Structures of the four avenacins, oat root resistance factors to ‘take-all’ disease

Crombie, Leslie; Crombie, W. Mary L.; Whiting, Donald A.

doi:10.1039/c39840000246

Cited by 35 publications

(30 citation statements)

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“…It is strong, environmentally tolerant and grows rapidly, so it can be planted anywhere, being cold hardy and resistant to dryness (Huh et al 1997). A rotenoid having the dihydrofuran ring with the isoprenoid side chain attached was isolated from Amorpha fruticosa L. for the first time (Crombie and Peace 1963;Crombie et al 1964). Methanol crude extract of Amorpha fruticosa L. seed was fractionated using dichloromethane to produce a rotenoid, 6a,12a-dihydro-a-toxicarol (Reisch et al 1976).…”

Section: Introductionmentioning

confidence: 99%

Effect of new rotenoid glycoside from the fruits of Amorpha fruticosa LINNE on the growth of human immune cells

et al. 2006

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A new compound, rotenoid isoflavone glycoside named, 6'-O-beta-D: -glucopyranosyl-12a-hydroxydalpanol was isolated from the methanolic (MeOH) fruit extract of Amorpha fruticosa LINNE by means of multi-stage column chromatography. Immuno-modulatory activities of this new glycoside were compared with the partitioned fractions of Amorpha fruticosa LINNE. Both of the fractions and purified single compound showed a 19% relatively low cytotoxicity at a maximum concentration of 1.0 g/L in a cultivated normal human lung cell line (HEL299). The purified single compound showed less cytotoxicity than the crude extracts, possibly because residual toxicants were eliminated during purification processes. Cell growth of human T cells was increased by about 15% by adding 0.5 g/L of the fractions compared to the control. Specific production rates of interleukin-6 (IL-6) and tumor necrosis factor (TNF-alpha) from T cell were higher as 1.16 x 10(-4) and 1.86 x 10(-4 )pg/cell, respectively, in the purified compound, compared to 1.38 x 10(-4) and 2.22 x 10(-4 )pg/cell, respectively, by adding 0.5 g/L of the dichloromethane fraction. Natural killer cell-92MI (NK-92MI) growth supplemented with the supernatant of human T cell was up to 19% higher with the dichloromethane fraction compared with a new single compound at a concentration of 0.5 g/L. Overall, the dichloromethane fraction showed relatively higher immuno-modulatory activities compared with a new single compound, probably due to the synergic effect given by other substances existing in the fractions.

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Section: Introductionmentioning

confidence: 99%

Effect of new rotenoid glycoside from the fruits of Amorpha fruticosa LINNE on the growth of human immune cells

et al. 2006

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“…6 Comparison of deuterated pyridine and deuterium oxide as NMR solvents shows no selective effects arising from pyridine complexation to one or other structure. Coupling constant data confirm the anomeric configurations (Glc J 1;2 values both 7.…”

Section: Resultsmentioning

confidence: 98%

Synthesis of l-arabinose-containing fragments of the oat root saponin Avenacin A-1

Mukhopadhyay

Field

2004

Carbohydrate Research

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“…In their glycosylated form, they are toxic and reduce herbivory in leguminous seeds (34). A group of more highly oxidized oleanene triterpenes, the averacins, are found in oat roots and are potent resistence factors to "take all" disease caused by the fungus Gaeumannomyces graminis (35). If Lespedeza and genistein exudation can be taken as representative, then it seems unlikely that quantities of these phenolics sufficient for the induction of haustoria would be exuded.…”

Section: The Chemistry Of Allelopathymentioning

confidence: 98%

The Involvement of Allelochemicals in the Host Selection of Parasitic Angiosperms

Lynn

1985

ACS Symposium Series

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Several compounds have now been found which are capable of inducing the differentiation of the haustorium-a specialized organ in parasitic angiosperms which functions to attach the parasite to its host. A detailed description of the chemical nature of these compounds is presented. Measurements of the levels of these compounds exuded by a host have been made and correlated with levels required for haustorial induction. The data support a strict structural requirement for the factors involved in the induction of the haustorium. Although more than one structural class may be involved, the compounds appear to be linked with the host's allelochemicals and constitutive antibiotics. The evidence for synergistic activity among several different components in host exudate suggests the possibility of a more highly sophisticated mechanism of host selection through haustorial differentiation than previously anticipated.As so many natural products chemists before us, we have become intrigued with the seemingly endless array of organic structures which are produced in nature. Over the past thirty years, questions directed primarily at the structures of these compounds and at their effects on man's physiology have led to profound technological advances. Man can now synthesize virtually any organic compound which exists in nature and has used these talents to develop new methods to study and combat human disease. We are now in a position to explore a fundamentally different frontier-the physiological and ecological significance of these compounds to the organisms which produce them. The greater our understanding of the chemical communication and chemical defenses inherent in all living organisms, the better we will be able to understand and maintain the intricate chemical nature of the world which surrounds us (1). A need for this understanding in the plant kingdom, the area on which so much of our food and oxygen supply is dependent, is becoming particularly apparent. We have focused our interest on the mechanisms of host selection in parasitic angiosperms-plants which have evolved the capability of parasitizing other plants. An earlier proposal (2) that 0097-6156/85/0268-0055$07.75/0

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Structures of the four avenacins, oat root resistance factors to ‘take-all’ disease

Cited by 35 publications

References 0 publications

Effect of new rotenoid glycoside from the fruits of Amorpha fruticosa LINNE on the growth of human immune cells

Effect of new rotenoid glycoside from the fruits of Amorpha fruticosa LINNE on the growth of human immune cells

Synthesis of l-arabinose-containing fragments of the oat root saponin Avenacin A-1

The Involvement of Allelochemicals in the Host Selection of Parasitic Angiosperms

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