Samuel O. Yeboah

Recent results from natural product research at the University of Botswana

Marketed plants are very important items of trade in many parts of the world. The community uses these for a variety of purposes such as foods, cosmetics, flavors, spices, and medicines. It seems that plants that are used for medicinal purposes form the most common category. Four plants used for treatment of microbial infections, viz., Bolusanthus speciosus, Erythrina latissima, Crotalaria podocarpa, and Elephantorrhiza goetzei, were investigated, and these yielded several known and novel structures, some with appreciable antibiotic activity against the test organisms. The activity of some of the isolated plants and the parts of the plant from which these were obtained lend support to their traditional use. Bulbine abyssinica and B. capitata yielded phenylanthraquinones, some of which were shown to possess strong antiplasmodial activity. In addition, these yielded isofuranonaphthoquinones, which were also found to be weakly antiplasmodial and antioxidant. Scilla nervosa yielded several known and novel homoisoflavoinds of the 3-benzylchroman-4-ones and 3-benzylidinechroman-4-one type, as well as some stilbenoids. The homoisoflavonoids showed strong antitumor activity against various cancer cell lines. Rhus pyroides gave a novel bichalcone, which showed weak antifeedant activity, consistent with the observation by farmers that the plant was avoided by corn cricket. Results from investigated Dorstenia species originating from Cameroon, Ethiopia, and Tanzania yielded styrenes, coumarins, chalcones, and flavonoids. The chalcones and flavonoids showed various levels of prenylation or geranylation, and an observation made so far is that prenylated flavonoids are only found in Dorstenia species of African origin. The only example of a bis-geranylated chalcone is found in Dorstenia.

Tylosema esculentum (Marama) Tuber and Bean Extracts Are Strong Antiviral Agents against Rotavirus Infection

Tylosema esculentum (marama) beans and tubers are used as food, and traditional medicine against diarrhoea in Southern Africa. Rotaviruses (RVs) are a major cause of diarrhoea among infants, young children, immunocompromised people, and domesticated animals. Our work is first to determine anti-RV activity of marama bean and tuber ethanol and water extracts; in this case on intestinal enterocyte cells of human infant (H4), adult pig (CLAB) and adult bovine (CIEB) origin. Marama cotyledon ethanolic extract (MCE) and cotyledon water extract (MCW) without RV were not cytotoxic to all cells tested, while seed coat and tuber extracts showed variable levels of cytotoxicity. Marama cotyledon ethanolic and water extracts (MCE and MCW, resp.) (≥0.1 mg/mL), seed coat extract (MSCE) and seed coat water extract (MSCW) (0.01 to 0.001 mg/mL), especially ethanolic, significantly increased cell survival and enhanced survival to cytopathic effects of RV by at least 100% after in vitro co- and pre-incubation treatments. All marama extracts used significantly enhanced nitric oxide release from H4 cells and enhanced TER (Ω/cm2) of enterocyte barriers after coincubation with RV. Marama cotyledon and seed coat extracts inhibited virion infectivity possibly through interference with replication due to accumulation of nitric oxide. Marama extracts are therefore promising microbicides against RV.

Chemical constituents of Croton oligandrum (Euphorbiaceae).

A new clerodane diterpene derivative named crotonoligaketone was obtained from the stem bark of Croton oligandrum along with eight known compounds including crotonadiol, imbricatadiol, crotonzambefuran B, 7-acetoxytrachiloban-18-oic acid, 3-O-acetylaleuritolic acid, lupeol, b-sitosterol, and stigmasterol. The structures of the isolated compounds were established on the basis of their spectral data and by comparison with those reported in the literature

Secondary metabolites with antiproliferative effects from Albizia glaberrima var glabrescens Oliv. (Mimosoideae)

Abstract A new 5-dehydroxyflavan, namely Albiziaflavan B or (+)-(2R, 3S, 4R)-3′,4′, 7-trihydroxy-4-methoxy-2,3-trans-flavan-3,4-trans-diol (1) was isolated from the root bark of Albizia glaberrima, together with six known compounds including three flavans: (+)-mollisacacidin (2), (+)-fustin (3) and butin (4); two steroids: chondrillasterol (5) and chondrillasterone (6), and a triterpenoid: lupeol (7). The structure of 1 was established by detailed analysis of its spectroscopic data, especially 1D and 2D NMR spectra, HRESIMS and CD data. Compounds 1–6 were assayed for their antiproliferative effects on two human cancer cells, HeLa at 50 μM (n = 2) and HL60 at 20 μM (n = 2). Compound 3 and 4 were the most active on HL60 with IC50 of 8.1 and 8.3 μM, respectively. Compound 6 was the most active with an IC50 of 4.6 μM on HeLa.

Thonningiiflavanonol A and thonningiiflavanonol B, two novel flavonoids, and other constituents of Ficus thonningii Blume (Moraceae).

Abstract A phytochemical study of Ficus thonningii has led to the isolation of two previously unreported compounds, thonningiiflavanonol A and thonningiiflavanonol B together with 16 known compounds: shuterin, naringenin, syringic acid, p-hydroxybenzoic acid, genistein, 5,7,3′,4′,5′-pentahydroxyflavanone, luteolin, methylparaben, aromadendrin, garbanzol, dihydroquercetin, 5,7,3′-trihydroxyflavanone, β-sitosterol, sitosterolglucoside, lupeol acetate, and taraxerol. Their structures were elucidated on the basis of spectroscopic data. The new compounds and extracts displayed potent antioxidant activity.

Antrocarines A-F, antiplasmodial ergostane steroids from the stem bark of Antrocaryon klaineanum.

During a study on the chemistry and biological activity of Antrocaryon klaineanum Pierre, six new sterols including 4,24(28)-ergostadiene-6α,7α-diol (1), 6α-methoxy-4,24(28)-ergostadiene-7α,20S-diol (2), 6α-methoxy-4,24(28)-ergostadien-7α-ol (3), 20S-hydroxy-24(28)-ergosten-3-one (4), 7α-hydroxy-4,24(28)-ergostadien-3-one (5), and 24(28)-ergostene-3β,6α-diol (6) were characterized by physical and spectroscopic means. The known steroids 7 and 8 were also isolated. The crude extract and the isolated compounds were evaluated for their ability to inhibit the 3D7 strain of Plasmodium falciparum. Compounds 2, 3, and 8 showed potent activity while that of the crude extract was moderate.

Elatumic acid: a new ursolic acid congener from Omphalocarpum elatum Miers (Sapotaceae).

A new triterpene diastereomer, 1, of the previously reported 3β,6β,19α-trihydroxy-urs-12-en- 28-oic acid-24-carboxylic acid methyl ester was obtained from the stem bark of Omphalocarpum elatum Miers (Sapotaceae) along with α-amyrin acetate (2), spinasterol (3), spinasterol 3-O-β-Dglucopyranoside (4), and tormentic acid (5). The structures of the isolates were established on the basis of NMR and mass spectrometric data and by comparison with those previously reported in the literature. Compound 1 showed weak antibacterial activity against E. aerogenes ATCC13048 and EA3, K. pneumoniae ATCC29916, and P. aeruginosa; it also displayed moderate cytotoxicity against CCRF-CEM, CEM=ADR5000, and MDA-MB231 cells.

Excelsoside: a new benzylic diglycoside from the leaves of Milicia excelsa.

A new benzylic diglycoside was isolated from the leaves of Milicia excelsa and identified as 3,4-dimethoxybenzyl ß-D-xylopyranosyl(1⃗2)-ß-D-glucopyranoside (1). It was oßtained together with four known secondary metaßolites including lupeol acetate (2), ursolic acid (3), triacontyl (E)- ferulate (4), and 2-(3,5-dihydroxyphenyl)ßenzofuran-5,6-diol (5). Their structures were determined ßased on their spectroscopic data and by comparison with those reported in the literature.