1 2 dioleoyl sn glycero 3 phospho rac 1 glycerol sodium salt

Cholesterol, 1,2-dioleoyl-sn-glycero-3-phospho-rac-(1-glycerol) sodium salt, chloroform, cisplatin, PtCl₄, polyvinylpyrrolidone (PVP, 40 k), HCl (37%, w/w), NaBH₄ and water were purchased from Sigma-Aldrich (St. Louis, MO, USA) in ACS purity. Hydrogenated phosphatidylcholine from soybean was a gift from Lipoid GMBH (Ludwigshafen, Germany). The deionised water was prepared using Aqual 25 (Aqual, Brno, Czech Republic) and was further purified using apparatus MilliQ Direct QUV equipped with the UV lamp (Merck Millipore, Merck KgaA, Darmstadt, Germany). The pH of the solutions was measured using a pH meter WTW inoLab (WTW GmbH, Weilheim, Germany).

Soybean-phosphatidylcholine (PC, 95%) was purchased from Avanti Polar Lipids (Alabaster, AL, USA). Tributyrin (TC4, 99%), Tricaprylin (TC8, 99%), Triolein (TC18, 99%), 1,2-dioleoyl-sn-glycero-3-phosphocholine (DOPC, ≥97%), l-α-phosphatidylinositol (PI, ≥99%), 1,2-diacyl-sn-glycero-3-phospho-l-serine (PS, ≥97%), l-α-phosphatidylethanolamine (PE, ≥99%), cardiolipin (CL, ≥98%), 3-sn-Phosphatidic acid sodium salt (PA, ≥98%), Sphingomyelin (SM, ≥98%), 1,2-dioleoyl-sn-glycero-3-phospho-rac-(1-glycerol) sodium salt (PG, ≥98%), 1,2-distearoyimonoglactosylglyceride (MGDG, ≥98%) were all from Sigma-Aldrich Corporation (St. Louis, MO, USA). Olive oil and sucrose esters were purchased from Aladdin Reagent Co. (Shanghai, China). Six pure chiral pseudoglycerides (didecanoyl-deoxyamino-O-methyl glycerol, DDGs) used in the present studies were synthesized according to the method reported before [23 (link)].

Amaranth seeds (Amaranthus hypochondriacus) of the Nutrisol variety were harvested in 2018 and donated by Mr. Everardo Lovera, president of the Maize Producers Federation of Mexico State, Mexico.
The following materials were purchased from Sigma-Aldrich (St. Louis, MO, USA): squalene, ≥98% purity; squalane, ≥95% purity; 1,2-dioleoyl-sn-glycero-3-phosphocholine (DOPC); 1,2-dioleoyl-sn-glycero-3-phospho-rac-(1-glycerol) sodium salt (DOPA) and cholesterol, ≥99% purity. Boron trifluoride (BF₃) (14% in methanol) was purchased from Alltech, Inc. (Deerfield, IL, USA) C8-C30 Fatty acid methyl ester (FAME) standards and triundecanoin were purchased from Nu-Check Prep (Elysian, MN, USA). Holey carbon grids for transmission electron microscopy (TEM) were purchased from Structure Probe, Inc. (SPI, West Chester, PA, USA). Cell Counting Kit-8 (CCK8) was acquired from Abcam (Cambridge, MA, USA). Amicon Ultra centrifugal filters (50 kDa cutoff) were purchased from Millipore (Burlington, MA, USA). Detergent-compatible (DC) protein assay was purchased from Bio-Rad (Hercules, CA, USA).