Biosynthesis, natural distribution, and biological activities of acyclic monoterpenes and their derivatives

Bergman, Matthew E.; Franks, Anya E.; Phillips, Michael A.

doi:10.1007/s11101-022-09849-6

Cited by 4 publications

(4 citation statements)

References 170 publications

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“…However, this interpretation is complicated by the compartmentalization of terpenoids in tansy. Tansy leaves, including the midribs (the main target site of aphid attack), are characterized by a high density of glandular cells, which serve as storage sites for monoterpenoids in particular (Guerreiro et al, 2016; Bergman et al, 2023). Jakobs et al (2018) showed plant organ-specific responses to aphid infestation, for example, the composition of sugars and organic acids in the phloem exudate of tansy was particularly influenced by aphids compared to leaves.…”

Section: Discussionmentioning

confidence: 99%

Exogenous stimulation ofTanacetum vulgareroots with pipecolic acid leads to tissue-specific responses in terpenoid composition

Rahimova,

Heinen,

Weber

et al. 2024

Preprint

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Tanacetum vulgare L., known as tansy, is a perennial plant with a highly variable terpenoid composition, with mono- and sesquiterpenoids being the most abundant. The high diversity of terpenoids is known to play an important role in mediating ecological interactions. However, the distribution of terpenoids in different tissues and the inducibility of terpenoids in these tissues by biotic stress are poorly understood. In this study, we investigated the changes in terpenoid profiles and concentrations in different plant organs following treatment of roots with pipecolic acid (Pip). Pipecolic acid is a non-proteinogenic amino acid that triggers defense responses in plants. It is often used to induce systemic resistance (SAR) in plants under controlled conditions. Examination of the tissues showed that the leaves and midribs contained mainly monoterpenoids, while the coarse and fine roots of the plants contained mainly sesquiterpenoids. The rhizomes occupied an intermediate position by presenting the terpenoid profiles of both the midribs and roots but also the unique compounds of its own. Treatment with pipecolic acid led to an increase in the concentration of mono- and sesquiterpenoids in all tissues except rhizomes. However, a significantly higher amount of sesquiterpenoids was formed in root tissues in response to Pip compared to shoots. The metabolic atlas for terpenoids presented here shows that there is an exceptionally strong differentiation of terpenoid patterns and terpenoid contents in the different tissues of tansy. This, together with the differential inducibility by biotic stress, suggests that the chemical diversity of terpenoids may play an important role in the ecological interactions of tansy and in the defense against biotic stressors that feed on the below- and above-ground organs of the plant.

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Section: Discussionmentioning

confidence: 99%

Exogenous stimulation ofTanacetum vulgareroots with pipecolic acid leads to tissue-specific responses in terpenoid composition

Rahimova,

Heinen,

Weber

et al. 2024

Preprint

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“…It is also known for its antibacterial, antimicrobial and antifungal activity (Carnesecchi et al, 2004;Li et al, 2017;Salvi et al, 2017). Essential oils of Cymbopogon are rich sources of acyclic monoterpenes (Bergman et al, 2023). Citronellol, a monoterpene alcohol, has vasorelaxant, anticonvulsive, analgesic, antibacterial and anti-inflammatory activity (de Sousa et al, 2006;Brito et al, 2012;Brito et al, 2015).…”

Section: Discussionmentioning

confidence: 99%

Research Article Chemical profile of essential oil in four <i>Cymbopogon</i> species grown in southern Brazil

Prochnow,

Santos,

Barros

et al. 2023

Genet. Mol. Res.

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Essential oils (EO) are substances used by pharmaceutical, cosmetic and food industries. These compounds have useful properties for human health and well-being. Among the species cultivated for production of these substances are those of the genus Cymbopogon. Several species, subspecies, varieties, and sub-varieties are used worldwide, and studies have been conducted to elucidate the chemical features of their EO, mainly for C. citratus and C. winterianus. However, there are still species with great potential that have not yet been fully chemically characterized. In addition, EO composition is influenced by genetic and environmental factors. Along this line, we examined the chemical profile of EO of four species of the genus Cymbopogon (C. citratus, C. distans, C. flexuosus and C. winterianus) grown in southern Brazil. The EO was obtained from fresh leaf tissues by hydrodistillation. Citral was identified as the main component of C. citratus, C. flexuosus, and C. distans, whereas citronellal, citronellol, cisgeraniol and elemol were predominant in C. winterianus. The absence of a large range of compounds was noted in C. distans, which may be useful for the semi-exclusive synthesis of citral and other compounds of interest. ©FUNPEC-RP www.funpecrp.com.br Genetics and Molecular Research 22 (4): gmr19160 D. Prochnow et al. 2

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“…In 2021, Silva et al reviewed the potential of 16 monoterpenes and their derivatives to affect various models of cardiovascular disease [90]. According to Bergman, Franks, and Philips (2023), certain acyclic monoterpenes and their derivatives have demonstrated notable anti-inflammatory potential [91]. Several monoterpene-coumarin conjugates showed good antiviral activity [92,93], while others demonstrated the capacity to inhibit the enzyme TDP1, which serves as a pivotal target in the realm of anticancer therapy [94,95].…”

Section: Therapeutic Potential Of Monoterpenoid Derivativesmentioning

confidence: 99%

“…Increasingly more literature data are available regarding new modifications of these natural compounds, including their biological effects and medical applications. However, information regarding the biological and pharmacological properties of monoterpene derivatives remains limited to several review articles, published in the last ten years [91,122,[146][147][148][149][150][151][152].…”

Section: Antitumor Potentialmentioning

confidence: 99%

Therapeutic Potential of Myrtenal and Its Derivatives—A Review

Dragomanova,

Andonova,

Volcho

et al. 2023

Life

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The investigation of monoterpenes as natural products has gained significant attention in the search for new pharmacological agents due to their ability to exhibit a wide range in biological activities, including antifungal, antibacterial, antioxidant, anticancer, antispasmodic, hypotensive, and vasodilating properties. In vitro and in vivo studies reveal their antidepressant, anxiolytic, and memory-enhancing effects in experimental dementia and Parkinson’s disease. Chemical modification of natural substances by conjugation with various synthetic components is a modern method of obtaining new biologically active compounds. The discovery of new potential drugs among monoterpene derivatives is a progressive avenue within experimental pharmacology, offering a promising approach for the therapy of diverse pathological conditions. Biologically active substances such as monoterpenes, for example, borneol, camphor, geraniol, pinene, and thymol, are used to synthesize compounds with analgesic, anti-inflammatory, anticonvulsive, antidepressant, anti-Alzheimer’s, antiparkinsonian, antiviral and antibacterial (antituberculosis) properties. Myrtenal is a perspective monoterpenoid with therapeutic potential in various fields of medicine. Its chemical modifications often lead to new or more pronounced biological effects. As an example, the conjugation of myrtenal with the established pharmacophore adamantane enables the augmentation of several of its pivotal properties. Myrtenal–adamantane derivatives exhibited a variety of beneficial characteristics, such as antimicrobial, antifungal, antiviral, anticancer, anxiolytic, and neuroprotective properties, which are worth examining in more detail and at length.

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Biosynthesis, natural distribution, and biological activities of acyclic monoterpenes and their derivatives

Cited by 4 publications

References 170 publications

Exogenous stimulation ofTanacetum vulgareroots with pipecolic acid leads to tissue-specific responses in terpenoid composition

Exogenous stimulation ofTanacetum vulgareroots with pipecolic acid leads to tissue-specific responses in terpenoid composition

Research Article Chemical profile of essential oil in four <i>Cymbopogon</i> species grown in southern Brazil

Therapeutic Potential of Myrtenal and Its Derivatives—A Review

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