Galinsosides A (1) and B (2), new flavanone glucosides together with two known flavanones, 7,3',4'-trihydroxyflavanone (3) and 3,5,7,3',4'-pentahydroxyflavanone (4) have been isolated from an ethyl acetate- soluble fraction of Galinsoga parviflora. Their structures were assigned on the basis of spectral studies. Compound 1 showed significant antioxidant and urease inhibitory activity while compound 2 was moderately active. On the other hand, 2 showed inhibitory potential against alpha-glucosidase.
A monocyclic "temple" synthetic lectin, with extended electron-rich aromatic surfaces, shows enhanced affinities for carbohydrates in water. The methoxy substituents favour binding to α-linked maltodextrins, against the all-equatorial substrates normally favoured by this family of receptors.
Haloxylon salicornicum (MOQ.-TAND.) Boiss belongs to the family Chenopodiaceae which comprises 100 genera and 1200 species. Most of the members of this family are weedy and grow in waste and unfertile areas of soil. In Pakistan, this family is represented by 35 genera. Only five species of genus Haloxylon are found in Pakistan. Haloxylon salicor-nicum is a diffuse shrub, pale, much branched, almost leaf-less, 25-60 cm tall, with woody stem. It is widely distributed in Egypt, Palestine, Jordan, Iraq, Kuwait, Iran, and Pak-istan. 1) The plant is traditionally reported for its toxicity and applied externally on insect stings. 2) The ash of the plant is used for internal ulcers. 3) Three alkaloids and a pyranone derivative have so far been reported from this species. 4-6) A methanolic extract of this plant showed strong cytotoxicity in brine shrimp lethality test. 7) On further fractionation, the major cytotoxicity was detected in the chloroform-soluble fraction. Further pharmacological screening of this fraction revealed strong antifungal and cholinesterase inhibiting activities. This prompted us to carry out bioassay-guided isolation of bioactive compounds from the chloroform-soluble fraction. As a result of these studies we have isolated two new piperidine alkaloids named as haloxylines A (1) and B (2). Both 1 and 2 showed antifungal and cholinesterase inhibiting activities. Results and Discussion The methanolic extract of the whole plant of H. salicor-nicum was processed as described in Experimental to afford new piperidine alkaloids named as haloxylines A (1) and B (2). Haloxyline A (1) was isolated as colorless crystals (14 mg). The high-resolution (HR) EI-MS of (1) showed the molecular ion peak at m/z 419.3749 (Calcd for C 27 H 49 NO 2 , 419.3763) possessing four degrees of unsaturation. The IR spectrum of 1 showed an amide carbonyl at 1640 cm 1 and conjugated double bonds at 1620 cm 1. The UV spectrum displayed absorption at 262 nm, indicating the presence of a conjugated dienamide system. The presence of unsubstituted piperidine ring was indicated by EI-MS and HR-EI-MS at m/z 84 and 84.0809 (C 5 H 10 N). The piperidine ring was further supported by the 1 H-NMR spectrum, which had three broad multiplets at d 3.49 (4H, m, H 2-2, H 2-6), d 1.60 (2H, m, H 2-4) and d 1.58 (4H, m, H 2-3, H 2-5). The 1 H-NMR further showed olefinic protons at d 5.32 (1H, d, J 2,3 11.5 Hz, H-2), d 7.42 (1H, dd, J 3,2 J 3,4 11.5 Hz, H-3), d 6.80 (1H, dd, J 4,3 J 4,5 11.5 Hz, H-4) and d 5.82 (1H, dt, J 5,4 11.5 Hz and J 5,6 7.2 Hz, H-5) indicative of a a, b, g, d-unsaturated amide. The values of coupling constant between the olefinic protons allowed us to assign Z configuration to both the double bonds. 8) The assignments of these protons were confirmed by analysis of the 1 H-1 H COSY spectrum and by homodecoupling experiments. Irradiation of the signal of H-2 (d 5.32) collapsed the double doublet of H-3 (d 7.42) into a doublet (J11.5 Hz). The irradiation at d 7.42 caused the doublet at d 5.32 to collapse into a singlet and that of H...
Background & Objective: The aim of present study was to evaluate herbal analgesic cream containing Nigella sativa oil as an active ingredient, standardization of Nigella sativa oil and evaluation of irritation/sensitization potential of formulation. Material & Method: For this, HPLC analysis of oil, skin irritation test on rabbits and patch testing on human skin was conducted. HPLC analysis using C-18 column, using an isocratic mobile phase of water: methanol (10:90) at flow rate of 1 ml/inactive ingredient: thymoquinone purified from the oil was found to be 1.42g (28.4 %). Safety assessment of analgesic cream was based on Primary Dermal Irritation Index (PDII) by Draize method. Result: According to Draize standard scoring system of reactions PDII was found 0.04 which comes under the category of non irritant. Patch testing on human volunteers revealed that none of volunteers showed any sign of skin reactions. Bangladesh Journal of Medical Science Vol.19(1) 2020 p.163-168
Silybum marianum GAERTH is an erect stout biennial, herb belonging to the family Compositae which comprises about 1000 genera and 20000 species. S. marianum is common in Kashmir at an altitude of 1800-4000 m and is cultivated for ornaments in gardens. The plant is used in the treatment of hepatitis, cirrhosis, regeneration from liver diseases, and liver poisoning.1) A decoction of this plant is also used by the local physicians for the treatment of a variety of viral diseases.1) A literature survey revealed that twenty compounds have so far been reported from S. marianum. The major constituents are, however, flavonoids, flavanolignans, diterpenes and flavanoglycosides.2,3) The ethnopharmacological and chemotaxonomic importance of the genus Silybum prompted us to investigate the chemical constituents of S. marianum. A methanolic extract of this plant showed strong toxicity in the brine shrimp lethality test, revealing the possible presence of bioactive compounds. Further pharmacological screening revealed significant inhibitory activity against the enzyme chymotrypsin. The inhibitory activity was most pronounced in the chloroform-soluble fraction. This prompted us to carry out bioassay-guided isolation of bioactive compounds from this fraction. As a result of these studies we have isolated marianine, a new lanostane-type triterpene (1) and marianosides A (2) and B (3), two new triterpenoidal glucosides, respectively. All three showed significant chymotrypsin inhibiting activity. This is the first report of the natural occurrence of lanostane-type triterpenes in the genus Silybum. Results and DiscussionMarianine (1) was isolated from the chloroform fraction of S. marianum as colorless crystals. It gave color reactions of triterpene and the molecular formula was determined to be C 31 H 50 O 3 by [M] ϩ peak in high-resolution ( H correlation spectroscopy (COSY) with two other protons limiting its location to either C-1 or C-3. However, it could be assigned to the usual C-3 position on the basis of heteronuclear multiple-bond connectivity (HMBC) as illustrated in Fig. 2. The larger coupling constant of this proton allowed us to assign b and equatorial configurations to the hydroxyl group which was substantiated by nuclear overhaueser effect (NOE) between H-3 and H-28. The loss of the side chain resulted in a fragment ion at m/z 329, showing the presence of one hydroxyl and an olefinic moiety in the side chain. Since both methyl groups at C-25 were observed downfield as singlets, the hydroxyl group could be referred to C-25 and confirmed by the HMBC correlations (Fig. 2). The methylene group could be assigned to C-24 Marianine, the new lanostane triterpene (1) and marianosides A (2) and B (3) have been isolated from the whole plant of Silybum marianum. Their structures were elucidated on the basis of extensive analysis of their one dimensional and two dimensional nuclear magnetic resonance (1D, 2D-NMR) spectral data. All inhibited chymotrypsin in a concentration-dependent manner.
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