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[Studies on the chemical constituents of Securidaca inappendiculata].

AIM: To investigate the chemical constituents of Securidaca inappendiculata. METHODS: Compounds were isolated by silica gel column chromatography and Medium Pressure Liquid Chromatography, respectively. Structures of the compounds were elucidated by chemical evidence and spectral (UV, IR, MS, 1HNMR and 13CNMR) analysis. RESULTS: Eight compounds (1-8) were isolated and identified. Seven of them (2-7) are known compounds: oleanolic acid, p-hydroxytruxinic acid, p-coumaric acid, ethyl p-methoxycinnamate, uridine, beta-sitosterol and daucosterol. One (1) is a new hemiterpenoic acid glycoside, named securiterpenoside. CONCLUSION: A new hemiterpenoic acid glycoside, named securiterpenoside, was isolated from Securidaca inappendiculata Hassk. Seven known compounds were isolated from genus Securidaca for the first time.

Butyrates↗

Antihyperglycaemic effect and acute toxicity of Securigera Securidaca L. seed extracts in mice.

The antihyperglycaemic activity of a Securigera securidaca aqueous infusion and an ethanol maceration extract of seeds was studied in normoglycaemic, glucose-induced hyperglycaemic and alloxan-induced diabetic mice. The acute toxicity of the ethanol extract was more than that of the aqueous one. The phytochemical analysis showed that the seed extracts were rich in flavonoids. The intraperitoneal and oral administration of the aqueous and ethanol extracts significantly reduced blood glucose in alloxan-induced diabetic mice. In normoglycaemic and glucose-induced hyperglycaemic mice, the blood glucose levels were not significantly different from the control. Glibenclamide was not able to lower blood glucose in alloxan-induced diabetic mice, while it significantly lowered the blood sugar in normoglycaemic mice. The results indicate that S. securidaca seed extracts significantly reduce blood glucose in alloxan-induced diabetic mice by a mechanism different from that of sulfonylurea agents.

Administration, Oral↗

Effect of volatile constituents from Securidaca longepedunculata on insect pests of stored grain.

Securidaca longepedunculata Fers (Polygalaceae) is commonly used as a traditional medicine in many parts of Africa as well as against a number of invertebrate pests, including insects infesting stored grain. The present study showed that S. longepedunculata root powder, its methanol extract, and the main volatile component, methyl salicylate, exhibit repellent and toxic properties to Sitophilus zeamais adults. Adult S. zeamais that were given a choice between untreated maize and maize treated with root powder, extract, or synthetic methyl salicylate in a four-way choice olfactometer significantly preferred the control maize. Methyl salicylate vapor also had a dose-dependant fumigant effect against S. zeamais, Rhyzopertha dominica, and Prostephanus truncates, with a LD100 achieved with a 60microl dose in a 1-l container against all three insect species after 24 hr of exposure. Probit analyses estimated LD50 values between 34 and 36 microl (95% CI) for all insect species. Furthermore, prolonged exposure for 6 days showed that lower amounts (30 microl) of methyl salicylate vapor were able to induce 100% adult mortality of the three insect species. The implications are discussed in the context of improving stored product pest control by small-scale subsistence farmers in Africa.

Animals↗

Antinociceptive and antidepressant like effects of Securidaca longepedunculata root extract in mice.

The aqueous root extract of Securidaca longepedunculata (polygalaceae) was investigated for possible antinociceptive and central nervous system (CNS) effects in mice. Three nociceptive models; acetic acid, formalin and tail-flick tests were used to study the antinociceptive activity. Rectal temperature test was employed as an adjunct to the nociceptive models. The extract at 200 and 400 mg/kg significantly and dose dependently reduced the nociception induced by the acetic acid and in the early phase of formalin test (P<0.05). The extract exerted significant (P<0.05) hypothermic effect in the 15 and 30 min of the rectal temperature test. The antinociceptive and hypothermic effects were partially reversed by naloxone (1mg/kg). The tail-flick test produced an insignificant increase in tail-flick latency at 400 mg/kg after 60 min of the test, but significantly (P<0.05) increase tail-flick latency in the 400mg/kg group of animals pre-treated with naloxone (1 mg/kg) after 120 min of the test. The extract also produced a significant (P<0.05) naloxone reversible antidepressant like effect in the forced swimming test (an animal model of depression). Collectively, these results suggest that the extract possess antinociceptive and antidepressant like effects with possible involvement of opioidergic pathways. The extract at limit dose of 2 g/kg body weight appeared to be safe in oral formulation.

Analgesics↗

Antimicrobial activity of Securidaca longipedunculata.

The folk herbal uses of Securidaca longipedunculata in the treatment of diarrhea, boils, gonorrhea, and cough prompted phytochemical analyses and antimicrobial activity screening of extracts of the root. Some flavonoids isolated showed activity against many micro-organisms. These flavonoids were isolated using chromatographic methods.

Anti-Infective Agents↗

New xanthone glycosides from Securidaca inappendiculata.

Three new xanthone glycosides, securixanside A (1), securixanside B (2), and securixanside C (3) were isolated from the stems of Securidaca inappendiculata. These compounds were characterized by spectrometric and chemical methods, including FABMS and one- and two-dimensional NMR experiments.

Glycosides↗

A new sterol glycoside from Securidaca inappendiculata.

From the roots of Securidaca inappendiculata, one new sterol glycoside securisteroside (1) has been isolated, along with two known sterols, spinasterol (2) and 3-O-beta-D-glucopyranosyl-spinasterol (3). The new sterol was characterized by chemical and spectrometric methods, including EIMS, FABMS and one- and two-dimensional NMR experiments.

Magnetic Resonance Spectroscopy↗

[Organic acid constituents from the stem of Securidaca inappendiculata Hassk].

OBJECTIVE: To investigate the organic acid constituents from the stem of Securidaca inappendiculata. METHOD: Column chromatographic techniques were used to isolate and purify the constituents. The structures were elucidated by spectra analysis. RESULT: Five compounds were isolated and identified as ferulic acid (I), cinnamic acid(II), palmitic acid(III), salicylic acid(IV) and benzoic acid(V). CONCLUSION: Compounds I-IV were isolated from the plant for the first time.

Cinnamates↗

[A new benzophenone from the root of Securidaca inappendiculata].

AIM: To study the benzophenones in the roots of Securidaca inappendiculata Hassk. METHODS: Column chromatography (including silica gel and Sephadex LH-20) was used to isolate benzophenones whose structures were elucidated by HREI-MS, NMR (1D and 2D) methods. RESULTS: A new benzophenone was isolated and identified as 2-methoxy-3,4-methylenedioxy-benzophenone (I), along with a known compound 4-hydroxy-2,6-dimethoxy-benzophenone (II). CONCLUSION: Compound I is a new one named as securiphenone B, compound II was isolated from the genus for the first time.

Benzophenones↗

Identification of methyl salicylate as the principal volatile component in the methanol extract of root bark of Securidaca longepedunculata Fers.

Securidaca longepedunculata Fers (Polygalaceae) is commonly used as a medicine in many parts of Africa and shows promise for protecting stored grain against insect pests. Analysis of a methanol extract of the root bark by gas chromatography linked to mass spectrometry (GC/MS) showed a major component accounting for over 90% of the volatile material. This was identified as methyl 2-hydroxybenzoate (methyl salicylate) by comparison of the GC retention times and mass spectrum with those of synthetic standards. This conflicts with an earlier report that the major component is methyl 4-hydroxybenzoate. Two minor components had mass spectra characteristic of 2-hydroxybenzoate esters and were identified as methyl 2-hydroxy-6-methoxybenzoate and its benzyl analogue, again conflicting with an earlier report.

Benzoates↗

New conjugated hydroxydienoic fatty acids and acetotriacylglycerols from Securidaca longipedunculata seed oil.

Like other members of the plant family Polygalaceae, Securidaca longipedunculata Fres., is a source of fatty acids and triacylglycerols with unusual structures. Its seed oil contains at least seven chromatographically distinct groups of triacylglycerols divided into two series: One series represents monoacetotriacylglycerols, and the other 'normal' triacylglycerols having only long-chain fatty acids. Each series has groups containing zero, one or two conjugated hydroxydienoic acids. In addition, there is a small amount of triacylglycerol incorporating three hydroxy acids. In addition to coriolic (13-hydroxyoctadeca-cis-9,trans-11-dienoic) acid (27%), two of its previously unknown homologs are present: 11-hydroxyhexadeca-cis-7,trans-9-dienoic acid (15%) and 9-hydroxytetradeca-cis-5,trans-7-dienoic acid (2%).

Chromatography, Gas↗

Xanthones from the stems of Securidaca inappendiculata.

From the stems of Securidaca inappendiculata, securixanthones A (1,3,7-trihydroxy-2,8-dimethoxyxanthone) and B (3,7-dimethoxy-4-hydroxyxanthone) along with ten known xanthones were isolated. Their structures were elucidated by analysis chemical and spectroscopic evidence, and the chemotaxonomic significance of these findings are also discussed.

Magnetic Resonance Spectroscopy↗

The effects of Securidaca longepedunculata root extract on ionic currents and contraction of cultured rat skeletal muscle cells.

The effects of the primary extract roots of Securidaca longepedunculata were tested on sodium, calcium and potassium currents in rat skeletal muscle cells developed in culture. In addition, they were tested on depolarisation-induced contraction and resting intracellular calcium levels. S. longepedunculata extract (10(-6) g/l) increases sodium current at all potentials. No clear effect was observed on calcium current except for a slight increase at negative potentials (-30, -10 mV) revealing a 5 mV shift towards negative potentials of the I(Ca)/V curve, as with potassium current. In contrast, at the same concentration, S. longepedunculata enhanced the contractile response elicited by durable depolarisation. This was not attributable to the slight increase in resting intracellular free calcium concentration which did not change during and following S. longepedunculata application. These results strongly suggest that S. longepedunculata root extract contains one or more components acting on the voltage-sensor of excitation-contraction coupling (dihydropyridine receptors), regardless of its implication as a calcium channel.

Animals↗

Macrophage-oriented cytotoxic activity of novel triterpene saponins extracted from roots of Securidaca inappendiculata.

It is recognized that macrophages in peripheral tissues often proliferate under pathological conditions such as tumors, inflammation and atherosclerosis. Because the growth state of macrophages is believed to be a factor regulating the pathological process of the diseases, substances that regulate macrophage growth or survival may be useful for disease control. In this paper, we identified the activity inhibiting macrophage growth in a hot water extract of roots of Securidaca inappendiculata. The extract markedly inhibited macrophage colony-stimulating factor (M-CSF/CSF-1)-induced growth of macrophages, whereas it exerted a less potent effect on growth of Concanavalin A (Con A)-stimulated thymocytes or M-CSF-stimulated bone marrow cells. The inhibition of macrophage growth was caused by a cytotoxic effect rather than a cytostatic effect. Cell death was due to the induction of apoptosis, as judged by staining with terminal deoxynucleotidyl transferase-mediated d-UTP nick end labelling (TUNEL). The cytotoxic activity seemed to be specific to peripheral macrophages; it showed a weak effect on the growth and survival of tumor cell lines including a macrophage-like cell line, J-774.1. Moreover, the saponin fraction induced apoptotic cell death of macrophages only when they were stimulated by M-CSF; it did not affect the viability of macrophages cultured without M-CSF or with granulocyte/macrophage-CSF. We determined the structures of the two active triterpene saponin compounds in the fraction, named securioside A and securioside B having a 3,4-dimethoxycinnamic group which is essential for the cell death-inducing activity. They are believed to be the primary compounds of new drugs for the treatment of pathological states in which macrophage proliferation occurs.

Animals↗

[Variability in the dormancy of seeds of Securigera securidaca (L.) Deg. et Dorfl. Preliminary note].

The germination rate of seeds of Securigera securidaca varied abruptly from 0% to 100% in different years of maturation, and this variability did not seem to be due to climatic differences during the period of seed maturation. These seeds showed also polymorphism in colour, which appeared to be related with varying depths of dormancy. This last one seemed to be increased by a short ageing of the seeds.

Fabaceae↗

New sucrose derivatives from the bark of Securidaca longipedunculata.

Two new bitter principles were isolated from the bark of Securidaca longipedunculata (Polygalaceae) and identified as beta-D-(3,4-disinapoyl)fructofuranosyl-alpha-D-(6-sinapoyl)g lucopyranoside and beta-D-(3-sinapoyl)fructofuranosyl-alpha-D-(6-sinapoyl)gluco pyranoside. The structures were elucidated by a combination of 1H nmr (1D, 2D COSY, 2D HOHAHA), 13C-nmr, and fabms spectra.

Carbohydrate Sequence↗