Peak AAA fatty acid homolog contaminants present in the dietary supplement l-Tryptophan associated with the onset of eosinophilia-myalgia syndrome.

The eosinophilia-myalgia syndrome (EMS) outbreak that occurred in the USA and elsewhere in 1989 was caused by the ingestion of Showa Denko K.K. (SD) L-tryptophan (L-Trp). "Six compounds" detected in the L-Trp were reported as case-associated contaminants. Recently the final and most statistically significant contaminant, "Peak AAA" was structurally characterized. The "compound" was actually shown to be two structural isomers resulting from condensation reactions of L-Trp with fatty acids derived from the bacterial cell membrane. They were identified as the indole C-2 anteiso (AAA1-343) and linear (AAA2-343) aliphatic chain isomers. Based on those findings, we utilized a combination of on-line HPLC-electrospray ionization mass spectrometry (LC-MS), as well as both precursor and product ion tandem mass spectrometry (MS/MS) to facilitate identification of a homologous family of condensation products related to AAA1-343 and AAA2-343. We structurally characterized eight new AAA1-XXX/AAA2-XXX contaminants, where XXX represents the integer molecular ions of all the related homologs, differing by aliphatic chain length and isomer configuration. The contaminants were derived from the following fatty acids of the bacterial cell membrane, 5-methylheptanoic acid (anteiso-C8:0) for AAA1-315; n-octanoic acid (n-C8:0) for AAA2-315; 6-methyloctanoic acid (anteiso-C9:0) for AAA1-329; n-nonanoic acid (n-C9:0) for AAA2-329; 10-methyldodecanoic acid (anteiso-C13:0) for AAA1-385; n-tridecanoic acid (n-C13:0) for AAA2-385; 11-methyltridecanoic acid (anteiso-C14:0) for AAA1-399; and n-tetradecanoic acid (n-C14:0) for AAA2-399. The concentration levels for these contaminants were estimated to be 0.1-7.9 µg / 500 mg of an individual SD L-Trp tablet or capsule The structural similarity of these homologs to case-related contaminants of Spanish Toxic Oil Syndrome (TOS) is discussed.

[Research on components of Cornus officinalis extracted by supercritical carbon dioxide].

OBJECTIVE: To study the chemical constituents of Cornus officinalis extracted by supercritical carbon dioxide fluid extraction (SFE). METHOD: The process was performed at 40 centigrade with pressures of 15 MPa for 2 hours and with CO2 fluid and gas at the flow rate of 22.0 kg x h(-1) and 18.0 kg x h(-1) respectively. The chemical constituents of the SFE extractions were determined by GC-MS. RESULT: The total amount of extractable substances or yields by SFE is 2.42% (mass). 31 Chemical constituents were identified and their relative contents were determined by normalization method of area. CONCLUSION: The major components identified in the extractions are 1,2-benzenedicarboxylic acid, butyl 2-methylpropyl ester, isopropyl myristate etc.

[Analysis of the volatile organic acids in 5 kinds of pericarpium Trichosanthis].

The volatile organic acids in the pericarps of Trichosanthes kirilowii, T. rosthornii, T. truncata, T. hupehensis and T. cucumeroides (Cucurbitaceae) were analyzed by methylation, GC and GC-MS-DS. The results showed that they were composed of fifteen long-chain fatty acids, such as palmitic, linolenic, linoleic, lauric, myristic acid, etc.