Structure and reactions of lactonic and acidic sophorosides of 17-hydroxyoctadecanoic acid

Tulloch, A. P.; Hill, Anthony F.; Spencer, J. F. T.

doi:10.1139/v68-551

Cited by 97 publications

(50 citation statements)

References 11 publications

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“…[15][16][17][18] Due to their reduced environmental impact biosynthesis, confirmed by a recent life cycle analysis study, 19 sophorolipids (SL) have attracted a fair attention of the home and skin-care industry. [20][21][22] Nevertheless, few recent studies have highlighted interesting anticancer 23 or self-assembly properties.…”

Section: Figure 1 -Acidic Form Of Sophorolipids (Sl) Obtained From Camentioning

confidence: 99%

Unusual, pH-Induced, Self-Assembly Of Sophorolipid Biosurfactants

et al. 2012

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International audienceAn increasing need exists for simple, bioderived, nontoxic, and up-scalable compounds with stimuli-responsive properties. Acidic sophorolipids (SL) are glucose-based biosurfactants derived from the yeast broth of Candida bombicola (teleomorph: Starmerella bombicola). The specific design of this molecule, a sophorose head with a free end-COOH group at the end of the alkyl chain, makes it a potentially interesting pH-responsive compound. We have specifically investigated this assumption using a combination of small angle neutron scattering (SANS), transmission electron microscopy under cryogenic conditions (Cryo-TEM), and nuclear magnetic resonance (NMR) techniques and found a strong dependence of SL self-assembly on the degree of ionization, α, of the COOH group at concentration values as low as 5 and 0.5 wt %. At least three regimes can be identified where the supramolecular behavior of SL is unexpectedly different: (1) at low α values, self-assembly is driven by concentration, C, and micelles are mainly identified as nonionic objects whose curvature decreases (sphere-to-rod) with C; (2) at mid α values, the formation of COO– groups introduces negative charges at the micellar surface inducing an increase in curvature (rod-to-sphere transition). Repulsive electrostatic long-range interactions appear at this stage. In both regimes 1 and 2, the cross-section radius of the micelles is below 25 Å. This behavior is concentration independent. (3) At α = 1, individual micelles seem to favor the formation of large netlike tubular aggregates whose size is above 100 nm. Such a complex behavior is very unique as it is generally not observed for common alkyl-based surfactants in concentration ranges below 5–10 wt %

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Section: Figure 1 -Acidic Form Of Sophorolipids (Sl) Obtained From Camentioning

confidence: 99%

Unusual, pH-Induced, Self-Assembly Of Sophorolipid Biosurfactants

et al. 2012

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“…The production of glycolipids (sophorose lipids) by the yeast Candida bornbicola (Spencer et al 1979) has been known for 30 years (Gorin et al 1961) and the structure of this family of compounds studied in great detail (Gorin etal. 1961;Jones 1967;Tulloch et al 1968;Asmer et al 1988). Much less information however is available on their production by fermentation (Spencer et al 1979;GObbert et al 1984), the main point investigated being the relationship between the nature of the carbon source and the structure of the sophorose lipids produced (Jones and Howe 1968;Klekner et al 1991).…”

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confidence: 99%

Kinetics and balance of a fermentation free from product inhibition: sophorose lipid production by Candida bombicola

Davila

Marchal

Vandecasteele

1992

Appl Microbiol Biotechnol

101

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The production of sophorose lipids from ethyl esters of rapeseed oil fatty acids and glucose by Candida bombicola CBS 6009 was studied. A kinetic description of the fermentation is presented, showing in particular two distinct phases of growth and, following nitrogen limitation, subsequent production of sophorose lipids, which were excluded from the aqueous phase. With the fed-batch fermentation technology used, a high production performance (320 g . l -1 sophorose lipids with a weight yield of 65°7o with respect to the carbon sources) was obtained. Detailed fermentation balances were established and their implications for energy metabolism during glycolipid production are discussed. The variations in the structure of the sophorose lipids during fermentation were also studied. Sophorolipid 1', 4"-lactone 6', 6"-diacetate was the major class compound produced (about 50o/o of the glycolipids). A correlation between the lipidic composition of the products and the nature of the fatty acids of the rapeseed esters was observed.

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“…Yeasts of the genus Torulopsis synthesize sophorose lipids (Table 1) during growth on glucose or on glucose with alkanes or derivatives of these as an additive [13][14][15]50) and with alkanes as the sole carbon source 51,821, respectively. The chain-length of the fatty acid in the glycolipid is determined by the carbon source and the additive.…”

Section: )mentioning

confidence: 99%