Sugar cane juice for the bioreduction of carbonyl compounds

Assunção, João Carlos C.; Machado, Luciana Lucas; Lemos, Telma L. G.; Cordell, Geoffrey A.; Monte, Francisco José Queiroz

doi:10.1016/j.molcatb.2008.01.004

Cited by 33 publications

(8 citation statements)

References 28 publications

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“…Recently, the asymmetric reduction of different kinds of prochiral ketones to produce the corresponding chiral alcohols have been realized with Apple ( Malus pumila ), carrot ( D. carota ), cucumber ( Cucumis sativus ), onion ( Allium cepa ), potato ( Solanum tuberosum ), radish ( Raphanus sativus ), tomato ( Lycopersicum esculentum ), and sweet potato ( Ipomoea batatas ) as biocatalysts. It was found that prochiral ketones could be reduced by these plant tissues with high enantioselectivity (Giri et al 2001;Villa et al 1998;Bruni et al 2002;Borges et al 2009, Blanchard & Weghe 2006Assun ç ã o et al 2008;Utsukihara et al 2006;Xu et al 2010;Liu et al 2012 coconut juice as a biocatalyst for selective reduction of aromatic and aliphatic carbonyl compounds has been reported and high enantioselectivities were obtained (Rammohan 2013). Both biological and organometallic enantioselective catalysts have been developed as complementary tools for the reduction of ketones.…”

Section: Introductionmentioning

confidence: 99%

Asymmetric reduction of ketones by biocatalysis using medlar (Mespilus germanicaL) fruit grown in Algeria

Bennamane

Zeror

Aribi‐Zouioueche

2014

Biocatalysis and Biotransformation

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The biocatalytic reduction of ketones was performed using medlar fruit (Mespilus germanica L) , which is grown in large amounts in Algeria. Experiments were performed using aqueous medium with fresh medlar. Prochiral heteroaryl ketones containing furan, thiophene, chroman, and thiochroman moieties were reduced with enantiomeric excess (ee) of up to 98%. High enantioselectivities have been observed especially for the bioreduction of tetralone 4 and thiochromanone 5 with ee of 89% and 98%, respectively. Bioreduction using different parts of medlar indicate that chromanone 6 was reduced with good asymmetric inductions 77% Ͻ ee Ͻ 85% whichever part of fruit was employed (whole, fl esh, or juice) and medlar juice exhibited the best activity.Biocatal Biotransformation Downloaded from informahealthcare.com by Monash University on 12/15/14For personal use only.

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Section: Introductionmentioning

confidence: 99%

Asymmetric reduction of ketones by biocatalysis using medlar (Mespilus germanicaL) fruit grown in Algeria

Bennamane

Zeror

Aribi‐Zouioueche

2014

Biocatalysis and Biotransformation

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“…At the beginning, (4R)-(-)-carvone (1) was subjected to biotransformation by means of five vegetables and three fruits. Based on the literature [15][16][17], we expected carveol as a biotransformation product, but we observed a mixture of products in each sample. Another course of biotransformation could lead to the formation of dihydrocarvone after the reduction of the double bond in the carvone ring.…”

Section: Biotransformation Of (4r)-(-)-carvone (1)mentioning

confidence: 85%

“…To transform carvone, the following plant fragments were used: roots of Manihot esculenta Crantz and Manihot dulcis Crantz [15], sugar cane juice from Saccharum officinarum L. [16], and coconut water from Cocos nucifera L. [17]. Only the reduction of carvone to carveol was observed, and the degree of substrate conversion did not exceed 15%.…”

Section: Introductionmentioning

confidence: 99%

Plant-Mediated Biotransformations of S(+)- and R(–)-Carvones

et al. 2018

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The enzymatic system of vegetables is well known as an efficient biocatalyst in the stereoselective reduction of ketones. Therefore, we decided to use the comminuted material of several plants including five vegetables (Apium graveolens L., Beta vulgaris L., Daucus carota L., Petroselinum crispum L., and Solanum tuberosum L.) and three fruits (Malus pumila L. “Golden” and “Kortland” as well as Pyrus communis L. “Konferencja”) to obtain enantiomerically pure carveol, which is commercially unavailable. Unexpectedly, all of the used biocatalysts not only reduced the carbonyl group of (4R)-(–)-carvone and (4S)-(+)-carvone, but also reduced the double bond in the cyclohexene ring. The results revealed that (4R)-(–)-carvone was transformed into (1R, 4R)- and (1S, 4R)-dihydrocarvones, and (1R,2R,4R)-dihydrocarveol. Although the enzymatic system of the potato transformed the substrate almost completely, the %de was not the highest. Potato yielded 92%; however, when carrot was used as the biocatalyst, it was possible to obtain 17% of (1R, 4R)-(+)-dihydrocarvone with 100% diastereomeric excess. In turn, the (4S)-(+)-carvone was transformed, using the biocatalysts, into (1R, 4S)- and (1S, 4S)-dihydrocarvones and dihydrocarveols. Complete substrate conversion was observed in biotransformation when potato was used. In the experiments using apple, (1R, 4S)-dihydrocarvone with 100% diastereomeric excess was obtained. Using NMR spectroscopy, we confirmed both diastereoisomers of 4(R)-1,2-dihydrocarveols, which were unseparated in the GC condition. Finally, we proved the high usefulness of vegetables for the biotransformation of both enantiomers of carvone as well as dihydrocarvone.

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“…Some other examples of the practical application of ecopharmacognosy include: i) the improved use of information systems to delineate what has been done and what needs to be done (not wasting resources by reinventing the wheel! ); ii) reducing the energy requirements for plant material extraction; iii) reducing the reliance on non-recyclable chromatographic supports and solvents; iv) determining the significance of individual plants in complex plant matrices to conserve species use; v) using network pharmacology [96,97] to develop new uses for established and sustainable plants, vi) studying the waste products of the industrial processing of plants for new applications; vii) developing natural pesticides and insecticides from renewable resources, viii) assessing whole organisms, plants, and microbial systems as renewable catalytic reagents showing high yield and high enantioselectivity for organic chemical processes [98][99][100][101]; ix) re-energizing the development of natural dyestuffs from sustainable resources; and x) investigating well-established commercial crops, such as turmeric, ginger, oregano, garlic, cinnamon, caraway, etc. for new biological responses.…”

Section: Abcs Of Ecopharmacognosymentioning

confidence: 99%

Alice, Benzene, and Coffee: The ABCs of Ecopharmacognosy

Cordell

2015

Natural Product Communications

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The sesquicentennial celebrations of the publication of "Alice's Adventures in Wonderland" and the structure of benzene offer a unique opportunity to develop a contemporary interpretation of aspects of Alice's adventures, illuminate the symbolism of benzene, and contextualize both with the globalization of coffee, transitioning to how the philosophy and sustainable practices of ecopharmacognosy may be applied to modulating approaches to the quality, safety, efficacy, and consistency (QSEC) of traditional medicines and dietary supplements through technology integration, thereby improving patient-centered health care.

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Sugar cane juice for the bioreduction of carbonyl compounds

Cited by 33 publications

References 28 publications

Asymmetric reduction of ketones by biocatalysis using medlar (Mespilus germanicaL) fruit grown in Algeria

Asymmetric reduction of ketones by biocatalysis using medlar (Mespilus germanicaL) fruit grown in Algeria

Plant-Mediated Biotransformations of S(+)- and R(–)-Carvones

Alice, Benzene, and Coffee: The ABCs of Ecopharmacognosy

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