2′-Epi-orobanchol and solanacol, two unique strigolactones, germination stimulants for root parasitic weeds, produced by tobacco

Journal of Agricultural and Food Chemistry

Volumn 55, Issue 20, 2007, Pages 8067-8072

  Xie, Xiaonan ^a,b   Kusumoto, Dai ^b   Takeuchi, Yasutomo ^b   Yoneyama, Kaori ^b   Yamada, Yoichi ^b   Yoneyama, Koichi ^b  

^a TOKYO UNIVERSITY OF AGRICULTURE AND TECHNOLOGY   (Japan)

^b UTSUNOMIYA UNIVERSITY   (Japan)

Author keywords

2 epi orobanchol; Germination stimulant; Orobanchol; Parasitic weeds; Solanacol; Strigolactone; Tobacco

Indexed keywords

NICOTIANA TABACUM; OROBANCHE; PHELIPANCHE;

(4 HYDROXY 5,8 DIMETHYL 3 (4 METHYL 5 OXO 2,5 DIHYDROFURAN 2 YLOXY)METHYLENE) 3A,4 DIHYDRO 3H INDENO(1,2 B)FURAN 2(8BH) ONE; (4-HYDROXY-5,8-DIMETHYL-3-(4-METHYL-5-OXO-2,5-DIHYDROFURAN-2-YLOXY)METHYLENE)-3A,4-DIHYDRO-3H-INDENO(1,2-B)FURAN-2(8BH)-ONE; LACTONE; OROBANCHOL; UNCLASSIFIED DRUG;

ARTICLE; CHEMISTRY; DRUG EFFECT; GERMINATION; GROWTH, DEVELOPMENT AND AGING; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OROBANCHE; PLANT ROOT; TOBACCO;

CHROMATOGRAPHY, LIQUID; GERMINATION; LACTONES; MAGNETIC RESONANCE SPECTROSCOPY; MASS SPECTROMETRY; OROBANCHE; PLANT ROOTS; TOBACCO;

EID: 38349045213     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf0715121     Document Type: Article

References (22)

1. Parker, C.; Riches, C. R. Parasitic Weeds of the World: Biology and Control; CAB International: Wallingford, U.K., 1993.
2. Joel, D. M.; Steffens, J. C.; Matthews, D. E. Germination of weedy root parasites. In Seed Development and Germination; Kigel, J., Galili, G., Eds.; Dekker: New York, 1995; pp 567-597.
3. Bouwmeester, H. J.; Matusova, R.; Zhongkui, S.; Beale, M. H. Secondary metabolite signalling in host-parasitic plant interactions. Curr. Opin. Plant Biol. 2003, 6, 358-364.
4. Akiyama, K.; Matsuzaki, K.-i.; Hayashi, H. Plant sesquiterpenes induce hyphal branching in arbuscular mycorrhizal fungi. Nature 2005, 435, 824-827.
5. Akiyama, K.; Hayashi, H. Strigolactones: chemical signals for fungal symbionts and parasitic weeds in plant roots. Ann. Bot. 2006, 97, 925-931.
6. Cook, C. E.; Whichard, L. P.; Turner, B.; Wall, M. E.; Egley, G. H. Germination of witchweed (Striga lutea Lour.): isolation and properties of a potent stimulant. Science 1966, 154, 1189-1190.
7. Cook, C. E.; Whichard, L. P.; Wall, M. E.; Egley, G. H.; Coggon, P.; Luhan, P. A.; McPhail, A. T. Germination stimulants. II. The structure of strigol - a potent seed germination stimulant for witchweed (Striga lutea Lour.). J. Am. Chem. Soc. 1972, 94, 6198-6199.
8. Müller, S.; Hauck, C.; Schildknecht, H. Germination stimulants produced by Vigna unguiculata Walp cv Saunders Upright. J. Plant Growth Regul. 1992, 11, 77-84.
9. Hauck, C.; Müller, S.; Schildknecht, H. A germination stimulant for parasitic flowering plants from Sorghum bicolor, a genuine host plant. J. Plant Physiol. 1992, 139, 474-478.
10. Yokota, T.; Sakai, H.; Okuno, K.; Yoneyama, K.; Takeuchi, Y. Alectrol and orobanchol, germination stimulants for Orobanche minor, from its host red clover. Phytochemistry 1998, 49, 1967-1973.
11. Awad, A. A.; Sato, D.; Kusumoto, D.; Kamioka, H.; Takeuchi, Y.; Yoneyama, K. Characterization of strigolactones, germination stimulants for the root parasitic plants Striga and Orobanche, produced by maize, millet and sorghum. Plant Growth Regul. 2006, 48, 221-227.
12. Xie, X.; Yoneyama, K. Kusumoto, D.; Yamada, Y.; Yokota, T.; Takeuchi, Y.; Yoneyama, K., Isolation and identification of alectrol as (+)-orobanchyl acetate, a novel germination stimulant for root parasitic plants. Phytochemistry 2007, in press.
13. Yoneyama, K.; Sato, D.; Takeuchi, Y.; Sekimoto, H.; Yokota, T.; Sassa, T. Search for germination stimulants and inhibitors for root parasitic weeds. ACS Symp. Ser. 2006, 927, 88-98.
14. Sato, D.; Awad, A. A.; Chae, S. H.; Yokota, T.; Sugimoto, Y.; Takeuchi, Y.; Yoneyama, K. Analysis of strigolactones, germination stimulants for Striga and Orobanche, by high-performance liquid chromatography/tandem mass spectrometry. J. Agric. Food Chem. 2003, 51, 1162-1168.
15. Sato, D.; Awad, A. A.; Takeuchi, Y.; Yoneyama, K. Confirmation and quantification of strigolactones, germination stimulants for root parasitic plants Striga and Orobanche, produced by cotton. Biosci., Biotechnol., Biochem. 2005, 69, 98-102.
16. Yoneyama, K.; Yoneyama, K.; Takeuchi, Y.; Sekimoto, H. Phosphorus deficiency in red clover promotes exudation of orobanchol, the signal for mycorrhizal symbionts and germination stimulant for root parasites. Planta 2007, 225, 1031-1038.
17. Zhou, W. J.; Yoneyama, K.; Takeuchi, Y.; Iso, S.; Rungmekarat, S.; Chae, S. H.; Sato, D.; Joel, D. M. In vitro infection of host roots by differentiated calli of the parasitic plant Orobanche. J. Exp. Bot. 2004, 55, 899-907.
18. Hirayama, K.; Mori, K. Plant bioregulators, 5. Synthesis of (+)-strigol and (+)-orobanchol, the germination stimulants, and their stereoisomers by employing lipase-catalyzed asymmetric acetylation as the key step. Eur. J. Org. Chem. 1999, 2211-2217.
19. Welzel, P.; Röhrig, S.; Milkova, Z. Strigol-type germination stimulants: the C-2′ configuration problem. J. Chem. Soc., Chem. Commun. 1999, 2017-2022.
20. Sugimoto, Y.; Wigchert, S. C. M.; Thuring, J. W. J. F.; Zwanenburg, B. Synthesis of all eight stereoisomers of the germination stimulant sorgolactone. J. Org. Chem. 1998, 63, 1259-1267.
21. Mangnus, E. M.; Dommerholt, F. J.; De Jong, R. L. P.; Zwanenburg, B. Improved synthesis of strigol analog GR24 and evaluation of the biological activity of its diastereomers. J. Agric. Food Chem. 1992, 40, 1230-1235.
22. Wigchert, S. C. M.; Zwanenburg, B. An expeditious preparation of all enantiopure diastereoisomers of aromatic A-ring analogs of strigolactones, germination stimulants for seeds of the parasitic weeds Striga and Orobanche. J. Chem. Soc., Perkin Trans. 1 1999, 2617-2623.