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A new oleanene glucuronide called melilotus-saponin O1 (1) was isolated together with three known ones from the roots of Melilotus officinalis (L.) PALLAS (Leguminosae). The structure of 1 was determined to be 3-O-alpha-L-rhamnopyranosyl-(1-->2)-alpha-L-arabinopyranosyl-(1--> 3)]- beta-D-galactopyranosyl-(1-->2)-beta-D-glucuronopyranosyl soyasapogenol B by spectroscopic and chemical methods.
A new oleanene glucuronide called melilotus-saponin O2 (1) was isolated together with three known ones (soyasaponin I, astragaloside VIII, wistariasaponin D) from the aerial parts of Melilotus officinalis (L.) Pallas (Leguminosae). The structure of 1 was determined to be 3-O-alpha-L-rhamnopyranosyl-(1-->2)-beta-D-xylopyranosyl- (1-->2)-beta-D-glucuronopyranosyl melilotigenin by spectroscopic and chemical methods.
OBJECTIVES: The aim of this clinical study was to verify the therapeutic activity of cumarinic extract of Melilotus officinalis (CEMO) in patients with chronic lymphedema of the upper arm caused by lymphadenectomy for breast cancer. Cumarine, in fact, has antiedemic properties due to macrophagic action that stimulates proteolysis in the tissues affected by chronic lymphedema. PATIENTS AND METHODS: In an open clinical study we enrolled 24 patients with chronic upper arm lymphedema due to post-lymphadenectomy of the axilla for breast cancer. 21 patients were eligible to receive 400 mg of CEMO containing 8 mg of cumarine in a sole daily administration for 6 months. We measure the circumference of the upper arm at 3 and 6 months from treatment. We evaluated the symptoms and tolerability through a questionnaire given to the patients at every clinical control. RESULTS: Of the 21 (87.5%) patients eligible, only 14 (66.6%) were treated with CEMO according to protocol. Of these 11 patients (52.3%) had a reduction of the circumference of the affected arm of 5% with respect to base values. Three patients (14.2%) had no change. In 12 patients (57.1%) symptoms improved. As for tolerability: 3 patients (14.2%) had transitory gastrointestinal side-effects. There was worsening of lymphedema and symptoms in 4 patients (19%) that did not receive CEMO and were followed as controls. Three patients (14.2%) were not evaluable because they were lost to follow-up. CONCLUSIONS: Cumarinic extract of Melilotus officinalis (CEMO) was effective in reducing lymphedema in 79% of the pts treated for a period of six months. The median reduction of the upper arm circumference was modest (5% with respect to initial values) but statistically significant (p = 0.048). Treatment with CEMO for lymphedema could be associated to the physiotherapy given to these patients such as manual lymph drainage (MLD).
The results of the exam at the light, the fluorescence and the scanning electron microscope of the endosperm of Melilotus alba mature impermeable seeds are reported. Cryostat sections, semithin sections and squashes are observed. Melilotus alba endosperm is variable in thickness and envelopes cotyledons and radicle. Its "aleurone" layer is one-cell thick, while the number of layers of its internal cells varies in relation to the location in the seed. In the aleurone cells, the cytoplasm and the outer portion of the wall are autofluorescent; tannic acid-ferric chloride stains the outer portion of the wall and allows to see clearly the inner thickenings, DAPI and haematoxylin demonstrate the presence of the nucleus. The cytoplasm of these cells is coloured by Sudan black b, and its fluorescence is enhanced by auramine and calcofluor white. Calcofluor white enhances the fluorescence of the outer portion of these walls, too, but is without effect on the non-autofluorescent thickening, indicating presence of cellulose only in the first case. Callose is absent. Also the thin autofluorescent walls of the endosperm inner cells react positively to calcofluor. These cells are very large, almost completely filled with "gelatinous" substances--the galactomannans--and very rarely contain a nucleus.
Our study investigated the effects of Melilotus officinalis L. extract, containing 0.25% coumarin, on acute inflammation induced with oil of turpentine in male rabbits. The results were compared with those from a group treated with hydrocortisone sodium hemisuccinate and one injected with coumarin before inflammation was induced. The effects were evaluated by measuring serum citrulline, a test of in vitro phagocytosis, total leukocyte count and differential leukocyte count expressed as a percentage. M. officinalis had antiinflammatory effects because it reduced the activation of circulating phagocytes and lowered citrulline production. These properties were similar to those of hydrocortisone sodium hemisuccinate and coumarin. In the bone marrow acute phase response, M. officinalis had an inhibitory action that was lower than that of hydrocortisone sodium hemisuccinate and similar to coumarin.
Agrobacterium strains have been frequently isolated from the root nodules of different legumes. Various possible mechanisms have been proposed to explain the existence of these bacteria in nodules, but there is no sufficient experimental evidence to support the estimations. In this work, we proved that the Agrobacterium strain CCBAU 81181, which was originally isolated from the root nodules of Onobrychis viciaefolia, and a symbiotic strain of Sinorhizobium meliloti CCBAU 10062 could coinhabit the root nodules of Melilotus dentatus. Analyses were performed by using a fluorescence marker, reisolation of bacteria from nodules, sodium dodecyl sulfate-polyacrylamide gel electrophoresis (SDS-PAGE) of whole cellular proteins, and polymerase chain reaction amplification of symbiotic genes. The inoculation of A. tumefaciens CCBAU 81181 did not affect the growth and nodulation of plants. CCBAU 81181 and 24 other Agrobacterium strains isolated from nodules were incapable of nodulating on their original or alternative host and 22 strains of these strains were endophytes in the roots and stems of their hosts. Also, the tumor-inducing A. tumefaciens strains IAM 13129(T) and C58 were found capable of entering the roots of Glycyrrhiza pallidiflora, but did not cause pathogenic symptoms. With these results, we conclude that A. tumefaciens strains could be endophytic bacteria in the roots, stems, and root nodules. This finding partially explains why Agrobacterium strains were frequently isolated from the surface-sterilized nodules.
Soxhlet extraction, ultrasound-assisted extraction (USAE) and microwaves-assisted extraction (MAE) in closed system have been investigated to determine the content of coumarin, o-coumaric and melilotic acids in flowering tops of Melilotus officinalis. The extracts were analyzed with an appropriate HPLC procedure. The reproducibility of extraction and of chromatographic analysis was proved. Taking into account the extraction yield, the cost and the time, we studied the effects of extraction variables on the yield of the above-mentioned compounds. Better results were obtained with MAE (50% v/v aqueous ethanol, two heating cycles of 5 min, 50 degrees C). On the basis of the ratio extraction yield/extraction time, we therefore propose MAE as the most efficient method.
In Ethiopian traditional medicine, Melilotus elegans Salzm. ex Ser. (Leguminosae) is used for the treatment of haemorrhoids and lacerated wounds. In view of its wide spread use and proven anti-inflammatory activity, 80% methanolic extract of the leaves was formulated into creams. HPLC/UV and MS studies revealed the presence of flavonoids, of which kaempferol was the major aglycone. Quantitative estimation of kaempferol in the hydrolyzed extract as determined by HPLC/UV was found to be 16.3+/-0.93 microg/mg (n=6, range) of extract. The in vitro release profiles of kaempferol glycosides (quantified as kaempferol equivalent) from the cream formulations in a multilayer membrane system indicated that a lipophilic cream of the extract provides higher release of kaempferol glycosides than hydrophilic and amphiphilic ones. Over a study period of 4h, the lipophilic cream released 66+/-5.70% of kaempferol glycosides, while the hydrophilic and amphiphilic creams resulted in 55+/-2.77 and 38+/-2.30% release, respectively.
Melilotus indica All. [Chopra, R.N., Nayar, S.L. and Chopra, I.C. (1956) Glossary Indian Med. Plants, 164 C.S.I.R. Publication New-Delhi; Kirtikar, K.R. and Basu, B.D. (1935) Indian Medicinal Plants, 2nd Ed., Vol. I, pp. 703-704 Lalit Mohan Basuan Co. Allahabad. The Wealth of India (1962) A Dictionary of Raw Materials and Industrial Products, Vol. VI, pp. 329-331 (C.S.I.R. Publication: New-Delhi)] belongs to family Leguminosae, which is commonly known as 'Banmethi' in Hindi. It is found in North India, extending into S. Persia, S. Europe and the Tropical zone of India. The seeds are used as an anthelmintic, an antipyretic, for curing heart diseases, bronchitis, leprosy, bowel complaints and infantile diarrhea. The plant has also been used as a discutient, emollient, and as a fomentation. It is also useful in a plaster for swelling. It is considered astringent and narcotic. Earlier workers have reported the presence of C-glycosides [Sayed, E.L., Ishak, M.S. and Mabry, T.J. (1997) Asian J. Chem., 9, 551], methylene-dioxypterocarpan (MIS6) [Saxena, V.K. and Nigam, S. (1997) Fitoterapia, 68, 343-345], pterocarpane (MIS2) [Saxena, V.K. and Nigam, S. (1996) J. Institution Chem. 68, 122-125] and prenylated pterocarpan [Saxena, V.K. and Nigam, S. (1997) Fitoterapia, 68, 403-407] from this plant. Here, we report the isolation of the new flavone glycoside 5,7,4'-trihydroxy-6,3'-dimethoxyflavone-7-O-alpha-L-arabinopyranosyl(1-->6)-O-beta-D-galactopyranoside (1) from the seeds of this plant.
Expansins are a highly conserved group of cell wall-localized proteins that appear to mediate changes in cell wall plasticity during cell expansion or differentiation. The accumulation of expansin protein or the mRNA for specific expansin gene family members has been correlated with the growth of various plant organs. Because expansin proteins are closely associated with plant cell wall expansion, and as part of a larger study to determine the role of different gene products in the legume-Rhizobium spp. symbiosis, we investigated whether a Melilotus alba (white sweetclover) expansin gene is expressed during nodule development. A cDNA fragment encoding an expansin gene (EXP) was isolated from Sinorhizobium meliloti-inoculated sweetclover root RNA by reverse-transcriptase polymerase chain reaction using degenerate primers, and a full-length sweetclover expansin sequence (MaEXP1) was obtained using 5' and 3' rapid amplification of cDNA end cloning. The predicted amino acid of the sweetclover expansin is highly conserved with the various alpha-expansins in the GenBank database. MaEXP1 contains a series of eight cysteines and four tryptophans that are conserved in the alpha-expansin protein family. Northern analysis and whole-mount in situ hybridization analyses indicate that MaEXP1 mRNA expression is enhanced in roots within hours after inoculation with S. meliloti and in nodules. Western and immunolocalization studies using a cucumber expansin antibody demonstrated that a cross-reacting protein accumulated in the expanding cells of the nodule.
An assessment was made of the impact of temporal separation on the composition of a population of Sinorhizobium meliloti associated with Medicago sativa (alfalfa) and Melilotus alba (sweet clover) grown at a single site that had no known history of alfalfa cultivation. Root nodules were sampled on six occasions over two seasons, and a total of 1620 isolates of S. meliloti were characterized on the basis of phage sensitivity using 16 typing phages. Plant infection tests indicated that symbiotic S. meliloti were deficient in the soil at the time of planting and that these bacteria were present at low density during the first season (<10(2)/g of soil); in the second season numbers increased markedly to about 10(5)/g of soil. Overall, 37 and 51 phage types, respectively, were encountered among the nodule isolates from M. sativa and M. alba. The data indicate significant temporal shifts in the frequency and diversity of types associated with the two legume species. Apparent temporal variation with respect to the frequency of types appeared largely unpredictable and was not attributable to any one sampling time. The results indicate an apparent reduction in phenotypic diversity over the course of the experiment. Differential host plant selection of specific types with respect to nodule occupancy was indicated by significant interactions between legume species and either the frequency or diversity of phage types. Isolates from M. sativa that were resistant to lysis by all typing phages (type 14) were unusual in that they were predominant on this host at all sampling times (between 53% and 82% nodule occupancy) and were relatively homogeneous on the basis of DNA hybridization with 98% of the isolates analysed sharing the same nod EFG hybridization profile. In contrast, those isolates from M. alba comprising type 14 were encountered at low total frequency (2%) and were genetically heterogeneous on the basis of Southern hybridization. The implications of the observed temporal and host plant variation for ecological studies are discussed.
BACKGROUND: The aim of this comparative clinical study was to evaluate the efficacy of the association of alphatocopherol, rutin, melilotus officinalis, and centella asiatica with oral administration in patients with chronic venous insufficiency. METHODS: Thirty patients with chronic venous insufficiency have been randomized in two groups of fifteen subjects (control and treatment group). During the period of treatment the patients didn't wear elastocompressive stockings. The therapeutic efficacy and the clinical tolerability of this association have been valued with clinical-instrumental evaluations and by a control after 15 and 30 days. Functional bothers, cramps and the edema have been valued in function presence and of their gravity with a clinical-score between 0 and 4. RESULTS: At the end of the observation period, a significant improvement of the clinical simptomatology was obtained, characterised by a diminution of the sovrafascial edema. CONCLUSIONS: The present study confirms previous clinical experiences regarding the described treatment and suggests its application in chronic venous insufficiency.
The crude methanol extract of Melilotus elegans Ser. (Fabaceae), a plant widely used in Ethiopian traditional medicine for the treatment of asthma, haemorrhoid and lacerated wounds showed a significant anti-inflammatory activity against carrageenin-induced rat paw oedema. At a dose corresponding to 333.3 mg per kg body weight of dry plant material, the methanol extract displayed a strong inhibitory effect that was comparable to the inhibitory effect of 1 mg/kg of indomethacin in the same test system. Bioassay guided fractionation of the alcoholic extract led to the isolation of an oleanene-type triterpene saponin identified as azukisaponin V (1) ((3-O-[alpha-L-rhamnopyranosyl-(1 --> 2)-beta-D-glucopyranosyl(1 --> 2)-beta-D-glucuronopyranosyl]-soyasapogenol B). The structure of the compound was identified by using MS and extensive one- and two-dimensional NMR experiments (1H, 13C, COSY, HMQC, HMBC and NOESY). One hour after injection of carrageenin, inhibition of oedema exerted by 1 was approximately ten times higher than that of indomethacin on a molar basis.
Biological and soil factors which contribute to the successful colonization of an annual legume species. Melilotus indica L., in soils with elevated selenium (Se) were studied. This species was introduced into the Kesterson Reservoir in the fresh top soil that was brought in under the Kesterson Cleanup Action to fill lowering pond sites and prevent the formation of ephemeral pools containing hazardous levels of Se. In 4 years since its introduction, it has expanded its range of colonization from the fresh soil fill sites to the native soil sites and contributed 10 to 50% of biomass to the grassland communities. The plant and nodule tissue Se concentrations of the field grown plants were found to be negatively correlated with the soil sulfate concentration. Nutrient solution culture studies discovered that M. indica was able to accumulate 500 micrograms Se g-1 dry weight without a reduction of growth rate. Plants without nodulation were found to accumulate a greater amount of Se and more vulnerable to Se toxicity. Acetylene reduction rate measurements indicate that the nitrogen fixation symbiotic activity appears to be more susceptible to an elevated Se concentration than its host plant. M. indica is a winter weed, and it occurs naturally in the Se-rich soils. It grows actively over the winter and spring and complete its life cycle in May. If the root nodules and root tissues are incorporated into the soil, the rate of soil Se volatilization may be accelerated over the warm summer months. For disposal of the Se-rich plant materials the plant shoot tissues may be harvested for Se-deficient forage supplementation. Therefore, this species may be useful for field management and reclamation of Se-contaminated soils.
Accumulation of specific groups of seleno-amino acids in plant tissue reflects not only the Se tolerance of a plant species, but also Se toxicity to animals. The distribution of seleno-amino acids in a Se-tolerant grassland legume species (Melilotus indica L.) grown in Se-laden soils was studied using high-resolution gas chromatography- and gas chromatography-mass spectrometry. Five seleno-amino acids including selenocystine, selenomethionine, selenocysteine, Se-methylselenocysteine, and gamma-glutamyl-Se-methylselenocysteine were identified and measured for their plant tissue concentrations. Se-methylselenocysteine, a nonprotein seleno-amino acid, was found in the plant tissue. Its concentration ranged from 15.3 mumol kg-1 for the plants growing in soil of low Se concentration to 109.8 mumol kg-1 for the plants grown in soil of high Se concentration. Accumulation of the nonprotein seleno-amino acid in this species resembles that in Se accumulator plants. gamma-Glutamyl-Se-methylselenocysteine was detected in the plant. However, its concentration was very low. It might not become a toxic element in the food chain. Results of plant tissue Se accumulation analysis indicated that there was a five-fold increase in tissue selenocysteine concentration when the total tissue Se increased from 5.07 to 22.02 mg kg-1, but there was no further increase in tissue selenocysteine concentration when the tissue total Se concentration increased from 22.0 to 117.4 mg kg-1. Selenomethinone constituted more than 50% of the total seleno-amino acid in the plant. More research is needed to reveal whether the mechanisms limiting the accumulation of selenocysteine and preferential accumulation of selenomethionine found in this study play any role in Se tolerance in this species.
Four new triterpene saponins of the oleanan series-melilotosides I, II, III, IV and nonglycosylated soyasapogenol B have been isolated from roots of Melilotus albus Medik. (Leguminosae) and four steroid saponins were isolated from M. tauricus (Bieb.) ser. seeds. The chemical structure of the saponins and of their aglycone was proved based on chemical transformations and spectral data. Melilotoside I has the structure of 3-O-[a-L-arabinopyranosyl] soyasapogenol B, melilotoside II that of 3-O-[beta-D-galactopyranosyl-(1-->2)-O-alpha-L-arabinopyranosyl] soyasapogenol B, melilotoside III that of 3-O-[alpha-L-rhamnopyranosyl-(1-->2)-O-beta-D-galactopyranosyl-(1-->2)-O -alpha-L-arabinopyranosyl] soyasapogenol B, and melilotoside IV that of 3-O-[alpha-L-rhamnopyranosyl-(1-->2)-[alpha-L-arabinopyranosyl-(1- ->3)]- O-beta-D-galactopyranosyl-(1-->2)-O-alpha-L-arabinopyranosyl soyasapogenol B. The steroid saponins have been identified as 3-O-beta-D-glucopyranoside-diosgenin (V); 3-O-alpha-L-rhamnopyranosyl (1-->2)-[alpha-L-rhamnopyranosyl(1-->3)-O-beta-D-glucopyranoside- diosgenin (VI),26-O-beta-D-glucopyranoside (25R)-furost-5-ene 3beta,22alpha, 26-triol (VII), and 3-O-alpha-L-rhamnopyranosyl(1-->4)-alpha-O-beta-D- glucopyranoside(25R)-furost-5-ene 3beta,22alpha,26-triol-26-O-beta-D- glucopyranoside (VIII).
A collection of chlorophyll (Chl)-deficient mutants of sweetclover (Melilotus alba) with defects in eight nuclear loci were grown at 17 or 26 degrees C. Plants grown at either temperature were examined for Chl content, Chl a/b ratio, expression of the light-harvesting complex II (LHC-II) apoproteins, and protochlorophyllide (Pchlide) biosynthetic capacity. Except for the ch4 mutant, the parental strain and all mutants accumulate more Chl when grown at 26 degrees C than at 17 degrees C. The ch5 mutants, lacking Chl b under any growth condition, and the ch12 mutant showed little temperature-dependent phenotypic plasticity, whereas this was a marked phenomenon in the other mutants. The ch10 and ch11 mutants demonstrated extreme temperature sensitivity with regard to the production of Chl b and the Chl b-binding LHC-II apoproteins. When excised trifoliolates were supplemented with exogenously supplied delta-aminolevulinic acid, only the ch4 mutant was markedly impaired in the ability to produce Pchlide. These data indicate that temperature-sensitive phenotypic plasticity is a common phenomenon of chlorphyll-deficient mutants and substantiate that only a minority of Chl-deficient mutants is impaired in the biosynthesis of Chl.
Of 42 rhizobial isolates from Medicago sativa and Melilotus spp. growing in arid saline fields in Xinjiang, China, 40 were identified as Sinorhizobium meliloti by a polyphasic approach. However, diverse groups were obtained from these isolates in numerical taxonomy and SDS-PAGE of proteins. They could grow at pH 10.5 and were tolerant to 2.5-4.0% (w/v) NaCl.