Structural Identification and Physicochemical Properties of Nonacetylated Sophorolipids Biosurfactant

doi:10.19894/j.issn.1000-0518.240021

Chinese Journal of Applied Chemistry ›› 2024, Vol. 41 ›› Issue (6): 878-889.DOI: 10.19894/j.issn.1000-0518.240021

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Structural Identification and Physicochemical Properties of Nonacetylated Sophorolipids Biosurfactant

Hao YANG¹^,², Xiao-Meng MA¹^,², Jin-Hua HUANG¹^,², Jun-Feng LI³, Sheng-Kang LIANG¹^,²()

^1.College of Chemistry and Chemistry Engineering，Ocean University of China，Qingdao 266100，China
^2.The Key Laboratory of Marine Chemistry Theory and Technology，Ministry of Education，Ocean University of China，Qingdao 266100，China
^3.College of Marine Science and Biological Engineering，Qingdao University of Science and Technology，Qingdao 266045，China

Received:2024-01-22 Accepted:2024-05-04 Published:2024-06-01 Online:2024-07-09
Contact: Sheng-Kang LIANG
About author:liangsk@ouc.edu.cn
Supported by:
the Shandong Province Major Science and Technology Innovation Engineering Project(2021CXGC010705);the Laoshan Laboratory's 14th Five Year Plan Major Project(2022QNLM040002)

Abstract

Abstract:

Sophorolipids （SLs） are a kind of biosurfactants with the highest potential for industrial application， and the degree of acetylation in their sugar chains has an important influence on their surface interface activity，and physicochemical properties. By homologous recombination， the research group constructed the acetyltransferase gene-deficient strain， and nonacetylated SLs was prepared by fermentation with oleic acid and glucose as biphasic carbon sources. In this paper， the structure of nonacetylated SLs was analyzed by high-performance liquid chromatography-tandem mass spectrometry （HPLC-MS/MS）， and the physicochemical properties of acetylated SLs produced by wild strains were compared. The results showed that the hydrophobic groups of nonacetylated SLs produced by nonacetylated strains were mainly octadecenoic acid， and the hydrophilic groups were mainly nonacetylated sophoricoside， in which the contents of lipoid， acidic and bola-type SLs were 26.99%， 49.98% and 23.03% respectively. The sophorolipids produced by wild strains are mainly acetylated sophorolipids， and the mass fractions of lactone and acid types are 97.86% and 2.14% respectively. Its hydrophobic group is mainly octadecenoic acid. The solubility of nonacetylated SLs in water is as high as 485.8 g/L， which is 14 times higher than acetylated SLs， and it has better foaming performance and foam stability. At the same time， the emulsifying performance of nonacetylated SLs is 26.7 times higher than acetylated SLs. Due to the increase of hydrophilicity of the missing acetyl group， the surface activity of deacetylation SLs decreased， and the surface tension of aqueous solution was reduced to 41.0 mN/m， which was higher than that of acetylated sophorolipid （36.2 mN/m）. The hydrophilic and lipophilic balance value is 13， which is higher than that of acetylation SLs （11）. Two kinds of sophorolipid have good hard water resistance， but weak acid and alkali resistance.

Key words: Candida, Sophorolipid, Deacetylation, Critical micelle concentration, Emulsibility

CLC Number:

O647.2

Hao YANG, Xiao-Meng MA, Jin-Hua HUANG, Jun-Feng LI, Sheng-Kang LIANG. Structural Identification and Physicochemical Properties of Nonacetylated Sophorolipids Biosurfactant[J]. Chinese Journal of Applied Chemistry, 2024, 41(6): 878-889.

Figures/Tables 11

References 33

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	Type		Molecular formula	m/z of ［M+H］⁺		Full name of component	w/%
	Fatty acid groups	L/A/B^*	Molecular formula	Measured value	Simulation value	Full name of component	w/%
Nonacetylated	C18∶2	A	C₃₀H₅₂O₁₃	621.342 1	621.340 8	17-L-［（2′-O-β-D-glucopyranosyl-β-D-glucopyranosyl）-O-］-octadecanodienoic acid	0.32
Monoacetylated	C16∶0	L	C₃₀H₅₂O₁₃	621.743 5	621.340 8	15-L-［（2′-O-β-D-glucopyranosyl-β-D-glucopyranosyl）-O-］-hexadecanoic acid-1′，4"- lactone-6"-monoacetyl ester	0.11
	C18∶0	L	C₃₂H₅₆O₁₃	649.369 7	649.372 2	17-L-［（2′-O-β-D-glucopyranosyl-β-D-glucopyranosyl）-O-］-octadecanoic acid-1′，4"- lactone-6"-monoacetyl ester	0.18
	C18∶1	L	C₃₂H₅₄O₁₃	647.358 1	647.356 5	17-L-［（2′-O-β-D-glucopyranosyl-β-D-glucopyranosyl）-O-］-oleic acid-1′，4"-lactone-6"- monoacetyl ester	5.29
	C18∶2	L	C₃₂H₅₂O₁₃	645.341 9	645.340 8	17-L-［（2′-O-β-D-glucopyranosyl-β-D-glucopyranosyl）-O-］-octadecanodienoic acid-1′，4"-lactone-6"-monoacetyl ester	1.60
Diacetylated	C16∶0	L	C₃₂H₅₄O₁₄	663.360 4	663.351 4	15-L-［（2′-O-β-D-glucopyranosyl-β-D-glucopyranosyl）-O-］-hexadecanoic acid-1′，4"- lactone-6′，6"-diacetyl ester	12.27
	C16∶1	L	C₃₂H₅₂O₁₄	661.338 6	661.335 7	15-L-［（2′-O-β-D-glucopyranosyl-β-D-glucopyranosyl）-O-］-hexadecenoic acid-1′，4"-lactone-6'，6"-diacetyl ester	0.15
	C18∶0	L	C₃₄H₅₈O₁₄	691.384 9	691.382 8	17-L-［（2′-O-β-D-glucopyranosyl-β-D-glucopyranosyl）-O-］-octadecanoic acid-1′，4"-lactone-6′，6"-diacetyl ester	16.97
	C18∶1	L	C₃₄H₅₆O₁₄	689.375 4	689.367 1	17-L-［（2′-O-β-D-glucopyranosyl-β-D-glucopyranosyl）-O-］-oleic acid-1′，4"-lactone-6′，6"-diacetyl ester	42.47
	C18∶2	L	C₃₄H₅₄O₁₄	687.356 3	687.351 4	17-L-［（2′-O-β-D-glucopyranosyl-β-D-glucopyranosyl）-O-］-octadecanodienoic acid-1′，4"-lactone-6'，6"-diacetyl ester	18.82
	C16∶2	A	C₃₂H₅₂O₁₅	677.331 9	677.330 6	15-L-［（2′-O-β-D-glucopyranosyl-β-D-glucopyranosyl）-O-］-hexadecanodienoic acid-6′，6″-diacetyl ester	1.29
	C18∶1	A	C₃₄H₅₈O₁₅	707.382 5	707.377 7	17-L-［（2′-O-β-D-glucopyranosyl-β-D-glucopyranosyl）-O-］-oleic acid-6′，6″-diacetylester	0.19
	C18∶2	A	C₃₄H₅₆O₁₅	705.351 6	705.362 0	17-L-［（2′-O-β-D-glucopyranosyl-β-D-glucopyranosyl）-O-］-octadecanodienoic acid-6′，6″- diacetyl ester	0.18
	C22∶1	A	C₃₈H₆₆O₁₅	745.432 9	745.429 9	21-L-［（2′-O-β-D-glucopyranosyl-β-D-glucopyranosyl）-O-］- docosenoic acid -6′，6″- diacetyl ester	0.16

	Type		Molecular formula	m/z of ［M+H］⁺		Full name of component	w/%
	Fatty acid groups	L/A/B^*	Molecular formula	Measured value	Simulation value	Full name of component	w/%
Nonacetylated	C18∶2	A	C₃₀H₅₂O₁₃	621.342 1	621.340 8	17-L-［（2′-O-β-D-glucopyranosyl-β-D-glucopyranosyl）-O-］-octadecanodienoic acid	0.32
Monoacetylated	C16∶0	L	C₃₀H₅₂O₁₃	621.743 5	621.340 8	15-L-［（2′-O-β-D-glucopyranosyl-β-D-glucopyranosyl）-O-］-hexadecanoic acid-1′，4"- lactone-6"-monoacetyl ester	0.11
	C18∶0	L	C₃₂H₅₆O₁₃	649.369 7	649.372 2	17-L-［（2′-O-β-D-glucopyranosyl-β-D-glucopyranosyl）-O-］-octadecanoic acid-1′，4"- lactone-6"-monoacetyl ester	0.18
	C18∶1	L	C₃₂H₅₄O₁₃	647.358 1	647.356 5	17-L-［（2′-O-β-D-glucopyranosyl-β-D-glucopyranosyl）-O-］-oleic acid-1′，4"-lactone-6"- monoacetyl ester	5.29
	C18∶2	L	C₃₂H₅₂O₁₃	645.341 9	645.340 8	17-L-［（2′-O-β-D-glucopyranosyl-β-D-glucopyranosyl）-O-］-octadecanodienoic acid-1′，4"-lactone-6"-monoacetyl ester	1.60
Diacetylated	C16∶0	L	C₃₂H₅₄O₁₄	663.360 4	663.351 4	15-L-［（2′-O-β-D-glucopyranosyl-β-D-glucopyranosyl）-O-］-hexadecanoic acid-1′，4"- lactone-6′，6"-diacetyl ester	12.27
	C16∶1	L	C₃₂H₅₂O₁₄	661.338 6	661.335 7	15-L-［（2′-O-β-D-glucopyranosyl-β-D-glucopyranosyl）-O-］-hexadecenoic acid-1′，4"-lactone-6'，6"-diacetyl ester	0.15
	C18∶0	L	C₃₄H₅₈O₁₄	691.384 9	691.382 8	17-L-［（2′-O-β-D-glucopyranosyl-β-D-glucopyranosyl）-O-］-octadecanoic acid-1′，4"-lactone-6′，6"-diacetyl ester	16.97
	C18∶1	L	C₃₄H₅₆O₁₄	689.375 4	689.367 1	17-L-［（2′-O-β-D-glucopyranosyl-β-D-glucopyranosyl）-O-］-oleic acid-1′，4"-lactone-6′，6"-diacetyl ester	42.47
	C18∶2	L	C₃₄H₅₄O₁₄	687.356 3	687.351 4	17-L-［（2′-O-β-D-glucopyranosyl-β-D-glucopyranosyl）-O-］-octadecanodienoic acid-1′，4"-lactone-6'，6"-diacetyl ester	18.82
	C16∶2	A	C₃₂H₅₂O₁₅	677.331 9	677.330 6	15-L-［（2′-O-β-D-glucopyranosyl-β-D-glucopyranosyl）-O-］-hexadecanodienoic acid-6′，6″-diacetyl ester	1.29
	C18∶1	A	C₃₄H₅₈O₁₅	707.382 5	707.377 7	17-L-［（2′-O-β-D-glucopyranosyl-β-D-glucopyranosyl）-O-］-oleic acid-6′，6″-diacetylester	0.19
	C18∶2	A	C₃₄H₅₆O₁₅	705.351 6	705.362 0	17-L-［（2′-O-β-D-glucopyranosyl-β-D-glucopyranosyl）-O-］-octadecanodienoic acid-6′，6″- diacetyl ester	0.18
	C22∶1	A	C₃₈H₆₆O₁₅	745.432 9	745.429 9	21-L-［（2′-O-β-D-glucopyranosyl-β-D-glucopyranosyl）-O-］- docosenoic acid -6′，6″- diacetyl ester	0.16

	Type		Molecular formula	m/z of ［M+H］⁺		Full name of component	w/%
	Fatty acid groups	L/A/B^*	Molecular formula	Measured value	Simulation value	Full name of component	w/%
Nonacetylated	C16∶2	L	C₂₈H₄₆O₁₂	575.310 4	575.298 8	15-L-［（2′-O-β-D-glucopyranosyl-β-D-glucopyranosyl）- O-］-hexadecanodienoic acid-1′，4″-lactone	8.73
	C18∶1	L	C₃₀H₅₂O₁₂	605.354 5	605.345 9	17-L-［（2′-O-β-D-glucopyranosyl-β-D-glucopyranosyl）- O-］-oleic acid-1′，4″-lactone	16.50
	C18∶3	L	C₃₀H₄₈O₁₂	637.365 2	637.335 7	17-L-［（2′-O-β-D-glucopyranosyl-β-D-glucopyranosyl）- O-］- octadecanotrienoic acid-1′，4″-lactone	1.76
	C16∶0	A	C₂₈H₅₂O₁₃	597.509 0	597.340 8	15-L-［（2′-O-β-D-glucopyranosyl-β-D-glucopyranosyl）- O-］-hexadecenoic acid	16.96
	C16∶0	A	C₂₈H₅₂O₁₃	597.347 9	597.340 8	16-L-［（2′-O-β-D-glucopyranosyl-β-D-glucopyranosyl）- O-］-hexadecenoic acid	1.74
	C18∶0	A	C₃₀H₅₆O₁₃	625.386 3	625.372 2	17-L-［（2′-O-β-D-glucopyranosyl-β-D-glucopyranosyl）- O-］-octadecanoic acid	6.37
	C18∶1	A	C₃₀H₅₄O₁₃	623.364 2	623.356 5	17-L-［（2′-O-β-D-glucopyranosyl-β-D-glucopyranosyl）- O-］-oleic acid	10.18
	C18∶2	A	C₃₀H₅₂O₁₃	621.356 7	621.340 8	17-L-［（2′-O-β-D-glucopyranosyl-β-D-glucopyranosyl）- O-］-octadecanodienoic acid	1.38
	C20∶1	A	C₃₂H₅₆O₁₂	651.395 8	651.387 9	19-L-［（2′-O-β-D-glucopyranosyl-β-D-glucopyranosyl）- O-］-eicosenoic acid	3.59
	C24∶0	A	C₃₆H₇₄O₁₂	709.496 9	709.466 4	23-L-［（2′-O-β-D-glucopyranosyl-β-D-glucopyranosyl）- O-］-lignoceric acid	1.49
	C16∶0	B	C₄₀H₇₂O₂₃	921.450 2	921.446 4	15-L-［（2′-O-β-D-glucopyranosyl-β-D-glucopyranosyl）-O-］-hexadecanoic acid-1-［（2′-O-β-D-glucopyranosyl-β-D-glucopyranosyl）-O-］-ester	6.60
	C16∶1	B	C₄₀H₇₀O₂₃	901.435 5	919.430 7	17-L-［（2′-O-β-D-glucopyranosyl-β-D-glucopyranosyl）-O-］- hexadecenoic acid -1-［（2′-O-β-D-glucopyranosyl-β-D-glucopyranosyl）-O-］-ester	10.16
	C18∶1	B	C₄₂H₇₄O₂₃	947.469 3	947.462 1	17-L-［（2′-O-β-D-glucopyranosyl-β-D-glucopyranosyl）-O-］-oleic acid-1-［（2′-O-β-D-glucopyranosyl-β-D-glucopyranosyl）-O-］-ester	2.74
	C18∶2	B	C₄₂H₇₂O₂₃	945.485 5	945.446 4	17-L-［（2′-O-β-D-glucopyranosyl-β-D-glucopyranosyl）-O-］-octadecanodienoic acid-1-［（2′-O-β-D-glucopyranosyl-β-D-glucopyranosyl）-O-］-ester	2.36
Monoacetylated	C18∶1	A	C₃₂H₅₆O₁₄	669.365 0	665.367 1	17-L-［（2′-O-β-D-glucopyranosyl-β-D-glucopyranosyl）-O-］-oleic acid-6″-monoacetyl ester	8.27
	C18∶1	B	C₄₄H₇₆O₂₃	989.478 5	989.472 7	17-L-［（2′-O-β-D-glucopyranosyl-β-D-glucopyranosyl）-O-］-oleic acid-1-［（2′-O-β-D-glucopyranosyl-β-D-glucopyranosyl）-O-］-ester-6″-monoacetyl ester	0.36
	C26∶0	B	C₅₂H₉₄O₂₃	1103.664 2	1103.614 0	25-L-［（2′-O-β-D-glucopyranosyl-β-D-glucopyranosyl）-O-］-hexacosanoic acid-1-［（2′-O-β-D-glucopyranosyl-β-D-glucopyranosyl）-O-］-ester-6″-monoacetyl ester	0.81

	Type		Molecular formula	m/z of ［M+H］⁺		Full name of component	w/%
	Fatty acid groups	L/A/B^*	Molecular formula	Measured value	Simulation value	Full name of component	w/%
Nonacetylated	C16∶2	L	C₂₈H₄₆O₁₂	575.310 4	575.298 8	15-L-［（2′-O-β-D-glucopyranosyl-β-D-glucopyranosyl）- O-］-hexadecanodienoic acid-1′，4″-lactone	8.73
	C18∶1	L	C₃₀H₅₂O₁₂	605.354 5	605.345 9	17-L-［（2′-O-β-D-glucopyranosyl-β-D-glucopyranosyl）- O-］-oleic acid-1′，4″-lactone	16.50
	C18∶3	L	C₃₀H₄₈O₁₂	637.365 2	637.335 7	17-L-［（2′-O-β-D-glucopyranosyl-β-D-glucopyranosyl）- O-］- octadecanotrienoic acid-1′，4″-lactone	1.76
	C16∶0	A	C₂₈H₅₂O₁₃	597.509 0	597.340 8	15-L-［（2′-O-β-D-glucopyranosyl-β-D-glucopyranosyl）- O-］-hexadecenoic acid	16.96
	C16∶0	A	C₂₈H₅₂O₁₃	597.347 9	597.340 8	16-L-［（2′-O-β-D-glucopyranosyl-β-D-glucopyranosyl）- O-］-hexadecenoic acid	1.74
	C18∶0	A	C₃₀H₅₆O₁₃	625.386 3	625.372 2	17-L-［（2′-O-β-D-glucopyranosyl-β-D-glucopyranosyl）- O-］-octadecanoic acid	6.37
	C18∶1	A	C₃₀H₅₄O₁₃	623.364 2	623.356 5	17-L-［（2′-O-β-D-glucopyranosyl-β-D-glucopyranosyl）- O-］-oleic acid	10.18
	C18∶2	A	C₃₀H₅₂O₁₃	621.356 7	621.340 8	17-L-［（2′-O-β-D-glucopyranosyl-β-D-glucopyranosyl）- O-］-octadecanodienoic acid	1.38
	C20∶1	A	C₃₂H₅₆O₁₂	651.395 8	651.387 9	19-L-［（2′-O-β-D-glucopyranosyl-β-D-glucopyranosyl）- O-］-eicosenoic acid	3.59
	C24∶0	A	C₃₆H₇₄O₁₂	709.496 9	709.466 4	23-L-［（2′-O-β-D-glucopyranosyl-β-D-glucopyranosyl）- O-］-lignoceric acid	1.49
	C16∶0	B	C₄₀H₇₂O₂₃	921.450 2	921.446 4	15-L-［（2′-O-β-D-glucopyranosyl-β-D-glucopyranosyl）-O-］-hexadecanoic acid-1-［（2′-O-β-D-glucopyranosyl-β-D-glucopyranosyl）-O-］-ester	6.60
	C16∶1	B	C₄₀H₇₀O₂₃	901.435 5	919.430 7	17-L-［（2′-O-β-D-glucopyranosyl-β-D-glucopyranosyl）-O-］- hexadecenoic acid -1-［（2′-O-β-D-glucopyranosyl-β-D-glucopyranosyl）-O-］-ester	10.16
	C18∶1	B	C₄₂H₇₄O₂₃	947.469 3	947.462 1	17-L-［（2′-O-β-D-glucopyranosyl-β-D-glucopyranosyl）-O-］-oleic acid-1-［（2′-O-β-D-glucopyranosyl-β-D-glucopyranosyl）-O-］-ester	2.74
	C18∶2	B	C₄₂H₇₂O₂₃	945.485 5	945.446 4	17-L-［（2′-O-β-D-glucopyranosyl-β-D-glucopyranosyl）-O-］-octadecanodienoic acid-1-［（2′-O-β-D-glucopyranosyl-β-D-glucopyranosyl）-O-］-ester	2.36
Monoacetylated	C18∶1	A	C₃₂H₅₆O₁₄	669.365 0	665.367 1	17-L-［（2′-O-β-D-glucopyranosyl-β-D-glucopyranosyl）-O-］-oleic acid-6″-monoacetyl ester	8.27
	C18∶1	B	C₄₄H₇₆O₂₃	989.478 5	989.472 7	17-L-［（2′-O-β-D-glucopyranosyl-β-D-glucopyranosyl）-O-］-oleic acid-1-［（2′-O-β-D-glucopyranosyl-β-D-glucopyranosyl）-O-］-ester-6″-monoacetyl ester	0.36
	C26∶0	B	C₅₂H₉₄O₂₃	1103.664 2	1103.614 0	25-L-［（2′-O-β-D-glucopyranosyl-β-D-glucopyranosyl）-O-］-hexacosanoic acid-1-［（2′-O-β-D-glucopyranosyl-β-D-glucopyranosyl）-O-］-ester-6″-monoacetyl ester	0.81

	Acetylated SLs	Nonacetylated SLs
Solubility/（g·L^-1）	33.8	485.8
Cloud point/℃	36	Not detected
Acid resistance	Conditional acid resistance	Non acid resistance
Alkali resistance	Non alkali resistance	Non alkali resistance
Hard water resistance/grade	5	5

Structural Identification and Physicochemical Properties of Nonacetylated Sophorolipids Biosurfactant

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Figures/Tables 11

References 33

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Sophorolipid	CMC/（mg·L^-1）	γ_CMC/（mN·m^-1）	Г_max/（μmol·m^-2）	A_min/nm²
Acetylated-SLs	30.3	36.2	2.55	0.653
Nonacetylated SLs	152.5	41.0	3.01	0.551

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