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Review
. 2020 Sep 25;21(19):7078.
doi: 10.3390/ijms21197078.

Monoterpenes and Their Derivatives-Recent Development in Biological and Medical Applications

Mariola Zielińska-Błajet  1 , Joanna Feder-Kubis  1
Affiliations
Review

Monoterpenes and Their Derivatives-Recent Development in Biological and Medical Applications

Mariola Zielińska-Błajet et al. Int J Mol Sci. .

Abstract

Monoterpenes, comprising hydrocarbons, are the largest class of plant secondary metabolites and are commonly found in essential oils. Monoterpenes and their derivatives are key ingredients in the design and production of new biologically active compounds. This review focuses on selected aliphatic, monocyclic, and bicyclic monoterpenes like geraniol, thymol, myrtenal, pinene, camphor, borneol, and their modified structures. The compounds in question play a pivotal role in biological and medical applications. The review also discusses anti-inflammatory, antimicrobial, anticonvulsant, analgesic, antiviral, anticancer, antituberculosis, and antioxidant biological activities exhibited by monoterpenes and their derivatives. Particular attention is paid to the link between biological activity and the effect of structural modification of monoterpenes and monoterpenoids, as well as the introduction of various functionalized moieties into the molecules in question.

Keywords: analgesic activity; anti-inflammatory activity; antiviral activity; biological activity; borneol; camphor; geraniol; myrtenal; pinene; thymol.

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Conflict of interest statement

The authors declare no conflict of interest.

Figures

Figure 1
Figure 1
Division of monoterpenes (acyclic, monocyclic, bicyclic).
Figure 2
Figure 2
The natural origin of monoterpenes and their biological applications.
Figure 3
Figure 3
Ester derivatives of naturally occurring geraniol.
Figure 4
Figure 4
Geraniol-based phenols/methoxyphenols.
Figure 5
Figure 5
The isomers of 6,7-dihydroxy-3,7-dimethyloct-2-enoic acid derivatives of geraniol.
Figure 6
Figure 6
Selected examples of geraniol-butanolide hybrid compounds.
Figure 7
Figure 7
Representative thymol’s derivatives with antimicrobial and antibacterial activities.
Figure 8
Figure 8
Representative thymol derivatives with antibacterial activity.
Figure 9
Figure 9
Selected aryl-azo-thymol derivatives with significant antibacterial and antifungal activities.
Figure 10
Figure 10
Selected thymol derivatives with significant antifungal activities.
Figure 11
Figure 11
Selected thymol derivatives with antioxidant activities.
Figure 12
Figure 12
Thymol derivatives with anticancer activity.
Figure 13
Figure 13
Thymol derivatives with anti-inflammatory activity.
Figure 14
Figure 14
Thymol derivatives with inhibitory effects on some metabolic enzymes.
Figure 15
Figure 15
Thymol derivatives with pharmacological activity.
Figure 16
Figure 16
Selected myrtenal’s derivatives with significant antifungal, herbicidal, antiviral, anticancer, and analgesic activities.
Figure 17
Figure 17
Monoterpene-based 1,2,4- and 1,3,4-oxadiazole derivatives.
Figure 18
Figure 18
Structural formulas of α-pinene and β-pinene enantiomers.
Figure 19
Figure 19
(–)-β-Pinene derivatives with antimicrobial and insecticidal activities.
Figure 20
Figure 20
Representative pinene derivatives with pharmacological activity.
Figure 21
Figure 21
α-Pinene-based dithiadiazole compounds.
Figure 22
Figure 22
The design strategy for (+)-camphor-based imines with effectiveness biological activity.
Figure 23
Figure 23
Camphecene—compound based on (+)-camphor and aminoethanol.
Figure 24
Figure 24
Aliphatic (+)-camphor imines with various lengths of the aliphatic chain.
Figure 25
Figure 25
Quaternary ammonium (+)-camphor derivatives.
Figure 26
Figure 26
(+)-Camphor imine and hydrazone derivatives.
Figure 27
Figure 27
(+)-Camphor N-acylhydrazones with various aliphatic, aromatic, and heterocyclic substituents.
Figure 28
Figure 28
α-Truxillic acid derivative with (+)-camphor fragment.
Figure 29
Figure 29
(+)-Camphor amide derivatives with the heterocyclic fragment.
Figure 30
Figure 30
(+)-Camphor based (–)-cytisine with the heterocyclic fragment.
Figure 31
Figure 31
Polycyclic nitrogen-containing heterocyclic compounds (121–124) being (+)-camphoric acid (120) derivatives.
Figure 32
Figure 32
Quaternary ammonium salts (126–128) derived from (1S)-(+)-camphor-10-sulfonic acid (125).
Figure 33
Figure 33
(1S)-(+)-Camphor-10-sulfonamide derivatives.
Figure 34
Figure 34
Aliphatic and aromatic esters of (–)-borneol derivatives were tested as antimicrobial agents [109] and as antiproliferative and antioedematogenic agents [108].
Figure 34
Figure 34
Aliphatic and aromatic esters of (–)-borneol derivatives were tested as antimicrobial agents [109] and as antiproliferative and antioedematogenic agents [108].
Figure 35
Figure 35
α-Truxillic acid derivative with (–)-borneol fragment.
Figure 36
Figure 36
Ester derivative of natural occurring (–)-borneol with hydrazinylidene group.
Figure 37
Figure 37
The design strategy for heterocyclic (–)-borneol-based esters with the effectiveness of the biological activity.
Figure 38
Figure 38
(–)-Borneol ester derivatives with different N- and S-nucleophiles.
Figure 39
Figure 39
(–)-Borneol and (–)-isoborneol derivatives with morpholine fragment.
Figure 40
Figure 40
N-Heterocyclic esters of (–)-borneol derivatives as antiulcerogenic agents.
Figure 41
Figure 41
N-Heterocyclic esters of (–)-borneol derivatives as vaccinia virus inhibitors.
Figure 42
Figure 42
(–)-Borneol derivative, 1,7,7-trimethylbicyclo[2.2.1]hept-2-yl methane sulfonate as antibacterial agent.
Figure 43
Figure 43
Borneol-based polymer.
See this image and copyright information in PMC

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