You are on page 1of 3

Roles of plant hormones

1. Regulatory
2. Chemical defense against pests

1-THC (tetrahydrocannabinol) responsible for mindaltering effect of Cannabis sativa


-

Synthesized by Mechoulam and Gaoni

Chemical messengers
1. Sex attractants (pheromones)
a. Insects differ in many insects
Concentration: 10-9 to 10-12
b. Terrestrial animals
c. Marine animals
d. Humans

Alexander Fleming isolated penicillin (antibiotic)


Penicillin active against tuberculosis
Waxman isolated streptomycin
Streptomycin used for treatment of tuberculosis

Egyptians
1. Opium
2. Castor oil
3. Rotten bread treat infections
Resembles antibiotics (produced by moulds
and fungi) usage

Conformational analysis designed by Derek Barton


-

Robert B. Woodward structural determination of


penicillin, strychnine, patalin, terramycin, aureomycin

Dioscorides Roman physician


-

Used for structural determinations of many


complex molecules (-amyrin and cycloartenol)

Synthesis of Vitamin B12

Wrote the first systemic material medica


Described medicinal properties of wines
A. Birch and R. Robinson studied biosynthesis of
polyketides having C6-C3-C6 backbones such as:

Shen Nung Pen Tsao oldest compilation of Chinese


herbs
-

Lists 385 materials

Pen Tsao Ma catalogue


-

Written by Li-Chen (Ming Dynasty)


1 898 herbal drugs and 8 160 prescriptions

Panax ginseng Ginseng root


-

For health maintenance


Treatment of various diseases

Ginkgo biloba from Ginkgo tree


-

a.
b.
c.
d.
e.

Plant phenolics
Polyene macrolides
Terpenoids and alkaloids
Sterols
Fatty acids and prostaglandins (from seminal
fluids)

Isoprene rule proposed by Otto Wallach


Paul Karrer established foundation of carotenoid
chemistry
Adolf Butenandt dealt with human sex hormones
-

Improve memory
Sharpen mental alertness

Bark of China tree treatment of malaria


Quinine isolated by Pelletia and Caventou
-

From China tree

Mescaline powerful hallucinogen


-

Used by American Indians

Cannabis sativa Indian hemp plant


-

Hallucinogen
Used as marijuana or hashish

Obtained:
a. Estrogen from pregnant women
b. Progesterone from sow ovaries
c. Androsterone from male urine
d. (with Peter Karlson) Ecdysone from
silkworm larvae

Ecdysone insect and crustacean molting hormone


Cortisone anti-arthritic hormone
-

Used as an important military medicine (WWII)

Carl Djerassi synthesis of the first oral contraceptive pill


for women
Koji Mori field of synthesis of pheromones

Strychnos and Chondrodendion contains strychnine


-

Used in arrow poisons

Rye infected by Claviceps porpurea produces ergotamine


and a number of ergot alkaloids these cause serious
illnesses
Bloch and Woodward suggested a mechanism for
cyclization of squalene to cholesterol

Photosynthesis primary synthetic process in


nature
Green plants utilize the energy of the sun for
the production of organic compounds from
CO2
Carbohydrates initial products of photosynthesis
-

Francis Crick and James Watson described the double


helix structure of proteins
Hodgkin determined the structure of vitamin B12 and of
penicillin
Paul Scheuer studied bioactive compounds from
mollusks and other marine sources
Luigi Minale, Raffaele Riccio, and Maria Iorizzi conducted
a comprehensive research on marine steroidal glycosides
Palytoxin most poisonous substance from the Hawaiian
soft coral (Palythoa toxica)
-

Isolated by Woodward
Contains 64 chiral centers, 7 double bonds
Capable of E/Z isomerism (271 possible
isomers close to Avogadros number)
Synthesized by Armstrong, et al.

Maitotoxin most toxic toxin


-

Empirical formula: C164H256O68S2NO2


Molecular weight: 3 422

Kinghorn and Balandrin described human medicinal


agents from plants

Classification of Natural Products


1. Classification based on the molecular skeletal
structure:
a. Open-chain aliphatic
b. Alicyclic and cycloaparaffinic
c. Aromatic
d. Benzenoid
e. Heterocyclic
2. Classification based on physiological activity
Morphine and Penicillin G alkaloids
3. Classification based on chemotaxonomy
Chemotaxonomy attempts to review plant
constituents according to plant taxa
Constituents are regarded as markers for
evolution as well as classification of plants
4. Classification based on biogenesis

When altered metabolically, they become


organic compounds of low molecular weight
and simple structures (e.g. carboxylic acids,
amino acids)

Carboxylic acids and amino acids form the


synthetic starting materials for specific, genetically
controlled, enzymatically catalyzed reactions that
lead to the complex compounds that characterize
the secondary metabolism of plants and mammals
Biosynthetic pathway reaction pathway leading
to a particular natural product
Biogenesis corresponding event
Different plant and animal species can employ
different biosynthetic pathways to produce the
same metabolite
4 Major Classes of Biochemicals
1.
2.
3.
4.

Carbohydrates
Proteins
Nucleic acids
Lipids

Carbohydrates, Proteins, and Nucleic acids could


have arisen through prebiotic chemistry
Acetate as a biosynthetic origin
a.
b.
c.

Fatty acids
Terpenes
Polyketide biosynthesis

Amino acids as biosynthetic origin


a.

Alkaloid biosynthesis

Fourier transform nuclear magnetic resonance (FTNMR)


and Fourier transform infrared (FTIR) allows recovery of
the sample in contrast to mass spectrometric
determination
Mass spectrometry (MS) destructive but a necessary
technique

Modern methods used to separate complex organic


mixtures utilizing:
a.
b.
c.

Gas-liquid chromatography (GLC)


High-pressure liquid chromatography (HPLC)
Droplet counter-current (DCC) chromatography

can separate samples rapidly and efficiently in the


pictogram range
Coupled chromatographic instruments (chromatographic
instruments + spectrometers)
1.
2.
3.
4.
5.
6.
7.
8.

GC-MS
GC-FTIR
GC-MI-FTIR
GC-UV-VIS
HPLC-MS
HPLC-FTIR
HPLC-FTNMR
MS-MS