Monoterpene chiral ratios: Chemotype diversity and interspecific commonality in Melaleuca alternifolia and M. linariifolia

Southwell, Ian A.; Dowell, Ashley; Morrow, Samantha; Allen, Gareth; Savins, Dale; Shepherd, Mervyn

doi:10.1016/j.indcrop.2017.09.057

Cited by 10 publications

(14 citation statements)

References 22 publications

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“…(-)-4-terpineol has not been reported as an antimicrobial volatile component from endophytes so far. It is similar chemically to terpene-4-alcohol (terpinen-4-ol), an isomer of (-)-4-terpineol, which has been reported as an antifungal and acts via disrupting cell walls, membranes, and cytoplasm, resulting in abnormal hyphae [30,31]. (-)-4-Terpineol may have similar antifungal mechanisms to terpene-4-alcohol.…”

Section: Discussionmentioning

confidence: 99%

An Endophytic Diaporthe apiculatum Produces Monoterpenes with Inhibitory Activity against Phytopathogenic Fungi

et al. 2019

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Volatile organic compounds (VOCs) from endophytic fungi are becoming a potential antibiotic resource. The inhibitive effects of VOCs produced by an endophytic fungus in Leucaena leucocephala were investigated on plant pathogens in this study. Using standard morphological methods and multigene phylogeny, the fungus was identified as Diaporthe apiculatum strain FPYF 3052. Utilizing a two- compartment Petri plate bioassay method, the VOCs from this fungus showed bioactivity ranging from 23.8% to 66.7% inhibition on eight plant pathogens within 24 hours. The SPME-GC/MS technique identified fifteen volatile compounds with dominant terpenoids γ-terpinene (39.8%), α-terpinene (17.2%), and (-)-4-terpineol (8.4%) from the VOCs. Commercial α-terpinene, γ-terpinene, and (-)-4-terpineol demonstrated inhibition on the tested pathogens at concentrations from 0.2 to 1.0 µl/ml within 72 h in the bioassay system. The inhibition rates were from 28% to 100% percent using 1.0 µl/ml within 48 h. (-)-4-Terpineol was the most active of the terpenoids causing up to 100% inhibition. The data illustrate that these monoterpenes play an important role in the inhibitive bioactivity of the VOCs of D. apiculatum FPYF 3052. Most importantly, (-)-4-terpineol is now for the first time, reported to have capability of strong antifungal activity and could be developed as an antibiotic substance.

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Section: Discussionmentioning

confidence: 99%

An Endophytic Diaporthe apiculatum Produces Monoterpenes with Inhibitory Activity against Phytopathogenic Fungi

et al. 2019

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“…Trees from the two species specified in the revised ISO Standard for tea tree oil production, M. alternifolia and M. linariifolia, were chosen for analysis. Trees from both ecotypes of M. alternifolia growing in a germplasm resource collection at SCU were initially screened using GC‐FID analysis of solvent extracts to identify representatives of each of the six known terpene chemotypes . Details of the collections of the seed parents used to generate this collection are given in ref.…”

Section: Methodsmentioning

confidence: 99%

“…, and botanical voucher specimens are held in the Southern Cross Plant Science Herbarium. A subset of 30 trees, referred to as the ‘diversity set’ were identified from this survey . A further twelve trees from the 3rd generation of the ATTIA tea tree breeding program were chosen to represent select trees used to produce high yielding cultivars of the commercial terpinen‐4‐ol‐type oil .…”

Section: Methodsmentioning

confidence: 99%

“…A further twelve trees from the 3rd generation of the ATTIA tea tree breeding program were chosen to represent select trees used to produce high yielding cultivars of the commercial terpinen‐4‐ol‐type oil . Five M. linariifolia , individuals, two of Chemotype 1, and three of Chemotype 5, with known provenance origins were sourced from either native stands, or plantations . This gave a total of 47 M. alternifolia or M. linariifolia trees for methyl eugenol analysis.…”

Section: Methodsmentioning

confidence: 99%

“…The individual tree chemotype determinations were based on GC‐FID analysis of ethanol extracts as described in ref. . Micro‐distillation was subsequently carried out on a subset so that distilled oils could be assessed for compliance with the ISO standard 4730:2017 and methyl eugenol determinations …”

Section: Methodsmentioning

confidence: 99%

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Ecotype Variation of Methyl Eugenol Content in Tea Tree (Melaleuca alternifolia and Melaleuca linariifolia)

Shepherd

Savins

Dowell

et al. 2017

Chemistry & Biodiversity

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Methyl eugenol is a natural phenylpropanoid compound found in a wide range of plants used for food, flavouring, cosmetics, and health-care. As a suspected rodent carcinogen, methyl eugenol may also be harmful to humans when present in significant concentrations. Consequently, its level has been restricted in some foodstuffs and cosmetics for some markets. In order to assess the potential to breed uniformly low methyl eugenol cultivars for an essential oil crop, tea tree, the source of 'Oil of Melaleuca, terpinene-4-ol type', we examine levels in individual trees (n = 30) from two geographic regions and six terpene chemotypes. Overall, methyl eugenol levels were low in this species (Mean [SD] 354 [239] ppm, n = 30), much lower than levels predicted to be of toxicological concern. Within each chemotype, there was a lack of evidence for correlations between terpenoid constituents and methyl eugenol levels. Further support for the independence of methyl eugenol and terpene biosynthesis was evident from similar mean levels in selected (Mean [SD] 586 [339] ppm, n = 12) and undomesticated Melaleuca alternifolia trees (Mean [SD] 480 [299] ppm, n = 5) with terpinen-4-ol type oils. By contrast, methyl eugenol level varied by geographic origin and chemotype. Trees from the upland region, where there is a prevalence of terpinolene type trees, had lower average methyl eugenol levels than trees from the coastal region, where there is a prevalence of terpinen-4-ol and 1,8-cineole type trees.

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Chemotypes and terpene synthase genes in Thymus genus: State of the art

Trindade

Pedro

Figueiredo

et al. 2018

Industrial Crops and Products

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Monoterpene chiral ratios: Chemotype diversity and interspecific commonality in Melaleuca alternifolia and M. linariifolia

Cited by 10 publications

References 22 publications

An Endophytic Diaporthe apiculatum Produces Monoterpenes with Inhibitory Activity against Phytopathogenic Fungi

An Endophytic Diaporthe apiculatum Produces Monoterpenes with Inhibitory Activity against Phytopathogenic Fungi

Ecotype Variation of Methyl Eugenol Content in Tea Tree (Melaleuca alternifolia and Melaleuca linariifolia)

Chemotypes and terpene synthase genes in Thymus genus: State of the art

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