The history and recent advances in research of polyprenol and its derivatives

The reduction pathway leading to the formation of dolichol was clarified in 2010 with the identification of SRD5A3, which is the polyprenol reductase. The finding inspired us to reanalyze the length of the major chain of polyprenol and dolichol from several plant leaves, including mangrove plants, as well as from animal and fish livers by 2D-TLC. Polyprenol- and dolichol derived metabolites such as polyprenylacetone and epoxydolichol were found together with rubber-like prenol. This review focuses on analyses of polyprenol and its derivatives, including recently found epoxypolyprenol and polyprenylacetone. Attention has also been paid to the chromatographic behavior of rubber-like prenol on TLC

Salinity Alters the Polyisoprenoid Alcohol Content and Composition of Both Salt-Secreting and Non–Salt-Secreting Mangrove Seedlings

The effects of salinity on the polyisoprenoid alcohol content and composition of the salt-secreting mangrove species Avicennia marina and Sonneratia alba and the non–salt-secreting species Bruguiera gymnorrhiza and Kandelia obovata were studied. The seedlings of mangroves were grown for 5 months under 0% and 3% salt concentrations. The occurrence, content, and distribution of four mangrove seedlings were analyzed by two-dimensional thin layer chromatography. The structural groups of the polyprenols and dolichols in the leaves and roots were classified into two types (I and II). In type I, dolichols predominated over polyprenols (more than 90%), whereas in type II, the occurrence of both polyprenols and dolichols was observed. Polyprenols were not detected in the leaves of A. marina and B. gymnorrhiza under 0% salt (control), but were detected in small amounts in K. obovata leaves; however, significant amounts were found in the 3% salinity group. This finding in A. marina, B. gymnorrhiza, and K. obovata leaves implies a change to the structural group: under 0% salt concentrations, the groups are classified as type I, but become type II under 3% salt concentrations. The occurrence of ficaprenol (C50–55) was found only in the leaves of the non–salt-secreting species B. gymnorrhiza and K. obovataunder 3% salinity and not in the salt-secreting species A. marina or S. alba. It is noteworthy that the polyisoprenoid type in the roots of the four species showed no change under salinity; the two salt-secreting species A. marina and S. alba contained type I under 0% and 3% salt concentrations. On the other hand, type II polyisoprenoids were identified in the non–salt-secreting species B. gymnorrhiza and K. obovata under 0% and 3% salinity conditions. This finding suggested that polyisoprenoids play a protective role against salinity in the mangrove leaves of both salt-secreting and non–salt-secreting species

Distribution, occurrence, and cluster analysis of new polyprenyl acetones and other polyisoprenoids from North Sumatran mangroves

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

Formation of lipid droplets induced by 2,3-dihydrogeranylgeranoic acid distinct from geranylgeranoic acid

Geranylgeranoic acid (GGA) and 2,3-dihydrogeranylgeranoic acid (2,3-diGGA) are geranylgeraniol-derived metabolites (Kodaira et al. (2002) J Biochem 132: 327-334). In the present study, we examined the effects of these acids on HL-60 cells. The cells were differentiated into neutrophils by GGA stimulation like retinoic acid stimulation. In the case of cells stimulated with 2,3-diGGA, neutrophils were not detected, but the formation of lipid droplets was induced. On the other hand, when the cells were cultured in the presence of 0.1% FBS instead of 10% FBS, apoptotic cells were induced not only by GGA stimulation but also with 2,3-diGGA. In the latter case, when the cells were cultured in the co-presence of a caspase-3 inhibitor (Ac-DMQD-CHO), the lipid droplets formation was observed in the cells. These results suggest that GGA and 2,3-diGGA are extremely different from each other with respect to their effects on HL-60 cells

Dolichols of the fern Matteucia struthiopteris.

Dolichols isolated from leaves of the fern Matteucia struthiopteris were present as a mixture of prenologues composed of 14 up to 20 isoprene units with Dol-16 dominating. They comprised approximately 0.004% of the fresh weight of fresh plant tissue and were accompanied by traces of polyprenols (Pren-14 up to Pren-17, Pren-16 dominating). Their structure was confirmed by electropray ionization mass spectrometry (ESI-MS). This is the first time that dolichols have been reported as dominating polyisoprenoid alcohols in plant photosynthetic tissue

Search for polyisoprenoids in the flowers and fruits of selected coastal plants using two-dimensional thin layer chromatography

Coastal plants are recognized to yield secondary metabolites including polyisoprenoid alcohols. Coastal plants have been shown to have biological and phytochemical activities. The present study reports the search for polyisoprenoids composition from flowers and fruits of selected coastal plants, Amorphophallus paeoniifolius, Guettarda speciosa, and Jatropha curcas. A two-dimensional thin layer chromatography (2D-TLC) was used to analyse the composition and occurrence of polyisoprenoid alcohols (polyprenols and dolichols) in coastal plants. The distribution of polyprenols and dolichols in the flowers and fruits were detected and classified into one type only, type-II. Type-II, having the presence of both polyprenols and dolichols, was found in all samples investigated: in the flowers and fruits of A. paeoniifolius, G. spiciosa, and J. curcas. It is interesting to note that no dominating dolichols over polyprenols (type-I) or predominance polyprenol over dolichols (type-III) detected in this study. The present study, therefore, suggested the diversity of polyisoprenoids in the generative tissues of tropical coastal plants