often only found in one or a few spp. Derived from 1˚ metabs, can be hard to draw line Can be up to 3% of dry weight: very expensive to the the plant!

>100,000 types; tremendous variety of functions Defense Herbivores Natural Products >100,000 types; tremendous variety of functions Defense Herbivores nicotine

>100,000 types; tremendous variety of functions Defense Herbivores Natural Products >100,000 types; tremendous variety of functions Defense Herbivores Pathogens Resveratrol Brassilexin = antifungal Berfberine = antibacterial

>100,000 types; tremendous variety of functions Defense Herbivores Natural Products >100,000 types; tremendous variety of functions Defense Herbivores Pathogens Other plants leptospermone leptospermone

Natural Products >100,000 types; tremendous variety of functions Defense Attractant Pollinators Odors Colors

Natural Products >100,000 types; tremendous variety of functions Defense Attractant Pollinators Symbionts

Natural Products >100,000 types; tremendous variety of functions Defense Attractant Pollinators Symbionts Seed dispersers Methyl anthranilate(strawberries) Pentyl butyrate (pears, apricots)

Natural Products >100,000 types; tremendous variety of functions Defense Attractant Pollinators Symbionts Seed dispersers “protectors” (tritrophic interactions)

Natural Products >100,000 types; tremendous variety of functions Defense Attractant Protecting from UV

Natural Products >100,000 types; tremendous variety of functions Defense Attractant Protecting from UV metal uptake and transport

Natural Products >100,000 types; tremendous variety of functions Defense Attractant Protecting from UV metal uptake and transport Hardening cell walls

Natural Products >100,000 types; tremendous variety of functions Some are made constitutively

Natural Products >100,000 types; tremendous variety of functions Some are made constitutively Others are induced, especially defense compounds

Natural Products >100,000 types; tremendous variety of functions Some are made constitutively, others are induced Made in many cellular locations Cytoplasm: most hydrophilics

Natural Products >100,000 types; tremendous variety of functions Some are made constitutively, others are induced Made in many cellular locations Cytoplasm: most hydrophilics Chloroplasts: terpenoids and some alkaloids

Natural Products >100,000 types; tremendous variety of functions Some are made constitutively, others are induced Made in many cellular locations Cytoplasm: most hydrophilics Chloroplasts: terpenoids and some alkaloids Mitochondria: some alkaloids and some amines

Natural Products >100,000 types; tremendous variety of functions Some are made constitutively, others are induced Made in many cellular locations Cytoplasm: most hydrophilics Chloroplasts: terpenoids and some alkaloids Mitochondria: some alkaloids and some amines Peroxisomes: some terpenoids, convert glucosinolates to active form upon pathogen attack

Natural Products >100,000 types; tremendous variety of functions Some are made constitutively, others are induced Made in many cellular locations Cytoplasm: most hydrophilics Chloroplasts: terpenoids and some alkaloids Mitochondria: some alkaloids and some amines Peroxisomes: some terpenoids, convert glucosinolates to active form upon pathogen attack Endoplasmic reticulum: fatty acid derivatives, other nonpolars

Natural Products >100,000 types; tremendous variety of functions Made in many cellular locations Made in many cell types Some in all

Natural Products >100,000 types; tremendous variety of functions Made in many cellular locations Made in many cell types Some in all Others in specialized cells or tissues

Natural Products >100,000 types; tremendous variety of functions Made in many cellular locations Made in many cell types Some in all Others in specialized cells or tissues Some are transported in xylem or phloem from site of synthesis to where they are stored

Natural Products >100,000 types; tremendous variety of functions Made in many cellular locations Made in many cell types Many are stored in vacuole

Natural Products >100,000 types; tremendous variety of functions Made in many cellular locations Made in many cell types Many are stored in vacuole Others in plastids or ER

Natural Products >100,000 types; tremendous variety of functions Made in many cellular locations Made in many cell types Some are stored in special cell types, eg trichomes

>100,000 types; tremendous variety of functions Natural Products >100,000 types; tremendous variety of functions Made in many cellular locations Made in many cell types Some are stored in special cell types Others in special cavities or ducts Left = lemon secretory cavity Right = pine resin duct Secretory cavity in lemon Pine resin duct

>100,000 types; tremendous variety of functions Natural Products >100,000 types; tremendous variety of functions Made in many cellular locations Made in many cell types Some are stored in special cell types Others in special cavities or ducts Others in flowers, leaves or fruits Left = lemon secretory cavity Right = pine resin duct

Natural Products >100,000 types; 3 main groups Terpenoids Alkaloids Phenolics

Natural Products >100,000 types; 3 main groups >30,000 terpenoids: made from isoprene units

Natural Products >100,000 types; 3 main groups >30,000 terpenoids: made from isoprene units Some with N, most w/o Monoterpenoids mostly essential oils

Natural Products >100,000 types; 3 main groups >30,000 terpenoids: made from isoprene units Some with N, most w/o Monoterpenoids mostly essential oils Longer ones have diverse functions Pigments Signals Defense

Natural Products >100,000 types; 3 main groups >30,000 terpenoids: made from isoprene units Longer ones have diverse functions Pigments Signals Defense Phytoecdysterones mimic ecdysone & cause molting

Natural Products >100,000 types; 3 main groups >30,000 terpenoids: made from isoprene units >12,000 Alkaloids: derived from amino acids: contain N

Natural Products >100,000 types; 3 main groups >30,000 terpenoids: made from isoprene units >12,000 Alkaloids: derived from amino acids: contain N Many drugs!

Natural Products >100,000 types; 3 main groups >30,000 terpenoids: made from isoprene units >12,000 Alkaloids: derived from amino acids: contain N Many drugs! Mainly for defense.

Natural Products >100,000 types; 3 main groups >30,000 terpenoids: made from isoprene units >12,000 Alkaloids: derived from amino acids: contain N >8,000 phenolics: contain phenol ring

Natural Products >100,000 types; 3 main groups >30,000 terpenoids: made from isoprene units >12,000 Alkaloids: derived from amino acids: contain N >8,000 phenolics: contain phenol ring Crucial for moving onto land! Strengthen cell wall enough to support wt on land & transport water

Phenolics >8,000 phenolics: contain phenol ring Crucial for moving onto land! Strengthen cell wall enough to support wt on land & transport water Comprise ~40% of organic C in the biosphere (most in cell walls)

Phenolics >8,000 phenolics: contain phenol ring Crucial for moving onto land! Strengthen cell wall enough to support wt on land & transport water Comprise ~40% of organic C in the biosphere (most in cell walls) Many serve other functions: Pigments

Phenolics >8,000 phenolics: contain phenol ring Crucial for moving onto land! Strengthen cell wall enough to support wt on land & transport water Comprise ~40% of organic C in the biosphere (most in cell walls) Many serve other functions: Pigments Signals

Phenolics >8,000 phenolics: contain phenol ring Crucial for moving onto land! Strengthen cell wall enough to support wt on land & transport water Comprise ~40% of organic C in the biosphere (most in cell walls) Many serve other functions: Pigments Signals Defense

Phenolics >8,000 phenolics: contain phenol ring Most are derived from phenypropanoid

Other natural products ~ 100 cyanogenic glycosides Release cyanide when plant is damaged Found in seeds of apricots, cherries, other fruits Laetrile

Other natural products > 100 glucosinolates: contain S and N

Other natural products > 100 glucosinolates: contain S and N Mainly found in Brassicaceae (crucifers)

Other natural products > 100 glucosinolates: contain S and N Mainly found in Brassicaceae (crucifers) Made from modified amino acids bonded to glucose

Other natural products > 100 glucosinolates: contain S and N Mainly found in Brassicaceae (crucifers) Made from modified amino acids bonded to glucose Function in defense

Other natural products > 100 glucosinolates: function in defense When damaged release Isothiocyanates nitriles and elemental sulfur Thiocyanates oxazolidine-thiones epithionitriles

Other natural products The genus Allium produces sulfoxides derived from cysteine

Other natural products The genus Allium produces sulfoxides derived from cysteine When plants are damaged they are converted to pungent volatiles