Natural synergism of acid and lactone type mixed sophorolipids in interfacial activities and cytotoxicities.
Sophorolipids (SLs) naturally produced from Candida bombicola are a mixture of lactonic (SL-lactone) and acidic (SL-acid) sophorosides of 17-L-hydroxydecanoic acid with an SL-lactone:SL-acid ratio of 72:28. SLs are biodegradable low-foaming surfactants with high detergency and hardness-tolerance properties. To analyze the effect of the SL-lactone:SL-acid ratio on these properties, SL-LXs containing X% SL-lactone, in which X varied from 0 to 100, were prepared and their interfacial activities and cytotoxicities examined. The minimum surface tension values for all SLs examined were comparable. The critical micelle concentration (CMC) was 680 mg/L for SL-L0 and 62-110 mg/L for the other SLs. Interestingly, natural SL (SL-L72) had the lowest surface tension and CMC among all of the SLs examined. The foaming ability and stability of the SLs were dependent on the SL-L content. SL-L0 and L17 had higher foaming values than the other SLs examined in 0-ppm hardness water. These values greatly reduced and became constant when the SL-L content increased over 55%. The detergencies of all of the SLs examined were comparable, except for those of SL-L0 and SL-L100, which were slightly lower than those of the other SLs. These results suggest that natural synergism between SLs creates a better balance for many interfacial activities. The cytotoxicity of SL-L72 was higher than that of SL-L0, but was comparable to that of surfactin, which is commercially available for cosmetic use. The low cytotoxicities and high interfacial properties of SLs increase their usefulness as biocompatible surface active agents for many applications.
Hirata
Yoshihiko
Y
Biochemical Laboratory, Saraya Co., LTD., Osaka, Japan. hirata@saraya.com
Ryu
Mizuyuki
M
Igarashi
Keisuke
K
Nagatsuka
Asami
A
Furuta
Taro
T
Kanaya
Shigenori
S
Sugiura
Masaki
M
D002175:Candida / Q000737:chemistry*; D002478:Cells, Cultured; D003652:Decanoic Acids / Q000737:chemistry / Q000633:toxicity*; D004357:Drug Synergism; D005227:Fatty Acids / Q000737:chemistry / Q000633:toxicity; D006017:Glycolipids / Q000737:chemistry / Q000633:toxicity*; D006801:Humans; D015603:Keratinocytes / Q000187:drug effects / Q000502:physiology; D007783:Lactones / Q000737:chemistry / Q000633:toxicity*; D013500:Surface Tension; D013501:Surface-Active Agents / Q000737:chemistry / Q000633:toxicity*
D003652:Decanoic Acids; D005227:Fatty Acids; D006017:Glycolipids; D007783:Lactones; D013501:Surface-Active Agents; C067958:16-(2'-O-glucopyranosylglucopyranosyloxy)hexadecanoic acid 1',4''-lactone 6',6''-diacetate