Isolation and identification of alectrol as (+)-orobanchyl acetate, a germination stimulant for root parasitic plants

Phytochemistry

Volumn 69, Issue 2, 2008, Pages 427-431

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

^a UTSUNOMIYA UNIVERSITY   (Japan)

^b TOKYO UNIVERSITY OF AGRICULTURE AND TECHNOLOGY   (Japan)

^c TEIKYO UNIVERSITY   (Japan)

Author keywords

Alectrol; Leguminosae; Orobanchaceae; Orobanche minor; Orobanchyl acetate; Strigolactone; Trifolium pratense

Indexed keywords

ALECTROL; LACTONE; STRIGOL; UNCLASSIFIED DRUG;

ARTICLE; CHEMISTRY; DRUG EFFECT; GERMINATION; GROWTH, DEVELOPMENT AND AGING; ISOLATION AND PURIFICATION; METABOLISM; OROBANCHE; PLANT ROOT; STEREOISOMERISM;

GERMINATION; LACTONES; OROBANCHE; PLANT ROOTS; STEREOISOMERISM;

FABACEAE; GLYCINE MAX; OROBANCHACEAE; OROBANCHE; OROBANCHE MINOR; TRIFOLIUM PRATENSE;

EID: 37549066296     PISSN: 00319422     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.phytochem.2007.07.017     Document Type: Article

References (19)

1. Akiyama K., Matsuzaki K., and Hayashi H. Plant sesquiterpenes induce hyphal branching in arbuscular mycorrhizal fungi. Nature 435 (2005) 824-827
2. Akiyama K., and Hayashi H. Strigolactones: chemical signals for fungal symbionts and parasitic weeds in plant roots. Ann. Bot. 97 (2006) 925-931
3. Bouwmeester H.J., Matusova R., Zhongkui S., and Beale M.H. Secondary metabolite signalling in host--parasitic plant interactions. Curr. Opin. Plant Biol. 6 (2003) 358-364
4. Chae S.H., Yoneyama K., Takeuchi Y., and Joel D.M. Fluridone and norflurazon, carotenoid-biosynthesis inhibitors, promote seed conditioning and germination of the holoparasite Orobanche minor. Physiol. Plant. 120 (2004) 328-337
5. Frischmuth K., Samson E., Kranz A., Welzel P., Meuer H., and Sheldrick W.S. Routes to derivatives of strigol (the witchweed germination factor) modified in the 5-position. Tetrahedron 47 (1991) 9793-9806
6. Müller S., Hauck C., and Schildknecht H. Germination stimulants produced by Vigna unguiculata Walp cv Saunders Upright. J. Plant Growth Regul. 11 (1992) 77-84
7. Hirayama K., and 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
8. Joel D.M., Steffens J.C., and Matthews D.E. Germination of weedy root parasites. In: Kigel J., and Galili G. (Eds). Seed Development and Germination (1995), Marcel Dekker, New York 567-597
9. Mori K., Matsui J., Bando M., Kido M., and Takeuchi Y. Synthetic disproof against the structure proposed for alectrol, the germination stimulant from Vigna unguiculata. Tetrahedron Lett. 39 (1998) 6023-6026
10. Ohashi, K., Sasago, H., Matsuura, H., Yoshihara, T., Kamata, K., 2006. Striga germination stimulant exuded from roots of cowpea. Abstr. Joint Meeting of Hokkaido and Tohoku Branches of Japan Society for Bioscience, Biotechnology, and Agrochemistry, C-1.
11. Parker C., and Riches C.R. Parasitic Weeds of the World: Biology and Control (1993), CAB International, Wallingford
12. Sato D., Awad A.A., Chae S.H., Yokota T., Sugimoto Y., Takeuchi Y., and Yoneyama K. Analysis of strigolactones, germination stimulants for Striga and Orobanche, by high-performance liquid chromatography/tandem mass spectrometry. J. Agric. Food Chem. 51 (2003) 1162-1168
13. Sato D., Awad A.A., Takeuchi Y., and Yoneyama K. Confirmation and quantification of strigolactones, germination stimulants for root parasitic plants Striga and Orobanche, produced by cotton. Biosci. Biotechnol. Biochem. 69 (2005) 98-102
14. Wigchert S.C.M., Kuiper E., Boelhouwer G.J., Nefkens G.H.L., Verkleij J.A.C., and Zwanenburg B. Dose-response of seeds of the parasitic weeds Striga and Orobanche toward the synthetic germination stimulants GR 24 and Nijmegen 1. J. Agric. Food Chem. 47 (1999) 1705-1710
15. Yokota T., Sakai H., Okuno K., Yoneyama K., and Takeuchi Y. Alectrol and orobanchol, germination stimulants for Orobanche minor, from its host red clover. Phytochemistry 49 (1998) 1967-1973
16. Yoneyama K., Takeuchi Y., and Yokota T. Production of clover broomrape seed germination stimulants by red clover root requires nitrate but is inhibited by phosphate and ammonium. Physiol. Plant. 112 (2001) 25-30
17. Yoneyama K., Yoneyama K., Takeuchi Y., and Sekimoto H. Phosphorus deficiency in red clover promotes exudation of orobanchol, the signal for mycorrhizal symbionts and germination stimulant for root parasites. Planta 225 (2007) 1031-1038
18. Yoneyama K., Sato D., Takeuchi Y., Sekimoto H., Yokota T., and Sassa T. Search for germination stimulants and inhibitors for root parasitic weeds. In: Duke S.O., and Rimando A. (Eds). Natural Products for Pest Management. ACS Symp. Ser. 927 (2006), American Chemical Society, Oxford 88-98
19. Zhou W.J., Yoneyama K., Takeuchi Y., Iso S., Rungmekarat S., Chae S.H., Sato D., and Joel D.M. In vitro infection of host roots by differentiated calli of the parasitic plant Orobanche. J. Exp. Bot. 55 (2004) 899-907