INTRODUCTION TO

PHYTOCHEMISTRY
Paolo Robert P. Bueno
 Ecology and Ecosystem
Natural Products and Phytochemistry
Phytochemicals and Bioactive compounds
Importance of Natural Products from Plants
Application in Phytochemicals in the Modern Setting

Introduction to Phytochemistry
• Recognize the difference between ecology and ecosystem
• Define Natural Products and phytochemistry
• Differentiate between primary and secondary metabolites
• Construct a map of the primary metabolic pathways that
lead to the secondary metabolic pathways
• Recognize the importance of natural products
• Enumerate the applications and sources of bioactive
compounds

Introduction to Phytochemistry
study of the distribution and abundance of organisms, the interaction between organisms, the
interaction between organisms and their environment, and structure and function of
ecosystems

Why is ecology important?

Understand how the world works

Provides evidence on the interdependence

between people and the natural world

Defines the essential basis for nature

conservation

Explains the consequences of human

activity on the environment
https://www.britishecologicalsociety.org/about/what-is-ecology/

Introduction to Phytochemistry
 a dynamic complex of plant, animal, and microorganism communities and the nonliving
environment interacting as a functional unit

TERRESTRIAL ECOSYSTEMS AQUATIC ECOSYSTEMS

Millennium Ecosystem Assessment: http://grimstad.uia.no/puls/climatechange/nng01/03nng01.htm
Introduction to Phytochemistry
an area inhabited by a particular an area inhabited by complex
species of animal or plant communities of interdependent
organisms

Introduction to Phytochemistry
 CHEMICAL CHARACTERISTICS
• Naturally-occurring small organic compounds
• including heterocyclic compounds, and peptides
• does not include proteins, carbohydrates, and nucleic acids
• MW: ~150 ~ <800 amu (“small molecule”)
• Methods of extraction, purification and structural determination
are generally similar to the techniques used for organic
compounds (TLC, HPLC, GC, NMR, MS, IR, X-ray, UV)

Introduction to Phytochemistry
 BIOLOGICAL CHARACTERISTICS
• Restricted occurrence: Compounds are generally
characteristic of a particular species or family
• No apparent utility: Non-essential (No nutritional or
structural function) to the source organism
• Functional roles may include:
- color (identification) - scent (attraction or repulsion)
- social communication - sexual attraction
- defense (e.g., plant toxins and antibiotics)
Introduction to Phytochemistry
 CARBOHYDRATES PHENOLICS TERPENOIDS
NUCLEOSIDES POLYKETIDES ALKALOIDS
AMINO ACIDS SAPONINS GLYCOSIDES
PROTEINS ANTHRAQUINONES TANNINS
ENZYMES FLAVONOIDS COUMARINS
FATTY ACIDS PROSTAGLANDINS

directly involved in the processes of perform various functions related to the

growth, development and protection, survival, fertility and
reproduction interspecies relations
Introduction to Phytochemistry
 CO2 + H2O

PHOTOSYNTHESIS

glucose & other carbohydrate polysaccharides

nucleosides RNA & DNA

PPP
GLYCOLYSIS
lignans, coumarins
phosphoenol pyruvate SHIKIMATE
aromatic AA’s proteins, enzymes, alkaloids
pyruvate
mevalonic acid terpenoids, steroids, carotenoids

acetyl coA
lipids, polyketides polyphenols, prostaglandins

TCA aliphatic AA’s proteins, enzymes, alkaloids

Introduction to Phytochemistry
 A brief history of natural products chemistry
Ancient Greek Materia Medica

19th century Pharmacognosy Pharmacology (to Medicine)

mid-20th century Pharmaceutical Medicinal Natural Mol Bio/Biotech

science chemistry products
chemistry Computational

21st century
Convergence
e.g., Metabolonomics, synergy

Introduction to Phytochemistry
Techniques used in natural products chemistry
1800 1850 1900 1950 1975 2000

Type of research undertaken:

Isolation, characterization
Pharmacognosy & Pharmacology
Organic synthesis
Chromatography Spectroscopy
Biogenetic studies
Biochemistry; Enzymology
Molecular Biology
Metabolonomics

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

Introduction to Phytochemistry
The study of natural products is multidisciplinary

Biology   Chemistry

Taxonomy . Botany Organic synthesis

Agriculture . Pharmacology . Pharmaceutical Science . Organic analytical chemistry

Entomology . Microbiology . Biotechnology/Molecular Biology . Biochemistry

Genomics .

Proteomics

Metabolonomics

Introduction to Phytochemistry
 study of phytochemicals

PHYTOCHEMICALS
- from the Greek word
“phytos” meaning plant)

Biologically active, naturally

occurring chemical
compounds found in plants

Introduction to Phytochemistry
• source of the most complex and fascinating chemical structures
• represent biological diversity
• expressions of the genome
• represent natural biological activity, whether as single compounds
or as complex mixtures
• part of the natural wealth of the country: can be important source of
livelihood, from agriculture and food, pharmaceuticals, fine chemicals
industry
• can be an effective bridge from tradition to modern scientific
developments, including genetics, molecular biology, biotechnology, and
pharmaceutical science

Introduction to Phytochemistry
The market for natural products is HUGE
• Pharmaceuticals
• Traditional herbal medicines:
US and Europe: gingko biloba, St. John’s wort, ginseng, garlic*, echinacea, saw
palmetto, soya*, kava-kava, golden seal, aloe*, gotu kola* (*also grown in the
Philippines)
India, China, Japan: Ayurverda, TCM, Kampo
Philippines: lagundi, sambong, ampalaya, banaba, malunggay
• Beverages: tea (e.g., green, chinese), herbal teas, coffee
• Food supplements and health products
• Fats and oils
• Herbs and spices, food flavor ingredients
• Perfumes and scents
• Essential oils, others
Introduction to Phytochemistry
Introduction to Phytochemistry
Overview of Herbal Medicine Regulation in the World

• WHO recognizes the important and historical role of herbal medicine in

health
• Herbal medicine is a major form of treatment for more than 70% of the
world's population

http://www.holisticonline.com/Herbal-Med/hol_herbalmed-drugreg.htm

Introduction to Phytochemistry
Overview of Herbal Medicine Regulation in the World

• USA: herbal products can be marketed only as food supplements.

Herbal products can make no specific health claims without FDA
approval

• Asia: use of patent herbal remedies composed of dried and powdered

whole herbs or herb extracts, also in tablet form
• China: wide-spread use of traditional herbals
• Japan: Kampo medicine is derived from Chinese medicine
• India: Ayurvedic medicine

http://www.holisticonline.com/Herbal-Med/hol_herbalmed-drugreg.htm
Introduction to Phytochemistry
The Changing Landscape of Herbal
Medicine, Food and Wellness
• Herbal Medicine: Makes therapeutic claim; includes crude herbal
materials, preparations and finished products, that contain as active
ingredients, parts of plants or combinations thereof. (WHO Traditional Medicine
Strategy 2002-2005). In Europe, also called “phytotherapy”.
• Dietary Supplement
• Nutriceutical
• Functional Food

Introduction to Phytochemistry
The Changing Landscape of Herbal
Medicine, Food and Wellness
• 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

Introduction to Phytochemistry
The Changing Landscape of Herbal
Medicine, Food and Wellness
• Herbal Medicine
• Dietary Supplement
• Nutraceutical: 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

Introduction to Phytochemistry
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)

Introduction to Phytochemistry
The Changing Landscape of Herbal
Medicine, Food and Wellness
• Herbal Medicine
• Dietary Supplement
• Nutriceutical
• Functional Food
 Natural Products and Phytochemistry
is key to all of these!

Introduction to Phytochemistry
Application of Phytochemistry
Medicines

CH2OH
OH N(H)CH3 O  glucoside

CH CH CH3

EPHEDRIN SALICIN
(aromatic alkaloid from Ephedra (aromatic alcohol from Salix species)
equisetrina and E. sinica; "ma huang") Structure and synthesis:
Structure and synthesis: 1906, Irvine
1920, Späth and Göring

(stimulant, appetite suppressant) (natural analogue of aspirin, anti-inflammatory)

Introduction to Phytochemistry
Application of Phytochemistry
Poisons, Insecticides, Pesticides
H N

N
N H
H H
H
10
O
H O

STRYCHNINE CONIINE
(aromatic alkaloid from Strychnos nux-vomica) (aliphatic alkaloid from hemlock, Conium maculatum)
Isolation: 1818, Pelletier & Caventou Isolation: 1886, Ladenburg
Structure: 1946, Robinson Structure: 1926, Koller
Synthesis: 1954, Woodward
2001, Eichberg

(pesticide, cause convulsion and asphyxia) (cause respiratory paralysis)

Introduction to Phytochemistry
Application of Phytochemistry
Narcotics
HO
3 1
4 CH3
N
12 10
CO2CH3
O 9
13 O
CH
65
5
15 N O
6
7 16 CH3
HO

MORPHINE COCAINE
(aromatic alkaloid from opium, Papaver (aliphatic alkaloid from Erythroxylon coca)
somniferum)
Isolation: 1859, Niemann
Isolation: 1806, Sertürner Synthesis: 1923: Willstätter
Structure: 1925, Robinson
Synthesis: 1954, Ginsberg
Biogenesis: 1959, Leete

Introduction to Phytochemistry
Application of Phytochemistry
Stimulant

CAFFEINE
(aromatic alkaloid from Coffea sp.)

Introduction to Phytochemistry
Application of Phytochemistry
Perfumes and Spices

Geraniol Cinnamaldehyde
(rose oil) (cinnamon)

diallyl disulphide
Eugenol (garlic)
(cloves)

Introduction to Phytochemistry
Dietary Supplements
Cosmetics
Modern directions in Phytochemistry:
• Structural determination of phytochemicals
• Genomics and Genetic engineering of plants
• Total synthesis or semi-synthesis of phytochemicals
• Determination of biosynthetic pathways using plant tissues, cell culture and
isotopic labeling
• Pharmaceutical science: pharmacologic effects
• Functional foods, herbal medicines
• Agricultural science
• Ethnobotany
• Plant chemistry and plant development
• Biodiversity and Ecology; Marine natural products
• Chemotaxonomy and genetic classification
Introduction to Phytochemistry
 SUMMARY
LEARNING OBJECTIVES
• Recognize the difference
between ecology and • ECOLOGY:
ecosystem
• Define Natural Products and • the scientific analysis and
phytochemistry study of interactions among
organisms and their
• Differentiate between primary and environment
secondary metabolites
• Construct a map of the primary
metabolic pathways that lead to • ECOSYSTEM:
the secondary metabolic
pathways • a community of living
• Recognize the importance of organisms interacting as a
natural products system
• Enumerate the applications and
sources of bioactive compounds

Introduction to Phytochemistry
 SUMMARY
LEARNING OBJECTIVES
• Recognize the difference between • NATURAL PRODUCTS:
ecology and ecosystem
• organic compounds of
• Define Natural Products and natural origin with restricted
phytochemistry
occurrence of no apparent
• Differentiate between primary and utility
secondary metabolites
• Construct a map of the primary
metabolic pathways that lead to
the secondary metabolic
• PHYTOCHEMISTRY:
pathways • study of biologically active,
• Recognize the importance of naturally occurring chemical
natural products compounds found in plants
• Enumerate the applications and
sources of bioactive compounds

Introduction to Phytochemistry
 SUMMARY
LEARNING OBJECTIVES
• Recognize the difference between • PRIMARY METABOLITES:
ecology and ecosystem • directly involved in the processes
• Define Natural Products and of growth, development and
phytochemistry reproduction
• Differentiate between primary
and secondary metabolites • SECONDARY METABOLITES:
• Construct a map of the primary • perform various functions related to
metabolic pathways that lead to the protection, survival, fertility and
the secondary metabolic interspecies relations
pathways
• Recognize the importance of
natural products
• Enumerate the applications and
sources of bioactive compounds

Introduction to Phytochemistry
 SUMMARY
LEARNING OBJECTIVES
• Recognize the difference between
ecology and ecosystem
• Define Natural Products and
phytochemistry
• Differentiate between primary and
secondary metabolites
• Construct a map of the primary
metabolic pathways that lead to
the secondary metabolic
pathways
• Recognize the importance of
natural products
• Enumerate the applications and
sources of bioactive compounds

Introduction to Phytochemistry
 SUMMARY
LEARNING OBJECTIVES
• Recognize the difference between • most complex and
ecology and ecosystem fascinating chemical
• Define Natural Products and structures which represent
phytochemistry
biological diversity with
• Differentiate between primary and
secondary metabolites natural biological activity
• Construct a map of the primary
metabolic pathways that lead to • This may be a source of
the secondary metabolic
pathways natural wealth and can be
• Recognize the importance of an effective bridge from
natural products tradition to modern
• Enumerate the applications and scientific developments
sources of bioactive compounds

Introduction to Phytochemistry
 SUMMARY
LEARNING OBJECTIVES
• Recognize the difference between • Phytochemicals are
ecology and ecosystem
developed as:
• Define Natural Products and
phytochemistry • Medicines
• Differentiate between primary and • Poisons, Insecticides,
secondary metabolites Pesticides
• Construct a map of the primary • Narcotics
metabolic pathways that lead to
the secondary metabolic • Perfumes and Spices
pathways • Stimulants
• Recognize the importance of • Dietary Supplements
natural products • Cosmetics
• Enumerate the applications and
sources of bioactive
compounds

Introduction to Phytochemistry
INTRODUCTION TO
PHYTOCHEMISTRY
THE END