NMR determination of site‐specific deuterium distribution (SNIF‐NMR) in squalene from different sources

Deiana, Monica; Corongiu, Francesco P.; Dessì, Ma; Scano, Paola; Casu, Mariano; Laı̈, Adolfo

doi:10.1002/1097-458x(200101)39:1<29::aid-mrc796>3.0.co;2-#

Cited by 10 publications

(12 citation statements)

References 16 publications

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“…We did not find significant differences between the δ 2 H values of olive oil (−165 ± 3‰) and those of shark squalene (−170 ± 10‰) (Table 1). The differences found by Deiana20 between olive oils and shark squalene concerned the 2 H pattern measured by SNIF‐NMR in the methyl/methylene/vinyl hydrogen atoms, but they are not evident if we consider the entire compound. The δ 2 H values of squalane samples were not taken into account because during the hydrogenation process of squalene, squalane would include exogenous hydrogen, which would mask the isotopic composition of the original hydrogen included in the biosynthesis.…”

Section: Resultsmentioning

confidence: 89%

“…In two previous studies,18, 19 it was shown that the presence of some minor steroid compounds can characterise the origin of squalene (‘stigmastane’ for olive oil and ‘colestane’ for shark), but recent advanced technological purification processes can cause a decrease or the total elimination of these marker compounds. A more recent study20 has highlighted that the deuterium ( 2 H) distribution, measured using SNIF‐NMR (site‐specific isotopic fractionation–nuclear magnetic resonance), in olefinic, methylene and methyl sites is different in olive oil, shark and synthetic squalene.…”

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confidence: 99%

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Stable isotope ratios of carbon and hydrogen to distinguish olive oil from shark squalene‐squalane

Camin

Bontempo

Ziller

et al. 2010

Rapid Comm Mass Spectrometry

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Squalene and its hydrogenated derivate squalane are widely used in the pharmaceutical and cosmetic fields. The two compounds are mainly produced from the liver oil of deep sea sharks and from olive oil distillates. Squalene and squalane from shark cost less than the same compounds derived from olive oil, and the use of these shark-derived compounds is unethical in cosmetic formulations. In this work we investigate whether (13)C/(12)C and (2)H/(1)H ratios can distinguish olive oil from shark squalene/squalane and can detect the presence of shark derivates in olive oil based products. The (13)C/(12)C ratios (expressed as delta(13)C values) of bulk samples and of pure compounds measured using isotope ratio mass spectrometry (IRMS) were significantly lower in authentic olive oil squalene/squalane (N: 13; -28.4 +/- 0.5 per thousand; -28.3 +/- 0.8 per thousand) than in shark squalene/squalane samples (N: 15; -20.5 +/- 0.7 per thousand; -20.4 +/- 0.6 per thousand). By defining delta(13)C threshold values of -27.4 per thousand and -26.6 per thousand for olive oil bulk and pure squalene/squalane, respectively, illegal addition of shark products can be identified starting from a minimum of 10%. (2)H/(1)H analysis is not useful for distinguishing the two different origins. Delta(13)C analysis is proposed as a suitable tool for detecting the authenticity of commercial olive oil squalene and squalane samples, using IRMS interfaced to an elemental analyser if the purity is higher than 80% and IRMS interfaced to a gas chromatography/combustion system for samples with lower purity, including solutions of squalane extracted from cosmetic products.

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Section: Resultsmentioning

confidence: 89%

mentioning

confidence: 99%

Stable isotope ratios of carbon and hydrogen to distinguish olive oil from shark squalene‐squalane

Camin

Bontempo

Ziller

et al. 2010

Rapid Comm Mass Spectrometry

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“…The known isolates, including two xanthones, 1,5-dihydroxy-6methoxyxanthone (5) [9] and 1,7-dihydroxy-3-methoxyxanthone (6) [10], a benzaldehyde, syringaldehyde (7) [11], a triterpenoid, squalene (8) [12], a-tocospiro B (9) [13], a benzoquinone, a-tocopherylquinone (10) [14], seven steroids, 6b-hydroxystigmast-4-en-3-one (11) [15], a mixture of b-sitosterol (12) and stigmasterol (13) [16], a mixture of b-sitostenone (14) and stigmasta-4,22-dien-3-one (15) [16], a mixture of 6a-hydroxystigmast-4-en-3-one (16) and 6a-hydroxystigmasta-4,22-dien-3one (17) [17] were readily identified by comparison of physical and spectroscopic data (UV, IR, 1 H-NMR, and mass spectrometry data) with corresponding authentic samples or literature values.…”

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confidence: 99%

Benzopyrans, Biphenyls and Xanthones from the Root ofGarcinia liniiand their Activity againstMycobacterium tuberculosis

Chen

Huang

et al. 2006

Planta Med

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A new benzopyran, (S)-3-hydroxygarcibenzopyran, and three new biphenyls, garcibiphenyl C, garcibiphenyl D, garcibiphenyl E, together with thirteen known compounds have been additionally isolated from the root of Garcinia linii. The structures of these new compounds were determined through spectral analyses. Among the isolates, 1,7-dihydroxy-3-methoxyxanthone and 1,5-dihydroxy-3-methoxyxanthone showed antitubercular activities with MICs of 3.1 +/- 0.5 and 6.3 +/- 1.0 microg/mL against Mycobacterium tuberculosis 90-221,387 in vitro, respectively.

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“…Significant amounts were later found in olive oil and olive leaves [ 8 , 9 , 10 , 11 , 12 ]. In addition, squalene is present in other diverse sources such as wheat germ oil, rice bran oil, carrots, Phycomyces blakesleeanus mold, alfalfa, elderberry, and lettuce [ 9 , 13 , 14 ]. Moreover, squalene is a main component of human sebum and a precursor of cholesterol biosynthesis [ 6 , 13 , 14 , 15 , 16 , 17 , 18 ].…”

Section: Introduction To Squalene and Emulsionsmentioning

confidence: 99%

“…In addition, squalene is present in other diverse sources such as wheat germ oil, rice bran oil, carrots, Phycomyces blakesleeanus mold, alfalfa, elderberry, and lettuce [ 9 , 13 , 14 ]. Moreover, squalene is a main component of human sebum and a precursor of cholesterol biosynthesis [ 6 , 13 , 14 , 15 , 16 , 17 , 18 ]. Interestingly, squalene from different sources has been shown to have characteristic deuterium distribution patterns, indicating varying synthesis and processing parameters [ 13 ].…”

Section: Introduction To Squalene and Emulsionsmentioning

confidence: 99%

Squalene Emulsions for Parenteral Vaccine and Drug Delivery

2009

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Squalene is a linear triterpene that is extensively utilized as a principal component of parenteral emulsions for drug and vaccine delivery. In this review, the chemical structure and sources of squalene are presented. Moreover, the physicochemical and biological properties of squalene-containing emulsions are evaluated in the context of parenteral formulations. Historical and current parenteral emulsion products containing squalene or squalane are discussed. The safety of squalene-based products is also addressed. Finally, analytical techniques for characterization of squalene emulsions are examined.

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NMR determination of site‐specific deuterium distribution (SNIF‐NMR) in squalene from different sources

Cited by 10 publications

References 16 publications

Stable isotope ratios of carbon and hydrogen to distinguish olive oil from shark squalene‐squalane

Stable isotope ratios of carbon and hydrogen to distinguish olive oil from shark squalene‐squalane

Benzopyrans, Biphenyls and Xanthones from the Root ofGarcinia liniiand their Activity againstMycobacterium tuberculosis

Squalene Emulsions for Parenteral Vaccine and Drug Delivery

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