Marchantin A, the first characterized macrocyclic bis(bibenzyls) found in the liverwort Marchantia polymorpha shows interesting biological activities such as antifungal, antimicrobial, cytotoxic, antioxidant and muscle relaxing activity. Previously, Zenk et al. reported the phenylpropane/polymalonate pathway in the biosynthesis of the marchantins in M. polymorpha. To clear this pathway, transcriptome sequencing and digital gene expression analyses of M. polymorpha were carried out by using Illumina RNA-seq system.
(a) AsakawaY. (1982) Chemical constituents of Hepaticae. In Progress in the Chemistry of Organic Natural Products.HerzW., GrisebachH., KirbyG.W. (Eds). Springer, Vienna, vol. 42, pp. 1–285. (b) Asakawa Y. (1995) Chemical constituents of bryophytes. In Progress in the Chemistry of Organic Natural Products, Herz W, Kirby WB, Moore RE, Steglich W, Tamm Ch. (Eds). Springer, Vienna, vol. 65, pp. 1–618; (c) Asakawa Y, Ludwiczuk A, Nagashima F. (2013) Chemical constituents of bryophytes: bio-and chemical diversity, biological activity, and chemosystematics. In Progress in the Chemistry of Organic Natural Products, Kinghorn DA, Falk H, Kobayashi J. (Eds.). Springer, Vienna, Austria, vol. 95, pp. 1–796; (d) Asakawa Y, Ludwiczuk A, Nagashima F (2013) Phytochemical and biological studies of bryophytes. Phytochemistry, 91, 52–80.
2.
FriederichS., MaierU.H., Deus-NeumannB., AsakawaY., ZenkM.H. (1999) Biosynthesis of cyclic bis(bibenzyls) in Marchantia polymorpha. Phytochemistry, 50, 589–598.
3.
FriederichS., RuefferM., AsakawaY., ZenkM.H. (1999) Cytochromes P-450 catalyze the formation of marchantins A and C in Marchantia polymorpha, Phytochemistry, 52, 1195–1202.
4.
CarochaV., SolerM., HeferC., Cassan-WangH., FevereiroP., MyburgA.A., PaivaJ.A.P., Grima-PettenatiJ. (2015) Genome-wide analysis of the lignin toolbox of Eucalyptus grandis. New Phytologist, 206, 1297–1313.
5.
GrabherrM.G., HaasB.J., YassourM., LevinJ.Z., ThompsonD.A., AmitI., AdiconisX., FanL., RaychowdhuryR., ZengQ., ChenZ., MauceliE., HacohenN., GnirkeA., RhindN., di PalmaF., BirrenB.W., NusbaumC., Lindblad-TohK., FriedmanN., RegevA. (2011) Full-length transcriptome assembly from RNA-Seq data without a reference genome. Nature Biotechnolgy, 29, 644–652.
6.
BelM.V., ProostS., NesteC.V., DeforceD., PeerY.V., VandepoeleK. (2013) TRAPID, an efficient online tool for the functional and comparative analysis of de novo RNA-Seq transcriptomes. Genome Biology, 14, R134.
TrapnellC1, WilliamsB.A., PerteaG., MortazaviA., KwanG., van BarenM.J., SalzbergS.L., WoldB.J., PachterL. (2010) Transcript assembly and quantification by RNA-Seq reveals unannotated transcripts and isoform switching during cell, differentiation., Nature Biotechnolgy, 28, 511–515.
9.
YuH.N., LiuX.Y., GaoS., HanX.J., ChengA.X., LouH-X. (2014) Molecular cloning and functional characterization of a phenylalanine ammonia-lyase from liverwort Plagiochasma appendiculatum. Plant Cell, Tissue and Organ Culture, 117, 265–277.
10.
HsiehL-S, HsiehY-L, YehC-S, ChengC-Y, YangC-C, LeeP-D. (2011) Molecular characterization of a phenylalanine ammonia-lyase gene (BoPAL1) from Bambusa oldhamii. Molecular Biology Reports, 38, 283–290.
11.
XuF., CaiR., ChengS., DuH., WangY. (2008) Molecular cloning, characterization and expression of phenylalanine ammonia-lyase gene from Ginkgo biloba. African Journal of Biotechnology, 7, 721–729.
12.
Bell-LelongD., CusumanoJ., MeyerK., ChappleC. (1997) Cinnamate-4-hydroxylase expression in Arabidopsis. Regulation in response to development and the environment. Plant Physiology, 113, 729–738.
13.
GaoS., YuH.N., XuR.X., ChengA.X., LouH.X. (2015) Cloning and functional characterization of a 4-coumarate CoA ligase from liverwort Plagiochasma appendiculatum. Phytochemistry, 111, 48–58.
14.
SilberM.V., MeimbergH., EbelJ. (2008) Identification of a 4-coumarate: CoA ligase gene family in the moss, Physcomitrella patens. Phytochemistry, 69, 2449–2456.
15.
AustinM.B., BowmanM.E., FerrerJ-L, SchröderJ., NoelJ.P. (2004) An Aldol switch discovered in stilbene synthases mediates cyclization specificity of type III polyketide synthases, Chemistry & Biology, 11, 1179–1194.
16.
EckermannC., SchroderG., EckermannS., StrackD., SchmidtJ., SchneiderB., SchroderJ. (2003) Stilbene carboxylate biosynthesis: a new function in the family of chalcone synthase-related proteins. Phytochemistry, 62, 271–286.
17.
KoduriP.K., GordonG.S., BarkerE.I., ColpittsC.C., AshtonN.W., SuhD.Y. (2010) Suh Genome-wide analysis of the chalcone synthase superfamily genes of Physcomitrella patens. Plant Molecular Biology, 72, 247–263.
18.
Hai-NaY., LeiW., BinS., ShuaiG., Ai-XiaC., Hong-XiangL. (2015) Functional characterization of a chalcone synthase from the liverwort Plagiochasma appendiculatum, Plant Cell Reports, 34, 233–245.
19.
IkezawaN., IwasaK., SatoF. (2008) Molecular cloning and characterization of CYP80G2, a cytochrome P450 that catalyzes an intramolecular C-C phenol coupling of (S)-reticuline in magnoflorine biosynthesis, from cultured Coptis japonica cells. Journal of Biological Chemistry, 283, 8810–8821.
