The Phytochemistry of Herbs

Home Introductory Intermediate Advanced PowerPoints Glossary LisaGanora

Welcome to the Phytochemical Glossary for Herbalists

If you arrived here by clicking on a word in the text, scroll down to find that particular definition. You can also search this page by hitting Ctrl F and typing the term into the box that pops up.

Active ingredient/constituent  One or more molecules which have been isolated from the plant matrix and scientifically established to have a specific physiological activity, both in isolation and within the context of the whole herb or extract. This concept comes from conventional pharmacy where an 'active ingredient' might be part of a solution containing a number of other ingredients including carriers or 'excipients.' Active ingredients generally exhibit a 'dose-dependent response' - in other words, the more one takes, the more activity one gets. Many herbalists think that the entire herb or extract is really the 'active ingredient/s' in which many constituents are acting together - synergistically.

Aglycone  Some molecules (such as anthocyanidins or isoflavones) can exist with or without a sugar group attached to them. When they are without the sugar group, they are known as aglycones ('a-' means 'without'). When they have the sugar group, they are known as glycosides.

Allyl group  A functional group composed of H2C=CH-CH2-R, found in many of the sulfur compounds of Garlic as well as in other organic molecules; this group was actually named after the Latin for Garlic, Allium, by a chemist researching Garlic oil in the 1840s.

Amino acid  An organic compound with an amine group (-NH2), a carboxylic acid group (-COOH), a hydrogen atom, and a varying 'R' group bonded to the central carbon atom (the 'alpha' carbon). There are 21 'standard' amino acids from which proteins are composed, and many additional modified types. Alliin, from Garlic, is an example of a modified amino acid.

Antioxidant  A substance which protects tissues from damage by stabilizing harmful free radicals. Free radicals have an unpaired electron, which is very reactive; antioxidants donate a companion electron to the free radical to 'calm it down' so that it doesn't try to react with - and damage - other sensitive molecules. The word 'antioxidant' arises from the chemical definitions of 'oxidation' and 'reduction.' A free radical is an 'oxidant,' 'oxidizer' or 'oxidizing agent,' a chemical that wants to take an electron away from another chemical and use that electron to stabilize itself. This damages, or 'oxidizes' the other chemical. An antioxidant is a 'reducer' or a 'reducing agent' that sacrifices one of its electrons to the free radical. When a free radical and an antioxidant react, the free radical is 'reduced' - it has gained an electron; and the antioxidant is 'oxidized' - it has lost an electron. You'd think it would be the other way around...reduction sounds like losing an electron rather than gaining one...but they did it this way just to confuse chemistry students ;>) See also Oxidation/Reduction and Lipid peroxidation.

Aromatic ring  A structure found in many kinds of phytochemicals, such as phenolic compounds, alkaloids, and terpenes; it consists of six carbon atoms in a flat, hexagonal pattern. It is represented like this:aromatic ringEach angle in the drawing stands for a carbon; the double lines alternating with single lines mean that the atoms are all sharing electrons. In many chemicals, different functional groups (such as -OH or -CH3) are attached to the ring, like this:
aromatic ring with substituents (It looks like there are double bonds alternating with single bonds in this ring, but in this special case, there really aren't - all atoms are sharing equally). The aromatic ring got its name from the fact that early chemists discovered it in fragrant substances; but not all phytochemicals containing this structure have an odor.  (? R)
 

Binding affinity  A measure of the strength of the attraction and 'sticking power' between a protein (i.e., an estrogen receptor) and its ligand (the molecule which binds to it - i.e., an isoflavone). For a technical explanation, see this.

Biosynthesized  A molecule is biosynthesized if it is made by living systems (plants, animals, etc); as opposed to laboratory synthesis.

Bond (covalent bond)
  When atoms in the molecules we discuss here are bonded, they are sharing one or more pairs of electrons, and maintain a particular relationship in space to one another.  When only one pair is shared, it's a single bond. When two pairs are shared, you have a double bond. See also  Hydrogen bond.

Broad spectrum extract An herbal extract designed to contain a wide range of the compounds found in the original plant, as opposed to a narrow spectrum extract, which focuses on achieving high levels of only one or a few compounds.

Carbonyl group  An oxygen atom double-bonded to a carbon atom.

Chromatography This word applies to various different methods of chemical analysis that separate and detect compounds or groups of compounds from a complex mixture. Types of chromatography include TLC (thin layer chromatography), HPTLC (high performance thin layer chromatography), HPLC (high performance liquid chromatography), GC (gas chromatography - or GC/MS: gas chromatography/mass spectrometry), and GLC (gas liquid chromatography). The word is made up of Greek roots meaning 'color' and 'writing,' because early chromatographs separated colored compounds into bands on a flat surface.

Compound
  A chemical composed of more than one type of atom. For example, Sulfur (S) is an element, but allicin is a compound containing sulfur, oxygen, carbon and hydrogen.

Deglycosylation  The removal of a sugar unit (i.e., glucose) from a larger molecule called a glycoside. For example, an enzyme called beta-glycosidase removes the sugar unit from the isoflavone glycoside daidzin, leaving the aglycone, daidzein.

Demethylation  The removal of a methyl group (-CH3) from a molecule; for example, when the methyl group is removed from the isoflavone biochanin A, the resulting molecule is called genistein.

Derivative  Chemicals which are made from their parent compounds are known as derivatives of the parent compound.

Double bond  Atoms are sharing two pairs of electrons in a double bond. This kind of bond is therefore called 'electron rich.' A double bond can become the site of chemical reactions. For example, this sulfide molecule from Garlic has a double bond at each end, represented by the double lines. (Each angle in the drawing represents a carbon atom; there is also a carbon atom at each end of the double lines). double bond

Endogenous  Biochemicals which are made by and within the human body are called 'endogenous'; as opposed to exogenous, those which come from outside. For example, estradiol is an endogenous estrogen, while any phytoestrogen or pharmaceutical estrogen would be considered exogenous. Exogenous estrogens are also known as xenoestrogens; this designation includes both beneficial phytoestrogens and harmful estrogenic chemical pollutants such as DDT.

Enteric coating 
A coating applied to tablets which prevents them from dissolving in the stomach, but allows them to dissolve when they reach the small intestine.

Enzyme
  A type of protein (almost always) that changes, constructs, or decomposes other molecules without being changed itself. A biological catalyst. Most biochemical reactions are mediated by enzymes, which help otherwise slow reactions proceed at a biologically useful pace. Enzymes are sensitive to high temperatures and extremes of pH. For example, alliinase, the enzyme that changes alliin to allicin in Garlic, is inactivated by heat (cooking) or low pH (stomach acid).

Estrogen receptor  A protein within certain cells which can bind to endogenous estrogens, phytoestrogens, or xenoestrogens. Once coupled with its estrogenic molecule, this protein communicates with other molecules and starts a process that ultimately leads to certain genes being switched on or off. The genes regulate many hormone-influenced systems.

Free radical  A free radical is an 'oxidant,' 'oxidizer' or 'oxidizing agent,' a molecule with one 'extra' electron that wants to take an electron away from another molecule and use that electron to stabilize itself (electrons are happiest in pairs). This process damages ('oxidizes') many biological chemicals including the lipids in cell membranes.

Freeze drying 
Plant materials are frozen, then subject to high vacuum. Water molecules sublimate (pass from solid to gas phase), and are removed from the material. The drying is all done at low temperature.

Functional group 
In organic molecules, particular groups of atoms where characteristic chemical reactions take place. There is a limited number of functional groups, and they can be found in many different kinds of molecules. Examples: Alcohol group, -OH; Amine group, -NH2; Sulfide group, C-S-C.

Glucoside  See glycoside, below.

Glycoside  Any of various kinds of molecules (including flavonoids) which have a sugar group attached to the main part of the molecule. The molecule without the sugar is known as the aglycone. A glycoside that has glucose as its sugar unit is called a glucoside.

Gram  One ounce contains 28.35 grams (g); a milligram (mg) is 1/1000 of a gram, so one ounce contains 28,349.5 milligrams. A microgram (µg) is 1/1,000,000 of a gram; one ounce contains 28,349,523 micrograms. Here's a great unit converter for translating one measurement into another.

Half-life 
The time it takes for half of a given quantity of a particular compound to decompose or transform into other compounds.

Hydrogen bond  A relatively weak kind of chemical bond where there is an attraction between a hydrogen atom on one molecule and an oxygen or nitrogen atom on another. Helps to stabilize the shape of molecules such as proteins (including enzymes) and DNA; accounts for the 'surface tension' of water.

Hydroxyl group  A hydroxyl group is a functional group consisting of an oxygen atom bonded to a hydrogen atom (-OH). It is very common in biomolecules.

In vitro  Literally, 'in glass': generally refers to scientific studies performed on cells cultured in Petri dishes. The results of in vitro studies suggest, but cannot predict, the effects a substance will have on a living organisms (such as a mouse or human being). This is contrasted to in vivo, which means 'in the living organism.'

Isomer Two compounds are isomers of each other when they have the same number and kinds of atoms, but those atoms are arranged in different ways.

Ligand  A (usually smaller) molecule which binds to a (usually larger) molecule such as an enzyme or protein, and is either transformed into something else or initiates a metabolic process (i.e., a phytoestrogen - the ligand - binds to an estrogen receptor - the protein - and initiates a process such as transcription of a particular gene).

Lipid  Fatty or oily substance, insoluble in water. Includes fatty acids and triglycerides. For more info, see Lipid Library and this outline.

Lipid peroxidation  Lipids (such as the phospholipids in cell membranes and fatty acids in the bloodstream) are subject to attack by free radicals, which damage them by oxidation; this process is called lipid peroxidation. Lipid peroxidation has been implicated in atherosclerosis and other diseases. Antioxidants help protect against lipid peroxidation.

Methoxy group  A functional group consisting of an oxygen atom attached to a methyl group (-OCH3).

Methyl group  A functional group consisting of a carbon atom with three hydrogen atoms attached (-CH3).

Microgram, see 'gram' above.
Milligram, see 'gram' above.

Moiety When referring to a molecule, a 'moiety' is a part or section of the whole.

Oligomeric   'Oligo' means short. It refers to a type of polymer with only a few subunits, as opposed to a 'monomer' - with one unit, or a 'polymer' - with many subunits. For example, an oligomeric proanthocyanidin is a short-chain polymer consisting of two to four or five flavanol subunits. Oligomers may be further classified as 'dimers' - having two subunits, or 'trimers' - having three subunits.

Organic  In chemistry, any carbon-containing compound (with the exception of molecules like carbon monoxide or carbon dioxide, and materials like graphite and diamonds) is said to be 'organic.'

Organosulfur  An organic compound containing sulfur.

Oxidation/Reduction  In phytochemistry, you can think of 'oxidation' as adding an atom of oxygen or removing an atom of hydrogen from a molecule. You can think of 'reduction' as removing an oxygen atom or adding a hydrogen atom to a molecule. For more detail, see this Oxidation/Reduction website.

Parent compound  A compound from which other compounds are derived. For example, alliin is the parent compound of allicin.

pH  A measure of the acidity or alkalinity of a substance. Neutral pH (pure water) is 7; acidic is less than 7 and basic, or alkaline, is above 7. Examples: vinegar, 2.4-3.4; stomach acid, 1.0-3.0; blood, 7.4; baking soda, 8.4.

Pharmacodynamics  The study of the physiological effects and mechanisms of action of a compound and how this varies with concentration/dosage. In other words, the study of how the drug acts upon the body.

Pharmacognosy  The study of medicinal plants and their extracts, constituents, and phytochemistry. Pharmacognosy (from the Greek words for drug or medicine and knowledge) is currently considered to be a branch of pharmacology and is studied in schools of pharmacy.

Pharmacokinetics   The study of how compounds are absorbed, distributed, metabolized and eliminated by the body. In other words, the study of how the body acts upon the drug.

Phenolic  A molecule containing an aromatic ring that bears one or more hydroxyl groups is referred to as 'phenolic.' Examples include flavonoids, isoflavonoids, and lignans. The word comes from 'phenol,' the name for the structure below which has one hydroxyl group attached to the ring:phenolic

Physiological concentrations  Concentrations of a substance likely to occur within the human body. Results from research that uses significantly higher or lower concentrations of the chemical being studied may not be applicable to the actual situation inside the body.

Phytoalexin  An antimicrobial, protective compound synthesized by a plant in response to bacterial, viral, or fungal infection. Many chemicals that are medicinal to humans are phytoalexins.

Phytochemistry  The branch of chemistry that focuses on the constituents of plants (phyto comes from the Greek word for plant). Often, phytochemistry deals specifically with the chemistry of medicinal plants. This discipline can also include studies of how to extract, concentrate, analyze, standardize, & preserve herbal products.

Polyhydroxylated  A molecule bearing more than one hydroxyl group is called polyhydroxylated.

Polymer  A large molecule consisting of a number of identical or similar subunits joined together. An example is the starch molecule, which is made up of numerous glucose units. Proteins can be thought of as polymers of amino acid units. Lignin, the polymer that gives wood its rigidity, is a polymer of cinnamyl alcohol units (lignans are made of two joined cinnamyl alcohols).

Precursor   Plants make phytochemicals by starting with one chemical, a 'parent compound,' and changing it into another, called a 'derivative' -- meaning 'derived from the parent compound.' There is a sometimes lengthy series of chemical transformations where the original molecule changes shapes, splits up, or joins with other molecules or atoms on the way to becoming the derivative. Biochemists call this chain of transformative relationships a 'pathway.' A pathway is organized by a specific group of enzymes that help change each form of the molecule into the next form 'downstream.' A molecule that is 'upstream' in this process is called a precursor of the final molecule.

Pro-oxidant  Opposite of an antioxidant; causes oxidation.

R In molecular structure, 'R' is a kind of shorthand that stands for a variable group; for example, in a set of related molecules that are mostly identical, you might find -CH3 attached to a particular spot in one molecule, -C3H5 in the corresponding place in the second molecule, and simply -H in that spot in the third molecule. R is a way of saying, 'this could be any one of a number of structures.'

Reactive oxygen species (ROS)  Damaging molecules, including oxygen radicals (i.e. superoxide radical) and other highly reactive forms of oxygen (i.e. singlet oxygen) that can harm biomolecules and contribute to disease states. Other oxygen-containing radicals, such as the hydroxyl and peroxyl radicals, are often classified as ROS too.

Significant  In a scientific study, significant means that a statistical analysis of the results has ruled out chance variation as the cause of an observed effect.

Stable  A stable compound remains unchanged for a relatively long period of time.

Standardize  To analyze a concentrated botanical extract so that predetermined levels of certain compounds (known as 'marker' compounds) are guaranteed to be present in every batch. These levels are generally chosen based on research results.

Steam distilling  In order to extract volatile or essential oils, plant material is either boiled in water or steam is passed through it. The volatiles are carried off in the steam and recovered in a condenser.

Stereoisomer  Two molecules are 'stereoisomers' of each other when they contain the exact same numbers and kinds of atoms, which are bonded to each other in the very same order; the only difference between them is the way certain bonds are oriented in space.

Sulfide  An organic compound containing sulfur bonded to carbon;  monosulfide: R-C-S-C-R; disulfide: R-C-S-S-C-R; Trisulfide: R-C-S-S-S-C-R (mono=one, di=two, tri=3; R= R group, see above)

Sulfoxide  An organic compound containing a sulfur atom bonded to an oxygen atom.

Synergy  In medicinal plants, constituents that somehow work together are said to be working in 'synergy' or 'synergistically.' Two or more constituents may result in an increased effect (potentiating synergy), or one constituent may modify the toxic effects of another (attenuating synergy); protective synergy is when one constituent stabilizes or protects another (i.e., an antioxidant may prevent the breakdown of another constituent). Synergy is thought to occur in addition to any additive effects the constituents of an herb may have (simplified as 1 + 1 > 2). Another type of synergy occurs when one constituent produces an effect upon an organism that allows a separate constituent to have an enhanced effect on that organism. For example, some herbs that produce the antimicrobial alkaloid berberine also produce a chemical that inhibits bacteria from pumping the berberine out of their cells. Some herbs (i.e., Valerian) do not have a prominent 'active ingredient' but instead achieve their effects through synergy of multiple constituents. Synergy can be found operating in formulas as well; for example, Nettle root & Pygeum bark work better together for BPH (benign prostatic hyperplasia) than either herb alone. Although the word synergy can have several definitions, there is a specific mathematical test for true synergistic interactions between constituents, known as the 'isobole method.'

Thiosulfinate  An organic compound containing two sulfur atoms bonded together, one of which is also double-bonded to an oxygen atom. Example: allicin.

Transformation products  Chemicals that are derived from a particular compound when it undergoes chemical changes during extraction, processing, or spontaneous decomposition.

Unstable  An unstable compound is one which will spontaneously decompose or transform into other compounds over a relatively short period of time.

Volatile  A substance which evaporates easily is said to be 'volatile.' Things with a strong aroma are generally volatile, because the molecules easily pass into the surrounding air.

Wedges  Some bonds are represented by wedges instead of by straight lines. This is a way of indicating the 3-dimensional structure of the molecule. The wedges represent the way the bond is oriented in space: imagine that the part of the molecule at the fat end of the dark wedge is coming out of the page towards you. The part of the molecule at the fat end of the dotted wedge is poking back into space behind the page:
wedge bond
In this particular molecule, the -OH group with the dark wedge is poking out of the plane of the page towards the viewer; the ring on the end of the dotted wedge is poking back behind the page.

Top

Home

Introductory

Intermediate

Advanced

Lisa Ganora

Links to Other Botanical Medicine Sites

© Lisa Ganora 2006