Synthesis of the germination stimulant (±)-strigol

MacAlpine, Gerald A.; Raphael, R. A.; Shaw, A.; Taylor, Andrew; Wild, Hans‐Jakob

doi:10.1039/p19760000410

Cited by 70 publications

(47 citation statements)

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“…Another strigolactone, orobanchol ( 3 ), was isolated from red clover, Trifolium pretense L., an Orobanche host 15. The structures of compounds 1 to 3 have been confirmed by total synthesis;16–25 however, the spectroscopic data of the synthetic compound26, 27 with structure 4 were not in accordance with those reported for natural alectrol 12. Since then, the true structure of alectrol has remained controversial, and a bridged structure 5 for this stimulant was proposed 28.…”

Section: Naturally Occurring Germination Stimulants—the Strigolactonementioning

confidence: 99%

Structure and function of natural and synthetic signalling molecules in parasitic weed germination

Zwanenburg

Mwakaboko

Reizelman

et al. 2009

Pest Management Science

220

192

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The structures of naturally occurring germination stimulants for seeds of the parasitic weeds Striga spp. and Orobanche spp. are described. The bioactiphore in this strigolactone family of stimulants is deduced from a structure-activity relationship and shown to reside in the CD part of the stimulant molecule. A molecular mechanism for the initial stages of seed germination is proposed. The influence of stereochemistry on the stimulant activity is significant. Combining this molecular information leads to a model for the design of synthetic strigolactones. Nijmegen-1 is a typical example of a highly active, newly designed synthetic stimulant. The occurrence of natural stimulants not belonging to the strigolactone family, such as cotylenin and parthenolide, is briefly described. The biosynthesis of natural strigolactones from beta-carotene is analysed in terms of isolated and predicted stimulants. This scheme will be helpful in the search for new strigolactones from root exudates. Protein fishing experiments to isolate and characterise the receptor protein using biotin-labelled GR 24 are described. A receptor protein of 60 kD was identified by this method. Nijmegen-1 has been tested as a suicidal germination agent in field trials on tobacco infested by Orobanche ramosa L. The preliminary results are highly rewarding. Finally, some future challenges in synthesis are described. These include synthesising new natural and synthetic stimulants and establishing the molecular connection between strigolactones as germination stimulants, as the branching factor for arbuscular mycorrhizal fungi and as an inhibitor of shoot branching.

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Section: Naturally Occurring Germination Stimulants—the Strigolactonementioning

confidence: 99%

Structure and function of natural and synthetic signalling molecules in parasitic weed germination

Zwanenburg

Mwakaboko

Reizelman

et al. 2009

Pest Management Science

220

192

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“…Heather et al (1974) ont Ct C les premiers h rCaliser sa synthkse, dont ils ont rapport6 les dCtails en 1976. MacAlpine et al (1974MacAlpine et al ( , 1976) sont Cgalement parvenus a synthCtiser la molCcule en utilisant une mCthode quelque peu differente.…”

Section: Le Stimulant De Germinationunclassified

La relation entre le Striga hermonthica et ses hôtes: une synthèse

Olivier¹

1996

Can. J. Bot.

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R&sumC : La mauvaise herbe parasite Striga hermonthica inflige des pertes de rendement considCrables au mais, au mil et au sorgho en Afrique. L'importance des dommages subis par les cultures est liCe B leur interaction Ctroite avec le parasite. La graine de S. hermonthica germe en rCponse B des stimulants de germination exsudCs par les racines de cCrCales. L'extrCmitC de la radicule se differencie ensuite en un haustorium qui s'attache B une racine de l'hate et pCnbtre ses tissus. Une connexion est alors Ctablie entre les systbmes vasculaires des deux plantes, ce qui permet au parasite de s'approvisionner en eau, en ClCments minCraux et en composCs organiques nkcessaires B son dCveloppement. Le S. hermonthica affecte Cgalement le mCtabolisme et la photosynthkse de son hate. Aucune mCthode de lutte efficace n'est actuellement accessible au paysan africain. L'application de stimulants de germination et d'herbicides, la pratique de rotations et d'associations culturales, la lutte biologique et la sClection de cultivars n'ont donnC jusqu'i maintenant que des rCsultats imparfaits. Une meilleure comprChension des mCcanismes de rCsistance de l'hbte est nCcessaire pour dCvelopper de nouvelles mCthodes de lutte contre le parasite. Abstract:The parasitic weed Striga hermonthica causes considerable yield losses in maize, pearl millet, and sorghum in Africa. The extent of the damage caused to crops is related to their close interaction with the parasite. The S. hermonthica seed germinates in response to germination stimulants exuded by cereal roots. The rootlet extremity then turns into a haustorium that attaches itself to the host root and penetrates its tissue. In this manner, a connection is established between the vascular systems of both plants, allowing absorption of water, minerals, and organic compounds that are essential for the parasite's development. S. hermonthica also affects the host's metabolism and photosynthesis. No effective control method against the parasite is available for the African peasants. The utilization of germination stimulants and herbicides, the rotation practice, and intercropping as well as biological control and varietal selection have given disappointing results so far. A better understanding of host resistance mechanisms is necessary to develop new methods for the control of the parasite.

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“…A racemic mixture of the AB-ring-truncated synthetic analog, GR5, was also prepared by a one-pot procedure involving the coupling of lactone with the suitable butenolide 32 (Macalpine et al, 1976) via an enol ether linkage (Fig. 4).…”

Section: Synthesis Of Sl Analogsmentioning

confidence: 99%

“…Prepared from tricycle 6 and 3-bromo-2-benzoyloxy-2(5H)-furanone 16 by the same procedure as for 19 to give the compound 27 (20 mg, 26%) as a white solid. Furanone 16 was obtained by bromation of 2-benzoyloxy-2-buten-4-olide (Limberg and Thiem, 1995) by the same procedure as for 5-bromo-3-methyl-2(5H)-furanone (Macalpine et al, 1976 …”

mentioning

confidence: 99%

Structure-Activity Relationship Studies of Strigolactone-Related Molecules for Branching Inhibition in Garden Pea: Molecule Design for Shoot Branching

et al. 2012

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Initially known for their role in the rhizosphere in stimulating the seed germination of parasitic weeds such as the Striga and Orobanche species, and later as host recognition signals for arbuscular mycorrhizal fungi, strigolactones (SLs) were recently rediscovered as a new class of plant hormones involved in the control of shoot branching in plants. Herein, we report the synthesis of new SL analogs and, to our knowledge, the first study of SL structure-activity relationships for their hormonal activity in garden pea (Pisum sativum). Comparisons with their action for the germination of broomrape (Phelipanche ramosa) are also presented. The pea rms1 SL-deficient mutant was used in a SL bioassay based on axillary bud length after direct SL application on the bud. This assay was compared with an assay where SLs were fed via the roots using hydroponics and with a molecular assay in which transcript levels of BRANCHED1, the pea homolog of the maize TEOSINTE BRANCHED1 gene were quantified in axillary buds only 6 h after application of SLs. We have demonstrated that the presence of a Michael acceptor and a methylbutenolide or dimethylbutenolide motif in the same molecule is essential. It was established that the more active analog 23 with a dimethylbutenolide as the D-ring could be used to control the plant architecture without strongly favoring the germination of P. ramosa seeds. Bold numerals refer to numbers of compounds.

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Synthesis of the germination stimulant (±)-strigol

Abstract: Two synthetic routes to the octahydroindeno[lV2-b]furanone derivative strigol (1 ), a germination stimulant of witchweed seeds, and its stereoisomers are described.

Cited by 70 publications

References 0 publications

Structure and function of natural and synthetic signalling molecules in parasitic weed germination

Structure and function of natural and synthetic signalling molecules in parasitic weed germination

La relation entre le Striga hermonthica et ses hôtes: une synthèse

Structure-Activity Relationship Studies of Strigolactone-Related Molecules for Branching Inhibition in Garden Pea: Molecule Design for Shoot Branching

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