Naturally Occurring Oxygen Heterocyclics. VII.¹ The Structure of Mammein.^2,3

Abstract

b) From epiisohaemanthamine: A solution of 200 mg. of epiisohaemanthamine (XIV, R = H ) in benzene was added to a dispersion of 250 mg. of potassium and finally was treated with 150 mg. of methyl p-toluenesulfonate, as in the 0-methylation of isohaemanthamine. A 150-mg. yield of crude product was chromatographed on alumina with ethyl acetate, producing 75 mg. of crystalline O-methylcoccinine which was sublimed a t 150" (5 1) and recrystallized from a small amount of ether, m.p. 122-123" alone or on admixture with 0-methylcoccinine derived from the 0methylation of coccinine. The infrared spectra (potassium bromide) of the two compounds also were identical. Subsequent elution with 20% methanol in ethyl acetate produced a trace of recovered epiisohaemanthamine. 0-MethyZ-a-isocrinamine (XII, OCH3 instead of OH). (a) From crinamine: A solution of 120 mg. of crinamine in 10 ml. of pyridine was treated with 0.20 ml. of methanesulfonyl chloride and finally with sodium methoxide in methanol under the conditions used in the conversion of haemanthamine to manthine. Chromatography of the crude reaction product on alumina with ethyl acetate produced 13 mg. (11%) of crystals, m.p. 171-172" (unchanged on [ a ]~~, -131°, [a]::, -342" (~0.36).crystallization from ethyl acetate). A mixture melting point with authentic 0-methyl-a-isocrinamine prepared below was not depressed, and the infrared spectra (potassium bromide) were identical.

Antiproliferative Constituents of Geopropolis from the Bee Melipona scutellaris

“…Cinnamoyloxy-mammeisin (6; NSC#781 051): a yellow solid; the 1 H and 13 C NMR data were identical with those reported elsewhere [7]. Mammein (7; NSC# 781 049): a yellow solid; the 1 H and 13 C NMR data were identical with those reported elsewhere [10]. ent-Nemorosone (8; NSC# 781 044): a white solid; [α] D 27 − 45 (c, 0.05, CHCl 3 ); the 1 H and 13 C NMR data were identical with those reported recently [11].…”

“…The other known compounds were isolated and their structures were determined by comparing spectroscopic data with literature values. They were identified as mammeigin (3) [8,9], hydroxymammeigin (4) [9], mammeisin (5) [6], cinnamoyloxymammeisin (6) [7], mammein (7) [10], and the benzophenone ent-nemorosone (8) [11]. All compounds were tested in the NCI 60-cell panel at an initial concentration of 10 −5 M. As shown in l " Table 2, at this concentration, compounds 5 and 7 showed a higher mean percent of inhibition, with 56 and 83% growth inhibition, respectively, and were submitted to the full five-dose screen; however, their cell line selectivity was modest (see Supporting Information).…”

Mammea B/BA Isolated From the Seeds of Mammea americana L. (Calophyllaceae) is a Potent Inhibitor of Methicillin-Resistant Staphylococcus aureus

“…Mammea B/BA was first isolated from M. americana by Morris M.P. and Pagán in 1952 from a sample called mamein, which also contained two other coumarins, mammea B/BB and mammea B/BC (Morris and Pagán, 1953;Djerassi et al, 1958Djerassi et al, , 1959Djerassi et al, , 1960Crombie and Games, 1966). Mammea B/BA was also isolated from the bark of Mammea africana, by Ouahouo et al (2004), who demonstrated its anti-staphylococcal effect using the disk diffusion method, presenting an inhibition halo of 18 mm (Ouahouo et al, 2004); it should be noted that at the time of writing this article, the MIC value for this compound was not reported in the literature reviewed, so it is considered that this is the first time that the MIC 90 of 0.5-1 μg/ml has been reported and a MIC 50 value of 0.25 μg/ml, in reference and clinical MSSA and MRSA.…”

Constitution of Mamey Wax

“…Several studies of this property of mamey seed extracts (2-5) led eventually to the isolation (6) of a crystalline active principle. Degradative and spectroscopic (7,8) as well as synthetic evidence (9) was adduced (8) in support of I for this substance which was named mamrnein (7). Subsequently, a yellow toxic (10) compound was isolated from the fruit peelings and shown (11) t o possess 11.…”