HOME HELP FEEDBACK SUBSCRIPTIONS ARCHIVE SEARCH TABLE OF CONTENTS		QUICK SEARCH:   [advanced] Author: Keyword(s): Year:  Vol:  Page:

J. Biol. Chem., Vol. 278, Issue 31, 28607-28611, August 1, 2003

This Article Full Text Full Text (PDF) All Versions of this Article: 278/31/28607    most recent M304185200v1 Alert me when this article is cited Alert me if a correction is posted Citation Map Services Email this article to a friend Similar articles in this journal Similar articles in PubMed Alert me to new issues of the journal Download to citation manager Citing Articles Citing Articles via HighWire Citing Articles via Google Scholar Google Scholar Articles by Dayan, F. E. Articles by Rimando, A. M. Search for Related Content PubMed PubMed Citation Articles by Dayan, F. E. Articles by Rimando, A. M. Social Bookmarking                      What's this?

Elucidation of the Biosynthetic Pathway of the Allelochemical Sorgoleone Using Retrobiosynthetic NMR Analysis^*

Franck E. Dayan , Isabelle A. Kagan and Agnes M. Rimando

From the United States Department of Agriculture/Agricultural Research Service, Natural Products Utilization Research Unit, University, Mississippi 38677

NMR analyses of the labeling pattern obtained using various ¹³C-labeled precursors indicated that both the lipid tail and the quinone head of sorgoleone, the main allelopathic component of the oily root exudate of Sorghum bicolor, were derived from acetate units, but that the two moieties were synthesized in different subcellular compartments. The 16:3 fatty acid precursor of the tail is synthesized by the combined action of fatty-acid synthase and desaturases most likely in the plastids. It is then exported out of the plastids and converted to 5-pentadecatriene resorcinol by a polyketide synthase. This resorcinol intermediate was identified in root hair extracts. The lipid resorcinol intermediate is then methylated by a S-adenosylmethionine-dependent O-methyltransferase and subsequently dihydroxylated by a P450 monooxygenase to yield the reduced form of sorgoleone.

Received for publication, April 22, 2003 , and in revised form, May 21, 2003.

^* The costs of publication of this article were defrayed in part by the payment of page charges. This article must therefore be hereby marked "advertisement" in accordance with 18 U.S.C. Section 1734 solely to indicate this fact.

To whom correspondence should be addressed. Tel.: 662-915-1039; Fax: 662-915-1035; E-mail: fdayan{at}ars.usda.gov.

CiteULike    Complore    Connotea    Del.icio.us    Digg    Reddit    Technorati    What's this?

This article has been cited by other articles:

				S. R. Baerson, F. E. Dayan, A. M. Rimando, N. P. D. Nanayakkara, C.-J. Liu, J. Schroder, M. Fishbein, Z. Pan, I. A. Kagan, L. H. Pratt, et al. A Functional Genomics Investigation of Allelochemical Biosynthesis in Sorghum bicolor Root Hairs J. Biol. Chem., February 8, 2008; 283(6): 3231 - 3247. [Abstract] [Full Text] [PDF]

				F. E. Dayan, S. B. Watson, and N. P. D. Nanayakkara Biosynthesis of lipid resorcinols and benzoquinones in isolated secretory plant root hairs J. Exp. Bot., October 10, 2007; (2007) erm173v1. [Abstract] [Full Text] [PDF]

				Z. Pan, A. M. Rimando, S. R. Baerson, M. Fishbein, and S. O. Duke Functional Characterization of Desaturases Involved in the Formation of the Terminal Double Bond of an Unusual 16:3{Delta}9, 12, 15 Fatty Acid Isolated from Sorghum bicolor Root Hairs J. Biol. Chem., February 16, 2007; 282(7): 4326 - 4335. [Abstract] [Full Text] [PDF]

				O. Sayanova, R. Haslam, I. Guschina, D. Lloyd, W. W. Christie, J. L. Harwood, and J. A. Napier A Bifunctional {Delta}12,{Delta}15-Desaturase from Acanthamoeba castellanii Directs the Synthesis of Highly Unusual n-1 Series Unsaturated Fatty Acids J. Biol. Chem., December 1, 2006; 281(48): 36533 - 36541. [Abstract] [Full Text] [PDF]

				C. K.Y. Yu, K. Springob, J. Schmidt, R. L. Nicholson, I. K. Chu, W. K. Yip, and C. Lo A Stilbene Synthase Gene (SbSTS1) Is Involved in Host and Nonhost Defense Responses in Sorghum Plant Physiology, May 1, 2005; 138(1): 393 - 401. [Abstract] [Full Text] [PDF]

				X. Yang, B. E. Scheffler, and L. A. Weston SOR1, a gene associated with bioherbicide production in sorghum root hairs J. Exp. Bot., October 1, 2004; 55(406): 2251 - 2259. [Abstract] [Full Text] [PDF]