Abstract:The presence of the tetracyclic diterpene 16alpha-hydroxykaurane (16alpha-hydroxy-ent-kaurane, C20H34O, CAS 5524-17-4) was detected in sterile cell cultures of the moss Physcomitrella patens (Hedw.) B.S.G. using gas chromatography and mass spectrometry. 16alpha-hydroxykaurane was found to be a major lipid compound in P. patens, with an estimated intracellular concentration of up to 0.84 mmol/l and an extracellular concentration of up to 9.3 micromol/l. The overall content of 16alpha-hydroxykaurane (in milligra… Show more
“…Mosses do not require gibberellins for growth (Yasumura et al 2007;Hirano et al 2007;Vandenbussche et al 2007), which is probably why growth was not inhibited in transgenic P. patens. P. patens produces two diterpenoids (ent-kaurene and 16-hydroxykaurane) as secondary metabolites (von Schwartzenberg et al 2004), which together can comprise up to 0.2% of its fresh weight (based on GC-MS analysis). Since the production of entkaurene and 16-hydroxykaurane still constitute a major portion of the diterpenoid pool in transgenic P. patens (Fig.…”
Taxadiene synthase gene from Taxus brevifolia was constitutively expressed in the moss Physcomitrella patens using a ubiquitin promoter to produce taxa-4(5),11(12)-diene, the precursor of the anticancer drug paclitaxel. In stable moss transformants, taxa-4(5),11(12)-diene was produced up to 0.05% fresh weight of tissue, without significantly affecting the amounts of the endogenous diterpenoids (ent-kaurene and 16-hydroxykaurane). Unlike higher plants that had been genetically modified to produce taxa-4(5),11(12)-diene, transgenic P. patens did not exhibit growth inhibition due to alteration of diterpenoid metabolic pools. Thus we propose that P. patens is a promising alternative host for the biotechnological production of paclitaxel and its precursors.
“…Mosses do not require gibberellins for growth (Yasumura et al 2007;Hirano et al 2007;Vandenbussche et al 2007), which is probably why growth was not inhibited in transgenic P. patens. P. patens produces two diterpenoids (ent-kaurene and 16-hydroxykaurane) as secondary metabolites (von Schwartzenberg et al 2004), which together can comprise up to 0.2% of its fresh weight (based on GC-MS analysis). Since the production of entkaurene and 16-hydroxykaurane still constitute a major portion of the diterpenoid pool in transgenic P. patens (Fig.…”
Taxadiene synthase gene from Taxus brevifolia was constitutively expressed in the moss Physcomitrella patens using a ubiquitin promoter to produce taxa-4(5),11(12)-diene, the precursor of the anticancer drug paclitaxel. In stable moss transformants, taxa-4(5),11(12)-diene was produced up to 0.05% fresh weight of tissue, without significantly affecting the amounts of the endogenous diterpenoids (ent-kaurene and 16-hydroxykaurane). Unlike higher plants that had been genetically modified to produce taxa-4(5),11(12)-diene, transgenic P. patens did not exhibit growth inhibition due to alteration of diterpenoid metabolic pools. Thus we propose that P. patens is a promising alternative host for the biotechnological production of paclitaxel and its precursors.
“…A tetracyclic diterpene, 16-hydroxykaurane (56), was released from the moss Physcomitrella patens into air. It has been proposed as an allelochemical with possible insect antifeeding property, although the ecological role has not been confirmed experimentally [48].…”
Bryophytes frequently grow in an unfavorable environment as the earliest land plants, and inevitably biosynthesize secondary metabolites against biotic or abiotic stress. They not only defend against the plant competition, microbial attack, and insect or animal predation, but also function in UV protection, drought tolerance, and freezing survival. This review covers the ecological aspect of secondary metabolites in bryophytes and is taxonomically presented according to the ecological significances.
“…Adapted from Schmidt et al (1999). metabolites in P. patens Hayashi et al, 2010;Miyazaki et al, 2014Miyazaki et al, , 2015, its CPS-KS catalyzes the biosynthesis of mostly 16a-hydroxy-ent-kaurane (Hayashi et al, 2006), which is extruded (Von Schwartzenberg et al, 2004). In any case, given the ability of M. polymorpha to give rise to functionally distinct diterpene synthases (i.e., MpDTPS1, 3, and 4), it is unclear why this liverwort recruited separate gene families to catalyze mono-and sesquiterpene cyclization rather than to rely on evolution of these genes from diterpene synthase genes as suggested by Trapp and Croteau (2001), but this could represent a fascinating case of adaptive gene evolution by horizontal transfer.…”
Section: Diterpene Synthases Provide An Anchor For Assessmentmentioning
Marchantia polymorpha is a basal terrestrial land plant, which like most liverworts accumulates structurally diverse terpenes believed to serve in deterring disease and herbivory. Previous studies have suggested that the mevalonate and methylerythritol phosphate pathways, present in evolutionarily diverged plants, are also operative in liverworts. However, the genes and enzymes responsible for the chemical diversity of terpenes have yet to be described. In this study, we resorted to a HMMER search tool to identify 17 putative terpene synthase genes from M. polymorpha transcriptomes. Functional characterization identified four diterpene synthase genes phylogenetically related to those found in diverged plants and nine rather unusual monoterpene and sesquiterpene synthase-like genes. The presence of separate monofunctional diterpene synthases for ent-copalyl diphosphate and ent-kaurene biosynthesis is similar to orthologs found in vascular plants, pushing the date of the underlying gene duplication and neofunctionalization of the ancestral diterpene synthase gene family to >400 million years ago. By contrast, the mono-and sesquiterpene synthases represent a distinct class of enzymes, not related to previously described plant terpene synthases and only distantly so to microbial-type terpene synthases. The absence of a Mg 2+ binding, aspartate-rich, DDXXD motif places these enzymes in a noncanonical family of terpene synthases.
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