Biotransformation of α-Pinene to Terpineol by Resting Cell Suspension of Absidia corulea

Siddhardha, Busi; Kumar, Mukesh; Murty, U. S. N.; Ramanjaneyulu, G.; Prabhakar, S.

doi:10.1007/s12088-011-0155-9

Cited by 9 publications

(3 citation statements)

References 14 publications

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“…and Penicillium sp. genera, are in agreement with studies of fungal tolerance to essential oils such as Cymbopogon citratus L. at low concentrations, and to terpenes such as citronellol, αand β-pinene, isoeugenol and mentone (Ramachandra Rao and Ravishankar 1999;Demyttenaere et al 2004;Helal et al 2006;Dambolena et al 2008;Rottava et al 2010;Siddhardha et al 2012).…”

Section: Discussionsupporting

confidence: 87%

Bioproduction of α‐terpineol and R‐(+)‐limonene derivatives by terpene‐tolerant ascomycete fungus as a potential contribution to the citrus value chain

Velázquez

Sadañoski

Zapata

et al. 2020

J. Appl. Microbiol.

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Aims: The aims of this article were to select fungal species with high tolerance and high growth rate in mediums supplemented with limonene and citrus essential oils (CEOs), and to test the bioconversion capability of the chosen isolates for the bioproduction of aroma compounds. Methods and Results: Based on the use of predictive mycology, 21 of 29 isolates were selected after assaying R-(+)-limonene and CEO tolerance (10 g l −1). With a dendrogram divisive coefficient of 0Á937, the subcluster two with isolates Aspergillus niger LBM 055, Penicillium sp. LBM 150, Penicillium sp. LBM 151 and Penicillium sp. LBM 154 gathered the highest tolerance and mycelia growth speed. Ultrastructural analysis indicated that culture media containing limonene had no visible toxic activity that could promote morphological changes in the fungal cell wall. The biomass of A. niger LBM055 was distinctive in liquid media supplemented with R-(+)-limonene (0Á57 AE 0Á07 g) and it was selected to prove bioconversion capacity, under static and agitated conditions, and converted up to 98% of limonene, yielding a wide variety of products that were quantified by GC-FID. It was obtained at molecular weights less than limonene (64-100%), between limonene and αterpineol (12-72%) and greater than α-terpineol (2-48%). Conclusions: Aspergillus niger LBM 055, Penicillium sp. LBM 150, Penicillium sp. LBM 151 and Penicillium sp. LBM 154 showed to the highest tolerance and growth rate in mediums supplemented with R-(+)-limonene and orange and lemon essential oils. Particularly, A. niger LBM055, showed limonene bioconversion capability and produced different molecular weights compounds such us α-terpineol. Significance and Impact of the Study: Different bioproducts can be obtained by changing operative condition with the same fungus, and this bioprocess aspect is a significant approach to be adopted on industrial scale leading to the creation of new natural flavours and fragrance compositions.

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Section: Discussionsupporting

confidence: 87%

Bioproduction of α‐terpineol and R‐(+)‐limonene derivatives by terpene‐tolerant ascomycete fungus as a potential contribution to the citrus value chain

Velázquez

Sadañoski

Zapata

et al. 2020

J. Appl. Microbiol.

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“…Limonene (39, 42) , a major constituent of citrus fruits, is added to many food products for its lemonlike flavor aside from its protective effect against multimodal intestinal inflammation . Comparable quantities of isoterpinolene (40, 45) and its precursor α-pinene (34) were detected, accounting for the positive correlation between their levels in the studied samples. α-Phellandrene (38) was detected only in P-01 and P-02 at 2.9 and 1.5%, respectively, with a minty, herbal, spicy note, suggestive to be a distinguishing component for these fennel accessions.…”

Section: Resultsmentioning

confidence: 95%

Gas Chromatography–Mass Spectrometry-Based Classification of 12 Fennel (Foeniculum vulgare Miller) Varieties Based on Their Aroma Profiles and Estragole Levels as Analyzed Using Chemometric Tools

et al. 2021

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Fennel (Foeniculum vulgare Miller) is a popular aromatic plant native to the Mediterranean basin and cultivated worldwide that is valued for the nutritional and health benefits of its fruits. Headspace solid-phase microextraction of 12 fennel accessions of cultivated (F. vulgare subsp. vulgare) and wild forms ( F. vulgare subsp. piperitum) of different origins was carried out for assessing their volatile distribution. Fifty-four volatiles were identified, with ethers amounting for the major class at ca. 52− 99% attributed to the abundance of (E)-anethole and estragole. Several subsp. vulgare accessions proved to be excellent sources of the chief aroma (E)-anethole (95.9−98.4%), whereas high levels of estragole at ca. 72% were observed in subsp. piperitum from Minia and Khartoum and must be considered in the safety assessment of fennel. Other volatile classes were detected including ketones, esters, aldehydes, alcohols, and hydrocarbons (monoterpenes, sesquiterpenes, and diterpenes). Fenchone exceeded 15% of the total volatiles in some fennel specimens, linked to a conspicuous bitter aftertaste. The members of subsp. piperitum were more enriched in monoterpene hydrocarbons with sabinene found exclusively in these, while subsp. vulgare comprised a higher content of ethers. Principle component analysis determined isoterpinolene as a special component in subsp. piperitum. In all specimens from the same group, estragole was the most distinguished volatile compound according to the findings from orthogonal partial least squares-discriminant analysis. The highest estimated estragole levels were detected in subsp. piperitum from Minia at 89.8 mg/g. This comparative study provides the first comprehensive insight into volatile profiling of 12 fennel fruit varieties.

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“…The possibility that these de novo compounds (especially α-terpineol and camphor) are a product or a biotransformation of the infecting fungal pathogen, however, cannot be discarded (Kusumoto et al 2014;Leufvén et al 1988;Siddhardha et al 2011;Tan and Day 1998). Furthermore, any terpene concentration found in the infected treatments could have been altered by fungal biotransformation or production.…”

Section: Discussionmentioning

confidence: 99%

Strong Induction of Minor Terpenes in Italian Cypress, Cupressus sempervirens, in Response to Infection by the Fungus Seiridium cardinale

Achotegui-Castells

Danti²,

Llusià

et al. 2015

J Chem Ecol

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Seiridium cardinale, the main fungal pathogen responsible for cypress bark canker, is the largest threat to cypresses worldwide. The terpene response of canker-resistant clones of Italian cypress, Cupressus sempervirens, to two differently aggressive isolates of S. cardinale was studied. Phloem terpene concentrations, foliar terpene concentrations, as well as foliar terpene emission rates were analyzed 1, 10, 30, and 90 days after artificial inoculation with fungal isolates. The phloem surrounding the inoculation point exhibited de novo production of four oxygenated monoterpenes and two unidentified terpenes. The concentrations of several constitutive mono-and diterpenes increased strongly (especially α-thujene, sabinene, terpinolene, terpinen-4-ol, oxygenated monoterpenes, manool, and two unidentified diterpenes) as the infection progressed. The proportion of minor terpenes in the infected cypresses increased markedly from the first day after inoculation (from 10 % in the control to 30-50 % in the infected treatments). Foliar concentrations showed no clear trend, but emission rates peaked at day 10 in infected trees, with higher δ-3-carene (15-fold) and total monoterpene (10-fold) emissions than the control. No substantial differences were found among cypresses infected by the two fungal isolates. These results suggest that cypresses activate several direct and indirect chemical defense mechanisms after infection by S. cardinale.

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Biotransformation of α-Pinene to Terpineol by Resting Cell Suspension of Absidia corulea

Cited by 9 publications

References 14 publications

Bioproduction of α‐terpineol and R‐(+)‐limonene derivatives by terpene‐tolerant ascomycete fungus as a potential contribution to the citrus value chain

Bioproduction of α‐terpineol and R‐(+)‐limonene derivatives by terpene‐tolerant ascomycete fungus as a potential contribution to the citrus value chain

Gas Chromatography–Mass Spectrometry-Based Classification of 12 Fennel (Foeniculum vulgare Miller) Varieties Based on Their Aroma Profiles and Estragole Levels as Analyzed Using Chemometric Tools

Strong Induction of Minor Terpenes in Italian Cypress, Cupressus sempervirens, in Response to Infection by the Fungus Seiridium cardinale

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