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Elisabeth Delbeke - One of the best experts on this subject based on the ideXlab platform.
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Lipid-Based Quaternary Ammonium Sophorolipid Amphiphiles with Antimicrobial and Transfection Activities.
ChemSusChem, 2019Co-Authors: Elisabeth Delbeke, Jonas Everaert, Olivier Lozach, Tony Le Gall, Tristan Montier, Paul-alain Jaffrès, Petra Rigole, Tom Coenye, Martha BrennichAbstract:Twelve new quaternary ammonium sophorolipids with long alkyl chains on the nitrogen atom were synthesized starting from oleic and Petroselinic Acid-based sophorolipids. These novel derivatives were evaluated for their antimicrobial activity against selected Gram-negative and Gram-positive bacteria and their transfection efficacies on three different eukaryotic cell lines in vitro as good activities were demonstrated for previously synthesized derivatives. Self-assembly properties were also evaluated. All compounds proved to possess antimicrobial and transfection properties, and trends could be observed based on the length of the nitrogen substituent and the total length of the sophorolipid tail. Moreover, all long-chain quaternary ammonium sophorolipids form micelles, which proved to be a prerequisite to induce antimicrobial activity and transfection capacity. These results are promising for future healthcare applications of long-chained quaternary ammonium sophorolipids.
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Characterization of French Coriander Oil as Source of Petroselinic Acid
Molecules, 2016Co-Authors: Evelien Uitterhaegen, Klicia Sampaio, Muriel Cerny, Elisabeth Delbeke, Philippe Evon, Thierry Talou, Othmane Merah, Wim De Greyt, Chris StevensAbstract:Coriander vegetable oil was extracted from fruits of French origin in a 23% yield. The oil was of good quality, with a low amount of free fatty Acids (1.8%) and a concurrently high amount of triacylglycerols (98%). It is a rich source of Petroselinic Acid (C18:1n-12), an important renewable building block, making up 73% of all fatty Acids, with also significant amounts of linoleic Acid (14%), oleic Acid (6%), and palmitic Acid (3%). The oil was characterized by a high unsaponifiable fraction, comprising a substantial amount of phytosterols (6.70 g/kg). The main sterol markers were β-sitosterol (35% of total sterols), stigmasterol (24%), and ∆7-stigmastenol (18%). Squalene was detected at an amount of 0.2 g/kg. A considerable amount of tocols were identified (500 mg/kg) and consisted mainly of tocotrienols, with γ-tocotrienol as the major compound. The phospholipid content was low at 0.3%, of which the main phospholipid classes were phosphatidic Acid (33%), phosphatidylcholine (25%), phosphatidylinositol (17%), and phosphatidylethanolamine (17%). About 50% of all phospholipids were non-hydratable. The β-carotene content was low at 10 mg/kg, while a significant amount of chlorophyll was detected at about 11 mg/kg. An iron content of 1.4 mg/kg was determined through element analysis of the vegetable oil. The influence of fruit origin on the vegetable oil composition was shown to be very important, particularly in terms of the phospholipids, sterols, and tocols composition.
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Petroselinic Acid purification and its use for the fermentation of new sophorolipids.
AMB Express, 2016Co-Authors: Elisabeth Delbeke, Evelien Uitterhaegen, Thierry Talou, Wim Soetaert, Inge N. A. Van Bogaert, Jonas Everaert, Stijn Verweire, Arno Verlee, Christian V. StevensAbstract:Petroselinic Acid, a positional isomer of oleic Acid, was isolated from the vegetable oil of Coriandrum sativum fruits. This uncommon fatty Acid was subsequently used as substrate for sophorolipid fermentation with a Starmerella bombicola lactone esterase overexpression (oe sble) strain. A Petroselinic Acid based diacetylated sophorolipid lactone was obtained in high purity without incorporation of de novo synthesized fatty Acids such as oleic Acid. A total production of 40 g/L was obtained. The Petroselinic Acid based sophorolipid lactone was subsequently hydrolyzed towards the Petroselinic Acid based sophorolipid Acid. For both compounds, their critical micelle concentration (CMC) and corresponding surface tension were compared to their oleic Acid based counterparts. Both Petroselinic Acid based sophorolipids displayed a much lower CMC value than their oleic Acid based counterparts, although their minimal surface tension was the same. Besides, the sophorolipid fermentation product was chemically modified towards a novel C12 sophorolipid aldehyde. This derivative constitutes an interesting building block for further modification towards new-to-nature sophorolipids with high potential for self-assembly applications.
Brahim Marzouk - One of the best experts on this subject based on the ideXlab platform.
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comparative assessment of phytochemical profiles and antioxidant properties of tunisian and egyptian anise pimpinella anisum l seeds
Plant Biosystems, 2018Co-Authors: Ines Bettaieb Rebey, Wissem Aidi Wannes, Brahim Marzouk, Soumaya Bourgou, Ibtissem Hamrouni Sellami, Moufida Saidani Tounsi, Marielaure Fauconnier, Riadh KsouriAbstract:AbstractAnis (Pimpinella anisum L.) seeds obtained from two geographic origins Tunisia (TAS) and Egypt (EAS) were studied regarding their biochemical composition and the antioxidant potential of their extracts. The results showed that the highest value of oil was detected with TAS compared to that of EAS ones. Ten (10) fatty Acids were identified for the two locations and Petroselinic Acid was the most prevalent in oil seeds and interestingly, TAS displayed a significantly higher level of this Acid than EAS. Besides, TAS exhibited slightly higher essential oil yield than the Egyptian variety and that trans-anethole was the dominant for the two provenances. In both accessions, the highest total phenolic, flavonoid and tannin content was obtained with ethyl acetate fraction. Therefore, TAS exhibited higher chelating and reducing powers than EAS which may be due to a slightly different phenolic composition between the two accession seed extracts. The phenolic compositions of TAS and EAS revealed that ethyl a...
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Biochemical Characterization of Coriander Cakes Obtained by Extrusion
Journal of Chemistry, 2013Co-Authors: Jazia Sriti, Thierry Talou, Manel Neffati, Kamel Msaada, Brahim MarzoukAbstract:This study was designed to examine the effect of operating conditions such as nozzle diameter on fatty Acid, sterol, and tocol composition of coriander cakes. Eight fatty Acids were identified, with Petroselinic Acid accounting for 75-77% of the total fatty Acids, followed by linoleic, oleic, and palmitic Acids, accounting for 12-13%, 5% and 3%, respectively, of the total fatty Acids. beta-Sitosterol was the major sterol in all oils with 33-35% of total sterols. The next major sterols in all oils were stigmasterol (24% of total sterols) and Delta(7)-stigmasterol (15% of total sterols). Coriander cake contained higher amounts of total tocotrienol where gamma-tocotrienol was the main compund.
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Biochemical Characterization of Coriander Cakes Obtained by Extrusion
Hindawi Limited, 2012Co-Authors: Jazia Sriti, Thierry Talou, Manel Neffati, Kamel Msaada, Brahim MarzoukAbstract:This study was designed to examine the effect of operating conditions such as nozzle diameter on fatty Acid, sterol, and tocol composition of coriander cakes. Eight fatty Acids were identified, with Petroselinic Acid accounting for 75–77% of the total fatty Acids, followed by linoleic, oleic, and palmitic Acids, accounting for 12-13%, 5%, and 3%, respectively, of the total fatty Acids.β-Sitosterol was the major sterol in all oils with 33–35% of total sterols. The next major sterols in all oils were stigmasterol (24% of total sterols) and Δ7-stigmasterol (15% of total sterols). Coriander cake contained higher amounts of total tocotrienol whereγ-tocotrienol was the main compound.
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essential oils and fatty Acids composition of tunisian and indian cumin cuminum cyminum l seeds a comparative study
Journal of the Science of Food and Agriculture, 2011Co-Authors: Iness Bettaieb, Jazia Sriti, Kamel Msaada, Soumaya Bourgou, Ferid Limam, Brahim MarzoukAbstract:BACKGROUND: Cumin (Cuminum cyminum L.) seeds of two geographic origins, Tunisia (TCS) and India (ICS), were studied regarding their fatty Acid and essentialoil composition. RESULTS: Oil yields were 17.77 and 15.40% for TCS and ICS respectively. Petroselinic Acid (C18:1n-12) was the major fatty Acid in both varieties, with a higher proportion being found in TCS (55.90% of total fatty Acids (TFA)) than in ICS (41.42% TFA).Moreover, themostpredominantfatty Acidswere palmitic,petroselenic andlinoleicAcids, accounting formorethan91% TFA in both varieties. The unsaturated fatty Acid content was high: 70.95% TFA in TCS and 62.17% TFA in ICS. Essential oil yields differed significantly (P < 0.05) between the two varieties: 1.21 and 1.62% for ICS and TCS respectively. A total of 40 compounds were identified, 34 of which were present in both essential oils. The two varieties displayed different chemotypes: γ-terpinene/1-phenyl-1,2-ethanediolfor TCS and cuminaldheyde/γ-terpinenefor ICS. CONCLUSION: The study revealed that the biochemical composition of cumin seeds is origin-dependent and that cumin seeds are rich in an unusual fatty Acid, Petroselinic Acid. Besides, cumin essential oil is a rich source of many compounds, including cuminaldehydeand γ-terpinene.Theoverallresultssuggesttheexploitationofcuminseedsasalow-costrenewablesourcefor industrial processing in thefields of cosmetics, perfumes and pharmaceuticals. c � 2011 Society of Chemical Industry
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comparative analysis of fatty Acid sterol and tocol composition of tunisian and canadian coriander coriandrum sativum l fruit
Analytical Chemistry Letters, 2011Co-Authors: Jazia Sriti, Thierry Talou, Kamel Msaada, Brahim MarzoukAbstract:Abstract Oils extracted from Tunisian (Tn) and Canadian (Can) coriander0 fruits were analysed for fatty Acid, sterol and tocol composition. Oil yields were 21.87 and 15.84 %for Tn and Can respectively. Petroselinic Acid (C 18:1n-12) was the major fatty Acid in two coriander fruit samples, with a higher proportion being found in Tn (75.66 % of total fatty Acid (TFA)) than in Can (73.23 % TFA). No difference was observed in phytosterol profiles between the both samples. A total of 7 sterols were identified, (3-sitosterol which constituted the major compound. Significant differences were found in total tocol contents among representing 27.78 mg/100 g oil in Tn and 21.14 mg/ 100 g oil in Can.
Martha Brennich - One of the best experts on this subject based on the ideXlab platform.
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Lipid-Based Quaternary Ammonium Sophorolipid Amphiphiles with Antimicrobial and Transfection Activities.
ChemSusChem, 2019Co-Authors: Elisabeth Delbeke, Jonas Everaert, Olivier Lozach, Tony Le Gall, Tristan Montier, Paul-alain Jaffrès, Petra Rigole, Tom Coenye, Martha BrennichAbstract:Twelve new quaternary ammonium sophorolipids with long alkyl chains on the nitrogen atom were synthesized starting from oleic and Petroselinic Acid-based sophorolipids. These novel derivatives were evaluated for their antimicrobial activity against selected Gram-negative and Gram-positive bacteria and their transfection efficacies on three different eukaryotic cell lines in vitro as good activities were demonstrated for previously synthesized derivatives. Self-assembly properties were also evaluated. All compounds proved to possess antimicrobial and transfection properties, and trends could be observed based on the length of the nitrogen substituent and the total length of the sophorolipid tail. Moreover, all long-chain quaternary ammonium sophorolipids form micelles, which proved to be a prerequisite to induce antimicrobial activity and transfection capacity. These results are promising for future healthcare applications of long-chained quaternary ammonium sophorolipids.
John B Ohlrogge - One of the best experts on this subject based on the ideXlab platform.
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an unusual seed specific 3 ketoacyl acp synthase associated with the biosynthesis of Petroselinic Acid in coriander
Plant Molecular Biology, 2001Co-Authors: Sergei Mekhedov, Edgar B Cahoon, John B OhlroggeAbstract:Petroselinic Acid (18:1 delta6) is the major component of the seed oil of Umbelliferae species such as coriander (Coriandrum sativum) as well as Araliaceae and Garryaceae species. This unusual fatty Acid is synthesized in plastids by the delta4 desaturation of palmitoyl-acyl carrier protein (16:0-ACP) and subsequent elongation of delta4-hexadecenoyl (16:1 delta4)-ACP. To characterize the enzymatic nature of the elongation reaction, an in vitro assay was developed with 16:1 delta4-ACP and 16:0-ACP as substrates. Extracts from developing coriander seeds elongated 16:1 delta4-ACP in a competitive assay at rates ten-fold greater than that with 16:0-ACP. In contrast, extracts from castor seeds, which do not synthesize Petroselinic Acid, displayed a strong preference for the elongation of 16:0-ACP rather than 16:1 A4-ACP. In addition, the elongation of 16:1 A4-ACP and 16:0-ACP by coriander seed extracts was strongly inhibited by cerulenin at concentrations as low as 10 microM. This finding suggested that the elongation of 16:1 A4-ACP and 16:0-ACP in coriander seed is catalyzed by a 3-ketoacyl-ACP synthase (KAS) 1-type enzyme(s), rather than a KAS II-type activity that is typically associated with 16:0-ACP elongation. Consistent with this, a cDNA for a diverged form of KAS I was isolated from a cDNA library prepared from developing coriander seed. Using a variety of heterologous probing techniques, no KAS II-type cDNAs could be identified in this library. Multiple alignment of KAS amino Acid sequences indicated that, although the polypeptide corresponding to the coriander cDNA is more closely related to KAS I. its active site motif deviates from those found in both KAS I and KAS II enzymes. Also suggestive of a possible role in Petroselinic Acid synthesis, antibodies raised to the recombinant protein recognize an abundant 45 kDa polypeptide in coriander endosperm that is not detected in coriander leaves. These antibodies also recognize a major band of similar size in developing seeds of English ivy (Hedera helix), an Araliaceae species that also accumulates Petroselinic Acid in a seed-specific manner.
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apparent role of phosphatidylcholine in the metabolism of Petroselinic Acid in developing umbelliferae endosperm
Plant Physiology, 1994Co-Authors: Edgar B Cahoon, John B OhlroggeAbstract:Studies were conducted to characterize the metabolism of the unusual fatty Acid Petroselinic Acid (18:1cis[delta]6) in developing endosperm of the Umbelliferae species coriander (Coriandrum sativum L.) and carrot (Daucus carota L.). Analyses of fatty Acid compositions of glycerolipids of these tissues revealed a dissimilar distribution of Petroselinic Acid in triacylglycerols (TAG) and the major polar lipids phosphatidylcholine (PC) and phosphatidylethanolamine (PE). Petroselinic Acid comprised 70 to 75 mol% of the fatty Acids of TAG but only 9 to 20 mol% of the fatty Acids of PC and PE. Although such data appeared to suggest that Petroselinic Acid is at least partially excluded from polar lipids, results of [1–14C]acetate radiolabeling experiments gave a much different picture of the metabolism of this fatty Acid. In time-course labeling of carrot endosperm, [1–14C]acetate was rapidly incorporated into PC in high levels. Through 30 min, radiolabel was most concentrated in PC, and of this, 80 to 85% was in the form of Petroselinic Acid. One explanation for the large disparity in amounts of Petroselinic Acid in PC as determined by fatty Acid mass analyses and 14C radiolabeling is that turnover of these lipids or the fatty Acids of these lipids results in relatively low accumulation of Petroselinic Acid mass. Consistent with this, the kinetics of [1–14C]acetate time-course labeling of carrot endosperm and “pulse-chase” labeling of coriander endosperm suggested a possible flux of fatty Acids from PC into TAG. In time-course experiments, radiolabel initially entered PC at the highest rates but accumulated in TAG at later time points. Similarly, in pulse-chase studies, losses in absolute amounts of radioactivity from PC were accompanied by significant increases of radiolabel in TAG. In addition, stereospecific analyses of unlabeled and [1–14C]acetate-labeled PC of coriander endosperm indicated that Petroselinic Acid can be readily incorporated into both the sn-1 and sn-2 positions of this lipid. Because Petroselinic Acid is neither synthesized nor further modified on polar lipids, the apparent metabolism of this fatty Acid through PC (and possibly through other polar lipids) may define a function of PC in TAG assembly apart from its involvement in fatty Acid modification reactions.
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metabolic evidence for the involvement of a delta 4 palmitoyl acyl carrier protein desaturase in Petroselinic Acid synthesis in coriander endosperm and transgenic tobacco cells
Plant Physiology, 1994Co-Authors: Edgar B Cahoon, John B OhlroggeAbstract:We have previously demonstrated that the double bond of Petroselinic Acid (18:1[delta]6cis) in coriander (Coriandrum sativum L.) seed results from the activity of a 36-kD desaturase that is structurally related to the [delta]9-stearoyl-acyl carrier protein (ACP) desaturase (E.B. Cahoon, J. Shanklin, J.B. Ohlrogge [1992] Proc Natl Acad Sci USA 89: 11184–11188). To further characterize the biosynthetic pathway of this unusual fatty Acid, 14C-labeling experiments were conducted using developing endosperm of coriander. Studies were also performed using suspension cultures of transgenic tobacco (Nicotiana tabacum L.) that express the coriander 36-kD desaturase, and as a result produce Petroselinic Acid and [delta]4-hexadecenoic Acid. When supplied exogenously to coriander endosperm slices, [1–14C]palmitic Acid and stearic Acid were incorporated into glycerolipids but were not converted to Petroselinic Acid. This suggested that Petroselinic Acid is not formed by the desaturation of a fatty Acid bound to a glycerolipid or by reactions involving acyl-coenzyme As (CoA). Instead, evidence was most consistent with an acyl-ACP route of Petroselinic Acid synthesis. For example, the exogenous feeding of [1–14C]lauric Acid and myristic Acid to coriander endosperm slices resulted in the incorporation of the radiolabels into long-chain fatty Acids, including primarily Petroselinic Acid, presumably through acyl-ACP-associated reactions. In addition, using an in vitro fatty Acid biosynthetic system, homogenates of coriander endosperm incorporated [2–14C]malonyl-CoA into Petroselinic Acid, of which a portion was detected in a putative acyl-ACP fraction. Furthermore, analysis of transgenic tobacco suspension cultures expressing the coriander 36-kD desaturase revealed significant amounts of Petroselinic Acid and [delta]4-hexadecenoic Acid in the acyl-ACP pool of these cells. Also presented is evidence derived from [U-14C]nonanoic Acid labeling of coriander endosperm, which demonstrates that the coriander 36-kD desaturase positions double bonds relative to the carboxyl end of acyl-ACP substrates. The data obtained in these studies are rationalized in terms of a biosynthetic pathway of Petroselinic Acid involving the [delta]4 desaturation of palmitoyl-ACP by the 36-kD desaturase followed by two-carbon elongation of the resulting [delta]4-hexadecenoyl-ACP.
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Specificities of the Acyl-Acyl Carrier Protein (ACP) Thioesterase and Glycerol-3-Phosphate Acyltransferase for Octadecenoyl-ACP Isomers (Identification of a Petroselinoyl-ACP Thioesterase in Umbelliferae).
Plant physiology, 1994Co-Authors: Peter Dörmann, Margrit Frentzen, John B OhlroggeAbstract:This study was designed to address the question: How specific for double bond position and conformation are plant enzymes that act on oleoyl-acyl carrier protein (ACP)? Octadecenoyl-ACPs with cis double bonds at positions [delta]6, [delta]7, [delta]8, [delta]9, [delta]10, [delta]11, or [delta]12 and elaidyl (18:1[delta]9trans)-ACP were synthesized and used to characterize the substrate specificity of the acyl-ACP thioesterase and acyl-ACP:sn-glycerol-3-phosphate acyltransferase. The two enzymes were found to be specific for the [delta]9 position of the double bond. The thioesterase was highly specific for the [delta]9 cis conformation, but the transferase was almost equally active with the cis and the trans isomer of 18:1[delta]9-ACP. In plants such as the Umbelliferae species coriander (Coriandrum sativum L.) that accumulate Petroselinic Acid (18:1[delta]6cis) in their seed triacylglycerols, a high petroselinoyl-ACP thioesterase activity was found in addition to the oleoyl-ACP thioesterase. The two activities could be separated by anion-exchange chromatography, indicating that the petroselinoyl-ACP thioesterase is represented by a distinct polypeptide.
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expression of a coriander desaturase results in Petroselinic Acid production in transgenic tobacco
Proceedings of the National Academy of Sciences of the United States of America, 1992Co-Authors: Edgar B Cahoon, John Shanklin, John B OhlroggeAbstract:Little is known about the metabolic origin of Petroselinic Acid (18:1 delta 6cis), the principal fatty Acid of the seed oil of most Umbelliferae, Araliaceae, and Garryaceae species. To examine the possibility that Petroselinic Acid is the product of an acyl-acyl carrier protein (ACP) desaturase, Western blots of coriander and other Umbelliferae seed extracts were probed with antibodies against the delta 9-stearoyl-ACP desaturase of avocado. In these extracts, proteins of 39 and 36 kDa were detected. Of these, only the 36-kDa peptide was specific to tissues which synthesize Petroselinic Acid. A cDNA encoding the 36-kDa peptide was isolated from a coriander endosperm cDNA library, placed under control of the cauliflower mosaic virus 35S promoter, and introduced into tobacco by Agrobacterium tumefaciens-mediated transformation. Expression of this cDNA in transgenic tobacco callus was accompanied by the accumulation of Petroselinic Acid and delta 4-hexadecenoic Acid, both of which were absent from control callus. These results demonstrate the involvement of a 36-kDa putative acyl-ACP desaturase in the biosynthetic pathway of Petroselinic Acid and the ability to produce fatty Acids of unusual structure in transgenic plants by the expression of the gene for this desaturase.
Jonas Everaert - One of the best experts on this subject based on the ideXlab platform.
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Lipid-Based Quaternary Ammonium Sophorolipid Amphiphiles with Antimicrobial and Transfection Activities.
ChemSusChem, 2019Co-Authors: Elisabeth Delbeke, Jonas Everaert, Olivier Lozach, Tony Le Gall, Tristan Montier, Paul-alain Jaffrès, Petra Rigole, Tom Coenye, Martha BrennichAbstract:Twelve new quaternary ammonium sophorolipids with long alkyl chains on the nitrogen atom were synthesized starting from oleic and Petroselinic Acid-based sophorolipids. These novel derivatives were evaluated for their antimicrobial activity against selected Gram-negative and Gram-positive bacteria and their transfection efficacies on three different eukaryotic cell lines in vitro as good activities were demonstrated for previously synthesized derivatives. Self-assembly properties were also evaluated. All compounds proved to possess antimicrobial and transfection properties, and trends could be observed based on the length of the nitrogen substituent and the total length of the sophorolipid tail. Moreover, all long-chain quaternary ammonium sophorolipids form micelles, which proved to be a prerequisite to induce antimicrobial activity and transfection capacity. These results are promising for future healthcare applications of long-chained quaternary ammonium sophorolipids.
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Petroselinic Acid purification and its use for the fermentation of new sophorolipids.
AMB Express, 2016Co-Authors: Elisabeth Delbeke, Evelien Uitterhaegen, Thierry Talou, Wim Soetaert, Inge N. A. Van Bogaert, Jonas Everaert, Stijn Verweire, Arno Verlee, Christian V. StevensAbstract:Petroselinic Acid, a positional isomer of oleic Acid, was isolated from the vegetable oil of Coriandrum sativum fruits. This uncommon fatty Acid was subsequently used as substrate for sophorolipid fermentation with a Starmerella bombicola lactone esterase overexpression (oe sble) strain. A Petroselinic Acid based diacetylated sophorolipid lactone was obtained in high purity without incorporation of de novo synthesized fatty Acids such as oleic Acid. A total production of 40 g/L was obtained. The Petroselinic Acid based sophorolipid lactone was subsequently hydrolyzed towards the Petroselinic Acid based sophorolipid Acid. For both compounds, their critical micelle concentration (CMC) and corresponding surface tension were compared to their oleic Acid based counterparts. Both Petroselinic Acid based sophorolipids displayed a much lower CMC value than their oleic Acid based counterparts, although their minimal surface tension was the same. Besides, the sophorolipid fermentation product was chemically modified towards a novel C12 sophorolipid aldehyde. This derivative constitutes an interesting building block for further modification towards new-to-nature sophorolipids with high potential for self-assembly applications.