The distribution and occurrence of polyisoprenoids (dolichols and polyprenols) in the leaves and roots of nine true Okinawan mangroves and the leaves of one associate mangrove were analyzed using two-dimensional thin layer chromatography. In the leaves, the distribution of three types (I, II, and III) of polyprenols and dolichols were detected. (I) The predominance of dolichols over polyprenols (more than 90%) was observed in Avicennia marina, Bruguiera gymnorrhiza, B. gymnorrhiza (yellow leaves), and Rhizophora stylosa. (II) The occurrence of both polyprenols and dolichols is observed in Excoecaria agallocha, Kandelia obovata, K. obovata (yellow leaves), Lumnitzera racemosa, Pemphis acidula, and Sonneratia alba. (III) The predominance of polyprenols over dolichols (more than 90%) is observed in Heritiera littoralis and Hibiscus tiliaceus. However, in the roots, a type-I distribution was observed in A. marina, B. gymnorrhiza, E. agallocha, H. littoralis and S. alba. A type-II distribution was observed in K. obovata, L. racemosa, P. acidula, and R. stylosa with no type-III distribution. The chain-length distribution of dolichols in the leaves and roots was C 50-C 140 and C 60-C 120 , respectively. A similar chain-length distribution of polyprenols of C 45-C 140 and C 65-C 85 was detected in the leaves and roots respectively. Taken together, sixteen out of twenty-one tissues indicated that dolichols are more abundant than polyprenols in both leaves and roots. The present study is the first to clarify the diversity of polyisoprenoids in both the leaves and roots of mangrove, suggesting the chemotaxonomic significance of polyisoprenoids in the mangrove tree species.

We report the inhibition of a human recombinant geranylgeranyl diphosphate synthase (GGPPSase) by 23 bisphosphonates and six azaprenyl diphosphates. The IC50 values range from 140 nM to 690 microM. None of the nitrogen-containing bisphosphonates that inhibit farnesyl diphosphate synthase were effective in inhibiting the GGPPSase enzyme. Using three-dimensional quantitative structure-activity relationship/comparative molecular field analysis (CoMFA) methods, we find a good correlation between experimental and predicted activity: R2 = 0.938, R(cv)2 = 0.900, R(bs)2 = 0.938, and F-test = 86.8. To test the predictive utility of the CoMFA approach, we used three training sets of 25 compounds each to generate models to predict three test sets of three compounds. The rms pIC50 error for the nine predictions was 0.39. We also investigated the pharmacophore of these GGPPSase inhibitors using the Catalyst method. The results demonstrated that Catalyst predicted the pIC50 values for the nine test set compounds with an rms error of 0.28 (R2 between experimental and predicted activity of 0.948).

Background. Mangrove forests have long been known as a source of phytochemical compounds producing various secondary metabolites. Despite the ubiquitous diversity of polyisoprenoids in the plant kingdom, few studies have focused on the distribution of polyisoprenoids in mangrove plants. The present study describes the distribution and occurrence of a new class of prenyl derivates -polyprenyl acetone as well as other polyisoprenoids in fourteen species of Indonesian mangroves, with an emphasis on chemotaxonomic importance. Material and methods. The leaves and roots of fourteen North Sumatran mangroves were analyzed using two-dimensional thin layer chromatography and electrospray ionization mass spectrometry. Results. In the leaves, the distribution of several types of polyprenyl acetones, polyprenols, and dolichols was detected and classified into types: type-I, having a predominance of dolichols over polyprenols (more than nine-fold), was observed in Acrostichum aureum (younger leaves), Avicennia alba, Av. lanata, Av. officinalis, Bruguiera parviflora, Ceriops tagal, Nypa fruticans, and Rhizophora mucronata; type-II, having the presence of both polyprenols and dolichols, was observed in Acanthus ilicifolius, Acr. aureum, B. cylindrica, and R. apiculata; type-III having a predominance of polyprenols over dolichols (more than nine-fold), was not observed in any North Sumatran mangroves; type-IV, having the presence of both polyprenyl acetones and dolichols, was observed in Aegiceras corniculatum; type-V, having the presence of polyprenyl acetones, polyprenols, and dolichols, was observed in Sonneratia caseolaris and Xylocarpus granatum. In the roots, type-I distribution was observed in Ae. corniculatum, Av. alba, Av. lanata, Av. officinalis, B. parviflora, C. tagal, N. fruticans, R. apiculata, R. mucronata, S. caseolaris, and X. granatum. Type-II distribution was observed in Ac. ilicifolius, Acr. aureum, and B. cylindrica. Type-III, -IV, and -V distributions were not observed in mangrove roots. Cluster analysis demonstrated that polyisoprenoid patterns in the leaves and roots form distinct separation into appropriate genera and tribe, suggesting that mangrove polyisoprenoids are chemotaxonomically significant. Conclusions. The major polyisoprenoid alcohols in Indonesian mangroves were found to be dolichols rather than polyprenols. The diversity of polyisoprenoids in both leaves and roots of mangroves may provide chemotaxonomic marker. The discovery of a new class of polyprenyl acetone is the first report from mangrove plants.

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