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

Abstract

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.

Antimicrobial activity of polyisoprenoids of sixteen mangrove species from North Sumatra, Indonesia

“…In this study, isolation of polyisoprenoid from 16 species of mangrove plants was performed using a previously described protocol (Basyuni 2016(Basyuni , 2017a(Basyuni , 2018c. As displayed in Table 1, polyisoprenoid in the form of polyprenol is predominantly detected in four species of mangroves, Ac.…”

“…Polyisoprenoid extraction method was performed as described previously (Sagami et al 1992;Basyuni et al 2016Basyuni et al , 2017aBasyuni et al , 2018c. The dried leaves (3-7 g) were first ground and extracted with 30 mL of chloroform-methanol (2: 1, v: v) for 48 h. The insoluble cell wall debris was removed following the method of Basyuni et al (2016).…”

“…Polyisoprenoid alcohols were a group of compounds that have an essential role in living things, including in mangrove plants that are firmly related to the biosynthesis of secondary metabolites of isoprenoid (Basyuni et al 2007(Basyuni et al , 2016(Basyuni et al , 2017a(Basyuni et al , 2018c. Isoprenoid and polyisoprenoid compounds are the most diverse plant secondary metabolites (Basyuni et al 2007(Basyuni et al , 2012(Basyuni et al , 2016(Basyuni et al , 2017aSkorupinska-Tudek et al 2008;Koch et al 2011). These compounds were encoded by oxidosqualene cyclase (OSC) gene (Basyuni et al 2012;Lodeiro et al 2007).…”

A Non‐Enzymatic Pathway with Superoxide in Intracellular Terpenoid Synthesis

“…Thus, compound 2 was determined to be (all‐ E )‐farnesylfarnesylacetone. Compound 2 has been identified via TLC and MS as a natural product from Laurus nobilis and Sonneratia caseolaris , as an oxidation product of solanesol, which is produced during air sampling for tobacco smoke, and as a minor artifact from tubercle bacilli . However, the isolation of compound 2 as a bacterial natural products and its NMR assignment were first reported in this study.…”

A Non‐Enzymatic Pathway with Superoxide in Intracellular Terpenoid Synthesis

“…HMBC data showed four isopentenyl moieties (represented by dotted squares in Figure 3) linked to each other. [18] Thus, compound 2 was determined to be (all-E)-farnesylfarnesylacetone.Compound 2 has been identified via TLC and MS as an atural product from Laurus nobilis and Sonneratia caseolaris, [19,20] as an oxidation product of solanesol, which is produced during air sampling for tobacco smoke, [21] and as am inor artifact from tubercle bacilli. An uclear Overhauser effect (NOE) was not observed for H-8/Me-28, H-12/Me-29, H-16/Me-30, or H-20/Me-31, indicating that prenyl residues in 2 were arranged in E-configuration, supported by chemical shifts (d C = 40.2 ppm) of C-10, C-14, C-18, and C-22 relative to previously reported shifts in ficaprenol (Z:c a.…”