Secondary metabolite

Secondary metabolites, also called specialised metabolites, secondary products, or natural products, are organic compounds produced by any lifeform, e.g. bacteria, archaea, fungi, animals, or plants, which are not directly involved in the normal growth, development, or reproduction of the organism. Instead, they generally mediate ecological interactions, which may produce a selective advantage for the organism by increasing its survivability or fecundity. Specific secondary metabolites are often restricted to a narrow set of species within a phylogenetic group. Secondary metabolites often play an important role in plant defense against herbivory and other interspecies defenses. Humans use secondary metabolites as medicines, flavourings, pigments, and recreational drugs.

The term secondary metabolite was first coined by Albrecht Kossel, the 1910 Nobel Prize laureate for medicine and physiology. 30 years later a Polish botanist Friedrich Czapek described secondary metabolites as end products of nitrogen metabolism.

Secondary metabolites commonly mediate antagonistic interactions, such as competition and predation, as well as mutualistic ones such as pollination and resource mutualisms. Usually, secondary metabolites are confined to a specific lineage or even species, though there is considerable evidence that horizontal transfer across species or genera of entire pathways plays an important role in bacterial (and, likely, fungal) evolution. Research also shows that secondary metabolism can affect different species in varying ways. In the same forest, four separate species of arboreal marsupial folivores reacted differently to a secondary metabolite in eucalypts. This shows that differing types of secondary metabolites can be the split between two herbivore ecological niches. Additionally, certain species evolve to resist secondary metabolites and even use them for their own benefit. For example, monarch butterflies have evolved to be able to eat milkweed (Asclepias) despite the presence of toxic cardiac glycosides. The butterflies are not only resistant to the toxins, but are actually able to benefit by actively sequestering them, which can lead to the deterrence of predators.

Plants are capable of producing and synthesizing diverse groups of organic compounds and are divided into two major groups: primary and secondary metabolites. Secondary metabolites are metabolic intermediates or products which are not essential to growth and life of the producing plants but rather required for interaction of plants with their environment and produced in response to stress. Their antibiotic, antifungal and antiviral properties protect the plant from pathogens. Some secondary metabolites such as phenylpropanoids protect plants from UV damage. The biological effects of plant secondary metabolites on humans have been known since ancient times. The herb Artemisia annua which contains Artemisinin, has been widely used in Chinese traditional medicine more than two thousand years ago. Plant secondary metabolites are classified by their chemical structure and can be divided into four major classes: terpenes, phenylpropanoids (i.e. phenolics), polyketides, and alkaloids.

Terpenes constitute a large class of natural products which are composed of isoprene units. Terpenes are only hydrocarbons and terpenoids are oxygenated hydrocarbons. The general molecular formula of terpenes are multiples of (C₅H₈)_n, where 'n' is number of linked isoprene units. Hence, terpenes are also termed as isoprenoid compounds. Classification is based on the number of isoprene units present in their structure. Some terpenoids (i.e. many sterols) are primary metabolites. Some terpenoids that may have originated as secondary metabolites have subsequently been recruited as plant hormones, such as gibberellins, brassinosteroids, and strigolactones.

Examples of terpenoids built from hemiterpene oligomerization are:

Phenolics are a chemical compound characterized by the presence of aromatic ring structure bearing one or more hydroxyl groups. Phenolics are the most abundant secondary metabolites of plants ranging from simple molecules such as phenolic acid to highly polymerized substances such as tannins. Classes of phenolics have been characterized on the basis of their basic skeleton.

An example of a plant phenol is: