Occurrence of rosmarinic acid, chlorogenic acid and rutin in Marantaceae species

doi:10.1016/j.phytol.2008.09.010

Phytochemistry Letters

Volume 1, Issue 4, 12 December 2008, Pages 199-203

https://doi.org/10.1016/j.phytol.2008.09.010 Get rights and content

Abstract

In a survey of the higher plants for families with rosmarinic acid-accumulating species we could show for the first time, that some species of the family Marantaceae of the order Zingiberales accumulate rosmarinic acid. Other compounds detected in Marantaceae are chlorogenic acid and rutin (quercetin 3-O-rutinoside). Out of 35 species coming from 9 different genera extracted and analysed, two species of Maranta (Maranta leuconeura, Maranta depressa) and one Thalia species (Thalia geniculata) showed the presence of rosmarinic acid. The two Maranta species additionally contained chlorogenic acid, which was also present in Stromanthe amabilis. Rutin was detected in the genera Calathea, Ctenanthe, Maranta, Pleiostachya and Thalia. For a comparison, species from six other families of the Zingiberales were analysed as well.

Graphical abstract

Maranta and Thalia species (Marantaceae, Zingiberales) were shown for the first time to contain rosmarinic acid.

Furthermore chlorogenic acid and rutin were detected in Marantaceae species.

Introduction

The family Marantaceae belongs to the order Zingiberales and is considered to be a sister group of the Cannaceae (Andersson and Chase, 2001). Nowadays, eight families are recognised in the order Zingiberales, namely the sister groups Zingiberaceae and Costaceae, the sister groups Strelitziaceae and Lowiaceae, the sister families Cannaceae and Marantaceae and the Heliconiaceae and Musaceae (Kress et al., 2001). The family Marantaceae includes about 31 genera with around 535 species (Prince and Kress, 2006). It is distributed all over the tropical regions of the world except Australia. Andersson (1998) divided the family into five informal groups on the basis of morphological characters, namely Phrynium, Maranta, Calathea, Myrosma and Donax group, however, some genera had an uncertain placement. Recent molecular investigations using the rps16 intron of the plastid DNA showed that this previous grouping is not supported by molecular data (Andersson and Chase, 2001). Most of the previously defined groups were shown to be para- or polyphyletic. Prince and Kress (2006) used different plastidic sequences (matK, trnL-F) to unravel the phylogenetic relationships of the Marantaceae. They identified on basis of their results five major clades (Calathea, Donax, Maranta, Stachyphrynium, Sarcophrynium) and revealed that four major genera (Calathea, Marantochloa, Phrynium, Schumannianthus) are not monophyletic. The genus Calathea was split into two groups within the Calathea clade. The two examined Schumannianthus species were placed into different clades, Schumannianthus virgatus into the Maranta clade and Schumannianthus dichotomus into the Donax clade. The phylogenetic branches of the genera Marantochloa (Stachyphrynium clade) and Phrynium (Donax clade) were interspersed with other genera.

Different phytochemical investigations of members of the family Marantaceae showed phenolic acids, flavonoids and steroids to be present (Merh et al., 1986, Gutierrez-Lugo et al., 2005, Lagnika et al., 2008). Flavonoids occur as O- and as C-glycosides of various aglyca which makes the Marantaceae special within the Zingiberales (Williams and Harborne, 1977). As another peculiarity of the Marantaceae, Williams and Harborne (1977) isolated sulphated flavonoids which was novel within the Zingiberales. Only Maranta arundinacea is of economical importance as its roots and tubers are used as a source of starch (Prince and Kress, 2006).

The occurrence of rosmarinic acid (RA) is well-known from members of the families Lamiaceae and Boraginaceae, although only one sub-family of the Lamiaceae, the Nepetoideae, is rich in rosmarinic acid-containing members. This restricted occurrence in only two families is, however, not the case since RA can be found in plant species throughout the plant kingdom from the hornworts (Anthocerotaceae), ferns of the family Blechnaceae to the dicotyledonous and monocotyledonous plants (see Petersen and Simmonds, 2003 for an overview). Within the dicotyledonous plants, RA is yet unknown in the Magnoliidae, but plants from several orders within the Rosidae synthesise and accumulate RA. Within the monocotyledonous plants, species of the orders Alismatales (Zostera, Anthurium, Potamogeton; Ravn et al., 1994, Aquino et al., 2001, Petersen and Simmonds, 2003), Zingiberales (Canna; Petersen and Simmonds, 2003, Yun et al., 2004) and Liliales (Paris; Lee et al., 2008) have been shown to contain RA. The pharmacological importance of RA can be summarised as antibacterial, antiviral, antioxidative and antiiflammatory activities (see Petersen and Simmonds, 2003 for an overview). In the plant, RA probably functions as a defense compound against infections and herbivores.

Chlorogenic acid (CA; caffeoylquinic acid) is one of the most abundant caffeic acid esters occurring in the plant kingdom. In some plant species, e.g. Coffea species or Solanum species, it is accumulated to high amounts (Clifford, 1999). The occurrence of CA in monocotyledonous plants is less well documented.

Rutin (quercetin 3-O-rutinoside) is a flavonol glycoside widely occurring in the plant kingdom. It was first isolated from Ruta graveolens (Rutaceae) in 1842 by the German pharmacist Weiss. Rutin is present as yellow pigment in many plants and is isolated for pharmaceutical purposes from Fagopyrum esculentum (Polygonaceae) and Sophora japonica (Fabaceae) where it can be found in amounts up to 20% of the dry matter. Rutin or its semi-synthetic derivative troxerutin are used against venous diseases. Williams and Harborne (1977) investigated the distribution of flavonoids in the Zingiberales and showed that only the Zingiberaceae and the Marantaceae are rich in flavonoids. A highly diverse flavonoid occurrence was found in the Marantaceae with flavone O- and C-glycosides, flavonols and anthocyanins in species with pigmented leaves.

In our search for RA-containing plant families within the Liliidae we came upon the family Marantaceae where species from two different genera were shown to contain RA. Additionally, the occurrence of CA and rutin was examined.

Section snippets

Occurrence of the caffeic acid esters rosmarinic acid and chlorogenic acid in Marantaceae and related families

In our ongoing search for plant species producing and accumulating RA (Fig. 1), we showed for the first time the presence of RA in Maranta leuconeura, a common ornamental plant that is grown in many varieties in Botanical Gardens and can be obtained from nurseries. Three varieties of this species, namely M. leuconeura “Fascinator”, kerchoviana and massangeana, showed levels of 0.78–0.87% of the dry weight RA in the leaves (Table 1). RA was identified and quantified by HPLC, verified by TLC and

Collection of plant material

Leaf material of Marantaceae, Heliconiaceae, Lowiaceae, Musaceae, Strelitziaceae and Zingiberaceae were collected and identified in the Botanical Gardens of the Universities of Marburg, Giessen and Kiel (all Germany); for registry numbers see Supplementary Table 1. T. dealbata was grown from seeds (H.G. Röpke, Seesen, Germany) in the Institute for Pharmaceutical Biology, Philipps-Universität Marburg (Germany). The leaves were frozen at −20 °C and lyophilised for 2 days (Christ L1, B. Braun

Acknowledgments

We are grateful to the Botanical Gardens of the Universities Marburg, Giessen and Kiel and their staff for providing us with leaf material for these investigations. The work of Yana Abdullah has been sponsored by a grant of the Syrian government, University of Damascus.

References (20)

L. Andersson et al.
Phylogeny and classification of Marantaceae
Bot. J. Linn. Soc.
(2001)
J.C. D’Auria
Acyltransferases in plants: a good time to be BAHD
Curr. Opin. Plant Biol.
(2006)
L. Hoffmann et al.
Purification, cloning, and properties of an acyltransferase controlling shikimate and quinate ester intermediates in phenylpropanoid metabolism
J. Biol. Chem.
(2003)
M. Petersen et al.
Rosmarinic acid
Phytochemistry
(2003)
C.A. Williams et al.
The leaf flavonoids of the Zingiberales
Biochem. Syst. Ecol.
(1977)
S.K. Adesina et al.
The occurrence and identification of flavonoids in Thaumatococcus daniellii Benth
Planta Med.
(1978)
L. Andersson
Marantaceae
R. Aquino et al.
Phenolic constituents and antioxidant activity of an extract of Anthurium versicolor leaves
J. Nat. Prod.
(2001)
E.C. Bate-Smith
Phenolic constituents of plants and their taxonomic significance. II. Monocotyledons
J. Linn. Soc. (Bot.)
(1968)
A. Berger et al.
Rosmarinic acid synthase is a new member of the superfamily of BAHD acyltransferases
Planta
(2006)

There are more references available in the full text version of this article.

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Phytochemistry Letters

Abstract

Graphical abstract

Introduction

Section snippets

Occurrence of the caffeic acid esters rosmarinic acid and chlorogenic acid in Marantaceae and related families

Collection of plant material

Acknowledgments

References (20)

Phylogeny and classification of Marantaceae

Bot. J. Linn. Soc.

Acyltransferases in plants: a good time to be BAHD

Curr. Opin. Plant Biol.

Purification, cloning, and properties of an acyltransferase controlling shikimate and quinate ester intermediates in phenylpropanoid metabolism

J. Biol. Chem.

Rosmarinic acid

Phytochemistry

The leaf flavonoids of the Zingiberales

Biochem. Syst. Ecol.

The occurrence and identification of flavonoids in Thaumatococcus daniellii Benth

Planta Med.

Marantaceae

Phenolic constituents and antioxidant activity of an extract of Anthurium versicolor leaves

J. Nat. Prod.

Phenolic constituents of plants and their taxonomic significance. II. Monocotyledons

J. Linn. Soc. (Bot.)

Rosmarinic acid synthase is a new member of the superfamily of BAHD acyltransferases

Planta

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Hunting and hallucinogens: The use psychoactive and other plants to improve the hunting ability of dogs