The volatile components from the thalloid liverwort, Marchantia paleacea subsp. diptera were investigated by HS-SPME-GC-MS analysis. The monocyclic monoterpene aldehyde, perillaldehyde was identified for the first time as the major component and its content was about 50% of the volatiles, along with β-pinene, limonene, β-caryophyllene, α-selinene and β-selinene as minor volatiles. Using MD (Multi-dimensional) GC-MS analysis equipped with a chiral column as the second column, the chirality was determined of both perillaldehyde and limonene, which was considered as the precursor of perillaldehyde,. Both compounds were (S)-(-)-enantiomers (over 99.0 %) and (R)-enantiomers (less than 0.5 %). This is the first report of the existence of perillaldehyde in liverworts.
AsakawaY. (1982) Chemical constituents of Hepaticae. In Progress in the Chemistry of Organic Natural Products. 42, HerzW, GrisebachH, KirbyGW. (Eds). Springer, Vienna, Austria. pp. 1–285;
2.
AsakawaY. (1995) Chemical constituents of bryophytes. In Progress in the Chemistry of Organic Natural Products, 65, HerzW, KirbyWB, MooreRE, SteglichW, TammCh. (Eds). Springer, Vienna, Austria. pp. 1–618;
3.
AsakawaY, LudwiczukA, NagashimaF. (2013) Chemical constituents of bryophytes: Bio- and chemical diversity, biological activity and chemosystematics. In Progress in the Chemistry of Organic Natural Products. 95, KinghornDA, FalkH, KobayashiJ. (Eds.). Springer, Vienna, Austria. pp. 1–796;
4.
AsakawaY, LudwiczukA, NagashimaF. (2013) Phytochemical and biological studies of bryophytes. Phytochemistry, 91, 52–80;
5.
AsakawaY. (2004) Odor and tasting substances from bryophytes. Aroma Research, 5, 204–212;
6.
AsakawaY. (2007) Scent substances from bryophytes. Bryological Research, 9, 198–203;
7.
LudwiczukA, AsakawaY. (2015) Chemosystematic value of essential oil components in liverwort species. A review. Flavour and Fragrance Journal, 30, 189–196.
8.
OchiaiN (2014) The poster presentation by high school student, In Proceedings of the 78th Annual Meeting of the Botanical Society of Japan, Kanagawa 2014, September 12–14. (H-15) p. 29;
9.
ChangHC, GageDA, OrielPJ. (1995) Cloning and expression of limonene degradation pathway from Bacillus stearothermophilus in Escherichia coli. Journal of Food Science, 60, 551–553.
10.
SavithiryN, OrielPJ. (1998) Method of production of monoterpene derivatives of limonene. USP–5,763,237
11.
TrytekM, FiedurekJ. (2005) A novel psychrotropic fungus Moritierella minutissima for D-limonene biotransformation. Biotechnology Letter, 27, 149–153;
12.
FujitaY, YamashitaT. (1942) Studies on the essential oils in the Southeast Asian countries (reports III), Essential oil of Limnophila aromatica L. Part 1. Journal of Chemical Society of Japan, 995–998;
