Antifungal Enantiomeric Styrylpyrones from Sanrafaelia ruffonammari and Ophrypetalum odoratum.

Phytochemical investigation of Sanrafaelia ruffonammari Verd and Ophrypetalum odoratum Diels that belongs to the rare genera confined to East African coastal forests led to the isolation of enantiomeric styrylpyrone dimer, (±)-5-methoxy-7-phenyl-[4-methoxy-2-pyronyl]-1-(E)-styryl-2-oxabicyclo-[4.2.0]-octa-4-en-3-one (1) alongside (+)-6-styryl-7,8-epoxy-4-methoxypyran-2-one (2) and the enantiomeric (+)- (3) and (-)-6-styryl-7,8-dihydroxy-4-methoxypyran-2-ones (4).

Diprenylated Indole Alkaloids from Fruits of Hexalobus monopetalus.

New hexalobine type alkaloid, 5-(2″,3″-epoxy-3″-methylbutyl)-3-(3'-hydroxy-3'-methyl-1'-acetyloxy-but-2'-yl)indole (1) alongside the known hexalobines 3-(2',3'-dihydroxy-3'-methylbutyl)-5-(3″-methylcrotonoyl) indole (2), 3,5-hexalobine C (3) and 3,5-hexalobine D (4) were isolated from fruits of Hexalobus monopetalus. Compounds 3 and 4 exhibited antifungal activity against Candida albicans.

New antimicrobial, mosquito larvicidal and other metabolites from two Artabotrys species.

Azabicycloheptenoylditerpene 1-((2E,6E,10E)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraenyl)-2-azabicyclo[2.2.1]hept-5-en-3-one (artamodamide, 1), diphenylpentanoid (E)-1,5-bis(4-hydroxyphenyl)-pent-1-en-3-one (artamenone, 2) and N-methoxy-5-oxoaporphinoid (artamonteirine, 3) were isolated as new metabolites from Artabotrys modestus Diels ssp macranthus Verdc.

Toussaintines A-E: antimicrobial indolidinoids, a cinnamoylhydrobenzofuranoid and a cinnamoylcyclohexenoid from Toussaintia orientalis leaves.

Toussaintine A (N-cinnamoyl-5,6-dehydro-4-hydroxyindolidin-2,7-dione), toussaintine B (N-cinnamoyl-5,6-dehydro-4,7-dihydroxyindolidin-2-one), toussaintine C (N-cinnamoyl-5,6-dehydro-4-hydroxyindolidin-7-one), toussaintine D (N-cinnamoyl-2-amino-4-hydroxy-7-oxo-2,3,8,9-tetrahydrobenzofuran) and toussaintine E (N-cinnamoyl-1-acetoxymethyl-2-amino-1-hydroxycyclox-5-en-4-one) were isolated as antibacterial and antifungal constituents of the leaves of Toussaintia orientalis Verdc. (Annonaceae) and their structures established from analysis of spectroscopic data. The compounds belong to a series of variously cyclized aminocinnamoyl tetraketide derivatives, showing the importance of rarely occurring Annonaceae species as sources of structurally diverse natural products.

Constituents of the essential oil of Suregada zanzibariensis leaves are repellent to the mosquito, Anopheles gambiae s.s.

In traditional African communities, repellent volatiles from certain plants generated by direct burning or by thermal expulsion have played an important role in protecting households against vectors of malaria and other diseases. Previous research on volatile constituents of plants has shown that some are good sources of potent mosquito repellents. In this bioprospecting initiative, the essential oil of leaves of the tree, Suregada zanzibariensis Verdc.

Geranylbenzoquinonoids from Lettowianthus stellatus fruits.

The geranylbenzoquinonoids 7-(3,7-dimethylocta-2,6-dienyl)-5-hydroxy-3H-benzofuran-2-one (lettowienolide), dimethyl 2,3-bis-[5-(3,7-dimethylocta-2,6-dienyl)-3,6-dioxocyclohexa-1,4-dienyl]-succinate (lettowiquinone), 2-(3,7-dimethylocta-2,6-dienyl)-6-[7-(3,7-dimethylocta-2,6-dienyl)-5-hydroxybenzofuran-2-yl]-[1,4]benzoquinone (lettowifuraquinone), methyl [3-(3,7-dimethylocta-2,6-dienyl)-6-methyl-5-(3-methylbut-2-enyl)-1,4-dioxo-1,5, 8,8a-tetrahydro-4H-nathphalen-4a-yl)]-acetate (lettowinone) and methyl [6-hydroxy-2-methyl-2-(4-methylpent-3-enyl)-2H-chromen-8-yl]-acetate (lettowipyraquinol) were isolated from fruits of Lettowianthus stellatus Diels, together with juvenile hormone III and 7-octadecen-9-ynoic acid. Lettowienolide and lettowiquinone exhibited mild in vitro activity against the Plasmodium falciparum malaria parasite (each IC(50) approximately 20 microg mL(-1)). Structural determination was achieved based on extensive analysis of spectroscopic data.

Aristolactams, 1-(2-C-methyl-beta-D-ribofuranosyl)-uracil and other bioactive constituents of Toussaintia orientalis.

The new aristolactam alkaloid toussalactam {2-hydroxy-1,6-dimethoxy-5H-dibenzo[cdf]indol-4-one} and the known ones, namely aristolactam AII, aristolactam BII, piperolactam C and aristolactam FII; 1-(2-C-methyl-beta-D-ribofuranosyl)-uracil, 3,4,5-trimethoxyphenyl-beta-D-glucopyranoside, and three catechinoids were isolated from the cytotoxic Toussaintia orientalis Verdc stem and root bark extracts, and their structures established based on analysis of spectroscopic data. The aristolactams exhibited antimicrobial and antiinflammatory activity, aristolactam FII showing almost the same level of activity as the standard anti-inflammatory agent Indomethacin. The compounds also exhibited either mild or no antiproliferative and cytotoxic activities, except aristolactam FII that showed the same level of cytotoxicity as the standard drug Camptothecin.

Antimosquito and antimicrobial clerodanoids and a chlorobenzenoid from Tessmannia species.

The clerodane diterpenoids trans-kolavenolic acid, 18-oxocleroda-3,13(E)-dien-15-oic acid, ent-(18-hydroxycarbonyl)-cleroda-3,13(E)-dien-15-oate, 2-oxo-ent-cleroda-3,13(Z)-dien-15-oic acid and trans-2-oxo-ent-cleroda-13(Z)-en-15-oic acid, and the chlorobenzenoid O-(3-hydroxy-4-hydroxycarbonyl-5-pentylphenyl)-3-chloro-4-methoxy-6-pentyl-2-oxybenzoic acid were isolated from Tessmannia martiniana var pauloi and T. martiniana var matiniana. Structures were established based on interpretation of spectroscopic data.

Cytotoxic, anti-proliferative and antimicrobial furanoditerpenoids from Stuhlmania moavi.

The furanoditerpenoids voucapane, voucapane-6alpha,7alpha-diol, voucapane-18,19-diol and 18-hydroxyvoucapan-19-al were isolated from the cytotoxic stem and root bark extracts of Stuhlmaniamoavi Verdc. (Ceasalpiniaceae) and their structures established based on analysis of spectroscopic data. The compounds exhibited anti-proliferative, cytotoxic, antibacterial and antifungal activities, 18-hydroxyvoucapan-19-al showing the highest anti-proliferative and cytotoxic properties.

Anti-mosquito and antimicrobial nor-halimanoids, isocoumarins and an anilinoid from Tessmannia densiflora.

The nor-halimane diterpenoid tessmannic acid and its methyl, 2-methylisopropyl and 1-methylbutyl esters, the unusual isocoumarins 8-hydroxy-6-methoxy-3-pentylisocoumarin and 7-chloro-8-hydroxy-6-methoxy-3-pentylisocoumarin, and 5-pentyl-3-methoxy-N-butylaniline were isolated from the stem and root bark extracts of Tessmannia densiflora Harms (Caesalpiniaceae) that showed mosquito larvicidal activity. The structures were determined on interpretation of spectroscopic data. Tessmannic acid and its methyl ester exhibited antibacterial and antifungal activity.

Larvicidal and IGR activity of extract of Tanzanian plants against malaria vector mosquitoes.

Background & Objectives: This paper reports the larvicidal activity of seventeen Tanzanian plant species against the malaria vector, Anopheles gambiae s.s. Giles larvae.

Mosquito larvicidal constituents from Lantana viburnoides sp viburnoides var kisi (A. rich) Verdc (Verbenaceae).

Background & Objectives: Lantana viburnoides sp viburnoides var kisi is used in Tanzania ethnobotanically to repel mosquitoes as well as in traditional medicine for stomach ache relief. Bioassay-guided fractionation and subtraction bioassays of the dichloromethane extract of the root barks were carried out in order to identify the bioactive components for controlling Anopheles gambiae s.s.

A new cytotoxic and larvicidal himachalenoid, rosanoids and other constituents of Hugonia busseana.

A new cytotoxic himachalene sesquiterpenoid 4alpha-methoxy-5,9-oxahimachal-9-ene (hugonianene A) which exhibited moderate activity against Anopheles gambiae mosquito larvae after 24 h at a concentration of 0.237 mg mL(-1), and at 48 h and 72 h contact time causing complete larval mortality up to a concentration as low as 0.01369 mg mL(-1), was isolated as the major constituent of the cytotoxic root bark extract of Hugonia busseana.

A novel antiplasmodial 3',5'-diformylchalcone and other constituents of Friesodielsia obovata.

Phytochemical investigation of the stem and root barks of Friesodielsia obovata Benth (Annonaceae) afforded new 3',5'-diformyl-2',4',6'-trihydroxychalcone and N-formyl-7-hydroxyglaucine together with five known compounds, 3',5'-dimethyl-2',4',6'-trihydroxychalcone, (-)-crotepoxide, demethoxymatteucinol, lawinal, and benzyl benzoate. 3',5'-diformyl-2',4',6'-trihydroxychalcone indicated significant antiplasmodial, cytotoxicity, and larvicidal activities.

Antifungal rosane diterpenes and other constituents of Hugonia castaneifolia.

The rosane diterpenoids hugorosenone [3beta-hydroxyrosa-1(10),15-dien-2-one], 18-hydroxyhugorosenone and 18-hydroxy-3-deoxyhugorosenone, and 12-hydroxy-13-methylpodocarpa-8,11,13-trien-3-one were isolated as antifungal constituents of H. castaneifolia Engl. root bark, together with the previously reported di-podocarpanoids hugonone A and hugonone B that were weakly active, and 1(10),15-rosadiene-2beta,3beta-diol (hugorosenol), 4alpha-methoxyhimachal-10-en-5beta-ol (hugonianene B) and 2-hydroxyhenpentacont-2-enal, and the known compounds tetracosyl-(E)-ferrulate and caryophyllene oxide, all of which were inactive.

C18 tetraynoic fatty acids and essential oil composition of Mkilua fragrans.

The fatty acids 17,18-dihydroxyoctadeca-9,11,13,15-tetraynoic acid (mkiluaynoic acid A) and 18-hydroxyoctadeca-9,11,13,15-tetraynoic acid (mkiluaynoic acid B), 5,7,3',4'-tetrahydroxyflavanol, 3,4-dihydroxybenzoic acid and a mixture of stearic and oleic acids were isolated from fruits and stem barks of Mkilua fragrans (Annonaceae). Mkiluaynoic acid A exhibited antifungal activity against Candida albicans comparable with that of the standard antifungal agent Ketoconazole. Structural determination was achieved by analysis of spectroscopic data.

Prenylindoles from Tanzanian Monodora and Isolona species.

6-(3-Methyl-but-2-enyl)-1,3-dihydro-indol-2-one, annonidine F [3-[6-(3-methyl-but-2-enyl)-1H-indolyl]-6-(3-methyl-but-2-enyl)-1H-indole], 1H-indole-5-carbaldehyde, 6-(3-methyl-2-butenyl)-1H-indole, 6-(3-methyl-buta-1,3-dienyl)-1H-indole, 6-(4-oxo-but-2-enyl)-1H-indole and 3-geranylindole were isolated from Monodora angolensis (Annonaceae) while 3-(1,1-dimethyl-but-2-enyl)-5-(3-methyl-but-2-enyl)-1H-indole (caulidine A), 4-[3-(1,1-dimethyl-but-2-enyl)-1H-indol-5-yl]-but-3-en-2-one (caulidine B), 5-(3-methyl-2-butenyl)-1H-indole and 5-(3-methylbuta-1,3-dienyl)-1H-indole were obtained from Isolona cauliflora (Annonaceae); structural determination by spectroscopic analysis. Some of the prenylindoles had antifungal and antimalarial activities.

(+/-)-Schefflone: a trimeric monoterpenoid from the root bark of Uvaria scheffleri.

The trimeric monoterpene and mildly mosquito larvicidal agent, (+/-)-schefflone, that is an apparent derivative of the antiparasitic aromatic monoterpene espintanol, was isolated from the antimalarial extracts of the root bark of Uvaria scheffleri, together with espintanol. Structural determination of (+/-)-schefflone was achieved from spectroscopic data and confirmed by single-crystal X-ray diffraction analysis. (+/-)-Schefflone can be considered a product of a non-enzymatic Diels-Alder-type cycloaddition reaction of the quinonemethide derivative of espintanol as the diene and dienophile.

The caulindoles: dimeric prenylindoles from Isolona cauliflora.

Four dimeric prenylindoles occurring in diastereomeric pairs, the caulindole A-D, 5-(3-methyl-2-butenyl)-1H-indole, and (E)-5-(3-methylbuta-1,3-dienyl)-1H-indole were isolated from the stem and root barks of Isolona cauliflora, an ecologically endangered Annonaceae species. Structural determination was achieved based on interpretation of spectroscopic data. Biogenetically, the caulindoles are considered as Diels-Alder-type cycloaddition products of mono- and/or bis-prenylindoles [e.

A novel phenanthrenolide and C-benzyl dihydrochalcones from Uvaria puguensis.

Two new natural products, the phenanthrenoid puguenolide (6-hydroxy-3-methoxy-4-oxapyren-5-one) and isoangoletin were isolated from the stem bark of the newly described Uvaria species, U. puguensis D.M.