Separation of Enantiomers of the Germination Stimulant Strigol on Cellulose Triacetate and Determination of their Biological Activity

Hauck, Christian; Schildknecht, H.

doi:10.1016/s0176-1617(11)81627-5

Cited by 35 publications

(12 citation statements)

References 5 publications

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“…For example, synthetic (+)-strigol, which is identical to the natural compound isolated from cotton (Gosspium hirsutum L.), induced seed germination of Striga asiatica (L). The (-)-strigol enantiomer was much less active (5). Germination of Alectra vogelii (Benth) seed was much higher with (-)-strigol than with (+)-strigol.…”

Section: Mode Of Actionmentioning

confidence: 97%

Triacontanol and Its Second Messenger 9-β-l(+)-Adenosine as Plant Growth Substances

Ries¹

1991

Plant Physiol.

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Triacontanol (TRIA), a common constituent of plant waxes, was first shown in 1977 to be an active growth substance which at nanomolar concentrations increased the growth and yield of crops. TRIA is used to increase crop yields on millions of hectares, particularly in Asia. Many investigators have shown that it affects several basic metabolic processes including photosynthesis, nutrient uptake, and enzyme activity. However, the initial site of action has not been elucidated. TRIA rapidly elicits a second messenger (TRIM) in rice (Oryza sativa L.), which at nanomolar concentrations causes plants to respond in a manner similar to TRIA. TRIM has been identified as 9-0-L(+)-adenosine (9H-purin-6-amine, 9-j0-L-ribofuranosyl). During the process of isolating and identifying 9-jf-L(+)-adenosine, it was shown that this enantiomer, which previously has not been reported as occurring in nature, made up about 1% of the total adenosine pool in roots from untreated rice seedlings.TRIA' and OCTA (Fig. 1) are primary alcohols which are ubiquitous in the environment. OCTA inhibits the activity of TRIA at equimolar concentrations (16), and both compounds elicit the second messengers, OCTAM and TRIM, respectively, in rice (Oryza sativa L.) seedlings (17). TRIM has been identified as L(+)-adenosine ( Fig. 1) 'Abbreviations: TRIA, triacontanol; OCTA, octacosanol; TRIM, triacontanol second messenger; OCTAM, octacosanol second messenger; D(-)-adenosine, 9-f3-D(-)-adenosine; L(+)-adenosine, 9-3-L(+)-adenosine or 9H-purin-6-amine, 9-f-L-ribofuranosyl.

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Section: Mode Of Actionmentioning

confidence: 97%

Triacontanol and Its Second Messenger 9-β-l(+)-Adenosine as Plant Growth Substances

Ries¹

1991

Plant Physiol.

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“…It was separated into its enantiomers by high-performance liquid chromatography (HPLC) on cellulose triacetate (Hauck et al 1990). …”

Section: Strigolmentioning

confidence: 99%

Germination stimulants produced by Vigna unguiculata Walp cv Saunders Upright

Müller

Hauck

Schildknecht

1992

J Plant Growth Regul

Self Cite

165

100

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Abstract.A germination stimulant, alectrol, for the seeds of the angiospermous root parasites Alectra vogelii Benth. and Striga gesnerioides (Willd.) Vatke has been isolated from root exudates of its genuine host plant Vigna unguiculata Walp cv Saunders Upright. Its spectroscopic data lead to a chemical structure closely related to (+)-strigol. The compound is more active than strigol in stimulating seeds of the respective parasites, Alectra vogelii and Striga gesnerioides.Root parasite flowering plants of the genera Alectra, Striga (Scrophulariaceae), and Orobanche (Orobanchaceae) have developed an interesting chemical ecology. Apparently, they have found an unchallenged ecophysiological and biochemical niche. The parasitic seeds are able to recognize their correct host plants, because they germinate only in their presence. Basic to this phenomenon is the chemical communication between parasite and host: seed germination is initiated by chemical substances occurring in the root exudates of their respective host plants. There seems to be a great variety of these so-called germination stimulants because different host plants produce different compositions of different stimulants, as demonstrated by chromatographic investigations (Sunderland 1960, Visser et al. 1974, 1987. The first stimulating compound, strigol (Fig. 1), was isolated from cotton, Gossypium hirsutum, a false host,

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“…The lactone rings, the linkage between them and the substituents on them, seem to be of crucial importance for germination stimulant activity. The shape of the molecule affects activity (stereoisomers are nonequivalent) (18). A molecular mechanism for stimulation of Striga seed germination by strigol and analogs has been proposed (39).…”

Section: Host Control Of Striga Development By Means Of Chemical Signalsmentioning

confidence: 99%

Chemical Communication Between the Parasitic Weed Striga and Its Crop Host

Butler

1994

ACS Symposium Series

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Adaptation of Striga to parasitism includes not only dependence upon a host plant for metabolic inputs such as water, minerals, and energy, but also for developmental signals. In this way parasite and host development are highly integrated. The early host-derived chemical signals Striga requires, for seed germination and for initiation of the haustorium by which it attaches to host roots, are exuded from host roots into the soil. After Striga penetrates the host root, subsequent developmental signals are apparently exchanged directly, through vascular tissue. Germination stimulants for most Striga hosts have been identified as strigol-type compounds (strigolactones). Sorghum genotypes which produce extremely low amounts of stimulant are resistant to Striga. The gene for this trait has been mapped and incorporated into improved sorghums being released for production. Subsequent host-derived signals required by Striga are being characterized for possible independent mechanisms of resistance.Plants that have surrendered their independence and adopted a parasitic lifestyle generally obtain their water, minerals, and/or energy (in the form of photosynthate) from their host plant. But successful parasitism involves much more than dependence upon a host for metabolic inputs. In addition to these essentials, the parasite's growth, morphological development and even its manner of reproduction must be compatible with that of the host. In effect, the entire life cycle of the parasite must, to a significant extent, be integrated with that of the host. This integration is necessarily more intimate, more molecular, than the integration of plants which depend upon other organisms for pollination or seed dispersal with the lifestyles and characteristics of the organisms which provide these services.Because their requirements are so specific and complex, parasitic plants would seem to be more vulnerable than independent, non-parasitic plants. Successful plant parasitism involves a series of stringent conditions and interactions, all of which 0097-6156/95/0582-0158$08.00/0

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Separation of Enantiomers of the Germination Stimulant Strigol on Cellulose Triacetate and Determination of their Biological Activity

Cited by 35 publications

References 5 publications

Triacontanol and Its Second Messenger 9-β-l(+)-Adenosine as Plant Growth Substances

Triacontanol and Its Second Messenger 9-β-l(+)-Adenosine as Plant Growth Substances

Germination stimulants produced by Vigna unguiculata Walp cv Saunders Upright

Chemical Communication Between the Parasitic Weed Striga and Its Crop Host

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