Secondary metabolite

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Structural formula for the amino acid pipecolic acid, which contrary to other amino acids is not used as a building block in proteins. In some plants, pipecolic acid act as a defense compound against microorganisms. Because of its limited presence, pipecolic acid is considered a secondary metabolite. Structural formula of pipecolic acid.svg
Structural formula for the amino acid pipecolic acid, which contrary to other amino acids is not used as a building block in proteins. In some plants, pipecolic acid act as a defense compound against microorganisms. Because of its limited presence, pipecolic acid is considered a secondary metabolite.
Structural formula for the amino acid proline, that in all living beings is a building block in proteins. Because of its universal presence, proline is considered a primary metabolite. Prolin - Proline.svg
Structural formula for the amino acid proline, that in all living beings is a building block in proteins. Because of its universal presence, proline is considered a primary metabolite .

Secondary metabolites, also called specialised metabolites, toxins, secondary products, or natural products, are organic compounds produced by any lifeform, e.g. bacteria, 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. [2]

Contents

The term secondary metabolite was first coined by Albrecht Kossel, the 1910 Nobel Prize laureate for medicine and physiology. [3] 30 years later a Polish botanist Friedrich Czapek described secondary metabolites as end products of nitrogen metabolism. [4]

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, [5] 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. [6] 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. [7] This shows that differing types of secondary metabolites can be the split between two herbivore ecological niches. [7] 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. [8] 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. [8]

Plant secondary metabolites

Plants are capable of producing and synthesizing diverse groups of organic compounds and are divided into two major groups: primary and secondary metabolites. [9] 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. [10] 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.[ citation needed ] 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. [11]

Chemical classes

Terpenoids

Structural formula for isopentenyl pyrophosphate (IPP), the carbon atoms of which constitute building blocks in terpenes. Because of the presence of five carbon atoms, the derived building block it is termed a C5 unit. Isopentenyl pyrophosphate.svg
Structural formula for isopentenyl pyrophosphate (IPP), the carbon atoms of which constitute building blocks in terpenes. Because of the presence of five carbon atoms, the derived building block it is termed a C5 unit.
Structural formula for humulene, a monocyclic sesquiterpene (called so because it contains 15 carbon atoms) that is built from three C5 units derived from isopentenyl pyrophosphate (IPP). Humulene.png
Structural formula for humulene, a monocyclic sesquiterpene (called so because it contains 15 carbon atoms) that is built from three C5 units derived from isopentenyl pyrophosphate (IPP).
Skeletal formula of the terpenoid taxol, an anticancer drug. Taxol structure.svg
Skeletal formula of the terpenoid taxol, an anticancer drug.

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.

Number of isoprene unitsNameCarbon atoms
1HemiterpeneC5
2 Monoterpene C10
3 Sesquiterpenes C15
4 Diterpene C20
5SesterterpeneC25
6 Triterpene C30
7SesquarterterpeneC35
8 Tetraterpene C40
More than 8Polyterpene

Examples of terpenoids built from hemiterpene oligomerization are:

Phenolic compounds

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.

No. of carbon atomsBasic skeletonClass
6C6Simple phenols
7C6 - C1 Phenolic acids
8C6 - C2 Acetophenone, Phenyle acetic acid
9C6 - C3 Phenylepropanoids, hydroxycinnamic acid, coumarins
10C6 - C4 Naphthoquinone
13C6 - C1- C6 Xanthone
14C6 - C2 - C6 Stilbene, anthraquinone
15C6 - C3 - C6 Flavonoids, isoflavanoids
18(C6 - C3 ) 2 lignans, neolignans
30( C6 - C3 - C6)2 Biflavonoids

An example of a plant phenol is:

Alkaloids

Structural formula for the alkaloid nicotine. The structure includes two nitrogen atoms both of which derives from amino acids. The nitrogen atom in the pyridine ring (to the left) derives from aspartate, whereas that in the pyrrolidine ring (to the right) derives from arginine (or ornithine)- Nikotin - Nicotine.svg
Structural formula for the alkaloid nicotine. The structure includes two nitrogen atoms both of which derives from amino acids. The nitrogen atom in the pyridine ring (to the left) derives from aspartate, whereas that in the pyrrolidine ring (to the right) derives from arginine (or ornithine)-
Skeletal formula of solanine, a toxic alkaloid which builds up in potatoes. Solanine.svg
Skeletal formula of solanine, a toxic alkaloid which builds up in potatoes.

Alkaloids are a diverse group of nitrogen-containing basic compounds. They are typically derived from plant sources and contain one or more nitrogen atoms. Chemically they are very heterogeneous. Based on chemical structures, they may be classified into two broad categories:

Examples of alkaloids produced by plants are:

Many alkaloids affect the central nervous system of animals by binding to neurotransmitter receptors.

Glucosinolates

Structural formula for glucosinolates. The side group R can vary. The structure includes a glucose molecules (to the left), a nitrogen atom derived from an amino acid, and two sulfur atoms, among which one derives from glutathione and the other from sulfate (seen to the left). Glucosinolate-skeletal.png
Structural formula for glucosinolates. The side group R can vary. The structure includes a glucose molecules (to the left), a nitrogen atom derived from an amino acid, and two sulfur atoms, among which one derives from glutathione and the other from sulfate (seen to the left).

Glucosinolates are secondary metabolites that include both sulfur and nitrogen atoms, and are derived from glucose, an amino acid and sulfate.

An example of a glucosinolate in plants is Glucoraphanin, from broccoli (Brassica oleracea var. italica).

Plant secondary metabolites in medicine

Many drugs used in modern medicine are derived from plant secondary metabolites.

Extraction of taxol from barks of Pacific Yew. Yew bark Taxol PD.jpg
Extraction of taxol from barks of Pacific Yew.

The two most commonly known terpenoids are artemisinin and paclitaxel. Artemisinin was widely used in Traditional Chinese medicine and later rediscovered as a powerful antimalarial by a Chinese scientist Tu Youyou. She was later awarded the Nobel Prize for the discovery in 2015. Currently, the malaria parasite, Plasmodium falciparum , has become resistant to artemisinin alone and the World Health Organization recommends its use with other antimalarial drugs for a successful therapy. Paclitaxel the active compound found in Taxol is a chemotherapy drug used to treat many forms of cancers including ovarian cancer, breast cancer, lung cancer, Kaposi sarcoma, cervical cancer, and pancreatic cancer. [14] Taxol was first isolated in 1973 from barks of a coniferous tree, the Pacific Yew. [15]

Morphine and codeine both belong to the class of alkaloids and are derived from opium poppies. Morphine was discovered in 1804 by a German pharmacist Friedrich Sertürner t. It was the first active alkaloid extracted from the opium poppy. It is mostly known for its strong analgesic effects, however, morphine is also used to treat shortness of breath and treatment of addiction to stronger opiates such as heroin. [16] [17] Despite its positive effects on humans, morphine has very strong adverse effects, such as addiction, hormone imbalance or constipation. [17] [18] Due to its highly addictive nature morphine is a strictly controlled substance around the world, used only in very severe cases with some countries underusing it compared to the global average due to the social stigma around it. [19]

Opium field in Afghanistan, the largest grower of opium. Afghanistan 16.jpg
Opium field in Afghanistan, the largest grower of opium.

Codeine, also an alkaloid derived from the opium poppy, is considered the most widely used drug in the world according to World Health Organization. It was first isolated in 1832 by a French chemist Pierre Jean Robiquet, also known for the discovery of caffeine and a widely used red dye alizarin. [21] Primarily codeine is used to treat mild pain and relief coughing [22] although in some cases it is used to treat diarrhea and some forms of irritable bowel syndrome. [22] Codeine has the strength of 0.1-0.15 compared to morphine ingested orally, [23] hence it is much safer to use. Although codeine can be extracted from the opium poppy, the process is not feasible economically due to the low abundance of pure codeine in the plant. A chemical process of methylation of the much more abundant morphine is the main method of production. [24]

Atropine is an alkaloid first found in Atropa belladonna , a member of the nightshade family. While atropine was first isolated in the 19th century, its medical use dates back to at least the fourth century B.C. where it was used for wounds, gout, and sleeplessness. Currently atropine is administered intravenously to treat bradycardia and as an antidote to organophosphate poisoning. Overdosing of atropine may lead to atropine poisoning which results in side effects such as blurred vision, nausea, lack of sweating, dry mouth and tachycardia. [25]

Resveratrol is a phenolic compound of the flavonoid class. It is highly abundant in grapes, blueberries, raspberries and peanuts. It is commonly taken as a dietary supplement for extending life and reducing the risk of cancer and heart disease, however there is no strong evidence supporting its efficacy. [26] [27] Nevertheless, flavonoids are in general thought to have beneficial effects for humans.[ citation needed ] Certain studies shown that flavonoids have direct antibiotic activity. [28] A number of in vitro and limited in vivo studies shown that flavonoids such as quercetin have synergistic activity with antibiotics and are able to suppress bacterial loads. [29]

Digoxin is a cardiac glycoside first derived by William Withering in 1785 from the foxglove (Digitalis) plant. It is typically used to treat heart conditions such as atrial fibrillation, atrial flutter or heart failure. [30] Digoxin can, however, have side effects such as nausea, bradycardia, diarrhea or even life-threatening arrhythmia.

Fungal secondary metabolites

The three main classes of fungal secondary metabolites are: polyketides, nonribosomal peptides and terpenes. Although fungal secondary metabolites are not required for growth they play an essential role in survival of fungi in their ecological niche. [31] The most known fungal secondary metabolite is penicillin discovered by Alexander Fleming in 1928. Later in 1945, Fleming, alongside Ernst Chain and Howard Florey, received a Nobel Prize for its discovery which was pivotal in reducing the number of deaths in World War II by over 100,000. [32]

Examples of other fungal secondary metabolites are:

Lovastatin was the first FDA approved secondary metabolite to lower cholesterol levels. Lovastatin occurs naturally in low concentrations in oyster mushrooms, [33] red yeast rice, [34] and Pu-erh. [35] Lovastatin's mode of action is competitive inhibition of HMG-CoA reductase, and a rate-limiting enzyme responsible for converting HMG-CoA to mevalonate.

Fungal secondary metabolites can also be dangerous to humans. Claviceps purpurea , a member of the ergot group of fungi typically growing on rye, results in death when ingested. The build-up of poisonous alkaloids found in C. purpurea lead to symptoms such as seizures and spasms, diarrhea, paresthesias, Itching, psychosis or gangrene. Currently, removal of ergot bodies requires putting the rye in brine solution with healthy grains sinking and infected floating. [36]

Bacterial secondary metabolites

Bacterial production of secondary metabolites starts in the stationary phase as a consequence of lack of nutrients or in response to environmental stress. Secondary metabolite synthesis in bacteria is not essential for their growth, however, they allow them to better interact with their ecological niche. The main synthetic pathways of secondary metabolite production in bacteria are; b-lactam, oligosaccharide, shikimate, polyketide and non-ribosomal pathways. [37] Many bacterial secondary metabolites are toxic to mammals. When secreted those poisonous compounds are known as exotoxins whereas those found in the prokaryotic cell wall are endotoxins.

An example of a bacterial secondary metabolite with a positive and negative effect on humans is botulinum toxin synthesised by Clostridium botulinum . This exotoxin often builds up in incorrectly canned foods and when ingested blocks cholinergic neurotransmission leading to muscle paralysis or death. However, botulinum toxin also has multiple medical uses such as treatment of muscle spasticity, migraine and cosmetics use.

Examples of other bacterial secondary metabolites are:

Phenazine

Polyketides

Nonribosomal peptides

Ribosomal peptides

Glucosides

Alkaloids

Biotechnological approaches

Plant tissue culture Oncidium leucochilum. Vinha retirada do artigo.jpg
Plant tissue culture Oncidium leucochilum.

Selective breeding was used as one of the first biotechnological techniques used to reduce the unwanted secondary metabolites in food, such as naringin causing bitterness in grapefruit. [38] In some cases increasing the content of secondary metabolites in a plant is the desired outcome. Traditionally this was done using in-vitro plant tissue culture techniques which allow for: control of growth conditions, mitigate seasonality of plants or protect them from parasites and harmful-microbes.[ citation needed ] Synthesis of secondary metabolites can be further enhanced by introducing elicitors into a tissue plant culture, such as jasmonic acid, UV-B or ozone. These compounds induce stress onto a plant leading to increased production of secondary metabolites.

To further increase the yield of SMs new approaches have been developed. A novel approach used by Evolva uses recombinant yeast S. cerevisiae strains to produce secondary metabolites normally found in plants. The first successful chemical compound synthesised with Evolva was vanillin, widely used in the food beverage industry as flavouring. The process involves inserting the desired secondary metabolite gene into an artificial chromosome in the recombinant yeast leading to synthesis of vanillin. Currently Evolva produces a wide array of chemicals such as stevia, resveratrol or nootkatone.

Nagoya protocol

With the development of recombinant technologies the Nagoya Protocol on Access to Genetic Resources and the Fair and Equitable Sharing of Benefits Arising from their Utilization to the Convention on Biological Diversity was signed in 2010. The protocol regulates the conservation and protection of genetic resources to prevent the exploitation of smaller and poorer countries. If genetic, protein or small molecule resources sourced from biodiverse countries become profitable a compensation scheme was put in place for the countries of origin. [39]

See also

Related Research Articles

<span class="mw-page-title-main">Alkaloid</span> Class of naturally occurring chemical compounds

Alkaloids are a class of basic, naturally occurring organic compounds that contain at least one nitrogen atom. This group also includes some related compounds with neutral and even weakly acidic properties. Some synthetic compounds of similar structure may also be termed alkaloids. In addition to carbon, hydrogen and nitrogen, alkaloids may also contain oxygen or sulfur. More rarely still, they may contain elements such as phosphorus, chlorine, and bromine.

The terpenoids, also known as isoprenoids, are a class of naturally occurring organic chemicals derived from the 5-carbon compound isoprene and its derivatives called terpenes, diterpenes, etc. While sometimes used interchangeably with "terpenes", terpenoids contain additional functional groups, usually containing oxygen. When combined with the hydrocarbon terpenes, terpenoids comprise about 80,000 compounds. They are the largest class of plant secondary metabolites, representing about 60% of known natural products. Many terpenoids have substantial pharmacological bioactivity and are therefore of interest to medicinal chemists.

<span class="mw-page-title-main">Terpene</span> Class of oily organic compounds found in plants

Terpenes are a class of natural products consisting of compounds with the formula (C5H8)n for n ≥ 2. Terpenes are major biosynthetic building blocks. Comprising more than 30,000 compounds, these unsaturated hydrocarbons are produced predominantly by plants, particularly conifers. In plants, terpenes and terpenoids are important mediators of ecological interactions, while some insects use some terpenes as a form of defense. Other functions of terpenoids include cell growth modulation and plant elongation, light harvesting and photoprotection, and membrane permeability and fluidity control.

<span class="mw-page-title-main">Resveratrol</span> Polyphenol with a stilbene skeleton

Resveratrol (3,5,4′-trihydroxy-trans-stilbene) is a stilbenoid, a type of natural phenol, and a phytoalexin produced by several plants in response to injury or when the plant is under attack by pathogens, such as bacteria or fungi. Sources of resveratrol in food include the skin of grapes, blueberries, raspberries, mulberries, and peanuts.

In molecular biology and pharmacology, a small molecule or micromolecule is a low molecular weight organic compound that may regulate a biological process, with a size on the order of 1 nm. Many drugs are small molecules; the terms are equivalent in the literature. Larger structures such as nucleic acids and proteins, and many polysaccharides are not small molecules, although their constituent monomers are often considered small molecules. Small molecules may be used as research tools to probe biological function as well as leads in the development of new therapeutic agents. Some can inhibit a specific function of a protein or disrupt protein–protein interactions.

<span class="mw-page-title-main">Pharmacognosy</span> Study of plants as a source of drugs

Pharmacognosy is the study of crude drugs obtained from medicinal plants, animals, fungi, and other natural sources. The American Society of Pharmacognosy defines pharmacognosy as "the study of the physical, chemical, biochemical, and biological properties of drugs, drug substances, or potential drugs or drug substances of natural origin as well as the search for new drugs from natural sources".

<span class="mw-page-title-main">Medicinal plants</span> Plants or derivatives used to treat medical conditions in humans or animals

Medicinal plants, also called medicinal herbs, have been discovered and used in traditional medicine practices since prehistoric times. Plants synthesize hundreds of chemical compounds for various functions, including defense and protection against insects, fungi, diseases, and herbivorous mammals.

<span class="mw-page-title-main">Phytoalexin</span> Class of chemical compounds

Phytoalexins are antimicrobial substances, some of which are antioxidative as well. They are defined, not by their having any particular chemical structure or character, but by the fact that they are defensively synthesized de novo by plants that produce the compounds rapidly at sites of pathogen infection. In general phytoalexins are broad spectrum inhibitors; they are chemically diverse, and different chemical classes of compounds are characteristic of particular plant taxa. Phytoalexins tend to fall into several chemical classes, including terpenoids, glycosteroids, and alkaloids; however the term applies to any phytochemicals that are induced by microbial infection.

In organic chemistry, polyketides are a class of natural products derived from a precursor molecule consisting of a chain of alternating ketone and methylene groups: [−C(=O)−CH2−]n. First studied in the early 20th century, discovery, biosynthesis, and application of polyketides has evolved. It is a large and diverse group of secondary metabolites caused by its complex biosynthesis which resembles that of fatty acid synthesis. Because of this diversity, polyketides can have various medicinal, agricultural, and industrial applications. Many polyketides are medicinal or exhibit acute toxicity. Biotechnology has enabled discovery of more naturally-occurring polyketides and evolution of new polyketides with novel or improved bioactivity.

<span class="mw-page-title-main">Natural product</span> Chemical compound or substance produced by a living organism, found in nature

A natural product is a natural compound or substance produced by a living organism—that is, found in nature. In the broadest sense, natural products include any substance produced by life. Natural products can also be prepared by chemical synthesis and have played a central role in the development of the field of organic chemistry by providing challenging synthetic targets. The term natural product has also been extended for commercial purposes to refer to cosmetics, dietary supplements, and foods produced from natural sources without added artificial ingredients.

<span class="mw-page-title-main">Phytochemistry</span> Study of phytochemicals, which are chemicals derived from plants

Phytochemistry is the study of phytochemicals, which are chemicals derived from plants. Phytochemists strive to describe the structures of the large number of secondary metabolites found in plants, the functions of these compounds in human and plant biology, and the biosynthesis of these compounds. Plants synthesize phytochemicals for many reasons, including to protect themselves against insect attacks and plant diseases. The compounds found in plants are of many kinds, but most can be grouped into four major biosynthetic classes: alkaloids, phenylpropanoids, polyketides, and terpenoids.

<span class="mw-page-title-main">Stilbenoid</span> Class of chemical compounds

Stilbenoids are hydroxylated derivatives of stilbene. They have a C6–C2–C6 structure. In biochemical terms, they belong to the family of phenylpropanoids and share most of their biosynthesis pathway with chalcones. Most stilbenoids are produced by plants, and the only known exception is the antihelminthic and antimicrobial stilbenoid, 2-isopropyl-5-[(E)-2-phenylvinyl]benzene-1,3-diol, biosynthesized by the Gram-negative bacterium Photorhabdus luminescens.

<span class="mw-page-title-main">Plant defense against herbivory</span> Plants defenses against being eaten

Plant defense against herbivory or host-plant resistance (HPR) is a range of adaptations evolved by plants which improve their survival and reproduction by reducing the impact of herbivores. Plants can sense being touched, and they can use several strategies to defend against damage caused by herbivores. Many plants produce secondary metabolites, known as allelochemicals, that influence the behavior, growth, or survival of herbivores. These chemical defenses can act as repellents or toxins to herbivores or reduce plant digestibility. Another defensive strategy of plants is changing their attractiveness. To prevent overconsumption by large herbivores, plants alter their appearance by changing their size or quality, reducing the rate at which they are consumed.

Phytotoxins are substances that are poisonous or toxic to the growth of plants. Phytotoxic substances may result from human activity, as with herbicides, or they may be produced by plants, by microorganisms, or by naturally occurring chemical reactions.

<span class="mw-page-title-main">Opiate</span> Substance derived from opium

An opiate is an alkaloid substance derived from opium. It differs from the similar term opioid in that the latter is used to designate all substances, both natural and synthetic, that bind to opioid receptors in the brain. Opiates are alkaloid compounds naturally found in the opium poppy plant Papaver somniferum. The psychoactive compounds found in the opium plant include morphine, codeine, and thebaine. Opiates have long been used for a variety of medical conditions, with evidence of opiate trade and use for pain relief as early as the eighth century AD. Most opiates are considered drugs with moderate to high abuse potential and are listed on various "Substance-Control Schedules" under the Uniform Controlled Substances Act of the United States of America.

<span class="mw-page-title-main">Naturally occurring phenols</span> Group of chemical compounds

In biochemistry, naturally occurring phenols are natural products containing at least one phenol functional group. Phenolic compounds are produced by plants and microorganisms. Organisms sometimes synthesize phenolic compounds in response to ecological pressures such as pathogen and insect attack, UV radiation and wounding. As they are present in food consumed in human diets and in plants used in traditional medicine of several cultures, their role in human health and disease is a subject of research. Some phenols are germicidal and are used in formulating disinfectants.

<span class="mw-page-title-main">Plant secondary metabolism</span>

Secondary metabolism produces a large number of specialized compounds that do not aid in the growth and development of plants but are required for the plant to survive in its environment. Secondary metabolism is connected to primary metabolism by using building blocks and biosynthetic enzymes derived from primary metabolism. Primary metabolism governs all basic physiological processes that allow a plant to grow and set seeds, by translating the genetic code into proteins, carbohydrates, and amino acids. Specialized compounds from secondary metabolism are essential for communicating with other organisms in mutualistic or antagonistic interactions. They further assist in coping with abiotic stress such as increased UV-radiation. The broad functional spectrum of specialized metabolism is still not fully understood. In any case, a good balance between products of primary and secondary metabolism is best for a plant’s optimal growth and development as well as for its effective coping with often changing environmental conditions. Well known specialized compounds include alkaloids, polyphenols including flavonoids, and terpenoids. Humans use many of these compounds for culinary, medicinal and nutraceutical purposes.

A meroterpene is a chemical compound having a partial terpenoid structure.

Medicinal fungi are fungi that contain metabolites or can be induced to produce metabolites through biotechnology to develop prescription drugs. Compounds successfully developed into drugs or under research include antibiotics, anti-cancer drugs, cholesterol and ergosterol synthesis inhibitors, psychotropic drugs, immunosuppressants and fungicides.

Chemical defenses in <i>Cannabis</i> Defense of Cannabis plant from pathogens

Cannabis (/ˈkænəbɪs/) is commonly known as marijuana or hemp and has two known strains: Cannabis sativa and Cannabis indica, both of which produce chemicals to deter herbivory. The chemical composition includes specialized terpenes and cannabinoids, mainly tetrahydrocannabinol (THC), and cannabidiol (CBD). These substances play a role in defending the plant from pathogens including insects, fungi, viruses and bacteria. THC and CBD are stored mostly in the trichomes of the plant, and can cause psychological and physical impairment in the user, via the endocannabinoid system and unique receptors. THC increases dopamine levels in the brain, which attributes to the euphoric and relaxed feelings cannabis provides. As THC is a secondary metabolite, it poses no known effects towards plant development, growth, and reproduction. However, some studies show secondary metabolites such as cannabinoids, flavonoids, and terpenes are used as defense mechanisms against biotic and abiotic environmental stressors.

References

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