Isolation of S-n-butylcysteine sulfoxide and six n-butyl-containing thiosulfinates from Allium siculum.
Isolation and identification of (S(S)R(C))-S-n-butylcysteine sulfoxide (1) from the bulbs of Allium siculum is reported. This compound was found in all parts of the plant (bulbs, stem, leaves, and flowers) along with known compounds (S(S)R(C))-S-methyl- and (R(S)R(C))-(E)-S-(1-propenyl)cysteine sulfoxides (2 and 3, respectively). In addition, six n-butyl-containing thiosulfinates (4-9) have been found in a CH2Cl2 extract of the bulbs. Structures were determined by a combination of spectral methods (primarily NMR and MS) and by comparison with authentic compounds obtained by synthesis. Antimicrobial activities of 4-7 and 9 are reported.
Department of Chemistry, State University of New York at Albany, Albany, New York 12222, USA.
Roman
R
Kubec
Seokwon
S
Kim
Denise M
DM
McKeon
Rabi A
RA
Musah
D000490:Allium / Q000737:chemistry*; D000900:Anti-Bacterial Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D001409:Bacillus cereus / Q000187:drug effects; D003545:Cysteine / Q000031:analogs & derivatives* / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D004926:Escherichia coli / Q000187:drug effects; D007711:Klebsiella pneumoniae / Q000187:drug effects; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D009518:New York; D019906:Nuclear Magnetic Resonance, Biomolecular; D010946:Plants, Medicinal; D011550:Pseudomonas aeruginosa / Q000187:drug effects; D017550:Spectroscopy, Fourier Transform Infrared; D013211:Staphylococcus aureus / Q000187:drug effects; D020615:Stenotrophomonas maltophilia / Q000187:drug effects; D013237:Stereoisomerism; D013292:Streptococcus agalactiae / Q000187:drug effects; D013441:Sulfinic Acids / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D013454:Sulfoxides
D000900:Anti-Bacterial Agents; C465288:S-n-butylcysteine sulfoxide; D013441:Sulfinic Acids; D013454:Sulfoxides; C100040:thiosulfinic acids; D003545:Cysteine