Bioactivity of natural O-prenylated phenylpropenes from Illicium anisatum leaves and their derivatives against spider mites and fungal pathogens

Plant Biology

Volumn 16, Issue 2, 2014, Pages 451-456

  Koeduka, T ^a   Sugimoto, K ^a   Watanabe, B ^a   Someya, N ^b   Kawanishi, D ^a   Gotoh, T ^c   Ozawa, R ^a   Takabayashi, J ^a   Matsui, K ^d   Hiratake, J ^a  

^a KYOTO UNIVERSITY   (Japan)

^b NATIONAL AGRICULTURAL RESEARCH CENTER FOR HOKKAIDO REGION   (Japan)

^c IBARAKI UNIVERSITY   (Japan)

^d YAMAGUCHI UNIVERSITY GRADUATE SCHOOL OF MEDICINE   (Japan)

Author keywords

Antifungal activity; O prenylation; Oviposition; Phenolic hydroxy groups; Volatiles

Indexed keywords

ANTIMICROBIAL ACTIVITY; BIOACTIVITY; FUNGUS; LEAF; MITE; OVIPOSITION; PATHOGEN; SECONDARY METABOLITE; VOLATILE ORGANIC COMPOUND;

ACARI; ILLICIUM ANISATUM; TETRANYCHIDAE;

DRUG DERIVATIVE; ESSENTIAL OIL; EUGENOL; ISOEUGENOL;

ANIMAL; ANTIFUNGAL ACTIVITY; ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; DISEASE RESISTANCE; EGG LAYING; FUNGUS; ILLICIUM; METABOLISM; MICROBIOLOGY; MITE; O-PRENYLATION; PHENOLIC HYDROXY GROUPS; PHYSIOLOGY; PLANT DISEASE; PLANT LEAF; PRENYLATION; STRUCTURE ACTIVITY RELATION; VOLATILES;

ANTIFUNGAL ACTIVITY; O-PRENYLATION; OVIPOSITION; PHENOLIC HYDROXY GROUPS; VOLATILES;

ANIMALS; DISEASE RESISTANCE; EUGENOL; FUNGI; ILLICIUM; MITES; MOLECULAR STRUCTURE; OILS, VOLATILE; PLANT DISEASES; PLANT LEAVES; PRENYLATION; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84897622345     PISSN: 14358603     EISSN: 14388677     Source Type: Journal    
DOI: 10.1111/plb.12054     Document Type: Article

References (24)

1. Akhtar Y., Yu Y., Isman M.B., Plettner E. (2010) Dialkoxybenzene and dialkoxyallylbenzene feeding and oviposition deterrents against the cabbage looper, Trichoplusia ni: potential insect behavior control agents. Journal of Agricultural and Food Chemistry, 58, 4983-4991.
2. Cho J.Y., Moon J.H., Seong K.Y., Park K.H. (1998) Antimicrobial activity of 4-hydroxybenzoic acid and trans 4-hydroxycinnamic acid isolated and identified from rice hull. Bioscience, Biotechnology, and Biochemistry, 62, 2273-2276.
3. Gang D.R., Wang J., Dudareva N., Nam K.H., Simon J.E., Lewinsohn E., Pichersky E. (2001) An investigation of the storage and biosynthesis of phenylpropenes in sweet basil. Plant Physiology, 125, 539-555.
4. Howell C.R., Beier R.C., Stipanovic R.D. (1988) Production of ammonia by Enterobacter cloacae and its possible role in the biological control of Pythium preemergence damping-off by the bacterium. Ecology and Epidemiology, 78, 1075-1078.
5. Howes M.J., Kite G.C., Simmonds M.S. (2009) Distinguishing Chinese star anise from Japanese star anise using thermal desorption-gas chromatography-mass spectrometry. Journal of Agricultural and Food Chemistry, 57, 5783-5789.
6. Itoigawa M., Ito C., Tokuda H., Enjo F., Nishino H., Furukawa H. (2004) Cancer chemopreventive activity of phenylpropanoids and phytoquinoids from Illicium plants. Cancer Letters, 214, 165-169.
7. Kim H.J., Chen F., Wang X., Rajapakse N.C. (2005) Effect of chitosan on the biological properties of sweet basil (Ocimum basilicum L.). Journal of Agricultural and Food Chemistry, 53, 3696-3701.
8. Kishimoto K., Matsui K., Ozawa R., Takabayashi J. (2008) Direct fungicidal activities of C6-aldehydes are important constituents for defense responses in Arabidopsis against Botrytis cinerea. Phytochemistry, 69, 2127-2132.
9. Koeduka T., Fridman E., Gang D.R., Vassão D.G., Jackson B.L., Kish C.M., Orlova I., Spassova S.M., Lewis N.G., Noel J.P., Baiga T.J., Dudareva N., Pichersky E. (2006) Eugenol and isoeugenol, characteristic aromatic constituents of spices, are biosynthesized via reduction of a coniferyl alcohol ester. Proceedings of the National Academy of Sciences USA, 103, 10128-10133.
10. Koeduka T., Louie G.V., Orlova I., Kish C.M., Ibdah M., Wilkerson C.G., Bowman M.E., Baiga T.J., Noel J.P., Dudareva N., Pichersky E. (2008) The multiple phenylpropene synthases in both Clarkia breweri and Petunia hybrida represent two distinct protein lineages. The Plant Journal, 54, 362-374.
11. Matsui K., Minami A., Hornung E., Shibata H., Kishimoto K., Ahnert V., Kindl H., Kajiwara T., Feussner I. (2006) Biosynthesis of fatty acid-derived aldehydes is induced upon mechanical wounding and its products show fungicidal activities in cucumber. Phytochemistry, 67, 649-657.
12. Morandi D. (1996) Occurrence of phytoalexins and phenolic compounds in endomycorrhizal interactions, and their potential role in biological control. Plant and Soil, 185, 241-251.
13. Mukai R., Horikawa H., Fujiura Y., Kwamura T., Nemoto H., Nikawa T., Terao J. (2012) Prevention of disuse muscle atrophy by dietary ingestion of 8-prenylnaringenin in denervated mice. PLoS ONE, 7, e45048.
14. Pasay C., Mounsey K., Stevenson G., Davis R., Arlian L., Morgan M., Vyszenski-Moher D., Andrews K., McCarthy J. (2010) Acaricidal activity of eugenol-based compounds against scabies mites. PLoS ONE, 5, e12079.
15. Pichersky E., Noel J.P., Dudareva N. (2006) Biosynthesis of plant volatiles: nature's diversity and ingenuity. Science, 311, 808-811.
16. Raguso R.A., Pichersky E. (1995) Floral volatiles from Clarkia breweri and C. concinna (Onagraceae): recent evolution of floral scent and moth pollination. Plant Systematics and Evolution, 194, 55-67.
17. Shibuya M., Abe K., Nakahashi Y., Kubota S. (1978) Phenolic components from leaf oil of Illicium anisatum L. Chemical and Pharmaceutical Bulletin, 26, 2671-2673.
18. Tahara S., Ibrahim R.K. (1995) Prenylated isoflavonoids - an update. Phytochemistry, 38, 1073-1094.
19. Tan K.H., Nishida R., Toong Y.C. (2002) Floral synomone of a wild orchid, Bulbophyllum cheiri, lures Bactrocera fruit flies for pollination. Journal of Chemical Ecology, 28, 1161-1172.
20. Tan K.H., Tan L.T., Nishida R. (2006) Floral phenylpropanoid cocktail and architecture of Bulbophyllum vinaceum orchid in attracting fruit flies for pollination. Journal of Chemical Ecology, 32, 2429-2441.
21. Tewary D.K., Bhardwaj A., Sharma A., Sinha A.K. (2006) Bioactivity and structure-activity relationship of natural methoxylated phenylpropenes and their derivative against Aphis craccivora Koch (Hemiptera: Aphididae). Journal of Pesticide Science, 79, 209-214.
22. Wang G.W., Hu W.T., Huang B.K., Qin L.P. (2011) Illicium verum: a review on its botany, traditional use, chemistry and pharmacology. Journal of Ethnopharmacology, 136, 10-20.
23. Yakushijin K., Tohshima T., Suzuki R., Murata H., Lu S.T., Furukawa H. (1983) Studies on the constituents of the plants Illicium species. II. Structures of phenolic components. Chemical and Pharmaceutical Bulletin, 31, 2879-2883.
24. Zahringer U., Schaller E., Grisebach H.Z. (1981) Induction of phytoalexin synthesis in soybean. Structure and reactions of naturally occurring and enzymatically prepared prenylated pterocarpans from elicitor-treated cotyledons and cell cultures of soybean. Zeitschrift für Naturforschung C, 36, 234-241.