Compound Class

Terpenoids

The largest class of plant compounds, built from five-carbon isoprene units — the essential-oil aromatics, resins, bitter principles, saponins, and plant sterols.

661 Constituents10 Subclasses190 Source herbs

Overview

What Are Terpenoids?

Terpenoids are the largest and most structurally varied class of plant compounds, all assembled from a single five-carbon building block: the isoprene unit. Joining and folding these units produces an enormous range of carbon skeletons.

They are found in virtually every plant. Terpenoids supply the volatile essence of aromatic herbs, the resins of conifers, the bitter principles of many roots and barks, and the sterols that build cell membranes — wherever a plant has a characteristic scent, resin or bitterness, terpenoids are usually behind it.

01

How Terpenoids Are Built

The class is organized by how many isoprene units a molecule contains, and whether its carbon chain closes into rings or stays open:

Monoterpenes
two units, ten carbons
Sesquiterpenes
three units, fifteen carbons
Diterpenes
four units, twenty carbons
Triterpenes
six units, thirty carbons
Tetraterpenes (carotenoids)
eight units, forty carbons

As a rule, the smaller and lighter the molecule, the more volatile it is — which is why the monoterpenes dominate essential oils while the triterpenes sit in resins and barks.

02

Where Terpenoids Occur

Terpenoids are close to universal, but certain families are famous for concentrating them, usually as defensive or aromatic chemistry.

Mints and their relatives (Lamiaceae)

Carrot and umbellifer family (Apiaceae)

Daisy family (Asteraceae)

Conifers (Pinaceae and relatives)

Citrus family (Rutaceae)

Beyond these, the saponin-rich roots of ginseng and liquorice and the carotenoid pigments of fruits and leaves show how far the class reaches.

03

Defining the Class

A compound is classed as a terpenoid when its carbon skeleton can be traced back to repeating isoprene units, typically with oxygen-bearing groups added. Strictly, the pure hydrocarbons are the terpenes and the broader oxygenated majority are the terpenoids, though the two words are often used interchangeably.

Structure, not botanical origin or biological activity, is the sorting criterion — which is why a fragrant monoterpene and a foaming saponin sit in the same class.

04

Pharmacological Importance

Terpenoids give herbal medicine much of its character. The aromatic monoterpenes and sesquiterpenes are the carminative, antimicrobial and anti-inflammatory actives of the essential-oil herbs, while the triterpenes and saponins supply adaptogenic, expectorant and vein-toning activity.

The sterols and carotenoids are more nutritional in character, acting as membrane components, antioxidants and, in the case of the provitamin-A carotenes, vitamin precursors.

05

Toxicity & Safety

As a class terpenoids tend towards the gentle end, and most are well tolerated at culinary and medicinal doses. The pattern is not uniform, however.

The monoterpene ketone thujone can provoke seizures; the sesquiterpene lactones of the daisy family are the principal cause of contact allergy to Asteraceae, and some, such as helenalin, are markedly toxic; and the diterpene esters of the spurge family are strong irritants. Concentrated essential oils deserve particular respect, since they carry these molecules at far higher levels than the whole herb.

Constituents

All Terpenoids

661 total

#

1,3,8-p-Menthatriene 1 herb 1,8-Cineole 20 herbs 10-Deacetylbaccatin III 1 herb 10-Desacetylasperulosidic Acid 10-Epicanin 1 herb 11-beta,13-Dihydrolactucin 2 herbs 11-Keto-beta-boswellic acid 1 herb 13-O-Acetylsolstitialin A 1 herb 13,18-Dehydroglaucarubinone 1 herb 14-Deoxy-11,12-didehydroandrographolide 1 herb 2-Acetoxyfuranodiene 1 herb 2-Methoxyfuranodiene 1 herb 2'-Acetylglaucarubinone 1 herb 20-Hydroxyecdysone 5 herbs 23-epi-26-deoxyactein 1 herb 3-Acetyl-beta-boswellic acid 1 herb 3-beta-Hydroxylanosta-8,24-dien-21-al 1 herb 3'-O-galloylpaeoniflorin 1 herb 4-Terpineol 1 herb 6'-O-benzoylpaeoniflorin 1 herb 6'-O-galloylalbiflorin 1 herb 6'-O-galloylpaeoniflorin 1 herb 7-alpha-Acetoxymarrubiin 1 herb 8-Coumaroylharpagide 1 herb
Open in filterable index

Source Plants

Herbs Containing Terpenoids

190 herbs

Plants in the materia medica documented to carry terpenoids, with the compounds each one is listed for. The bar counts how many DISTINCT terpenoids are on record for a plant, relative to the best-documented — it measures breadth of record, not potency, so a plant with one well-studied compound can outrank a richer source that has simply been analysed less. Where a measured concentration is on record it is quoted inline; most entries have none yet.

Feverfew Tanacetum parthenium Documented for camphor (0–57 % of oil), parthenolide (0.2–0.5 % dry wt), 1,8-cineole and 42 more terpenoids. 45 Terpenoids Muira Puama Ptychopetalum olacoides Documented for allo-aromadendrene, alpha-copaene, alpha-elemene and 32 more terpenoids. 35 Terpenoids Gotu Kola Centella asiatica Documented for asiatic acid (0.02–0.29 % dry wt), asiaticoside (0.04–2.41 % dry wt), madecassic acid (0.02–0.72 % dry wt), madecassoside (0.15–5.3 % dry wt) and 26 more terpenoids. 30 Terpenoids Chaste Tree Vitex agnus-castus Documented for 1,8-cineole, agnuside, aucubin and 26 more terpenoids. 29 Terpenoids Cannabis Cannabis sativa Documented for 1,8-cineole, alpha-terpinene, alpha-terpineol and 25 more terpenoids. 28 Terpenoids Stevia Stevia rebaudiana Documented for austroinulin, beta-carotene, beta-sitosterol and 22 more terpenoids. 25 Terpenoids Asian Ginseng Panax ginseng Documented for ginsenoside Re (0.15 % dry wt), compound K, dammarane saponins and 20 more terpenoids. 23 Terpenoids Yarrow Achillea millefolium Documented for 1,8-cineole, achillicin, achillin and 19 more terpenoids. 22 Terpenoids Peppermint Mentha × piperita Documented for 1,8-cineole (3.5–14 % of EO), limonene (1–5 % of oil), menthol (30–55 % of oil) and 18 more terpenoids. 21 Terpenoids Pine Pinus sylvestris Documented for abietic acid, alpha-pinene, alpha-terpineol and 18 more terpenoids. 21 Terpenoids Angelica Angelica archangelica Documented for alpha-bisabolene, alpha-phellandrene, alpha-pinene and 15 more terpenoids. 18 Terpenoids Rosemary Rosmarinus officinalis Documented for 1,8-cineole (15–55 % of EO), alpha-pinene (13.5–37.7 % of oil), borneol (0.3–21 % of oil), camphor (5–31 % of oil) and 14 more terpenoids. 18 Terpenoids

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