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.

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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Basyuni M, Wati R, Sagami H, Sumardi, Baba S, Oku H. 2018. Diversity and abundance of polyisoprenoid composition in plant species from North Sumatra, Indonesia. Biodiversitas 19: 1-11. The distribution and abundance of polyprenols (pol) and dolichols (dol) in the leaves and roots of fourteen coastal plants from North Sumatra, Indonesia were analysed using two-dimensional thin layer chromatography. In the leaves, with respect to the distribution of pol and dol were detected and categorized into three-types. In type-I, the predominance of dol over pol, was observed in Barringtonia asiatica, Calophyllum inophyllum, Pandanus odoratissimus, and Stachytarpheta jamaicensis. In type-II, the presence of both pol and dol, was observed in Casuarina equisetifolia, Melastoma candidum, Morinda citrifolia, Scyphiphora hydrophyllacea, Sesuvium portulacastrum and Terminalia catappa. In type-III, the predominance of pol over dol, was observed in Acacia auriculiformis, Hibiscus tiliaceus, Ricinus communis, and Pongamia pinnata. However, in the roots, a type-I distribution was observed in eleven species, while three species, A. auriculiformis, M. candidum, and M. citrifolia, corresponded to a type-II distribution instead of type-III. The diversity of polyisoprenoid composition in the leaves was noted, whereas 79% of root tissues indicated that dol occur more abundantly than pol. The range of the contents of polysioprenoid was 12-300 mg/g dw. The present study indicated that pol and dol could be useful in the classification of mangroves and other coastal forests and in phylogenetic studies. The diversity and presence of polyisoprenoids in coastal plants suggested that plant polyisoprenoids are chemotaxonomically important.

Mangrove plants are distributed in the intertidal zone of tropical or subtropical areas and rich sources of triterpenoids alcohols, which are derived mostly from the oleanane, lupane, and ursane classes of terpenoids [1,2] Oleanane-type triterpene is one of the most widespread triterpenes found in plants, together with the lupane type, and these two types often occur together in the same plant. Bruguiera gymnorrhiza (L.) Lamk. and Rhizophora stylosa Griff. (Rhizophoraceae) are known to produce both types of triterpenes. Four oxidosqualene cyclase cDNAs were cloned from the leaves of B. gymnorrhiza and R. stylosa by a homology-based PCR method. The ORFs of full-length clones termed BgbAS (2280 bp, coding for 759 amino acids), BgLUS (2286 bp, coding for 761 amino acids), RsM1 (2280 bp, coding for 759 amino acids) and RsM2 (2316 bp coding for 771 amino acids) were ligated into yeast expression plasmid pYES2 under the control of the GAL1 promoter. Expression of BgbAS and BgLUS in GIL77 resulted in the production of b-amyrin and lupeol, suggesting that these genes encode b-amyrin and lupeol synthase (LUS), respectively. Furthermore, RsM1 produced germanicol, b-amyrin, and lupeol in the ratio of 63 : 33 : 4, whereas RsM2 produced taraxerol, b-amyrin, and lupeol in the proportions 70 : 17 : 13. This result indicates that these are multifunctional triterpene synthases. Phylogenetic analysis and sequence comparisons revealed that BgbAS and RsM1 demonstrated high similarities (78-93%) to b-amyrin synthases, and were located in the same branch as b-amyrin synthase. BgLUS formed a new branch for lupeol synthase that was closely related to the b-amyrin synthase cluster, whereas RsM2 was found in the first branch of the multifunctional triterpene synthase evolved from lupeol to b-amyrin synthase. Based on these sequence comparisons and product profiles, we discuss the molecular evolution of triterpene synthases and the involvement of these genes in the formation of terpenoids in mangrove leaves.Abbreviations

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