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010 Introduction To Natural Products Chemistry PDF
010 Introduction To Natural Products Chemistry PDF
Introduction to the
Chemistry of Natural Products
RA Macahig
FM Dayrit
SY 2012-2013, Summer
"And the earth brought forth grass, and herb
yielding seed after his kind, and the tree yielding
fruit after his kind, whose seed was in itself, and
after his kind: and God saw that it was good."
-Genesis 1:12
http://www.holisticonline.com/Herbal-Med/hol_herbalmed-drugreg.htm
http://www.holisticonline.com/Herbal-Med/hol_herbalmed-drugreg.htm
Herbal Medicine
Dietary Supplement: A product that is intended to
supplement the diet and that bears or contains one or more
of the following dietary ingredients: a vitamin, mineral, herb
or other botanical material, an amino acid, a dietary
substance to supplement the diet by increasing the total
daily intake. (US Dietary Supplement Health and Education
Act, 1994). Philippine FDA uses a very similar definition.
Nutriceutical
Functional Food
Herbal Medicine
Dietary Supplement
Nutriceutical: Term coined by Stephen DeFelice in
1989 from "Nutrition" and "Pharmaceutical". Zeisel (Science
1999): Nutraceuticals are dietary supplements administered
in large dosages in order to obtain pharmacological effects.
Nutraceuticals deliver a concentrated orm of a presumed
bioactive agent from food, presented in a non-food matrix,
in dosages that exceed those that can be obtained in
normal food.
Functional Food
1. Introduction to the Chemistry of Natural Products 20
The Changing Landscape of Herbal Medicine,
Food and Wellness
Herbal Medicine
Dietary Supplement
Nutriceutical
Functional Food: A food that is consumed as part of a
normal diet and which is claimed to have health-promoting or
disease-preventing properties beyond the basic function of
supplying nutrients. Examples include probiotics (fermented
foods with live cultures), prebiotics (e.g., inulin). This term
was first used in Japan in the 1980s where there is a
government approval process for functional foods called
Foods for Specified Health Use (FOSHU).
Herbal Medicine
Dietary Supplement
Nutriceutical
Functional Food
Natural Products Chemistry
is key to all of these!
Biology Chemistry
Genomics . Proteomics
Metabolonomics
Antifungals
Symbiosis Symbiosis
Antifungals Chemotaxis
Chemotaxis Bacteria Communication
Communication
Fungi Antibacterials
th
19 century Pharmacognosy Pharmacology (to Medicine)
th
mid-20 century Pharmaceutical Medicinal Natural Mol Bio/Biotech
science chemistry products
chemistry Computational
st
21 century
Convergence
e.g., Metabolonomics, synergy
Techniques used:
basic physico-chemical measurements
TLC column chrom GC HPLC / Electrophoresis
X-ray UV-vis IR MS / NMR
Radioisotopes
Enzymes Computational methods
Tissue culture
Mol Bio / Biotech
Combinatorial chem
H
HO
3 1 N
H
4
N
HO
12 10
O H
13 9
N H CH3O
5
H H
15 N 10
6
7 16 CH3 O O
H N
HO
Morphine Strychnine
Quinine
(aromatic alkaloid from opium, (aromatic alkaloid from (quinoline alkaloid from
Papaver somniferum) Strychnos nux-vomica)
Cinchona species)
Isolation: 1806, Sertrner Isolation: 1818, Pelletier &
Isolation: 1820, Pelletier &
Structure: 1925, Robinson Caventou
Caventou
Synthesis: 1954, Ginsberg Structure: 1946, Robinson
Synthesis: 1944, Woodward
Biogenesis: 1959, Leete Synthesis: 1954, Woodward
2001, Eichberg
10
CH3
CH3 N
1 CO2CH3
2 O N
O
9
C6 H5
7 8 H
CH3 CH3 O
4 Coniine
Cocaine
Camphor (aliphatic alkaloid from
(aliphatic alkaloid from
(monoterpene from hemlock, Conium
Erythroxylon coca)
Cinamomum camphora) maculatum)
Isolation: 1859, Niemann
Isolation: 1845, Bouchardat Isolation: 1886, Ladenburg
Synthesis: 1923: Willsttter
Structure: 1926, Koller
21
24
20 23 26
18
CH3 25 OH N(H)CH3
27
CH2OH 19
11 13 17 CH CH CH3
CH3
14
O glucoside 1 9
10 8
3 5
6
HO
Ephedrin
Cholesterol (aromatic alkaloid from
Salicin (steroid from gallstones) Ephedra equisetrina and
(aromatic alcohol from
Isolation: 1909, Windaus E. sinica; "ma huang")
Salix species)
Structure: 1932, Wieland Structure and synthesis:
Structure and synthesis: Synthesis: 1964, Johnson 1920, Spth and Gring
1906, Irvine Biogenesis: 1966, Cornforth
O O
. . .
O O
. . CHO
O . O O . . O
. O
O
Taxol
(antitumor diterpene from Dynemicin A
Pacific yew, Taxus species) (antibiotic polyketide from
Micromonospora chersina)
Isolation: 1971, Wani et al.
Structure: 1971, Wani et al. Structure: 1989, Matsumoto and Clardy
Synthesis: 1991, Nicolau
Biosynthesis: 1992, Tokiwa et al.
OH
OH
O
H
H OH O
H
O
O O
O
OH
O H O
O OH
O
OH
(+)-Absinthin O
(dimeric diterpene from Artemisia (-)-Littoralisone
absinthium L., an anthelmintic)
(neurotrophic growth factor, iridoid
Isolation: 1953, Herout from Verbena littoralis L.)
Structure: NMR: 1980, Beauharie,
Isolation and structure: 2001, Li
X-ray: 1985, Karimov
Synthesis: 2005, Mangion
Synthesis: 2004, Zhang
O
OH
Oleic acid
9
O
OH
Linolenic acid
15 12 9
O
H CH3
H CH3 H CH3
CH3
CH3 CH3
CH3 CH3
HO HO CH2
Cholesterol 7-Dehydrocholesterol
(Provitamin D) Vitamin D3
HO
Taxonomy
Pharmaceutical Science
Entomology
Biochemistry
Natural
Products Combinatorial
Chemistry Chemistry
Biotechnology
Chemical synthesis