The first isolation of lignans, megacerotonic acid and anthocerotonic acid, from non-vascular plants, anthocerotae (hornworts)

Takeda, Reiji; Hasegawa, Jiro; Shinozaki, Masateru

doi:10.1016/s0040-4039(00)97569-5

Cited by 58 publications

(38 citation statements)

References 5 publications

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“…Rosmarinic acid is a well-known constituent found in plant families all over the higher plant kingdom (Petersen and Simmonds 2003 and literature cited therein) and even in lower plants like hornworts (Takeda et al 1990a(Takeda et al ,1990bPetersen 2003). Less ubiquitous are glucosides of rosmarinic acid which have-to our knowledge-so far only been published from Helicteres isora (Sterculiaceae; Satake et al 1999).…”

Section: Discussionmentioning

confidence: 99%

Production of rosmarinic acid and a new rosmarinic acid 3′-O-β-D-glucoside in suspension cultures of the hornwort Anthoceros agrestis Paton

Vogelsang

Schneider

Petersen

2005

Planta

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Cell suspension cultures of the hornwort Anthoceros agrestis Paton (Anthocerotaceae) were cultivated and characterized in CB-media containing 2 and 4% sucrose. The suspension cells accumulated rosmarinic acid up to 5.1% of the cell dry weight as well as caffeoyl-4¢-hydroxyphenyllactate. Moreover, a more hydrophilic compound was detected which was isolated and identified as rosmarinic acid 3¢-O-b-D-glucoside, a new rosmarinic acid derivative. This new rosmarinic acid derivative was found up to 1.0% of the cell dry weight in suspension cells of A. agrestis.

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Section: Discussionmentioning

confidence: 99%

Production of rosmarinic acid and a new rosmarinic acid 3′-O-β-D-glucoside in suspension cultures of the hornwort Anthoceros agrestis Paton

Vogelsang

Schneider

Petersen

2005

Planta

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“…Rosmarinic acid as well as the lignan-like compounds, anthocerotonic and megacerotonic acid, isolated and identified in A. punctatus (Takeda et al 1990a(Takeda et al , 1990b as well as other species of the genus Anthoceros (data not shown), are derived from 4-coumaric acid or higher hydroxylated cinnamic acid derivatives. This is a first indication that the general phenylpropanoid pathway has to be present in this hornwort.…”

Section: Isolation and Identification Of C4hmentioning

confidence: 94%

“…flavonoids (see Lewis and Davin 1994). Moreover, Anthoceros and some other species of the hornworts are able to synthesize and accumulate rosmarinic acid (RA), an ester of caffeic acid and 3,4-dihydroxyphenyllactic acid (DHPL), as well as lignan-like compounds such as anthocerotonic acid and megacerotonic acid (Takeda et al 1990a(Takeda et al , 1990bTrennha¨user 1992). Therefore, the phenylpropanoid pathway, delivering hydroxycinnamic acid units for the further biosynthesis of these compounds, must be present in the Anthocerotopsida.…”

Section: Introductionmentioning

confidence: 99%

Cinnamic acid 4-hydroxylase from cell cultures of the hornwort Anthoceros agrestis

Petersen

2003

Planta

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“…Dendroceros japonicus and Megaceros flagellaris (12,13), with the latter recently being classified as originating in the Silurian period (14). Interestingly, evolution of both gymnosperms and angiosperms was accompanied by major changes in the structural complexity and oxidative modifications of the lignans (9,15).…”

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confidence: 99%

(+)-Pinoresinol/(+)-Lariciresinol Reductase from Forsythia intermedia

Dinkova‐Kostova

Gang

Davin

et al. 1996

Journal of Biological Chemistry

183

104

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Lignans are a widely distributed class of natural products, whose functions and distribution suggest that they are one of the earliest forms of defense to have evolved in vascular plants; some, such as podophyllotoxin and enterodiol, have important roles in cancer chemotherapy and prevention, respectively.Entry into lignan enzymology has been gained by the ϳ3000-fold purification of two isoforms of (؉)-pinoresinol/(؉)-lariciresinol reductase, a pivotal branchpoint enzyme in lignan biosynthesis. Both have comparable (ϳ34.9 kDa) molecular mass and kinetic (V max /K m ) properties and catalyze sequential, NADPH-dependent, stereospecific, hydride transfers where the incoming hydride takes up the pro-R position.The gene encoding (؉)-pinoresinol/(؉)-lariciresinol reductase has been cloned and the recombinant protein heterologously expressed as a functional ␤-galactosidase fusion protein. Its amino acid sequence reveals a strong homology to isoflavone reductase, a key branchpoint enzyme in isoflavonoid metabolism and primarily found in the Fabaceae (angiosperms). This is of great evolutionary significance since both lignans and isoflavonoids have comparable plant defense properties, as well as similar roles as phytoestrogens. Given that lignans are widespread from primitive plants onwards, whereas the isoflavone reductase-derived isoflavonoids are mainly restricted to the Fabaceae, it is tempting to speculate that this branch of the isoflavonoid pathway arose via evolutionary divergence from that giving the lignans.

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The first isolation of lignans, megacerotonic acid and anthocerotonic acid, from non-vascular plants, anthocerotae (hornworts)

Cited by 58 publications

References 5 publications

Production of rosmarinic acid and a new rosmarinic acid 3′-O-β-D-glucoside in suspension cultures of the hornwort Anthoceros agrestis Paton

Production of rosmarinic acid and a new rosmarinic acid 3′-O-β-D-glucoside in suspension cultures of the hornwort Anthoceros agrestis Paton

Cinnamic acid 4-hydroxylase from cell cultures of the hornwort Anthoceros agrestis

(+)-Pinoresinol/(+)-Lariciresinol Reductase from Forsythia intermedia

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