A γ-pyronyl-triterpenoid saponin from Pisum sativum

Tsurumi, Seiji; Takagi, Toshikazu; Hashimoto, Tohru

doi:10.1016/0031-9422(92)83294-9

Cited by 56 publications

(28 citation statements)

References 9 publications

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“…The soyasaponin content was reported to be very high in soybean seed hypocotyls 41,42) and pea seedlings. 43) These results suggest that the induction of soyasaponin biosynthesis during germination is common in these legumes. In addition, the b-amyrin synthase mRNA level and soyasaponin production were up-regulated by MeJA in cultured cells of M. truncatula and G. glabra.…”

Section: Discussionmentioning

confidence: 80%

“…5) Soyasaponin I was also reported to be a phytochrome killer in pea. 46) Chromosaponin I, a conjugate of soyasaponin I and 2,3-dihydro-2,5-dihydroxy-6-methyl-4H-pyran-4-one, 43,47) was shown to stimulate elongation of roots in a variety of plants. 6,7) Although the general role of soyasaponin is not yet established, soyasaponin plays an important role in leguminous plants.…”

Section: Discussionmentioning

confidence: 99%

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Differential Expression of Three Oxidosqualene Cyclase mRNAs in Glycyrrhiza glabra

Hayashi

Huang

Takada

et al. 2004

Biological & Pharmaceutical Bulletin

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Higher plants produce not only sterols but also various triterpenes, which are derived from six isoprene units, 1) and some triterpenes are further glycosylated to produce various triterpene saponins.2) These triterpenes and triterpene saponins are believed to participate in the plant defence systems against microbial pathogens or insects. [3][4][5] An interesting effect that has also been reported is that an exogenous triterpene saponin stimulates the growth of roots in several plants. 6,7) In addition to the benefit for plants themselves, these triterpenes and saponins are beneficial for human beings as medicines, sweeteners, detergents, and cosmetics. Although structural elucidation of triterpenes and saponins has been extensively studied, 1,2) our understanding about the regulation of their biosyntheses is quite limited at the molecular level. 8)Oxidosqualene cyclases (OSCs) catalyze the cyclization of 2,3-oxidosqualene, a common intermediate of both sterols and triterpenes. Lanosterol synthase, playing a crucial role in cholesterol biosynthesis, is a unique OSC in mammals. In higher plants, on the other hand, some OSCs responsible for triterpene biosynthesis co-exist with cycloartenol synthase corresponding to lanosterol synthase in mammals. 8,9) Up to now, cDNAs of OSCs including cycloartenol synthase, bamyrin synthase, lupeol synthase and multifunctional triterpene synthase have been functionally characterized from various plant species. 8) After cloning of these OSC genes, our interest has shifted the regulatory roles of these OSCs in triterpene and saponin biosyntheses in higher plants. 8,[10][11][12][13] In our study, licorice (Glycyrrhiza glabra L., Fabaceae) was used as a model plant to elucidate the regulation of triterpene biosyntheses in higher plants (Fig. 1). Cultured licorice cells lacked the ability to produce glycyrrhizin, a sweet oleanane-type triterpene saponin produced in the roots of the mother plant, but produced phytosterols and two structurally different triterpenoid constituents, soyasaponins and betulinic acid. 15,16) Glycyrrhizin is localized exclusively in the woody parts of the thickened roots and stolons, whereas soyasaponins, oleanane-type triterpene saponins, are localized mainly in the seeds and rootlets of licorice.17) On the other hand, the content of betulinic acid, a lupane-type triterpene, is high in the cork layer of thickened licorice roots. 15) cDNAs of cycloartenol synthase, an OSC involved in sterol biosynthesis, and b-amyrin synthase, an OSC involved in both glycyrrhizin and soyasaponin biosynthesis, have been cloned from G. glabra. 18,19) In addition to these two OSCs, the third OSC, lupeol synthase, which is responsible for the biosynthesis of betulinic acid, most likely exists in cultured licorice cells. In the present study, an OSC cDNA for lupeol synthase was isolated by heterologous hybridization with that of olive lupeol synthase, 20) and the patterns of mRNA expression of the three OSCs in the cultured cells and the intact plants of G. glabra were examined. ...

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Section: Discussionmentioning

confidence: 80%

Section: Discussionmentioning

confidence: 99%

Differential Expression of Three Oxidosqualene Cyclase mRNAs in Glycyrrhiza glabra

Hayashi

Huang

Takada

et al. 2004

Biological & Pharmaceutical Bulletin

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“…We recently reported that chromosaponin I (CSI), a ␥-pyronyl-triterpenoid saponin isolated from pea (Pisum sativum) and other leguminous plants (Tsurumi et al, 1991(Tsurumi et al, , 1992Kudou et al, 1992Kudou et al, , 1993Massiot et al, 1992), specifically interacts with auxin influx carrier AUX1 (Bennett et al, 1996) and changes the response of Arabidopsis roots toward auxin and ethylene by controlling auxin uptake (Rahman et al, 2001a). Application of 60 m CSI inhibited the auxin uptake in the roots of Arabidopsis expressing the wild-type AUX1 protein and slowed down the gravitropic response of roots.…”

mentioning

confidence: 99%

Auxin and Ethylene Response Interactions during Arabidopsis Root Hair Development Dissected by Auxin Influx Modulators

Rahman

Hosokawa²,

Oono³

et al. 2002

Plant Physiology

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214

164

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The plant hormones auxin and ethylene have been shown to play important roles during root hair development. However, cross talk between auxin and ethylene makes it difficult to understand the independent role of either hormone. To dissect their respective roles, we examined the effects of two compounds, chromosaponin I (CSI) and 1-naphthoxyacetic acid (1-NOA), on the root hair developmental process in wild-type Arabidopsis, ethylene-insensitive mutant ein2-1, and auxin influx mutants aux1-7, aux1-22, and double mutant aux1-7 ein2. ␤-Glucuronidase (GUS) expression analysis in the BA-GUS transgenic line, consisting of auxin-responsive domains of PS-IAA4/5 promoter and GUS reporter, revealed that 1-NOA and CSI act as auxin uptake inhibitors in Arabidopsis roots. The frequency of root hairs in ein2-1 roots was greatly reduced in the presence of CSI or 1-NOA, suggesting that endogenous auxin plays a critical role for the root hair initiation in the absence of an ethylene response. All of these mutants showed a reduction in root hair length, however, the root hair length could be restored with a variable concentration of 1-naphthaleneacetic acid (NAA). NAA (10 nm) restored the root hair length of aux1 mutants to wild-type level, whereas 100 nm NAA was needed for ein2-1 and aux1-7 ein2 mutants. Our results suggest that insensitivity in ethylene response affects the auxin-driven root hair elongation. CSI exhibited a similar effect to 1-NOA, reducing root hair growth and the number of root hair-bearing cells in wild-type and ein2-1 roots, while stimulating these traits in aux1-7and aux1-7ein2 roots, confirming that CSI is a unique modulator of AUX1.Root hairs are tip-growing, tubular-shaped outgrowths that help to anchor roots, interact with soil microorganisms, and assist in the uptake of water and nutrients (Cutter, 1978). The relatively simple and invariant cellular organization of the primary roots of Arabidopsis and the ease of isolation and characterization of mutants make it a very attractive material for studying the root hair developmental process. The first committed step for root hair development is epidermal cell specification. In many species, including Arabidopsis, the root epidermis consists of two epidermal cell types, root hair-forming trichoblast cells and hairless atrichoblast cells (Cormack, 1947(Cormack, , 1949Bunning, 1951;Cutter, 1978). Within the Arabidopsis root epidermis, cells adopt distinct fates in a position-dependent manner. Epidermal cells that overlay the junction between two cortical cell files adopt a root hair cell fate, whereas the epidermal cells that contact only one cortical cell file become hairless cells (Dolan et al., 1994;Galway et al., 1994; Berger et al., 1998).Once the immature epidermal cell adopts a root hair cell fate, it goes through characteristic changes in its shape and size (Schiefelbein, 2000). Genetic analysis revealed that the root hair initiation mutations axr2 ), axr3 (Leyser et al., 1996, and ctr1 (Kieber et al., 1993) exhibit changes in their response to two i...

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“…Bidesmodic saponins have two sugar chains, often with one attached through an ether linkage at C-3 and the other either attached through an ester linkage at C-28 or through an ether linkage at C-20 (pentacyclic and tertacyclic triterpene saponins, respectively), or through an ether linkage at C-26 (furostane saponins) (Güçlü-Üstündag and Mazza, 2007). During the last decade some results have come up to suggest that some triterpenoid saponins genuinely may occur as pyronyl-derivatives (chromosaponins) (Tsurumi et al, 1992;Kudou et al, 1994).…”

Section: Chemistry Of Saponinsmentioning

confidence: 99%

Saponins in Madhuca Longifolia as undesirable substances in animal feed

2009

EFSA Journal

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SUMMARYSaponins are a diverse group of low molecular-weight secondary plant metabolites that are widely distributed in the plant kingdom. The chemical structure of saponins consists of an aglycone of either steroidal or a triterpenoid nature and one or more sugar chains (glycosides). Saponins can form stable foam in aqueous solutions, hence the name "saponin" from the Latin word for soap (sapo). Traditionally, they have been used as detergents, piscicides and molluscicides in addition to industrial applications as foaming and surface active agents.Madhuca longifolia and other Madhuca species are large evergreen or semi-evergreen trees with a dense spreading crown extensively cultivated in warm climates for their oil-containing seeds. The present opinion deals with saponins in Madhuca longifolia and other Madhuca species as potentially undesirable compounds in feed. Possible occurrence of saponins and also cyanogenic glycosides in "unhusked beech mast" from Fagus silvatica with regard to its listing as an undesirable substance in animal feed was also included in the request. However, since it does not contain saponins or cyanogenic glycosides in significant amounts and its reported toxicity in cattle and horses can most likely be attributed to its high content of oxalates, beech mast is not further discussed in this opinion. Saponins in Madhuca longifolia L. as undesirable substances in animal feedThe EFSA Journal (2009) Results from studies on Madhuca seed cakes, which contain saponins, on ruminants indicate that they are more tolerant to Madhuca saponins than monogastric animals and can tolerate inclusion levels of up to a maximum of 20% of the total diet. Toxicity studies of Madhuca seeds on monogastric target animals are scarce. Madhuca seed cake in chick mash at approximately 12% level was lethal. No studies have been conducted on horses, pigs, rabbits or dogs. Except for piscicidal effect of Madhuca saponins by water exposure in guppy fish, no toxicity studies after dietary exposure were identified in fish.Data on occurrence of Madhuca as a botanical impurity in feed are not available. Because of its limited value as feed for livestock Madhuca is not imported into the EU either as whole seeds or as meal. In producing countries, Madhuca cake is used mainly as a fertiliser and to a limited extent as feed because of its protein content. Data for the carry-over and residues of Madhuca saponins are not available. Madhuca products are not consumed by humans as part of the diet and human dietary exposure to Madhuca saponin through the consumption of animal products is very unlikely as the only potential source would be imported food of animal origin from animals fed Madhuca. The CONTAM Panel concludes that human dietary exposure to Madhuca saponins in the EU can be considered as negligible.

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A γ-pyronyl-triterpenoid saponin from Pisum sativum

Cited by 56 publications

References 9 publications

Differential Expression of Three Oxidosqualene Cyclase mRNAs in Glycyrrhiza glabra

Differential Expression of Three Oxidosqualene Cyclase mRNAs in Glycyrrhiza glabra

Auxin and Ethylene Response Interactions during Arabidopsis Root Hair Development Dissected by Auxin Influx Modulators

Saponins in Madhuca Longifolia as undesirable substances in animal feed

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