Actualities in the phytochemical research on selected terpenes

Jerković, Igor; Maleš, Željan; Friščić, Maja

doi:10.2478/acph-2019-0036

Cited by 2 publications

(2 citation statements)

References 32 publications

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“…The intermediate 79 , in a few steps, affords furanoeremophilane ( 67 ), whereas 80 , after a Favorskii-like rearrangement, produces the hydroxy acid 81 . Finally, compound 81 , after dehydration and few more steps, produces bakkenolide A ( 72 ) [ 83 , 84 , 85 ].…”

Section: Discussionmentioning

confidence: 99%

The Leaf Essential Oil of Gynoxys buxifolia (Kunth) Cass. (Asteraceae): A Good Source of Furanoeremophilane and Bakkenolide A

Cumbicus

Malagón

Cumbicus

et al. 2023

Plants

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The present study describes the chemical and enantiomeric composition of a new essential oil, distilled from the dry leaves of Gynoxys buxifolia (Kunth) Cass. The chemical analysis was conducted by GC-MS and GC-FID, on two orthogonal capillary columns. A total of 72 compounds were detected and quantified with at least one column, corresponding to about 85% by weight of the whole oil mass. Of the 72 components, 70 were identified by comparing the respective linear retention indices and mass spectra with data from the literature, whereas the two main constituents were identified by preparative purification and NMR experiments. The quantitative analysis was carried out calculating the relative response factor of each compound according to their combustion enthalpy. The major constituents of the EO (≥3%) were: furanoeremophilane (31.3–28.3%), bakkenolide A (17.6–16.3%), caryophyllene oxide (6.0–5.8%), and (E)-β-caryophyllene (4.4%). Additionally, the hydrolate was also analyzed with respect to the dissolved organic phase. About 40.7–43.4 mg/100 mL of organic compounds was detected in solution, of which p-vinylguaiacol was the main component (25.4–29.9 mg/100 mL). Finally, the enantioselective analysis of some chiral terpenes was carried out, with a capillary column based on β-cyclodextrin chiral stationary phase. In this analysis, (1S,5S)-(−)-α-pinene, (1S,5S)-(−)-β-pinene, (S)-(+)-α-phellandrene, (S)-(+)-β-phellandrene, and (S)-(−)-terpinen-4-ol were detected as enantiomerically pure, whereas (S)-(−)-sabinene showed an enantiomeric excess of 69.2%. The essential oil described in the present study is a good source of two uncommon volatile compounds: furanoeremophilane and bakkenolide A. The former lacks bioactivity information and deserves further investigation, whereas the latter is a promising selective anticancer product.

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Section: Discussionmentioning

confidence: 99%

The Leaf Essential Oil of Gynoxys buxifolia (Kunth) Cass. (Asteraceae): A Good Source of Furanoeremophilane and Bakkenolide A

Cumbicus

Malagón

Cumbicus

et al. 2023

Plants

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“…Because of the multiple impacts of the latter on humans, Z. tritici is considered as a model for the development of biosourced pesticides. Terpenes and phenolic compounds are widespread groups of secondary metabolites that can be found in various species of plants 7–8 . Among these groups, many interesting compounds are extensively applied in industrial sectors, such as flavors, spices, cosmetics or food additives.…”

Section: Introductionmentioning

confidence: 99%

Sesamol‐based terpenoids as promising bio‐sourced crop protection compounds against the wheat pathogen Zymoseptoria tritici

Damiens

Léonard

Fayeulle

et al. 2021

Pest Management Science

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BACKGROUND Research into environmentally friendly alternatives to conventional plant protection products, to promote sustainable agriculture and healthy food, is strongly encouraged. RESULTS In this context, 20 naturally occurring terpenoids and phenolic compounds were selected and evaluated in vitro as crop protection compounds against Zymoseptoria tritici, the causal agent of Septoria tritici blotch of wheat. After selection of the most active compounds, some hemisynthetic modifications were conducted to modify their lipophilicity. These modifications led to the discovery of sesamol esters as promising antifungal agents, with IC50 around 10 μg/mL and a total absence of cytotoxicity against human cells. CONCLUSION These sesamol‐based derivatives should be selected for further evaluations in planta to validate their use as wheat crop protection agents. Moreover, the importance of a balanced hydrophily/lipophilicity ratio should be further studied. © 2021 Society of Chemical Industry

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Actualities in the phytochemical research on selected terpenes

Cited by 2 publications

References 32 publications

The Leaf Essential Oil of Gynoxys buxifolia (Kunth) Cass. (Asteraceae): A Good Source of Furanoeremophilane and Bakkenolide A

The Leaf Essential Oil of Gynoxys buxifolia (Kunth) Cass. (Asteraceae): A Good Source of Furanoeremophilane and Bakkenolide A

Sesamol‐based terpenoids as promising bio‐sourced crop protection compounds against the wheat pathogen Zymoseptoria tritici

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