Succinoyl trehalose lipids (STLs) are promising glycolipid biosurfactants produced from n-alkanes by Rhodococcus sp. These compounds show not only unique interfacial properties but also versatile biochemical actions. In this study, we determined for the first time the complete structure of the main component, namely STL-1, based on NMR, MALDI-TOF/MS and GC-MS analyses. The present STL-1 produced from n-hexadecane was identified as 3,4-di-O-alkanoyl-2-O-succinoyl-alpha-D-glucopyranosyl-2'-O-succinoyl-alpha-D-glucopyranoside. The major fatty acid of STL-1 was C(16), indicating that n-hexadecane as the carbon source is directly incorporated into the carbohydrate moiety via terminal oxidation. We also investigated its surface active properties using a Whilhelmy method at 25 degrees C. The estimated CMC and gamma(CMC) values for STL-1 were 5.6x10(-6) M and 19.0 mN/m, and those for sodium salt (NaSTL-1) were 7.7x10(-6) M and 23.7 mN/m, respectively. The high activity of STL-1 was probably due to the unique molecular structure resulting from its multiple functional groups including succinic acids and two long fatty acids. Accordingly, STL-1 and its sodium salt were demonstrated to exhibit an excellent surface-activity at remarkably low concentrations, and should have great potential for environmentally friendly surfactants.

01 Jan 1997·Bioscience, Biotechnology, and BiochemistryQ4 · ENGINEERING & TECHNOLOGY

Microbial Extracellular Glycolipid Induction of Differentiation and Inhibition of the Protein Kinase C Activity of Human Promyelocytic Leukemia Cell Line HL60

Q4 · ENGINEERING & TECHNOLOGY

Article

Author: Hiroko Isoda ; Tadaatsu Nakahara ; Dai Kitamoto ; Masatoshi Matsumura ; Hiroshi Shinmoto

The biological activities of 7 microbial extracellular glycolipids including mannosylerythritol lipid (MEL)-A, MEL-B, polyol lipid (PL), rhamnolipid (RL), sophorose lipid (SL), succinoyl trehalose lipid (STL)-1, and STL-3 were investigated. All glycolipids except for RL were found to induce cell differentiation instead of cell proliferation in the human promyelocytic leukemia cell line HL60. To identify the differentiation direction of the induced cells, the leukocyte esterase activities were cytologically investigated, and the results showed that MEL-A, MEL-B, and PL induced HL60 to differentiate into granulocytes, while SL, STL-1, and STL-3 induced differentiation into monocytes. The 6 effective glycolipids also increased nitroblue tetrazolium (NBT) reducing ability, which is a common differentiation-associated characteristic in monocytes and granulocytes. Furthermore, it was also observed that these 6 glycolipids inhibited the activity of phospholipid- and Ca(2+)-dependent protein kinase. Additionally, the 6 effective glycolipids also induced the human myelogenous leukemia cell line K562 and the human basophilic leukemia cell line KU812 to differentiate into monocytes, granulocytes, and megakaryocytes.

01 Jan 1996·CytotechnologyQ4 · BIOLOGY

Succinoyl trehalose lipid induced differentiation of human monocytoid leukemic cell line U937 into monocyte-macrophages

Q4 · BIOLOGY

Article

Author: Hiroshi Shinmoto ; Tadaatsu Nakahara ; Hiroko Isoda ; Masatoshi Matsumura

A novel type of succinoyl trehalose lipid (STL-1) prepared from n-hexadecane-culture of Rhodococcus erythropolis SD-74 markedly inhibited the growth of a human monocytoid leukemic cell line, U937, and induced its morphological alteration along a monocyte-macrophage lineage. STL-1 markedly increased differention-associated characteristics in macrophage, such as nitroblue tetrazolium reducing ability, appearance of Fc receptor, phagocytic activities in U937. Furthermore, U937 cells, which were activated with STL-1 exhibited cytotoxic activity against human lung carcinoma cell line A549. However, STL-1 did not affect growth of a normal human fetal lung cell line TIG-1. The individual components of STL-1, neither sugar moiety nor fatty acids in the free form, were effective at inducing the differentiation of U937 cell. From these results, we concluded that STL-1 has low cytotoxicity against normal human cells and the ester molecule itself is responsible for the activity of inducing differentiation of human monocytoid leukemic cell line U937 into monocyte-macrophage which results in the stimulation of the production of some cytotoxic substances.

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Multiple Myeloma	Preclinical	CN	Medical College of Soochow University	-

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