Phytochemistry is the study of phytochemicals, which are chemicals derived from

plant Plants are predominantly photosynthetic eukaryotes of the kingdom Plantae. Historically, the plant kingdom encompassed all living things that were not animals, and included algae and fungi; however, all current definitions of Plantae exclu ...

s. Phytochemists strive to describe the structures of the large number of

secondary 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 norma ...

s 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 Insects (from Latin ') are pancrustacean hexapod invertebrates of the class Insecta. They are the largest group within the arthropod phylum. Insects have a chitinous exoskeleton, a three-part body ( head, thorax and abdomen), three ...

attacks and

plant disease Plant pathology (also phytopathology) is the scientific study of diseases in plants caused by pathogens (infectious organisms) and environmental conditions (physiological factors). Organisms that cause infectious disease include fungi, oomy ...

s. The compounds found in plants are of many kinds, but most can be grouped into four major biosynthetic classes:

alkaloid 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 ...

s, phenylpropanoids,

polyketide Polyketides are a class of natural products derived from a precursor molecule consisting of a chain of alternating ketone (or reduced forms of a ketone) and methylene groups: (-CO-CH2-). First studied in the early 20th century, discovery, biosynth ...

s, and

terpenoid 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" ...

s. Phytochemistry can be considered a subfield of

botany Botany, also called , plant biology or phytology, is the science of plant life and a branch of biology. A botanist, plant scientist or phytologist is a scientist who specialises in this field. The term "botany" comes from the Ancient Greek w ...

or chemistry. Activities can be led in

botanical garden A botanical garden or botanic gardenThe terms ''botanic'' and ''botanical'' and ''garden'' or ''gardens'' are used more-or-less interchangeably, although the word ''botanic'' is generally reserved for the earlier, more traditional gardens, an ...

s or in the wild with the aid of ethnobotany. Phytochemical studies directed toward human (i.e. drug discovery) use may fall under the discipline of pharmacognosy, whereas phytochemical studies focused on the ecological functions and evolution of phytochemicals likely fall under the discipline of

chemical ecology A chemical substance is a form of matter having constant chemical composition and characteristic properties. Some references add that chemical substance cannot be separated into its constituent elements by physical separation methods, i.e., wit ...

. Phytochemistry also has relevance to the field of plant physiology.

Techniques

Techniques commonly used in the field of phytochemistry are extraction, isolation, and

structural elucidation A chemical structure determination includes a chemist's specifying the molecular geometry and, when feasible and necessary, the electronic structure of the target molecule or other solid. Molecular geometry refers to the spatial arrangement of at ...

( MS,1D and 2D NMR) of

natural products 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 sy ...

, as well as various

chromatography In chemical analysis, chromatography is a laboratory technique for the separation of a mixture into its components. The mixture is dissolved in a fluid solvent (gas or liquid) called the ''mobile phase'', which carries it through a system ( ...

techniques (MPLC, HPLC, and LC-MS).

Phytochemicals

Many plants produce chemical compounds for defence against herbivores. The major classes of pharmacologically active phytochemicals are described below, with examples of medicinal plants that contain them. Human settlements are often surrounded by weeds containing phytochemicals, such as

nettle {{redirect, Nettle Nettle refers to plants with stinging hairs, particularly those of the genus '' Urtica''. It can also refer to plants which resemble ''Urtica'' species in appearance but do not have stinging hairs. Plants called "nettle" includ ...

dandelion ''Taraxacum'' () is a large genus of flowering plants in the family Asteraceae, which consists of species commonly known as dandelions. The scientific and hobby study of the genus is known as taraxacology. The genus is native to Eurasia and Nor ...

and

chickweed ''Stellaria media'', chickweed, is an annual and perennial flowering plant in the family Caryophyllaceae.Fernald, M. L. 1950. “Gray's Manual of Botany”. Eight Edition. American Book Company, New York, NY. 1632 pp. It is native to Euras ...

. Many phytochemicals, including

curcumin Curcumin is a bright yellow chemical produced by plants of the ''Curcuma longa'' species. It is the principal curcuminoid of turmeric (''Curcuma longa''), a member of the ginger family, Zingiberaceae. It is sold as a herbal supplement, cosmet ...

, epigallocatechin gallate,

genistein Genistein (C15H10O5) is a naturally occurring compound that structurally belongs to a class of compounds known as isoflavones. It is described as an angiogenesis inhibitor and a phytoestrogen. It was first isolated in 1899 from the dyer's bro ...

, and resveratrol are pan-assay interference compounds and are not useful in drug discovery.

Alkaloids

Alkaloids are bitter-tasting chemicals, widespread in nature, and often toxic. There are several classes with different modes of action as drugs, both recreational and pharmaceutical. Medicines of different classes include atropine, scopolamine, and hyoscyamine (all from nightshade), the traditional medicine berberine (from plants such as ''

Berberis ''Berberis'' (), commonly known as barberry, is a large genus of deciduous and evergreen shrubs from tall, found throughout temperate and subtropical regions of the world (apart from Australia). Species diversity is greatest in South Amer ...

'' and ''

Mahonia ''Mahonia'' is a genus of approximately 70 species of evergreen shrubs and, rarely, small trees in the family Berberidaceae, native to eastern Asia, the Himalaya, North and Central America. They are closely related to the genus ''Berberis'' and ...

''),

caffeine Caffeine is a central nervous system (CNS) stimulant of the methylxanthine class. It is mainly used recreationally as a cognitive enhancer, increasing alertness and attentional performance. Caffeine acts by blocking binding of adenosine to ...

(''

Coffea ''Coffea'' is a genus of flowering plants in the family Rubiaceae. ''Coffea'' species are shrubs or small trees native to tropical and southern Africa and tropical Asia. The seeds of some species, called coffee beans, are used to flavor vario ...

''),

cocaine Cocaine (from , from , ultimately from Quechua: ''kúka'') is a central nervous system (CNS) stimulant mainly used recreationally for its euphoric effects. It is primarily obtained from the leaves of two Coca species native to South Ameri ...

(''

Coca Coca is any of the four cultivated plants in the family Erythroxylaceae, native to western South America. Coca is known worldwide for its psychoactive alkaloid, cocaine. The plant is grown as a cash crop in the Argentine Northwest, Bolivia, ...

''),

ephedrine Ephedrine is a central nervous system (CNS) stimulant that is often used to prevent low blood pressure during anesthesia. It has also been used for asthma, narcolepsy, and obesity but is not the preferred treatment. It is of unclear benefit in ...

(''

Ephedra Ephedra may refer to: * Ephedra (medicine), a medicinal preparation from the plant ''Ephedra sinica'' * ''Ephedra'' (plant), genus of gymnosperm shrubs See also * Ephedrine Ephedrine is a central nervous system (CNS) stimulant that is of ...

''),

morphine Morphine is a strong opiate that is found naturally in opium, a dark brown resin in poppies (''Papaver somniferum''). It is mainly used as a pain medication, and is also commonly used recreationally, or to make other illicit opioids. T ...

( opium poppy),

nicotine Nicotine is a natural product, naturally produced alkaloid in the nightshade family of plants (most predominantly in tobacco and ''Duboisia hopwoodii'') and is widely used recreational drug use, recreationally as a stimulant and anxiolytic. As ...

(

tobacco Tobacco is the common name of several plants in the genus '' Nicotiana'' of the family Solanaceae, and the general term for any product prepared from the cured leaves of these plants. More than 70 species of tobacco are known, but the ...

), reserpine ('' Rauvolfia serpentina''),

quinidine Quinidine is a class I antiarrhythmic agent, class IA antiarrhythmic agent used to treat heart rhythm disturbances. It is the enantiomer of Antimalarial medication, antimalarial agent quinine, originally derived from the bark of the cinchona tre ...

and

quinine Quinine is a medication used to treat malaria and babesiosis. This includes the treatment of malaria due to '' Plasmodium falciparum'' that is resistant to chloroquine when artesunate is not available. While sometimes used for nocturnal le ...

('' Cinchona''),

vincamine Vincamine is a monoterpenoid indole alkaloid found in the leaves of ''Vinca minor'' (lesser periwinkle), comprising about 25-65% of its indole alkaloids by weight. It can also be synthesized from related alkaloids. Uses Vincamine is sold in Eur ...

(''

Vinca minor ''Vinca minor'' (common names lesser periwinkle or dwarf periwinkle) is a species of flowering plant in the dogbane family, native to central and southern Europe, from Portugal and France north to the Netherlands and the Baltic States, east to ...

''), and

vincristine Vincristine, also known as leurocristine and marketed under the brand name Oncovin among others, is a chemotherapy medication used to treat a number of types of cancer. This includes acute lymphocytic leukemia, acute myeloid leukemia, Hodgkin's ...

(''

Catharanthus roseus ''Catharanthus roseus'', commonly known as bright eyes, Cape periwinkle, graveyard plant, Madagascar periwinkle, old maid, pink periwinkle, rose periwinkle, is a species of flowering plant in the family Apocynaceae. It is native and endemic to M ...

''). File:Opium poppy.jpg, The opium poppy ''

Papaver somniferum ''Papaver somniferum'', commonly known as the opium poppy or breadseed poppy, is a species of flowering plant in the family Papaveraceae. It is the species of plant from which both opium and poppy seeds are derived and is also a valuable orname ...

'' is the source of the alkaloids

and codeine. File:Nicotine.svg, The alkaloid

from

binds directly to the body's

Nicotinic acetylcholine receptor Nicotinic acetylcholine receptors, or nAChRs, are receptor polypeptides that respond to the neurotransmitter acetylcholine. Nicotinic receptors also respond to drugs such as the agonist nicotine. They are found in the central and peripheral ner ...

s, accounting for its pharmacological effects. File:Koeh-018.jpg, Deadly nightshade, ''Atropa belladonna'', yields

tropane alkaloid Tropane alkaloids are a class of bicyclic .2.1alkaloids and secondary metabolites that contain a tropane ring in their chemical structure. Tropane alkaloids occur naturally in many members of the plant family Solanaceae. Certain tropane alkaloid ...

s including atropine, scopolamine and hyoscyamine. File:DMT.svg, N,N-Dimethyltryptamine ( DMT) a powerful psychedelic compound which is present in several plant species found across the globe, commonly found in

Mimosa ''Mimosa'' is a genus of about 590 species of herbs and shrubs, in the mimosoid clade of the legume family Fabaceae. The generic name is derived from the Greek word (''mimos''), an "actor" or "mime", and the feminine suffix -''osa'', "resemb ...

and Acacia species but has also been discovered in grasses such as Philaris Aquatica.

Glycosides

Anthraquinone Anthraquinone, also called anthracenedione or dioxoanthracene, is an aromatic organic compound with formula . Isomers include various quinone derivatives. The term anthraquinone however refers to the isomer, 9,10-anthraquinone (IUPAC: 9,10-dioxoan ...

glycosides are found in senna, rhubarb, and '' Aloe''. The

cardiac glycoside Cardiac glycosides are a class of organic compounds that increase the output force of the heart and decrease its rate of contractions by inhibiting the cellular sodium-potassium ATPase pump. Their beneficial medical uses are as treatments for c ...

s are phytochemicals from plants including

foxglove ''Digitalis'' ( or ) is a genus of about 20 species of herbaceous perennial plants, shrubs, and biennials, commonly called foxgloves. ''Digitalis'' is native to Europe, western Asia, and northwestern Africa. The flowers are tubular in shap ...

and

lily of the valley Lily of the valley (''Convallaria majalis'' (), sometimes written lily-of-the-valley, is a woodland flowering plant with sweetly scented, pendent, bell-shaped white flowers borne in sprays in spring. It is native throughout the cool temperate No ...

. They include digoxin and

digitoxin Digitoxin is a cardiac glycoside used for the treatment of heart failure and certain kinds of heart arrhythmia. It is a phytosteroid and is similar in structure and effects to digoxin, though the effects are longer-lasting. Unlike digoxin, w ...

which act as

diuretic A diuretic () is any substance that promotes diuresis, the increased production of urine. This includes forced diuresis. A diuretic tablet is sometimes colloquially called a water tablet. There are several categories of diuretics. All diuretics i ...

s. File:Senna alexandrina Mill.-Cassia angustifolia L. (Senna Plant).jpg, '' Senna alexandrina'', containing anthraquinone glycosides, has been used as a

laxative Laxatives, purgatives, or aperients are substances that loosen stools and increase bowel movements. They are used to treat and prevent constipation. Laxatives vary as to how they work and the side effects they may have. Certain stimulant, lubri ...

for millennia. Digitalis purpurea2.jpg, The

, ''Digitalis purpurea'', contains digoxin, a

. The plant was used to treat heart conditions long before the glycoside was identified. File:Digoxin.svg, Digoxin is used to treat atrial fibrillation,

atrial flutter Atrial flutter (AFL) is a common abnormal heart rhythm that starts in the atrial chambers of the heart. When it first occurs, it is usually associated with a fast heart rate and is classified as a type of supraventricular tachycardia. Atrial f ...

and sometimes heart failure.

Polyphenols

Polyphenol Polyphenols () are a large family of naturally occurring organic compounds characterized by multiples of phenol units. They are abundant in plants and structurally diverse. Polyphenols include flavonoids, tannic acid, and ellagitannin, some o ...

s of several classes are widespread in plants, including anthocyanins,

phytoestrogen A phytoestrogen is a plant-derived xenoestrogen (see estrogen) not generated within the endocrine system, but consumed by eating plants or manufactured foods. Also called a "dietary estrogen", it is a diverse group of naturally occurring nonstero ...

s, and

tannin Tannins (or tannoids) are a class of astringent, polyphenolic biomolecules that bind to and precipitate proteins and various other organic compounds including amino acids and alkaloids. The term ''tannin'' (from Anglo-Norman ''tanner'' ...

s. File:Angelica sylvestris 3.jpg,

Angelica ''Angelica'' is a genus of about 60 species of tall biennial and perennial herbs in the family Apiaceae, native to temperate and subarctic regions of the Northern Hemisphere, reaching as far north as Iceland, Lapland, and Greenland. They gr ...

, containing

s File:Phytoestrogens2.png,

s include

s (top and middle) File:Figure 1 Chemical structures of the three main types of anthocyanins.jpg,

Anthocyanins Anthocyanins (), also called anthocyans, are water-soluble vacuolar pigments that, depending on their pH, may appear red, purple, blue, or black. In 1835, the German pharmacist Ludwig Clamor Marquart gave the name Anthokyan to a chemical com ...

are a class of polyphenol that contributes to the color of many plants. File:Tannic acid.svg, Tannic acids are one example of many complex polyphenolic structures produced by plants.

Terpenes

Terpenes Terpenes () are a class of natural products consisting of compounds with the formula (C5H8)n for n > 1. Comprising more than 30,000 compounds, these unsaturated hydrocarbons are produced predominantly by plants, particularly conifers. Terpenes ar ...

and terpenoids of many kinds are found in

resin In polymer chemistry and materials science, resin is a solid or highly viscous substance of plant or synthetic origin that is typically convertible into polymers. Resins are usually mixtures of organic compounds. This article focuses on n ...

ous plants such as the conifers. They are aromatic and serve to repel herbivores. Their scent makes them useful in

essential oils An essential oil is a concentrated hydrophobic liquid containing volatile (easily evaporated at normal temperatures) chemical compounds from plants. Essential oils are also known as volatile oils, ethereal oils, aetheroleum, or simply as the o ...

, whether for

perfume Perfume (, ; french: parfum) is a mixture of fragrant essential oils or aroma compounds (fragrances), fixatives and solvents, usually in liquid form, used to give the human body, animals, food, objects, and living-spaces an agreeable scent. Th ...

s such as

rose A rose is either a woody perennial flowering plant of the genus ''Rosa'' (), in the family Rosaceae (), or the flower it bears. There are over three hundred species and tens of thousands of cultivars. They form a group of plants that can be ...

and

lavender ''Lavandula'' (common name lavender) is a genus of 47 known species of flowering plants in the mint family, Lamiaceae. It is native to the Old World and is found in Cape Verde and the Canary Islands, and from Europe across to northern and easte ...

, or for

aromatherapy Aromatherapy is based on the usage of aromatic materials including essential oils and other aroma compounds, with claims for improving psychological and physical well-being. It is offered as a complementary therapy or as a form of alternative ...

. Some have had medicinal uses:

thymol Thymol (also known as 2-isopropyl-5-methylphenol, IPMP), , is a natural monoterpenoid phenol derivative of ''p''-Cymene, isomeric with carvacrol, found in oil of thyme, and extracted from ''Thymus vulgaris'' (common thyme), ajwain, and vari ...

is an antiseptic and was once used as a

vermifuge Anthelmintics or antihelminthics are a group of antiparasitic drugs that expel parasitic worms (helminths) and other internal parasites from the body by either stunning or killing them and without causing significant damage to the host. They may ...

(anti-worm medicine). File:Thymian.jpg, The essential oil of common thyme (''Thymus vulgaris''), contains the

monoterpene Monoterpenes are a class of terpenes that consist of two isoprene units and have the molecular formula C10H16. Monoterpenes may be linear (acyclic) or contain rings (monocyclic and bicyclic). Modified terpenes, such as those containing oxygen func ...

, an

antiseptic An antiseptic (from Greek ἀντί ''anti'', "against" and σηπτικός ''sēptikos'', "putrefactive") is an antimicrobial substance or compound that is applied to living tissue/skin to reduce the possibility of infection, sepsis, or putre ...

and antifungal. File:Thymol2.svg, Thymol is one of many

terpene Terpenes () are a class of natural products consisting of compounds with the formula (C5H8)n for n > 1. Comprising more than 30,000 compounds, these unsaturated hydrocarbons are produced predominantly by plants, particularly conifers. Terpenes ...

s found in plants. File:Isoprene Structural Formulae V.1.svg, Terpenes are polymer of isoprene

Genetics

Contrary to bacteria and fungi, most plant

metabolic pathway In biochemistry, a metabolic pathway is a linked series of chemical reactions occurring within a cell. The reactants, products, and intermediates of an enzymatic reaction are known as metabolites, which are modified by a sequence of chemical reac ...

s are not grouped into biosynthetic gene clusters, but instead are scattered as individual genes. Some exceptions have been discovered: steroidal glycoalkaloids in ''

Solanum ''Solanum'' is a large and diverse genus of flowering plants, which include three food crops of high economic importance: the potato, the tomato and the eggplant (aubergine, brinjal). It is the largest genus in the nightshade family Solanaceae ...

'',

s in

Pooideae The Pooideae are the largest subfamily of the grass family Poaceae, with about 4,000 species in 15 tribes and roughly 200 genera. They include some major cereals such as wheat, barley, oat, rye and many lawn and pasture grasses. They are often ...

, benzoxazinoids in '' Zea mays'',

triterpene Triterpenes are a class of chemical compounds composed of three terpene units with the molecular formula C30H48; they may also be thought of as consisting of six isoprene units. Animals, plants and fungi all produce triterpenes, including squa ...

s in ''

Avena sativa The oat (''Avena sativa''), sometimes called the common oat, is a species of cereal grain grown for its seed, which is known by the same name (usually in the plural, unlike other cereals and pseudocereals). While oats are suitable for human co ...

'',

Cucurbitaceae The Cucurbitaceae, also called cucurbits or the gourd family, are a plant family consisting of about 965 species in around 95 genera, of which the most important to humans are: *''Cucurbita'' – squash, pumpkin, zucchini, some gourds *'' Lagen ...

, '' Arabidopsis'', and momilactone diterpenes in ''

Oryza sativa ''Oryza sativa'', commonly known as Asian rice or indica rice, is the plant species most commonly referred to in English as ''rice''. It is the type of farmed rice whose cultivars are most common globally, and was first domesticated in the Yan ...

''.

References

{{Authority control Phytochemicals Biochemistry Chemistry Botany Herbalism Branches of botany Pharmacognosy