Chemistry of Natural Products A Biosynthetic approach

An Outline of most significant Information

Prof. M.H Elnagd Visiting professor of Chemistry Kuwait university (2012-2013)

By Prof.M.H El-Nagd .....................

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Chemistry of Natural Products A Biosynthetic approach

->What are natural products?

1- In fact nature produces plenty of chemicals, some like:-

Carbohydrates Proteins Poly petites- Fats steroids and nucleic acids, all are essential for life and manufactured by every organism chemistry leading to their in vivo information which is a major concern of biochemistry and are called: Natural products (Mainly from essential metabolic routes) 2- Nature produces thousands of other chemicals through secondary metabolism , These are not essential for life of organisms, Although they make it better . Every organism produces chemical characteristic for his species. Example: a) Colored flowers b) Nicotine in tobacco c) Caffeine in coffee and tea etc. These are Called Natural products and are subject of studies of a Natural products chemists 3- The starting materials needed for biosynthesis of these products are produced during the main stream metabolism This is summarized in Scheme (Next page)

By Prof.M.H El-Nagd .....................

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Chemistry of Natural Products A Biosynthetic approach

Why do living matter manufacture natural products and why do secondary metabolic process occur?
-This bring us to science of chemical ecology 1- Initially and for some time it was thought that NPs are made aimlessly? This theory is now rejected and it is believed that any compound made by nature in a secondary metabolic way although its not essential for life but it help to adopt to the environment including fighting predators some may extinct but the plants and animals continued their production. 2- Natural products and chemistry of pollination fertilization step in plants is performed by insects or some birds, bats and mice. These search for nectar insects from a distance. There are three types of pollination stimulates. Examples:(a)Aromatics (polypeptide bath way)

CH2CO2H

CHO

CO2Me

CH2CHO

OMe OMe

OMe NO2

OMe NH2

OH CO2Me

By Prof.M.H El-Nagd .....................

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Chemistry of Natural Products A Biosynthetic approach

(b)Mono and diterpens

CH2OH

Geraniol

Garene

Colors:
At short distance the insect is attracted to colored butterflies it prefers vivid-bright colored bees while, yellow and blue birds prefer scarlet blossoms There is group of compounds responsible for colors: 1-Flavones: (e.g) Fravonone and chalcone

OH

OH

By Prof.M.H El-Nagd .....................

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Chemistry of Natural Products A Biosynthetic approach

OH HO HO OH OH

CA280nm

382nm

2-Carotenes: (e.g):

R=H R=OH

-Carotene Zeaxanthin

484nm 483nm

3-Quinones: (e.g):

By Prof.M.H El-Nagd .....................

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Chemistry of Natural Products A Biosynthetic approach

O CH3

Animal-animal relationship: Chemical defense and warfare

-Animals produce poisons as self-defense or as a weapon (e.g): Butterflies of see of lack defense but is made as protector
N=C

Many Compounds are made.

By Prof.M.H El-Nagd .....................

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Chemistry of Natural Products A Biosynthetic approach

Ants and termites live in social colonies to sterile defense soldiers are equipped with range glands amounting to 10-30% of their weight these bite energy and inject chemicals. Examples:
R H R R O

NO2

Mycene

-pirene

*Defense chemicals vary and include:

Oviposition pheromones :-The deter insects from laying their eggs in already invaded fruits This include verbenone

By Prof.M.H El-Nagd .....................

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Chemistry of Natural Products A Biosynthetic approach

O
Territorial: Pheromones:To define animal territory some animals make special chemicals Plant animal relationship:Alarm and aggregation Pheromones.

How did trade in NPs shaped world history: An outline:

1-Anciant history;The discovery of some plants rich in NPs in burial sites suggest that these plants were of value for antint in Euphrates barks in Syria a few cloves in a charred vessel dated to about 1700 Bc have been discovered.Since cloves grow thousands of miles away in spice islands (known now as Indonesia) it is believed that these were traded at these days

2-The Indo-Iranian cultures:

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Chemistry of Natural Products A Biosynthetic approach

Eridence for interest in NPs containing plants goes back in history of these cultures to beyond 2500Bc and was extended to nowadays Pakistani during a later period (18000-1000 Bc)

3-Mediterrcenean cultures:
To demand for NPs groups in from 500 Bc Greek became also involved then rumination Rome concealed Greek in 15013 C. around 120 ships were involved in trade between Rome and India handed 1000 tons a year. This huge trade placed strain on roman economy as the prices were paid in cash (Gold and Silver) in 22 AD Romans condemned use of these luxuries. Then came the arabs and trades was dominated by Arab and north Africa

The Arabian control of spices:

The Byzantium and Jewish spice traders were to be increasingly marginalized by the remarkable growth and power of the Arab, and subsequently Muslim traders. The Arabs had been very successful in gaining influence further to the east of the spice route-in the Indian subcontinent and beyond. There were Arab-speaking merchants in Sri-lanka by the fourth century AD and by the eighth century the arabs even had their own commercial enclave on the Chinese main land at Guangzhou ( Known formerly as Canton). However,

By Prof.M.H El-Nagd .....................

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Chemistry of Natural Products A Biosynthetic approach

the founding of Islam forged a powerful set of links between wealth, power, culture and NPs. Mohammed (570-632 AD) brought his religious insights to many Arab tribes

and united them under Islam. Mohammed had worked briefly for Khadija, taking charge of one of her caravans taking goods to the Syrian ports. The favorable reports of his character and ability encouraged the older Khadija to subsequently marry Mohammed . Given Khadijas business as a trader in spices, it is not surprising that the new religion spread along the existing spice routed as well as locally. There was Arab community established on the Malabar coast of India 500 years before Moghuls came from the north to bring Islam to other parts of that subcontinent (The Indian coast was also the home to the oldest Jewish community outside the Middle east because of the involvement of Jews in the spice trade). Because the spice route stretched to the country now known as Indonesia, Arab traders and their Islam religion became established in Indonesia. So the human quest for NPs explains why Indonesia was eventually to become the worlds most populous Islamic country. By AD 700, the Arabs had pushed the Byzantium Empire back to an area around current turkey and the Byzantium influence in Europe was confined to few enclaves (including Rome, Naples, and some ports on the northern Adriatic coast). However, this limited access to the European trade routes enabled Byzantium to continue its profitable spice trading to mainland Europe until it lost control of its European ports in the eighth century. Byzantium lost trade into Europe to a community of fishermen living on some easily defended marshy islands on the gulf at the north of Adriatic

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