HPLC determination of phenolic acids in the water-soluble extract of Zostera marina L. (eelgrass)

doi:10.1016/0304-3770(86)90119-1

Aquatic Botany

Volume 24, Issue 1, March 1986, Pages 83-89

https://doi.org/10.1016/0304-3770(86)90119-1 Get rights and content

Abstract

Six phenolic acids were quantitatively assessed in the water-soluble extract of Zostera marina L. (eelgrass) from Puget Sound, Washington, using high-performance liquid chromatography (HPLC). Ferulic (4-hydroxy, 3-methoxycinnamic), vanillic (4-hydroxy, 3-methoxybenzoic), p-hydroxybenzoic (4-hydroxybenzoic), caffeic (3,4-dihydroxycinnamic), gallic (3,4,5-trihydroxybenzoic) and protocatechuic (3,4-dihydroxybenzoic) acids were in suceedingly lower quantities. Gentisic (2,5-dihydroxybenzoic) acid was also found to be present in the extract. However, its quantification was not possible using this method.

References (21)

L. Cariello et al.
Posidonia Ecosystems. V. Phenolic compounds from marine phanerograms, Cymodocea nodosa and Posidonia oceanica
Comp. Biochem. Physiol.
(1979)
H.G.C. King et al.
The chemical analysis of small samples of leaf material and the relationship between the disappearance and composition of leaves
Pedobiologia
(1967)
O. Zapata et al.
Phenolic acids in seagrasses
Aquat. Bot.
(1979)
L. Cariello et al.
Effect of Posidonia oceanica extracts on the growth of Straphylococcus aureus
Bot. Mar.
(1979)
R.I. Davies et al.
Polyphenols in plant, humus, and soil. III. Stabilization of gelatin by polyphenol tanning
J. Soil. Sci.
(1964)
E.K. Demos et al.
The effects of ten phenolic compounds on hypocotyl growth and mitochondrial metabolism of mung bean
Am. J. Bot.
(1975)
L.S. Ettre
The nomenclature of liquid chromatography. II. Liquid chromatography
J. Chromatogr.
(1981)
J.B. Harborne
Introduction to Ecological Biochemistry
P.G. Harrison
Control of microbial growth and of amphipod grazing by watersoluble compounds from leaves of Zostera marina
Mar. Biol.
(1982)
P.G. Harrison et al.
Inhibition of the growth of micro-algae and bacteria by extracts of eelgrass (Zostera marina) leaves
Mar. Biol.
(1980)

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

Cited by (49)

Anti-phototoxicity and anti-melanogenesis activities of eelgrass Zostera marina and its phenolic constituents
2024, Fitoterapia
The eelgrass Zostera marina L. has several economic roles, from its earlier usage in the insulation industry to protecting the earth from global warming. In this study, we aimed to discover the cosmetic potential of Z. marina. A methanolic extract of Z. marina showed anti-phototoxicity and anti-melanogenesis activity with an IC₅₀ of 17.5 μM, followed by a phytochemical analysis of its phenolic constituents. Ten compounds (1−10) were isolated by several chromatographic techniques and identified by means of nuclear magnetic resonance spectroscopy (NMR) as well as high-resolution mass spectrometry (HR/MS). The identified compounds are caffeic acid (1), 3,4-dihydroxybenzoic acid (protocatechuic acid) (2), luteolin (3), diosmetin (4), 4-coumaroyl-4′-hydroxyl phenyllactic acid (5), rosmarinic acid (6), caffeoyl-4′-hydroxy-phenyllactic acid (isorinic acid) (7), apigenin 7-O-β-D-glucopyranoside (8), luteolin 7-O-β-D-glucopyranoside (9), and luteolin 7-sulfate (10). This is the first report to identify compounds 5 and 7 from the family Zosteraceae. The isolated compounds were assessed for their anti-aging abilities and were found to exhibit good anti-phototoxicity and anti-melanogenesis activities by increasing the viability of UVB-irradiated HaCaT cells by 6% to 34% and by inhibiting melanin synthesis in B16 melanoma cells by 44% to 65%.
Phenolic chemistry of the seagrass Zostera marina Linnaeus: First assessment of geographic variability among populations on a broad spatial scale
2023, Phytochemistry
The variability of the phenolic content of thirteen populations of Zostera marina L. (six narrow-leaved and seven wide-leaved ecotypes) from different geographical zones, i.e., Baltic Sea, Mediterranean, East and West Atlantic, and East Pacific coasts was evaluated. Depending on the location, three to five phenolic acids and nine to fourteen flavonoids were identified of which an undescribed flavonoid sulfate. The phenolic concentrations of the thirteen populations differ among countries and among sites within countries. However, the same individuals were found almost everywhere. Substantial phenolic concentrations were found at all study sites with the exception of Puck Bay (Baltic Sea). Some geographical differences in the flavonoid content were observed. The highest phenolic diversity was found with specimens from the French Atlantic coast and the lowest with the Northeastern American sample (Cape Cod, MA). Regardless of their leaf width, the content of phenolic compounds was found to be similar and mainly characterized by rosmarinic acid and luteolin 7,3′-disulfate. The results demonstrate that geographic origin influences the phenolic composition of Z. marina primarily in terms of concentration, but not in terms of individual compound identity, despite the large geographic scale and the contrasting climatic and environmental conditions associated with it. This work is the first study to consider the spatial variability of phenolic compounds for a seagrass species on a spatial scale covering four bioregions. This is also the first to compare the phenolic chemistry of the two ecotypes of Z. marina.
Nutritional and bioactive potential of seagrasses: A review
2021, South African Journal of Botany
Citation Excerpt :
Examples of the natural products isolated from Zostera marina L. (eelgrass) include flavone sulphates (Harborne and Williams, 1976), the 7-sulphates of luteolin, diosmetin, apigenin, chrysoeriol, the 7,3′- disulphate of luteolin and several non-sulphated phenolic acids; p-coumaric, ferulic, caffeic, vanillic, gallic, protocatechuic, gentisic,4‑hydroxy benzoic and o-pyrocatechuic acids (Quackenbush et al., 1986; Zapata and McMillan, 1979). A total of six phenolic acids were quantified in the water-soluble extracts of Zostera marina L. from Puget Sound, Washington using high-performance liquid chromatography (HPLC) techniques (Quackenbush et al., 1986). Halophila ovalis of the Pacific Ocean contains sulphated flavonoids (McMillan, 1986).
Seagrasses, one of the most threatened yet overlooked ecosystems on Earth, are the only flowering plants to recolonising the seabed. Apart from their critical ecological prominence on the life of many marine organisms, seagrasses are also used as an alternative or complementary medicine to manage an array of pathological disorders such as muscle aches, wounds, abdominal pain, indigestion, hangover, and mental disorders. However, a compilation of existing work on their ethnopharmacological uses, nutritional values, pharmacological propensities and bioactive compounds is lacking. Thus, this review aims at elaborating on the biochemical composition, phytochemical analysis, and biological properties including antioxidant, antimicrobial activities of various species of seagrasses. Seagrasses harbour several metabolites with multiple bioactivities. The phytochemical compounds isolated from Zostera marina L., Thalassia testudinum K. D. Koenig. and Thalassodendron ciliatum (Forssk.) exhibit a plethora of biological activities, including cytotoxicity against cancer cell lines, anti-human immunodeficiency virus (HIV), antimicrobial, and skin regenerating properties. This review also identifies vital lacuna in seagrass research. For instance, the mechanism and site of action of compounds displaying potent biological activities has not been adequately addressed together with optimisation of extraction methods to isolate minor metabolites and applying technological advancements in biological assays. In conclusion, this review provides a synthesis of current knowledge and highlights future work that needs to be undertaken for the biomedical application of such natural resources.
Analytical determination of the reducing and stabilization agents present in different Zostera noltii extracts used for the biosynthesis of gold nanoparticles
2018, Journal of Photochemistry and Photobiology B: Biology
Citation Excerpt :
Therefore, recycling this flotsam as raw material for nanoparticles synthesis may lead to a solution. On the other hand, looking for their biomedical applications, previous chemical studies on Zostera noltii led to the isolation of several natural products of special interest for their antioxidant, antibiotic, antifungal or antiparasitic activities [21–26]. In this context, the method proposed here gives a new way for the application of Z. noltii.
The objective of this work was to ascertain the nature of the components responsible for the reducing and stabilizing properties of Zostera noltii extracts that lead to gold nanoparticle formation using chemical techniques of analysis. In order to achieve this aim, we try the synthesis of AuNPs with three different extracts from plants collected in the Bay of Cádiz (Spain). The n-butanol extract produced the best results. Taking this into account, four fractions were isolated by Sephadex LH-20 column chromatography from this extract and we studied their activity. The chemical study of these fractions led to the isolation of several flavone sulfates and these were identified as the species' responsible for the formation and stabilization of the AuNPs. Flavone sulfates were purified by high performance liquid chromatography and the structures were established by means of spectroscopic methods nuclear magnetic resonance and mass spectroscopy. AuNPs have an average lifetime of about 16 weeks. Additionally, the morphology and crystalline phase of the gold nanoparticles were characterized by transmission electron microscopy. The composition of the nanoparticles was evaluated by electron diffraction and energy dispersive X-ray spectroscopy. An 88% of the gold nanoparticles has a diameter in the range 20–35 nm, with an average size of 26 ± 2 nm.
Secondary metabolites of seagrasses (Alismatales and Potamogetonales; Alismatidae): Chemical diversity, bioactivity, and ecological function
2016, Phytochemistry
Citation Excerpt :
Harborne’s (1975) review on flavonoid sulfates contains neither additional data for the occurrence of these compounds in Zostera nor for other seagrass genera. Quackenbush et al. (1986) described an early RP-HPLC method for phenolic acids in Z. marina. Based on retention times, the authors detected 10, 13, 14, 16, 18, 28, and 29 in an extract of Z. marina collected off the coast of the US state of Washington.
Seagrasses are the only higher plants living in fully marine environments; they play a significant role in coastal ecosystems. Seagrasses inhabit the coastal shelves of all continents except Antarctica and can grow in depths of up to 90 m. Because of their eminent ecological importance, innumerous studies have been dedicated to seagrasses and their ecology. However, the phytochemistry has not been equally well investigated yet and many of the existing studies in chemical ecology are only investigating the chemistry at the level of compound classes, e.g. phenolics, and not at the level of chemically defined metabolites. In the present review, the existing literature on secondary metabolites of seagrasses, their known source seagrasses, their bioactivity, and ecological function are compiled and critically assessed. Moreover, research gaps are highlighted and avenues for future research are discussed.
Currently, a total of 154 chemically defined natural products have been reported from the about 70 seagrass species known worldwide. Compounds reported include simple phenols derivatives (four compounds), phenylmethane derivatives (14 compounds), phenylethane derivatives (four compounds), phenylpropane derivatives including their esters and dimers (20 compounds), chalkones (four compounds), flavonoids including catechins (57 compounds), phenylheptanoids (four compounds), one monoterpene derivative, one sesquiterpene, diterpenoids (13 compounds), steroids (31 compounds), and one alkaloid.
Most of the existing bioactivity studies of seagrass metabolites and extracts have been directed to potential cytotoxic, antimicrobial, or antimacrofouling activity. Antimicrobial studies have been performed towards panels of both human pathogens and ecologically relevant pathogens. In the antimacrofouling studies, investigations of the potential of zosteric acid from the genus Zostera are the most numerous and have yielded so far the most interesting results.
Studies on the chemical ecology of seagrasses often have been focused on variation in phenolic compounds and include but are not limited to studies on variation due to abiotic factors, seasonal variation, variation in response to grazing by fish or sea urchins, or following microbial attack.
Assessing the ecological status of seagrasses using morphology, biochemical descriptors and microbial community analyses. A study in Halophila stipulacea (Forsk.) Aschers meadows in the northern Red Sea
2016, Ecological Indicators
Seagrasses are one of the most valuable marine ecosystems on earth, yet they are declining worldwide at alarming rates. With most of seagrass monitoring based on long term responses to environmental pressures, there is growing interest in developing alternative diagnostic tools that more effectively identify changes in seagrass ecological status at an early stage. Besides morphological indicators, functional and biochemical descriptors may provide a good understanding of plant's responses to environmental changes. Moreover, the epiphytic microbial communities of seagrasses may also shift in response to changes in environmental conditions, although these have been seldom used as a descriptor of environmental change. In this study three Halophila stipulacea (Forsk.) Aschers meadows, found in the Gulf of Aqaba (northern Red Sea), were characterized using an integrated approach to highlight possible differences in the meadows ecological status. Plant descriptors, including leaves morphometrics (leaf size, leaf number/plant, leaves with lost apex), photosynthetic pigments (Chlorophylls, Carotenoids) and total phenols contents, were investigated and coupled with the plants’ epiphytic microbial community structure and composition, studied using pyrosequencing. The entire suite of descriptors highlighted differences among the meadows ecological status based on changes in plants’ morphology and biochemistry, and their associated microbial communities, in response to the different environmental conditions (water column turbidity, seawater and sediment nutrients) and the geomorphological features (bottom slope, granulometry) of the stations. Leaf morphology and photosynthetic pigment content were modulated in H. stipulacea in response to light availability and hydrodynamics in the Gulf of Aqaba. The highest leaf surface area and photosynthetic pigment contents were observed at the lowest irradiance and hydrodynamics/granulometry among stations. Total phenol content showed differences among stations with increasing concentrations from north to south. The microbial communities showed differences among stations and plant compartments, with high incidence of Gammaproteobacteria and Bacteroidetes in light limiting conditions, while Cyanobacteria and Rhodobacteraceae thrived in conditions of high light availability and hydrodynamics. The mutual response of the seagrass plants and the microbial communities provided evidence of their functional relationship, which undoubtedly needs further investigation. To the best of our knowledge, this is the first time that such descriptors have been used in an integrated approach. We provide evidence of their effectiveness in discriminating seagrass ecological status, even at small spatial scales. This work constitutes a new approach to the assessment of seagrasses and a stepping stone in the application of microbial communities as a putative marker in a changing environment.

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Aquatic Botany

Abstract

References (21)

Posidonia Ecosystems. V. Phenolic compounds from marine phanerograms, Cymodocea nodosa and Posidonia oceanica

Comp. Biochem. Physiol.

The chemical analysis of small samples of leaf material and the relationship between the disappearance and composition of leaves

Pedobiologia

Phenolic acids in seagrasses

Aquat. Bot.

Effect of Posidonia oceanica extracts on the growth of Straphylococcus aureus

Bot. Mar.

Polyphenols in plant, humus, and soil. III. Stabilization of gelatin by polyphenol tanning

J. Soil. Sci.

The effects of ten phenolic compounds on hypocotyl growth and mitochondrial metabolism of mung bean

Am. J. Bot.

The nomenclature of liquid chromatography. II. Liquid chromatography

J. Chromatogr.

Introduction to Ecological Biochemistry

Control of microbial growth and of amphipod grazing by watersoluble compounds from leaves of Zostera marina

Mar. Biol.

Inhibition of the growth of micro-algae and bacteria by extracts of eelgrass (Zostera marina) leaves

Mar. Biol.

Cited by (49)

Anti-phototoxicity and anti-melanogenesis activities of eelgrass Zostera marina and its phenolic constituents

Phenolic chemistry of the seagrass Zostera marina Linnaeus: First assessment of geographic variability among populations on a broad spatial scale

Nutritional and bioactive potential of seagrasses: A review

Analytical determination of the reducing and stabilization agents present in different Zostera noltii extracts used for the biosynthesis of gold nanoparticles

Secondary metabolites of seagrasses (Alismatales and Potamogetonales; Alismatidae): Chemical diversity, bioactivity, and ecological function

Assessing the ecological status of seagrasses using morphology, biochemical descriptors and microbial community analyses. A study in Halophila stipulacea (Forsk.) Aschers meadows in the northern Red Sea