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The steam-volatile constituents from leaves of Japanese pepper were separated by column chromatography and GLC, and their chemical structures were studied by IR, NMR, and mass spectrometry. The volatile oil was found to be composed of about 100 components; those identified were as follows: 15 hydrocarbons (α- and β-pinene, camphene, sabinene, myrcene, α- and β-phellandrene, limonene, p-cymene, terpinolene, α-copaene, caryophyllene, humulene, α-muurolene, and γ-cadinene), 16 alcohols (2-penten-1-ol, n-hexanol, 3-hexen-1-ol, trans- and cis-sahinene hydrate, cis-linalool oxide, linalool, isopulegol, neoisopulegol, terpinen-4-ol, α- and δ-terpineol, limonen-4-ol, benzyl alcohol, β-phenylethyl alcohol, and nerolidol), 2 aldehydes (2-hexenal and citronellal), 1 ketone (cryptone), 7 esters(isobutyl caproate, linalyl acetate, citronellyl acetate, terpinyl acetate, geranyl acetate, methyl salicylate, and methyl cinnamate) and 2 ethers (1,8-cineol and methyl chavicol).

Enantiomeric differentiations of various (R)-and (5')ammonium and (R)and (S)-a-amino acid ester salts bySUMMARY The interactions of the hydrobromides of (R)and (S)-alanine-N-methylanilides (1) with 24-, 27and 36-membered ring pseudopeptides (H-24, H-27 and H-36, respectively) derived from glycine and (2 S, 3'S)-4-methyl-2-(2'-0~0-3'-isobutyl-l'-piperazinyl)pentanoic acid were studied by means of ' H and I3C NMR measurements in CDCI, . It was found from these results that H-24 and H-27 distinguished ( R )and (S)-isomers of 1, while H-36 did not entirely. Moreover, the enantioface-differentiating abilities of these cyclic peptides were investigated by means of 'H NMR measurements in CDCI, using ( R )and (S)-1-phenylethylammonium and ( R )and (S)-p-methoxy-1-phenylethylammonium bromides as the substrates, showing that the enantioselectivity of H-36 is superior to those of H-24 and H-27. Also, the chiral recognition ability of H-24 for the hydrochlorides of (R)and (S)-alanine (Ala), -leucine (Leu), -methionhe (Met), -phenylalanine (Phe), -proline (Pro) and -valine (Val) methyl esters were examined by 'H and I3C NMR measurements in CDCI, . Among these hydrochlorides, HCI . Phe-OCH, was distinguished more effectively with H-24.

27-and 36-membered ring peptides were prepared using glycine, (2S, 3'S)4methyL2-(2'-oxo-3'-isobutyl-l '-piperaziny1)pentanoic acid (2) and (2 S,3' S)-3-pheny1-2-(2'-0~0-3'-benzyl-l '-pipera-ziny1)propanoic acid as the units of peptides. The interactions of 1-phenylethylammonium (1) and p-methoxy-I-phenylethylammonium bromides (11) with these cyclic peptides were studied by 'H and 13C NMR measurements in CDCI,. It was found from these results that the peptides distinguish the enantiomers (Rand S-isomers) of the substrates. Furthermore, it was shown that the enantioface-differentiating abilities of 36-membered ring peptides are superior to those of , 27-membered rings. 0 1990, HUthig & Wepf Verlag, Basel CCC 0025-1 16X/90/$03.00

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