Crinum biflorum Rottb. (syn. Crinum distichum ) is an Amaryllidaceae plant used in African traditional medicine but very few studies have been performed on this species from a chemical and applicative point of view. Bulbs of C. biflorum , collected in Senegal, were extracted with ethanol by Soxhlet and the corresponding organic extract was purified using chromatographic methods. The pure compounds were chemically characterized by spectroscopic techniques (1D and 2D 1 H and 13 C NMR, HR MS and ECD) and X-ray analysis. Four homoisoflavonoids ( 1 - 4 ) and one alkylamide ( 5 ) were isolated and characterized as 5,6,7-trimethoxy-3-(4-hydroxybenzyl)chroman-4-one ( 1 ), as 3-hydroxy-5,6,7-trimethoxy-3-(4-hydroxybenzyl)chroman-4-one ( 2 ), as 3-hydroxy-5,6,7-trimethoxy-3-(4-methoxybenzyl)chroman-4-one ( 3 ) and as 5,6,7-trimethoxy-3-(4-methoxybenzyl)chroman-4-one ( 4 ), and the alkylamide as ( E )- N -(4-hydroxyphenethyl)-3-(4-hydroxyphenyl)acrylamide ( 5 ), commonly named N - p -coumaroyltyramine. The relative configuration of compound 1 was verified thanks to the X-ray analysis which also allowed us to confirm its racemic nature. The absolute configurations of compounds 2 and 3 were assigned by comparing their ECD spectra with those previously reported for urgineanins A and B. Flavanoids 1 , 3 and 4 showed promising anticancer properties being cytotoxic at low micromolar concentrations towards HeLa and A431 human cancer cell lines. The N - p -coumaroyltyramine ( 5 ) was selectively toxic to A431 and HeLa cancer cells while it protected immortalized HaCaT cells against oxidative stress induced by hydrogen peroxide. Compounds 1 - 4 also inhibited acetylcholinesterase activity with compound 3 being the most potent. The anti-amylase and the strong anti-glucosidase activity of compound 5 were confirmed. Our results show that C. biflorum produces compounds of therapeutic interest with anti-diabetic, anti-tumoral and anti-acetylcholinesterase properties.

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Crinum asiaticum Linn. has been used in Thai traditional medicine to relieve inflammatory symptoms and treat osteoarthritis. There have been reports on its potent anti-inflammatory property but nothing on the effects of different pretreatments on its chemical properties and anti-inflammatory activity. Pretreatment of herbal raw materials is an important step which affects the overall quality of Thai traditional medicine. The objectives of this study were to investigate different treatments of C. asiaticum leaves prior to ethanolic extraction and to compare the extracts for their anti-inflammatory activity and chemical properties. The treatments included hot air drying in an oven, microwave drying, traditional grilling on a charcoal stove before drying in an oven, and temperature shock in hot and cold water before hot air drying. The anti-inflammatory activity and chemical properties of the extracts were analyzed using the established methods. Results showed that 95% ethanolic extract of hot air oven-dried leaves had the highest anti-inflammatory activity and total phenolic and lycorine contents. We recommend hot air drying as a preextraction treatment for C. asiaticum leaves for its simplicity, best retention of the herbal quality, and suitability for scaling up to an industrial process.

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Crinum abyscinicum Hochst. ExA. Rich bulb is traditionally used in Ethiopia for the treatment of various ailments including internal parasites, mastitis, rabies, colic diseases of animals, and cancer. Despite its importance in traditional cancer treatment, no research work has been reported on the antiproliferative activity of the bulb extract and its major constituents. Phytochemical investigation of the bulb extract of C. abyscinicum by PTLC over silica gel resulted in the isolation of two alkaloids, which were unequivocally identified as 6-hydroxycrinamine and lycorine on the basis of 1 H- and 13 C-NMR and MS analysis. The bulb extract, 6-hydroxycrinamine, and lycorine possessed significant antiproliferative activity, lycorine being the most active exhibiting GI 50 values of 2.8 μ g/ml and 3.4 μ g/ml against A2780 and MV4-11 cells, respectively. Cell cycle analysis and annexin V/propidium iodide double staining in A2780 cells revealed that both compounds increased the percentage of cells in the S-phase at 30 μ g/ml without inducing apoptosis. Our results suggest that the antiproliferative activities of the bulb extract of C. abyscinicum, 6-hydroxycrinamine, and lycorine could support the traditional claim of the plant against cancer.

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A new pyran derivative, 6-hydroxy-2H-pyran-3-carbaldehyde, has been isolated from the methanolic extract of Crinum yemense along with the known alkaloid haemanthamine, benzoic acid and 1,1'-bis(1,1'-carboxyethyl) ether which is isolated from a natural source for the first time. Structure elucidation of these compounds based on spectroscopicevidences. The pyran derivative was found to be a tyrosinase inhibitor more potent than kojic acid.

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The 80% aqueous methanolic extract from the bulbs of Crinum yemense showed a potent inhibitory effect on nitric oxide production in lipopolysaccharide-activated macrophages. Three new crinine-type alkaloids, yemenines A (1), B (2), and C (3), were isolated from the herbal extract together with six known alkaloids. The absolute configurations of 1-3 were determined on the basis of chemical and physicochemical evidence. The effects of the isolated alkaloids on nitric oxide production in lipopolysaccharide-activated macrophages were examined, and several alkaloids, e.g. 1, (+)-bulbispermine (6), (+)-crinamine (7), (+)-6-hydroxycrinamine (8), and (-)-lycorine (9), showed inhibitory effects on nitric oxide production and induction of inducible nitric oxide synthase.

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