Combretastatins D-3 and D-4, New Macrocyclic Lactones fromGetonia floribunda

Abstract

Chemical investigation of biologically active compounds of Getonia floribunda led to the isolation of two new macrocyclic lactones, combretastatins D-3 (1) and D-4 (2). The structures of these compounds were confirmed by spectroscopic analyses. Combretastatin D-3 (1) exhibited cytotoxicity towards the small-cell lung cancer cell line (NCI-H187, IC50=13.0 +/- 0.2 microg/mL) but was inactive against KB, BC-1, and Vero cell lines. Combretastatin D-3 (1) showed weak antitubercular activity with a minimum inhibitory concentration (MIC) of 100.0 microg/mL, and was inactive towards the malarial parasite. Combretastatin D-4 (2) was inactive in all antitubercular, antiplasmodial, and cytotoxic assays.

Components from the Leaves and Twigs of Mangrove Lumnitzera racemosa with Anti-Angiogenic and Anti-Inflammatory Effects

“…From analyses of the NMR, UV ( Figure S5 ), and IR data, compound 1 was determined to be a neolignan. Compound 1 showed similar 1 H and 13 C NMR signals ( Table 1 ), partially similar to those of corniculatolide A, which has an ether bridge between two propylphenyl moieties [ 22 , 23 ]—except for the presence of two unusual quaternary carbon signals at δ c 126.6 and δ c 127.2 instead of two signals at δ c 149.0 and δ c 154.2 in corniculatolide A. This indicated a new carbon–carbon linkage formation in the target molecule.…”

Applications of Mitsunobu Reaction in total synthesis of natural products

“…For a long time, this mangrove has been utilized as a folk medicine in the treatment of different inflammatory and metabolic disordere as well as showing a series of striking biological potencies . Notably, from five isolated natural products, just corniculatolide A attracted the attention of the synthetic organic chemists …”

“…[152,153] Notably, from five isolated natural products, just corniculatolide A attracted the attention of the synthetic organic chemists. [154] The total synthesis the 83 initiated by the reaction of easily available ester 84 with para-fluorocinnamaldehyde 85 which after several steps gave diarylether 86. [155] Then, under the Mitsunobu reaction [10,156] conditions, in the presence of PPh 3 , DIAD in toluene as solvent at ambient temperature the desired natural product target, macrocycle 83 was obtained in 65% yield (Scheme 19).…”

Antimalarial compounds isolated from plants used in traditional medicine

“…No cytotoxicity was observed with 51. [32] A xanthone derivative, gaboxanthone (53), was isolated from the seed shells of Symphonia globulifera L.f. (Clusiaceae), together with known compounds, symphonin (54) and globuliferin (55). The antiplasmodial activity of the phenolic compounds was evaluated against W2.…”

“…Table 1 gives the tested phenolic derivatives presenting low or no activity in vitro against various strains of P. falciparum. [12,13,16,17,25,26,28,29,32,34,37,[40][41][42]47,48,[50][51][52][53][54][55][56][57][58][59][60][61][62][63][64][65][66] metabolites were isolated from the root extract of Bauhinia purpurea L. (Leguminosae). Among the isolated metabolites, two compounds exhibited antimalarial activity against K1, bauhinoxepin I (84) (IC50 = 10.5 mM) and bauhinoxepin J (85) (IC50 = 5.8 mM).…”