A forgotten vegetable (Smyrnium olusatrum L., Apiaceae) as a rich source of isofuranodiene

Maggi, Filippo; Barboni, Luciano; Papa, Fabrizio; Caprioli, Giovanni; Ricciutelli, Massimo; Sagratini, Gianni; Vittori, Sauro

doi:10.1016/j.foodchem.2012.07.027

Cited by 45 publications

(19 citation statements)

References 27 publications

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“…Compounds 1-3 act as typical olfactory cues, showing characteristic odors when exposed to air. It is noteworthy that isofuranodiene (1), often misleadingly called furanodiene (6), also occurs in marine organisms (7)(8)(9)(10)(11)(12), but it is better known for contributing to the smell of several terrestrial flowering plants, including myrrh and white turmeric, some of which are commonly used as food additives and fragrance ingredients (6). Furthermore, atractylon (2), which has also been found in marine animals (10), is a major odor-active compound from Significance This report gives empirical evidence indicating that chemoreception of volatile/odorant lipophilic compounds, almost insoluble in water, can occur in aquatic environments, by means of "tactile" forms of olfaction.…”

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confidence: 99%

Volatile secondary metabolites as aposematic olfactory signals and defensive weapons in aquatic environments

Giordano

Carbone

Ciavatta

et al. 2017

Proc. Natl. Acad. Sci. U.S.A.

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Olfaction is considered a distance sense; hence, aquatic olfaction is thought to be mediated only by molecules dissolved in water. Here, we challenge this view by showing that shrimp and fish can recognize the presence of hydrophobic olfactory cues by a "tactile" form of chemoreception. We found that odiferous furanosesquiterpenes protect both the Mediterranean octocoral Maasella edwardsi and its specialist predator, the nudibranch gastropod Tritonia striata, from potential predators. Food treated with the terpenes elicited avoidance responses in the cooccurring shrimp Palaemon elegans. Rejection was also induced in the shrimp by the memory recall of postingestive aversive effects (vomiting), evoked by repeatedly touching the food with chemosensory mouthparts. Consistent with their emetic properties once ingested, the compounds were highly toxic to brine shrimp. Further experiments on the zebrafish showed that this vertebrate aquatic model also avoids food treated with one of the terpenes, after having experienced gastrointestinal malaise. The fish refused the food after repeatedly touching it with their mouths. The compounds studied thus act simultaneously as (i) toxins, (ii) avoidance-learning inducers, and (iii) aposematic odorant cues. Although they produce a characteristic smell when exposed to air, the compounds are detected by direct contact with the emitter in aquatic environments and are perceived at high doses that are not compatible with their transport in water. The mouthparts of both the shrimp and the fish have thus been shown to act as "aquatic noses," supporting a substantial revision of the current definition of the chemical senses based upon spatial criteria. T raditionally, the sense of smell has been regarded as a distance sense (like vision), whereas the sense of taste has been treated as a contact sense (like touch). This classification of the chemical senses (olfaction and gustation) based on their spatial range persists in contemporary literature. Accordingly, biomolecules smaller than ∼300 Da, which can be transported through air, and which finally bind to odorant receptors expressed in olfactory neurons, are generally considered odorant molecules. Conversely, the molecules sensed by taste have to be in solution and in contact with the receptor (1). However, the claim that "only olfaction can provide information on the identity of the water mass encountered" by marine organisms (2) implies that water-soluble compounds, which are typically "tasted" by the tongues of terrestrial animals, act as olfactory cues in aquatic environments. Consequently, it may be asked how typical odorant molecules such as small terpenes from plants and marine sponges that combine high volatility in air with insolubility in water can produce olfactory sensations in marine organisms, thereby giving protection from predators and cues to finding food and mates.

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confidence: 99%

Volatile secondary metabolites as aposematic olfactory signals and defensive weapons in aquatic environments

Giordano

Carbone

Ciavatta

et al. 2017

Proc. Natl. Acad. Sci. U.S.A.

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“…The molecular structure was confirmed by comparison of 1 H and 13 C-NMR data obtained on a Varian Mercury plus 400 Spectrometer, using CDCl 3 as solvent and the solvent signals as internal references, with those reported in the literature [9]. Isofuranodiene was the major constituent, accounting for 48% of the volatile oil (Figure 2).…”

Section: Methodsmentioning

confidence: 61%

“…From the whole plant, it is possible to obtain essential oils mainly constituted by furanogermacrane-type sesquiterpenes [9]. Their occurrence can be explained by the fact that these molecules are considered to be precursors of sesquiterpene lactones [10] which are in turn regarded as marker compounds of the genus Smyrnium [11].…”

Section: Introductionmentioning

confidence: 99%

Antiproliferative Evaluation of Isofuranodiene on Breast and Prostate Cancer Cell Lines

Buccioni

Ben

Lambertucci

et al. 2014

The Scientific World Journal

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The anticancer activity of isofuranodiene, extracted from Smyrnium olusatrum, was evaluated in human breast adenocarcinomas MDA-MB 231 and BT 474, and Caucasian prostate adenocarcinoma PC 3 cell lines by MTS assay. MTS assay showed a dose-dependent growth inhibition in the tumor cell lines after isofuranodiene treatment. The best antiproliferative activity of the isofuranodiene was found on PC 3 cells with an IC50 value of 29 μM, which was slightly less than the inhibition against the two breast adenocarcinoma cell lines with IC50 values of 59 and 55 μM on MDA-MB 231 and BT 474, respectively. Hoechst 33258 assay was performed in order to study the growth inhibition mechanism in prostate cancer cell line; the results indicate that isofuranodiene induces apoptosis. Overall, the understudy compound has a good anticancer activity especially towards the PC 3. On the contrary, it is less active on Chinese hamster ovary cells (CHO) and human embryonic kidney (HEK 293) appearing as a good candidate as a potential natural anticancer drug with low side effects.

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“…Recently, the chemical composition of AEO has been fully characterized 8 and its in vitro biological activity assessed . The AEO composition is dominated mainly by furanogermacrane‐type sesquiterpenes, among which isofuranodiene is the most abundant compound . It has been reported that AEO possesses good antiproliferative activity against human colon carcinoma (HCT116) and human breast adenocarcinoma cells (MDA‐MB 231) .…”

Section: Introductionmentioning

confidence: 99%

Microemulsions enhance the shelf‐life and processability of Smyrnium olusatrum L. essential oil

Cespi

Quassinti

Perinelli

et al. 2016

Flavour & Fragrance J

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Smyrnium olusatrum L. is a horticultural crop cultivated during the Roman age for culinary and curative uses. The essential oil extracted from this plant (AEO) is rich in bioactive constituents such as isofuranodiene and germacrone. Several previous studies revealed that AEO and its isolated components possess interesting therapeutic features, such as antiproliferative, neuritogenic, hepatoprotective and antioxidant properties. Nevertheless, AEO has stability problems because of the high concentration of its main components. This issue makes AEO very difficult to handle and use. Thus, AEO was formulated as microemulsions known for their thermodynamic stability and easiness of preparation. AEO was hydrodistilled from inflorescences of S. olusatrum and its composition determined by different chromatographic methods. The microemulsions were developed using a central composite design and their activity tested using the MTT assay. The present study demonstrated the possibility to formulate stable AEO microemulsions where the crystallization of isofuranodiene is avoided, and the AEO biological activity is maintained. Copyright © 2016 John Wiley & Sons, Ltd.

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A forgotten vegetable (Smyrnium olusatrum L., Apiaceae) as a rich source of isofuranodiene

Cited by 45 publications

References 27 publications

Volatile secondary metabolites as aposematic olfactory signals and defensive weapons in aquatic environments

Volatile secondary metabolites as aposematic olfactory signals and defensive weapons in aquatic environments

Antiproliferative Evaluation of Isofuranodiene on Breast and Prostate Cancer Cell Lines

Microemulsions enhance the shelf‐life and processability of Smyrnium olusatrum L. essential oil

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