The Fungicidal Terpenoids and Essential Oil from Litsea cubeba in Tibet

A new C9 monoterpenoid acid (litseacubebic acid, 1) and a known monoterpene lactone (6R)-3,7-dimethyl-7-hydroxy-2-octen-6-olide (2), along with three known compounds – vanillic acid (3), trans-3,4,5-trimethoxylcinnamyl alcohol (4), and oxonantenine (5) – were isolated with bioassay-guided purification from the fruit extract of Litsea cubeba collected in Tibet. The structure of 1 was elucidated by MS, 1H-NMR, 13C-NMR, COSY, HSQC, HMBC, NOE spectral data as 2,6-dimethyl-6-hydroxy-2E,4E-hepta-2,4-diene acid. Additionally 33 compounds were identified from the essential oil of L. cubeba. The preliminary bioassay results showed that 1 and 2 have good fungicidal activities against Sclerotinia sclerotiorum, Thanatephorus cucumeris, Pseudocer-cospora musae and Colletotrichum gloeosporioides at the concentration of 588 and 272 μM, and the essential oil has good fungicidal activities against T. cucumeris and S. sclerotiorum, with IC50 values of 115.58 and 151.25 μg/mL, repectively.

[1]  M. Isman,et al.  Comparative toxicity of essential oils of Litsea pungens and Litsea cubeba and blends of their major constituents against the cabbage looper, Trichoplusia ni. , 2009, Journal of agricultural and food chemistry.

[2]  C. Duh,et al.  Litebamine, a novel phenanthrene alkaloid from Litsea cubeba☆ , 1991 .

[3]  M. Tomita,et al.  [Studies on the alkaloids of Formosan lauraceous plants. V. alkaloids of litsea cubeba persoon]. , 1965, Yakugaku zasshi : Journal of the Pharmaceutical Society of Japan.

[4]  Zi-Tao Jiang,et al.  Complexation and molecular microcapsules of Litsea cubeba essential oil with β-cyclodextrin and its derivatives , 2009 .

[5]  J. Anzai,et al.  Tyrosinase inhibitor from black rice bran. , 2003, Journal of agricultural and food chemistry.

[6]  Chien-Kuang Chen,et al.  Two Dibenzopyrrocoline Alkaloids from Litsea cubeba , 1996 .

[7]  M. Luo,et al.  Acute and genetic toxicity of essential oil extracted from Litsea cubeba (Lour.) Pers. , 2005, Journal of food protection.

[8]  Chi-Hung Huang,et al.  Litebamine, a phenanthrene alkaloid from the wood of Litsea cubeba, inhibits rat smooth muscle cell adhesion and migration on collagen. , 2008, European journal of pharmacology.

[9]  Sun Young Lee,et al.  Lactones from the leaves of Litsea japonica and their anti-complement activity. , 2003, Journal of natural products.

[10]  N. T. Tam,et al.  Chemical Variability of Litsea cubeba Leaf Oil from Vietnam , 2005 .

[11]  Chien-Kuang Chen,et al.  Quaternary Alkaloids from Litsea cubeba and Cryptocarya konishii , 1993 .

[12]  G. Cabrera,et al.  Neric acid derivatives produced by the honey bee fungal entomopathogen Ascosphaera apis , 2008 .

[13]  H. Surburg,et al.  Constituents of commercial Labdanum oil , 1998 .

[14]  H. Matsuura,et al.  Isolation of α-glusosidase inhibitors from hyssop (Hyssopus officinalis) , 2004 .

[15]  J. Gaddum Probit Analysis , 1948, Nature.

[16]  S. S. Lee,et al.  Litebamine N-homologues: preparation and anti-acetylcholinesterase activity. , 1998, Journal of natural products.