Functional genomics approach to the study of triterpene biosynthesis

Ebizuka, Yutaka; Katsube, Yuji; Tsutsumi, Takehiko; Kushiro, Toshio; Shibuya, Masabumi

doi:10.1351/pac200375020369

Cited by 59 publications

(58 citation statements)

References 8 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…16) No OSC yielding aamyrin as a sole product has been reported and all OSCs whose products include a-amyrin are multifunctional. They are OEA from O. europaea (this study), PSM from Pisum sativum, 17) At1g78960 18) and At1g78500 19,20) from Arabidopsis thaliana, KcMS from Kandelia candel, 21) and two OSCs from Taraxacum officinale (our unpublished results). Furthermore, most of the phytochemical studies reported the presence of ursane type triterpenes together with oleanane type triterpenes.…”

mentioning

confidence: 63%

“…Some callus cultures produce no trace of the metabolites found in the mother plants but produce those metabolites that are not produced by the mother plants. This situation is exemplified by Glycyrrhiza glabra cell cultures, which did not produce glycyrrhizin (18), a major triterpene saponin of the mother plant, but produced betulinic acid (16) 8) and soyasaponin I (19). 9) It is quite interesting to know what kinds and how much of triterpenes cultured cells produce.…”

mentioning

confidence: 99%

See 1 more Smart Citation

Production of Triterpene Acids by Cell Suspension Cultures of Olea europaea

Saimaru

Orihara

Tansakul

et al. 2007

CHEMICAL & PHARMACEUTICAL BULLETIN

Self Cite

View full text Add to dashboard Cite

Olive (Olea europaea) is a well-known evergreen tree native to the Mediterranean coast, whose fruits and oil have been used for foods and cooking. Olive contains large quantity of triterpene acids including oleanolic acid (6) as a major one.1,2) Recently, much attention has been paid for triterpene acids from pharmaceutical viewpoints because of their anti-HIV, 3) anti-inflammatory, 4) anti-tumor-promoting 5) activities and antagonist activity for an endothelin receptor, 6) etc. Wax of olive fruits contains predominantly oleanolic acid, 1) whereas that of the leaves contains a mixture of oleanolic acid and betulinic acid (16) in a ratio of 7 : 2.2) In addition to these triterpene acids, triterpene-diols, such as erythrodiol (8: oleanane type) and uvaol (15: ursane type) are also contained, even though in less quantity than the corresponding acids. 2)Successful production of triterpene acids by plant cell cultures has been documented. Production of bryonolic acid (17), an anti-allergic triterpene acid, by cultured cells of several cucurbitaceous plants 7) is a good example. Cell cultures of plants, however, do not always produce the same secondary metabolites as those in the mother plants. Some callus cultures produce no trace of the metabolites found in the mother plants but produce those metabolites that are not produced by the mother plants. This situation is exemplified by Glycyrrhiza glabra cell cultures, which did not produce glycyrrhizin (18), a major triterpene saponin of the mother plant, but produced betulinic acid (16) 8) and soyasaponin I (19).9) It is quite interesting to know what kinds and how much of triterpenes cultured cells produce. If they produce any particular ones in large quantity, such production system would benefit the supply of triterpene acids for clinical use, since purification and isolation of triterpenes from complex mixtures are generally laborious. Thus we induced cell cultures of O. europaea and investigated the production of triterpene metabolites.Triterpenes are biosynthesized from a common precursor, (3S)-oxidosqualene (1). Over one hundred of diverse triterpene skeletons reported from nature 10) are constructed at the cyclization step of oxidosqualene catalyzed by oxidosqualene cyclase (OSC). Thus, the studies on their product specificity, in particular, would lead to better understanding of the structural diversity of natural triterpenes. As a continuation of our studies on OSCs 11) in this direction, cDNA clonig of OSCs from Olive cell cultures was also conducted.In this paper, we report induction of cell cultures, isolation Olive (Olea europaea) contains large quantity of triterpene acids including oleanolic acid (6) as a major one. Varieties of biological activities exhibited by triterpene acids attracted our attentions, especially from pharmaceutical viewpoints. Cell culture of olive plant was induced and its triterpene constituents were studied. From the cell suspension cultures, six ursane type triterpene acids; ursolic acid (9), pomolic acid (10), rotundic acid (11)...

show abstract

mentioning

confidence: 63%

mentioning

confidence: 99%

Production of Triterpene Acids by Cell Suspension Cultures of Olea europaea

Saimaru

Orihara

Tansakul

et al. 2007

CHEMICAL & PHARMACEUTICAL BULLETIN

Self Cite

View full text Add to dashboard Cite

show abstract

“…Although 13 OSC genes were identified in the Arabidopsis thaliana genome, 31) five OSC genes, which have been functionally identified, encode one cycloartenol synthase 32) and four multifunctional triterpene synthases, 31,[33][34][35] respectively. The multifunctional triterpene synthase produces multi-triterpene-products from 2,3-oxidosqualene, the common substrate for OSCs, and this type of OSC was also cloned from pea, 36) Costus speciosus 37) and Lotus japonicus.…”

Section: Discussionmentioning

confidence: 99%

Differential Expression of Three Oxidosqualene Cyclase mRNAs in Glycyrrhiza glabra

Hayashi

Huang

Takada

et al. 2004

Biological & Pharmaceutical Bulletin

Self Cite

View full text Add to dashboard Cite

Higher plants produce not only sterols but also various triterpenes, which are derived from six isoprene units, 1) and some triterpenes are further glycosylated to produce various triterpene saponins.2) These triterpenes and triterpene saponins are believed to participate in the plant defence systems against microbial pathogens or insects. [3][4][5] An interesting effect that has also been reported is that an exogenous triterpene saponin stimulates the growth of roots in several plants. 6,7) In addition to the benefit for plants themselves, these triterpenes and saponins are beneficial for human beings as medicines, sweeteners, detergents, and cosmetics. Although structural elucidation of triterpenes and saponins has been extensively studied, 1,2) our understanding about the regulation of their biosyntheses is quite limited at the molecular level. 8)Oxidosqualene cyclases (OSCs) catalyze the cyclization of 2,3-oxidosqualene, a common intermediate of both sterols and triterpenes. Lanosterol synthase, playing a crucial role in cholesterol biosynthesis, is a unique OSC in mammals. In higher plants, on the other hand, some OSCs responsible for triterpene biosynthesis co-exist with cycloartenol synthase corresponding to lanosterol synthase in mammals. 8,9) Up to now, cDNAs of OSCs including cycloartenol synthase, bamyrin synthase, lupeol synthase and multifunctional triterpene synthase have been functionally characterized from various plant species. 8) After cloning of these OSC genes, our interest has shifted the regulatory roles of these OSCs in triterpene and saponin biosyntheses in higher plants. 8,[10][11][12][13] In our study, licorice (Glycyrrhiza glabra L., Fabaceae) was used as a model plant to elucidate the regulation of triterpene biosyntheses in higher plants (Fig. 1). Cultured licorice cells lacked the ability to produce glycyrrhizin, a sweet oleanane-type triterpene saponin produced in the roots of the mother plant, but produced phytosterols and two structurally different triterpenoid constituents, soyasaponins and betulinic acid. 15,16) Glycyrrhizin is localized exclusively in the woody parts of the thickened roots and stolons, whereas soyasaponins, oleanane-type triterpene saponins, are localized mainly in the seeds and rootlets of licorice.17) On the other hand, the content of betulinic acid, a lupane-type triterpene, is high in the cork layer of thickened licorice roots. 15) cDNAs of cycloartenol synthase, an OSC involved in sterol biosynthesis, and b-amyrin synthase, an OSC involved in both glycyrrhizin and soyasaponin biosynthesis, have been cloned from G. glabra. 18,19) In addition to these two OSCs, the third OSC, lupeol synthase, which is responsible for the biosynthesis of betulinic acid, most likely exists in cultured licorice cells. In the present study, an OSC cDNA for lupeol synthase was isolated by heterologous hybridization with that of olive lupeol synthase, 20) and the patterns of mRNA expression of the three OSCs in the cultured cells and the intact plants of G. glabra were examined. ...

show abstract

“…A selected number of genes are provided in Table 2 and include those involved in both aliphatic and aromatic metabolic pathways associated with suberin formation. Genes potentially linked with suberin biosynthesis found to be downregulated in both myb9 and myb107 seeds include those encoding SUS (the putative suberin synthase); an SGNH hydrolase-type esterase superfamily protein (likely involved in lipid metabolic processes; Li-Beisson et al, 2013); CASP-LIKE PROTEIN 1B2 (CASPL1B2, showing strong homology to CASP proteins involved in casparian strip metabolism); LACCASE3 (a member of the laccase family of which LACCASE4 has been demonstrated to be involved in lignin metabolism; Zhao et al, 2013;Schuetz et al, 2014); DIHYDROFLAVONOL 4-REDUCTASE-LIKE1 (DFR-like1; involved in phenylpropanoid metabolism and previously linked to pollen wall development and seed production (Lallemand et al, 2013); and LUPEOL SYNTHASE5 (LUP5; a multifunctional triterpene synthase; Ebizuka et al, 2003). While genes downregulated in myb107 seeds (but not myb9 seeds) encode GPAT5 and ASFT (known to act in suberin formation); 3-KETOACYL-COA SYNTHASE17 (KCS17; a very-long-chain fatty acid synthase); 4-COUMARATE:COA LIGASE5 (4CL5; involved in phenylpropanoid metabolism); and GLYCOSYLPHOSPHATIDYLINOSITOL-ANCHORED LIPID PROTEIN TRANSFER5 (LTPG5; a homolog to the lipid transporter LTPG1; Debono et al, 2009;Edstam and Edqvist, 2014).…”

Section: Myb107 and Myb9 Are Required For Suberin-associated Gene Expmentioning

confidence: 99%

MYB107 and MYB9 Homologs Regulate Suberin Deposition in Angiosperms

et al. 2016

View full text Add to dashboard Cite

Suberin, a polymer composed of both aliphatic and aromatic domains, is deposited as a rough matrix upon plant surface damage and during normal growth in the root endodermis, bark, specialized organs (e.g., potato [Solanum tuberosum] tubers), and seed coats. To identify genes associated with the developmental control of suberin deposition, we investigated the chemical composition and transcriptomes of suberized tomato (Solanum lycopersicum) and russet apple (Malus x domestica) fruit surfaces. Consequently, a gene expression signature for suberin polymer assembly was revealed that is highly conserved in angiosperms. Seed permeability assays of knockout mutants corresponding to signature genes revealed regulatory proteins (i.e., AtMYB9 and AtMYB107) required for suberin assembly in the Arabidopsis thaliana seed coat. Seeds of myb107 and myb9 Arabidopsis mutants displayed a significant reduction in suberin monomers and altered levels of other seed coat-associated metabolites. They also exhibited increased permeability, and lower germination capacities under osmotic and salt stress. AtMYB9 and AtMYB107 appear to synchronize the transcriptional induction of aliphatic and aromatic monomer biosynthesis and transport and suberin polymerization in the seed outer integument layer. Collectively, our findings establish a regulatory system controlling developmentally deposited suberin, which likely differs from the one of stressinduced polymer assembly recognized to date.

show abstract

Functional genomics approach to the study of triterpene biosynthesis

Cited by 59 publications

References 8 publications

Production of Triterpene Acids by Cell Suspension Cultures of Olea europaea

Production of Triterpene Acids by Cell Suspension Cultures of Olea europaea

Differential Expression of Three Oxidosqualene Cyclase mRNAs in Glycyrrhiza glabra

MYB107 and MYB9 Homologs Regulate Suberin Deposition in Angiosperms

Contact Info

Product

Resources

About