Herbicidal activity of 4-chloroindoleacetic acid and other auxins on pea, barley and mustard

The natural auxins, 4-chloroindoleacetic acid and its methyl ester have strong herbicidal effects on pea, Pisum sativum , a plant in which they occur naturally. The standard herbicide, 2,4-dichlorophenoxyacetic acid (2,4-D) is only 5 times more effective than 4-chloroindoleacetic acid. The I₅₀, the dose inhibiting yield by 50%, for 4-chloroindoleacetic acid and its methyl ester is 0.5 kg ha⁻¹ or 15 mg kg⁻¹ fresh weight, close to the concentration of 4-chloroindoleacetic acid methyl ester in maturing pea seeds. Naphthaleneacetic acid and indoleacetic acid are also inhibitory, but at much higher concentrations. In its inhibiting effect on white mustard, Sinapis alba , 4-chloroindoleacetic acid approximates that of 2,4-D, whereas in barley, Hordeum vulgare , it is a stronger herbicide than 2,4-D. All auxins tested killed white mustard at low doses, but none killed barley. Both 4-chloroindoleacetic acid and 2,4-D killed pea. The chloroindole auxins of pea may be the hypothetic death hormones or senescence factors that are secreted from the developing seeds into the parent plant which is strongly inhibited or killed and from which the nutrients are mobilized and translocated to the seeds. The action mechanism of auxin type herbicides may be to simulate the action of endogenous herbicides.     

Determination of 4-chloroindole-3-acetic acid methyl ester in Lathyrus, Vicia and Pisum by gas chromatography – mass spectrometry

4-Chloroindole-3-acetic acid methyl ester was identified unequivocally in Lathyrus latifolius L., Vicia faba L. and Pisum sativum L. by thin layer chromatography, gas chromatography and mass spectrometry. The gas chromatographic system was able to separate underivatized chloroindole-3-acetic acid methyl ester isomers. The quantitative determination of 4-chloroindole-3-acetic acid methyl ester in immature seeds of these three species was performed by gas chromatography – mass spectrometry using deuterium labelled 4-chloro-indole-3-acetic acid methyl ester as an internal standard. P. sativum contained approximately 25 mg kg^-1, V. faba 1–2 mg kg^-1 and L. latifolius 2 mg kg^-1 dry weight.     

Amino acids in seeds and seedlings of the genus Lens

The amino acid content of seeds and 4-day-old seedlings were studied in five species of lentil: Lens culinaris, L. orientalis, L. ervoides, L. nigricans and L. odemensis. Free amino acid and also total protein amino acid content after HCl hydrolysis were determined by HPLC. The nonprotein UV-absorbing amino acids were determined by capillary zone electrophoresis (CZE). The content of free protein amino acids in seeds varied among species and increased dramatically after germination. Asparagine is quantitatively most important in both seed and seedling. The content of free nonprotein amino acids is variable in seeds and seedlings. gamma-Hydroxyarginine, gamma-hydroxyornithine, alpha-aminobutyric acid and taurine were found in both seeds and seedlings. Homoarginine was found in four species but not in L. orientalis while gamma-aminobutyric acid (GABA), alpha-aminoadipic acid (alpha-aaa) and three isoxazolinone derivatives: beta-(isoxazolin-5-on-2-yl)-alanine (BIA), gamma-glutamyl-BIA (gamma-glu-BIA) and 2-carboxymethyl-isoxazolin-5-one (CMI) were found exclusively in the seedlings. CMI was identified for the first time in lentil species. Lathyrine, beta-(2-amino-pyrimidine-4-yl)-alanine, which was reported to be in the seeds of some Lathyrus species was confirmed to be present also in the seedling of L. culinaris (trace amount), L. nigricans and L. odemensis. Trigonelline (N-methyl-nicotinic acid), a plant hormone, is present both in seeds and seedlings in different concentrations except in L. ervoides. The different combination of nonprotein amino acids among the species gives indication of their genetic relationship and might partly explain the varying compatibility for interspecies crossing.     

Simple identification of the neutral chlorinated auxin in pea by thin layer chromatography

One of the neutral chlorinated auxins of immature pea seeds was readily identified by thin layer procedures simple enough to serve in student's laboratory courses. 4-Chloroindole-3-acetic acid methyl ester was extracted from 50 g of commercial, frozen peas by either water or acetone, concentrated to small volumes and chromatographed in CHCl₃ or CCl₄ solvent systems separating the chlorinated auxin from indoleacetonitrile and the methyl or ethyl esters of indoleacetic acid. Colour reaction was carried out with some of the Salkowski FeCl₃ sprays of which Ehmann's FeCl₃/dimethylaminobenzaldehyde modification gave the most stable blue colour.     

Identification of 4-Chloroindole-3-acetic Acid and Its Methyl Ester in Immature Seeds of Vicia amurensis (the Tribe Vicieae), and Their Absence from Three Species of Phaseoleae

The natural chlorinated auxins 4-chloroindole-3-acetic acid(4-Cl-IAA) and its methyl ester (4-Cl-IAA Me ester) were found,in addition to IAA and its Me ester, by gas chromatography-massspectrometry in immature seeds of Vicia amurensis, a Vicieaespecies. In contrast, only non-chlorinated, IAA and IAA Me esterwere present in immature seeds of three Phaseoleae species.These results are further evidence of the wide distributionof 4-Cl-IAA and its Me ester in various Vicieae. (Received October 3, 1986; Accepted December 22, 1986)     

藏红花花瓣和雄蕊挥发油化学成分GC-MS分析及比较

采用水蒸气蒸馏法从藏红花花瓣和雄蕊中提取挥发油,用GC-MS技术结合计算机检索对其二者化学成分进行分离和鉴定,用色谱峰面积归一化法计算各组分的相对含量.花瓣中共鉴定出16种化合物,主要成分为正二十六烷(11.60％)、正十五烷(11.31％)、棕榈酸甲酯(10.82％)、油酸甲酯(10.35％)、2,4-二叔丁基苯酚(9.63％)、亚油酸甲酯(7.18％)、藏红花醛(5.66％);雄蕊中共鉴定出20种化合物,主要成分为油酸甲酯(30.83％)、亚油酸甲酯(24.12％)、环已醇(16.80％)、硬脂酸甲酯(12.88％)、棕榈酸甲酯(8.97％)、花生酸甲酯(1.18％)、苯并噻唑(1.01％).     

山黧豆及其神经毒素(ODAP)的研究进展

山黧豆具有耐寒、耐旱等优良生产性状，且营养丰富，在恶劣的天气条件下仍能维持较高的产量，因此它是半干旱地区的潜在粮食作物。但长期食用山黧豆会引起中毒，这是由于山黧豆中含有的神经毒素（ＯＤＡＰ）所致，因此筛选无毒品系具有重要意义。本文对山黧豆神经毒素（ＯＤＡＰ）的生物合成毒素异构化等方面作简要综述。     

Further characterization of monoclonal antibody 6,F-8 reacting with Lathyrus, Lens and Pisum lectins

The murine monoclonal antibody (MoAB) 6,F-8 made against the glucose/mannose-specific Lathyrus odoratus mitogen has previously been shown to react with Lens culinaris and Pisum sativum lectins, but not with the lectin from Vicia faba [(1988) Biol. Chem. Hoppe-Seyler 369, 365-370]. The reactivity against seven other completely sequenced Lathyrus lectins has now been tested after separation of the subunits by SDS-polyacrylamide gel electrophoresis and electroblotting to nitrocellulose filters. Two of these lectins reacted with the antibody. Comparison of the amino acid sequences of the examined lectins and the predicted hydrophilic, flexible and accessible regions of Pisum sativum suggest that valine-147 is involved in antibody binding.     

Lathyrus sativus (grass pea) and its neurotoxin ODAP

Lathyrus sativus (grass pea) is a high-yielding, drought-resistant legume consumed as a food in Northern India and neighboring countries as well as in Ethiopia. Its development into an important food legume, however, has been hindered by the presence of the neurotoxin - beta-N-oxalyl-L-alpha,beta-diaminopropionic acid (beta-ODAP) in seeds which, if consumed in large quantities for prolonged periods, can cause irreversible paralysis. Recently, some low-toxin lines have been developed that may prove safe for both animal and human foods. Cultivation of L. sativus should thus be considered in suitable regions because the demand for legume animal feed protein products is expected to increase. This paper addresses advances in understanding L. sativus from the perspective of its taxonomy, genetics, ecology, chemistry, nutrition, medicine, biology and for animal nutrition.     

Fatty acid composition of seeds of Satureja thymbra and S. cuneifolia

The chemical composition of fatty acid methyl esters (FAMEs) from seeds of S. thymbra and S. cuneifolia were analyzed by GC/MS. 7 FAMEs were identified from the seeds of S. thymbra mainly as 9-octadecenoic acid methyl ester (43.9%), hexadecanoic acid methyl ester (11.4%), 9,12,15-octadecatrienoic acid methyl ester (Z,Z,Z) (30.2%), and octadecanoic acid methyl ester (14.1%), while from the seed of S. cuneifolia 10 FAMEs were obtained with the main components, similar to S. thymbra. These were identified as 9-octadecenoic acid methyl ester (10.1%), hexadecanoic acid methyl ester (methyl palmitate, 34.6%), 9,12,15-octadecatrienoic acid methyl ester (Z,Z,Z) (6.3%) and octadecanoic acid methyl ester (1.8%).     

Purification and characterization of lectins from Vicia hirsuta

The presence of three lectins in the seeds of Vicia hirsuta (L.) S. F. Gray, a wild-growing vetch, was shown. The main lectin was purified to homogeneity by buffer extraction, ammonium sulfate precipitation, affinity chromatography on Sephadex G-100 and isoelectric focusing in granulated gel. By chromatofocusing instead of isoelectric focusing the yield was increased 5-fold. The lectin has a pi of 6.4. It is composed of large β-subunits (M_r 19.200) and small α-subunits (M_r 12.800) in a 1:1 ratio. The subunits can be separated on Sephadex G-75 when equilibrated with 6 M guanidine-HCl. The amino acid composition of the two different subunits has been determined. No sulfur-containing amino acids are present. The lectin resembles the lectins from legumes from the same cross-inoculation group, i.e. Lens culinaris, Lens esculenta, Pisum satiyum and several Vicia spp. by the same type of sugar specificity and amino acid composition.     

Monomethyl-4-chloroindolyl-3-acetyl-L-aspartate and absence of indolyl-3-acetic acid in immature seeds of Pisum sativum

Summary A new auxin-related metabolite has been isolated from immature seeds of Pisum sativum and its structure has been determined as monomethyl-4-chloroindolyl-3-acetyl-L-aspartate. Neither indolyl-3-acetic acid nor its methyl ester have been detected in immature seeds by gas-liquid chromatographic analysis.     

Purification and characterization of insulin-mimetic inositol phosphoglycan-like molecules from grass pea (Lathyrus sativus) seeds.

BACKGROUND: Signal transduction through the hydrolysis of glycosyl-phosphatidylinositol (GPI) leading to the release of the water-soluble inositol phosphoglycan (IPG) molecules has been demonstrated to be important for mediating some of the actions of insulin and insulin-like growth factor-I (IGF-I). MATERIALS AND METHODS: In the present study, GPI from grass pea (Lathyrus sativus) seeds has been purified and partially characterized on the basis of its chromatographic properties and its compositional analysis. RESULTS: The results indicate that it shows similarities to GPI previously isolated from other sources such as rat liver. IPG was generated from L. sativus seed GPI by hydrolysis with a GPI-specific phospholipase D (GPI-PLD). This IPG inhibited protein kinase A (PKA) in an in vitro assay, caused cell proliferation in explanted cochleovestibular ganglia (CVG), and decreased 8-Br-cAMP-induced phosphoenolpyruvate carboxykinase (PEPCK) mRNA expression in cultured hepatoma cells. CONCLUSIONS: Our data indicate that L. sativus seed IPG possess insulin-mimetic activities. This may explain why L. sativus seeds have been used in some traditional medicines to ameliorate diabetic symptoms.     

Identification by gc-ms of 4-chloroindolylacetic acid and its methyl ester in immature Vicia faba seeds

4-Chloroindolylacetic acid and its methyl ester have been converted to the N′-heptafluorobutyryl methyl ester derivative. An extract of immature seeds of Vicia faba has been similarly derivatized. It gave in its mass spectrum the same fragmentation pattern as the synthetic heptafluorobutyryl derivative. The chlorine atom was assigned to the 4-position on the indole ring after comparison by GLC of the extract and of four monochlorinated IAA isomers.     

A method for determining the presence of inverted repeats in the chloroplast genome of higher plants]

A plasmid containing fragments of rp12 and rps19 genes from the chloroplast genome of Arabidopsis thaliana was developed. The presence of inverted repeats in the chloroplast DNA of A. thaliana and Vicia sativa, and their absence from two species of Fabaceae family (Lathyrus sativus, Lens esculenta) were shown with the help of this plasmid.     

Lead accumulation in the roots of grass pea (Lathyrus sativus L.): a novel plant for phytoremediation systems?

Eleven day-old grass pea plants (Lathyrus sativus L.) were grown hydroponically for 96 h in the presence of 0.5 mM lead nitrate (Pb(NO(3))(2)). The survival rate was 100%. The mean lead content (measured by ICP-OES) in root tissues was 153 mg Pb g(-1) dry matter. Over three quarters of the lead was not labile. Compared with control plants, lead-exposed plants showed a six-fold, two-fold and three and a half-fold reduction in their root calcium, zinc and copper contents, respectively. Together, these results suggested that Lathyrus sativus L. was tolerant to a deficiency in essential nutrients and able to store large amounts of lead in its root tissues. Therefore, it could be used for the development of new rhizofiltration systems.     

Natural Chlorinated Auxins Labelled with Radioactive Chloride in Immature Seeds

Immature seeds were harvested from 15 species grown in perlite/vermiculite containing ³⁶Cl^-, but with very low levels of cold Cl^-. Autoradiograms of one- and two-dimensional thin layer chromatograms of butanol extracts of lyophilized seeds indicated several radioactive compounds besides the ³⁶Cl^- in many species. In pea the radioactivity cochromatographed with 4-(or 6-)chloroindolyl-3-acetic acid and its methyl ester; in other species radioactivity was found near these chlorinated indolyl-acetic acid markers.     

60Coγ射线与EMS复合处理对山黧豆抗氧化酶活力及ODAP含量的影响

1　引　　言山黧豆抗寒、抗旱、耐贫瘠 ,尤其适于干旱、半干旱地区种植 .但山黧豆中含有的毒素 β ＯＤＡＰ会导致下肢瘫痪 .由于这个原因限制了山黧豆的大面积栽培 .我们采用 60 Ｃｏγ射线和ＥＭＳ单因子、复因子诱变的方法选育丰产、低毒、无毒山黧豆新品系 .近年来对生物辐射敏感性的研究表明 ,其抗性除与本身ＤＮＡ损伤修复能力有关外 ,还与体内所含防护物质有关 ,ＳＯＤ、ＰＯＤ、ＣＡＴ即是重要的保护物质 .关于抗氧化酶活性与辐射剂量、诱变剂浓度关系的研究很少 ,因此本实验对山黧豆成苗率、抗氧化酶活性、和 β ＯＤＡＰ含量进行…     

Effects of chlorosubstituted indoleacetic acids on root growth, ethylene and ATP formation

7-Chloroindoleacetic acid and dichloroindoleacetic acids with a Cl in the 7 position showed anti-auxinic activity and promoted root growth in wheat ( Triticum aestivum L. cv. Diamant II). In contrast, 4-, 5- and 6-chloroindoleatetic acids acted as strong auxins inhibiting the growth of wheat roots. Flax ( Linum usitatissimum L. cv. Concurrent) and cucumber ( Cucumis sativus L. cv. Favör) roots showed similar, but less clear-cut responses. 7-Chloroindoleacetic acid and 4,7-dichloroindoleacetic acid alleviated root growth inhibition in wheat caused by IAA, monochloroindoleacetic acids and benzyladenine. 2,4-D, 4- and 6-chloroindoleacetic acids strongly induced ethylene formation in cucumber seedlings; 4,7- and 6,7-dichloroindoleacetic acids did not, except at high concentrations. The more lipid-soluble dichloroindoleacetic acids were stronger inhibitors of ATP formation in cucumber mitochondria than monochloroindoleacetic acids, while IAA itself had only a very slight effect.     

^60Coγ射线与EMS复合处理对山黎豆抗氧化酶活力及ODAP含量的影响

Lathyrus sativus seeds were treated with 60Co gamma-ray and EMS(ethyl methane sulfonate), and their emergence rate and SOD, POD and CAT activities were determined. The result indicated that the treatment decreased the emergence rate. The activities of SOD and POD were changed in accordance with the increase of irradiation dose and EMS concentration, while that of CAT had no obvious change. After treatment, the ODAP content in Lathyrus sativus decreased. Amutant was developed, with toxin content of 0.1%, compared to 0.2% in control.