PIGMENTS, PERFUMES AND POISONS

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• Today
• Quiz 6 Discussion
• Plant medicines (concl.)
• Plant fibers
• Thursday
• Plant dyes

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• Quiz 6 High 22 Low 3 Class Average 16.2
• 1) Glucosinolates are sulfur-containing volatile
  compounds produced by plants in the mustard plant
  family.
• What is the meaning of volatile?
• What is typical of the molecules of volatile
  compounds?
• 2) Name and write one functional group that is
  always found
• in carbohydrates (sugars)
• b) in amino acids
• (On both quizzes)
• a) What is an alkaloid (define)?
• b) Name two examples of alkaloids

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• (On both quizzes)
• Name two extraordinary properties of the compound
  H2O
• b) Where in the Periodic Chart do you find
  metals?
• 5) Below is the structure of Vitamin E
  (tocopherol). Vitamin E is found in nuts and
  seeds.

• How can you see from the molecule structure of
  Vitamin E that it is water-insoluble (i.e. fat
  soluble)?
• What makes Vitamin E a phenolic?
• Extra Credit (2 points) Label clearly two chiral
  centers in the molecule of Vitamin E above.

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1) The leaves of cherry trees and the pits of
cherries and plums contain cyanogenic
glycosides. a) What is a glycoside? b) What does
a cyanogenic glycoside always produce when
interacting with the proper enzyme? 4) Below is
the structure of Vitamin A or retinol which our
body can synthesize from b-carotene
a) How can you see from its chemical structure
that vitamin A is colored (yellow)? b) How can
you see from its chemical structure that Vitamin
A is water-insoluble (i.e. fat-soluble)?
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5) Vitamin C or ascorbic acid (see structure
below) is found in citrus fruit.

• What makes Vitamin C water-soluble?
• b) Vitamin C is an acid. What is an acid?
• Extra Credit (2 pts.)
• Label clearly the two chiral centers in Vitamin C.

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Chemistry of Plant Medicines (Concl.)

• History Traditional plant medicines
• Procedures to obtain plant-derived
  pharmaceuticals
• Pharmacologically Active Plant Compounds
  Isolated in the19th Century (Morphine, quinine,
  atropine, scopolamine)
• Herbal medicines
• More Recent Discoveries of Complex Plant
  Compounds With Pharmacological Activity
  (reserpine, vinblastine, taxol)
• Drugs from Nonmedicinal Plants
• Antibiotics
• (Refer to Appendix in your Reader Old yet new
  pharmaceuticals)

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Using the Natural Molecule as a Template Drugs
from Nonmedicinal Plants

• Steroids from Yams

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Steroids from Yams (Dioscorea spp.)

• Cortisones, contraceptives, anabolics
• Carl Djerassi and the Pill
• Steroids Made It Possible

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STEROID STRUCTURE

• basic structure of
• 3 fused cyclohexanes and a fused cyclopentane
• (many chiral centers!)

• Steroid Functions in Humans
• membrane components cholesterol
• hormones
• sex hormones
• cortisones

D
C
A
B
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Figure 1. Steroids from Plants
a plant saponin (as the glycoside)
_
an oral contraceptive
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Figure 1. Steroids from Plants
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Antibiotics

• chemical compounds derived from a microorganism
  (mold or bacterium) that kill bacteria
• All are organic compounds
• Chemical structures are very different from plant
  compounds

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Antibiotics from Molds
Penicillium spp. Aspergillus spp.
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Penicillin
Penicillin G Potassium Salt
Alexander Fleming 1928
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Practice

• Name an OTC pharmaceutical that was originally
  derived from plants
• What is an antibiotic?

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Plant Fibers
Chemistry topics Polymers. Carbohydrates.
Proteins
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Types of Fibers

• Plant Fibers
• Cotton, ramie, hemp, linen
• Animal Fibers
• Wool, silk, hair
• Artificial fibers
• Polyester, rayon, nylon ..

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Chemistry of Fibers Polymers !

• Plant fibers
• mostly cellulose
• Animal fibers
• proteins
• Artificial fibers
• various polymers polyesters, polyamides,

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Chemistry of Fibers Polymers !
Plant fibers are (mostly) cellulose
segment of the cellulose molecule
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Chemistry of Fibers
Animal fibers are fibrous proteins S!
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Experiment!Nylon-6,6, an artificial proteina
polymer!
Peptide Bond (A polyamide)
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Artificial Polymers
Slime from polyvinyl alcohol and borax solution
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Artificial Polymers
Slime
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Thursday Plant dyes