1. 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?

2. 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

3. 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.

4. 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

5. 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

6. 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

7. 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

8. 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

9. 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!

10. >100,000 types; tremendous variety of functions Defense Herbivores
Natural Products
>100,000 types; tremendous variety of functions
Defense
Herbivores
nicotine

11. >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

12. >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

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

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

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

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

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

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

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

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

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

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

23. 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

24. 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

25. 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

26. 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

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

28. 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

29. 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

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

31. 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

32. 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

33. >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

34. >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

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

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

37. 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

38. 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

39. 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

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

41. 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!

42. 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.

43. 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

44. 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

45. 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)

46. 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

47. 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

48. 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

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

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

51. Other natural products
> 100 glucosinolates: contain S and N

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

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

54. 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

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

56. Other natural products
The genus Allium produces sulfoxides derived from cysteine

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