Medically Useful Plant Terpenoids: Biosynthesis, Occurrence, and Mechanism of Action

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Abstract

Specialized plant terpenoids have found fortuitous uses in medicine due to their evolutionary and biochemical selection for biological activity in animals. However, these highly functionalized natural products are produced through complex biosynthetic pathways for which we have a complete understanding in only a few cases. Here we review some of the most effective and promising plant terpenoids that are currently used in medicine and medical research and provide updates on their biosynthesis, natural occurrence, and mechanism of action in the body. This includes pharmacologically useful plastidic terpenoids such as p-menthane monoterpenoids, cannabinoids, paclitaxel (taxol ^®), and ingenol mebutate which are derived from the 2- C-methyl- d-erythritol-4-phosphate (MEP) pathway, as well as cytosolic terpenoids such as thapsigargin and artemisinin produced through the mevalonate (MVA) pathway. We further provide a review of the MEP and MVA precursor pathways which supply the carbon skeletons for the downstream transformations yielding these medically significant natural products.

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Structure of a cannabinoid receptor and functional expression of the cloned cDNA.

L Matsuda, S Lolait, M J Brownstein … (1990)

Marijuana and many of its constituent cannabinoids influence the central nervous system (CNS) in a complex and dose-dependent manner. Although CNS depression and analgesia are well documented effects of the cannabinoids, the mechanisms responsible for these and other cannabinoid-induced effects are not so far known. The hydrophobic nature of these substances has suggested that cannabinoids resemble anaesthetic agents in their action, that is, they nonspecifically disrupt cellular membranes. Recent evidence, however, has supported a mechanism involving a G protein-coupled receptor found in brain and neural cell lines, and which inhibits adenylate cyclase activity in a dose-dependent, stereoselective and pertussis toxin-sensitive manner. Also, the receptor is more responsive to psychoactive cannabinoids than to non-psychoactive cannabinoids. Here we report the cloning and expression of a complementary DNA that encodes a G protein-coupled receptor with all of these properties. Its messenger RNA is found in cell lines and regions of the brain that have cannabinoid receptors. These findings suggest that this protein is involved in cannabinoid-induced CNS effects (including alterations in mood and cognition) experienced by users of marijuana.

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Plant defense against herbivores: chemical aspects.

Axel Mithöfer, Wilhelm Boland (2012)

Plants have evolved a plethora of different chemical defenses covering nearly all classes of (secondary) metabolites that represent a major barrier to herbivory: Some are constitutive; others are induced after attack. Many compounds act directly on the herbivore, whereas others act indirectly via the attraction of organisms from other trophic levels that, in turn, protect the plant. An enormous diversity of plant (bio)chemicals are toxic, repellent, or antinutritive for herbivores of all types. Examples include cyanogenic glycosides, glucosinolates, alkaloids, and terpenoids; others are macromolecules and comprise latex or proteinase inhibitors. Their modes of action include membrane disruption, inhibition of nutrient and ion transport, inhibition of signal transduction processes, inhibition of metabolism, or disruption of the hormonal control of physiological processes. Recognizing the herbivore challenge and precise timing of plant activities as well as the adaptive modulation of the plants' metabolism is important so that metabolites and energy may be efficiently allocated to defensive activities.

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Recruitment of entomopathogenic nematodes by insect-damaged maize roots.

Sergio Rasmann, Tobias G Köllner, Jörg Degenhardt … (2005)

Plants under attack by arthropod herbivores often emit volatile compounds from their leaves that attract natural enemies of the herbivores. Here we report the first identification of an insect-induced belowground plant signal, (E)-beta-caryophyllene, which strongly attracts an entomopathogenic nematode. Maize roots release this sesquiterpene in response to feeding by larvae of the beetle Diabrotica virgifera virgifera, a maize pest that is currently invading Europe. Most North American maize lines do not release (E)-beta-caryophyllene, whereas European lines and the wild maize ancestor, teosinte, readily do so in response to D. v. virgifera attack. This difference was consistent with striking differences in the attractiveness of representative lines in the laboratory. Field experiments showed a fivefold higher nematode infection rate of D. v. virgifera larvae on a maize variety that produces the signal than on a variety that does not, whereas spiking the soil near the latter variety with authentic (E)-beta-caryophyllene decreased the emergence of adult D. v. virgifera to less than half. North American maize lines must have lost the signal during the breeding process. Development of new varieties that release the attractant in adequate amounts should help enhance the efficacy of nematodes as biological control agents against root pests like D. v. virgifera.

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Author and article information

Contributors

Ewa Swiezewska: Role: Academic Editor

Liliana Surmacz: Role: Academic Editor

Bernhard Loll: Role: Academic Editor

Journal

Journal ID (nlm-ta): Molecules

Journal ID (iso-abbrev): Molecules

Journal ID (publisher-id): molecules

Title: Molecules

Publisher: MDPI

ISSN (Electronic): 1420-3049

Publication date (Electronic): 01 November 2019

Publication date Collection: November 2019

Volume: 24

Issue: 21

Electronic Location Identifier: 3961

Affiliations

[1 ]Department of Cellular and Systems Biology, University of Toronto, Toronto, ON M5S 3G5, Canada; matthew.bergman@ 123456mail.utoronto.ca (M.E.B.); benjamin.davis@ 123456mail.utoronto.ca (B.D.)

[2 ]Department of Biology, University of Toronto–Mississauga, Mississauga, ON L5L 1C6, Canada

Author notes

[* ]Correspondence: michaelandrew.phillips@ 123456utoronto.ca ; Tel.: +1-905-569-4848

Author information

Matthew E. Bergman https://orcid.org/0000-0002-4071-3166

Michael A. Phillips https://orcid.org/0000-0001-7276-119X

Article

Publisher ID: molecules-24-03961

DOI: 10.3390/molecules24213961

PMC ID: 6864776

PubMed ID: 31683764

SO-VID: b9e6869e-7577-486b-bedf-8ee21e77da8e

License:

Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license ( http://creativecommons.org/licenses/by/4.0/).

History

Date received : 03 October 2019

Date accepted : 30 October 2019

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Medically Useful Plant Terpenoids: Biosynthesis, Occurrence, and Mechanism of Action

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Abstract

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Most cited references 163

Structure of a cannabinoid receptor and functional expression of the cloned cDNA.

Plant defense against herbivores: chemical aspects.

Recruitment of entomopathogenic nematodes by insect-damaged maize roots.

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Cited by 77

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