Constituents of Mammea americana L. IV. The Structure of Mammeigin<sup>1,2</sup>

Finnegan, R.A.; Mueller, W. H.

doi:10.1021/jo01018a053

Cited by 24 publications

(7 citation statements)

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“…In popular medicine, this plant is used for the treatment of stomach pains, scabies and others skin diseases, rheumatic pain and cough (Raponda-Walker and Sillans, 1961). The results of previous detailed studies on the chemistry of M. africana have revealed the presence of a large number of 4-alkyl and 4-arylcoumarins that are almost invariably substituted, at C-6 and C-8, by a variety of isoprene-type side-chains (Carpenter et al, 1971;Crombie et al, 1972;Finnegan and Mueller, 1965;Games, 1972;Crichton and Waterman, 1978;Vichai et al, 2003). In some cases, the isoprene side-chain can cyclize to give chromene, hydroxypyran or hydroxyfuran moieties (Carpenter et al, 1971).…”

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confidence: 99%

Cytotoxic and antimicrobial coumarins fromMammea africana

Ouahouo

Azebaze

Meyer

et al. 2004

Annals of Tropical Medicine & Parasitology

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Six coumarin derivatives [three 4-phenylcoumarins (Mammea A/AA, Mammea A/BA and MAB 3), two 4-n-propylcoumarins (Mammea B/BB and Mammea B/BA) and one 4-n-pentylcoumarin (Mammea C/OB)], 1,5-dihydroxyxanthone and 1-methoxy-5-hydroxyxanthone have been isolated from the stem bark of Mammea africana Sabine collected in Cameroon. Although known, the structures of the coumarin derivatives were confirmed by spectral analysis, including two-dimensional nuclear magnetic resonance. All the coumarin compounds showed noteworthy cytotoxicity against the human 9-KB cell line. Both of the 4-n-propylcoumarins were also found to exhibit significant activity against Staphylococcus aureus.

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confidence: 99%

Cytotoxic and antimicrobial coumarins fromMammea africana

Ouahouo

Azebaze

Meyer

et al. 2004

Annals of Tropical Medicine & Parasitology

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“…H 2 SO 4 [143,170] and catalytic hydrogenation of mammeigin 190 [170]. of the resulting oxime acetates annelated the isoxazole ring to form substituted angular pyrano[1,2]benzisoxazoles 208 [178].…”

Section: Methods Of Modifying 4-arylcoumarinsmentioning

confidence: 99%

Neoflavones. 2. Methods for Synthesizing and Modifying 4-Arylcoumarins

Garazd

Khilya

2005

Chem Nat Compd

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Literature data up to 2003 were presented and information on methods for preparing and modifying natural 4-arylcoumarins and their synthetic analogs were systematized.The first part of this review [1] presented data on the physicochemical and pharmacological properties of natural 4-arylcoumarins. Natural neoflavones and their synthetic analogs can be used as medical preparations because of their wide spectrum of biological activity and low toxicity. However, this necessitates the development of preparative synthetic methods. Therefore, the second part reviews completely all presently known synthetic approaches to the construction and modification of neoflavones.

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“…Isolation of Mammein Mixture from Mamey Oil-The preparation of mamey oil has been described before (3). In this work, various samples of oil were chromatographed quickly through a column of alumina (Merck, acid washed, deactivated with 5% water).…”

Section: Experimental6mentioning

confidence: 99%

“…The extensive efforts of Djerassi and his collaborators (1,8,9), which culminated in Structure I for mammein and revealed in detail the variegated chemistry of this polyfunctional molecule, established a precedent which greatly facilitated access to Structures I1 for mammeisin (2) and I11 for mammeigin (3). Thus, Structure I1 was secured relatively quickly on the basis of experiments conducted in the mammein mold, while Structure 111, although based principally on its NMR spectrum, was easily verified by a chemical interconversion whh 11.…”

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confidence: 99%