The first identification of isoflavones from a bryophyte

Anhut, Siegbert; Zinsmeister, Hans Dietmar; Mues, Rüdiger; Barz, Wolfgang; Mackenbrock, Klaus; Köster, Johannes; Markham, Kenneth R.

doi:10.1016/s0031-9422(00)82611-4

Cited by 42 publications

(20 citation statements)

References 6 publications

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“…-4H-chromen-4-one (5',8"-biluteolin or 5',3'''-dihydroxyamentaflavone), previously identified in other moss species. 12,13,14 According to Seeger et al 1990, 14 the most common methanol-soluble moss biflavonoids are dimers of luteolin and their 2,3-or 2'',3''-dihydro derivatives.…”

Section: Resultsmentioning

confidence: 99%

Antarctic Moss Biflavonoids Show High Antioxidant and Ultraviolet-Screening Activity

Waterman¹,

Nugraha²,

Hendra³

et al. 2017

J. Nat. Prod.

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Ceratodon purpureus is a cosmopolitan moss that survives some of the harshest places on Earth: from frozen Antarctica to hot South Australian deserts. In a study on the survival mechanisms of the species, nine compounds were isolated from Australian and Antarctic C. purpureus. This included five biflavonoids, with complete structural elucidation of 1 and 2 reported here for the first time, as well as an additional four known phenolic compounds. Dispersion-corrected DFT calculations suggested a rotational barrier, leading to atropisomerism, resulting in the presence of diastereomers for compound 2. All isolates absorbed strongly in the ultraviolet (UV) spectrum, e.g., biflavone 1 (UV-A, 315-400 nm), which displayed the strongest radical-scavenging activity, 13% more efficient than the standard rutin; p-coumaric acid and trans-ferulic acid showed the highest UV-B (280-315 nm) absorption. The more complex and abundant 1 and 2 presumably have dual roles as both UV-screening and antioxidant compounds. They are strongly bound to Antarctic moss cell walls as well as located inside the cells of moss from both locations. The combined high stability and photoprotective abilities of these isolates may account for the known resilience of this species to UV-B radiation and its survival in some of the toughest locations in the world.

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Section: Resultsmentioning

confidence: 99%

Antarctic Moss Biflavonoids Show High Antioxidant and Ultraviolet-Screening Activity

Waterman¹,

Nugraha²,

Hendra³

et al. 2017

J. Nat. Prod.

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“…Based on electron spray ionization-mass spectrometry, 1 H NMR and 13 C NMR spectral data, the purified compound was verified as orobol 7-O-d-glucoside ( Fig. 1; Anhut et al 1984).…”

Section: Bioassay-guided Fractionation and Isolation Of Active Princimentioning

confidence: 99%

Inhibitory effects of orobol 7-O-d-glucoside from banaba (Lagerstroemia speciosa L.) on human rhinoviruses replication

Choi

Bae

Song

et al. 2010

Letters in Applied Microbiology

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Aims: The anti‐human rhinovirus (HRV) activity of orobol 7‐O‐d‐glucoside (O7G) from Lagerstroemia speciosa L. (Lythraceae) was evaluated in Hela cells. Methods and Results: We tested anti‐HRV activity of O7G using a cytopathic effect (CPE) reduction method, which exhibited broad‐spectrum anti‐HRVs activity with a 50% inhibitory concentration (IC50) ranging from 0·58 to 8·80 μg ml−1. The 50% cytotoxicity concentration (CC50) of O7G is more than 100 μg ml−1, and the derived therapeutic indices are more than 12. Ribavirin didn’t possess antiviral activity against HRV15, HRV3 and HRV5, but exhibited weak antiviral activity against HRV2 and HRV3, and showed strong anti‐HRV6 and ‐14 activities. Conclusions: These results suggest that O7G is a novel drug class with broad spectrum antiviral activity against HRV species A (HRV1B, HRV2, HRV15 and HRV40) and species B (HRV3, HRV6 and HRV14), as well as pleconaril‐resistant virus (HRV5). Significance and Impact of the Study: Therefore, these findings provide important information for the utilization of Q7G promising broad spectrum for human rhinovirus treatment.

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“…Again, 4-O-caffeoylquinic, 5-O-caffeoylquinic and caffeic acids were detected in the two mosses Brachytheciastrum velutinum and Kindbergia praelonga [ 77 ]. Besides these compounds, bryophytes are known to produce derivatives of benzoic acids [ 42 , 84 ], stilbenes [ 85 ], coumarins [ 86 , 87 ] and different flavonoids, including flavones (apigenin and luteolin derivatives for example) [ 77 ]; flavonols (quercetin) [ 77 ], isoflavones [ 88 ], dihydroflavonols [ 89 ] and aurones [ 90 , 91 ]. Interestingly, genes involved in phenylpropanoid-polyamine biosynthesis are not found in bryophytes [ 92 ].…”

Section: Phytochemistry Of Bryophyte’s Antifungal Metabolitesmentioning

confidence: 99%

Bryo-Activities: A Review on How Bryophytes Are Contributing to the Arsenal of Natural Bioactive Compounds against Fungi

Commisso

Guarino

Marchi

et al. 2021

Plants

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Usually regarded as less evolved than their more recently diverged vascular sisters, which currently dominate vegetation landscape, bryophytes seem having nothing to envy to the defensive arsenal of other plants, since they had acquired a suite of chemical traits that allowed them to adapt and persist on land. In fact, these closest modern relatives of the ancestors to the earliest terrestrial plants proved to be marvelous chemists, as they traditionally were a popular remedy among tribal people all over the world, that exploit their pharmacological properties to cure the most different diseases. The phytochemistry of bryophytes exhibits a stunning assortment of biologically active compounds such as lipids, proteins, steroids, organic acids, alcohols, aliphatic and aromatic compounds, polyphenols, terpenoids, acetogenins and phenylquinones, thus it is not surprising that substances obtained from various species belonging to such ancestral plants are widely employed as antitumor, antipyretic, insecticidal and antimicrobial. This review explores in particular the antifungal potential of the three Bryophyta divisions—mosses (Musci), hornworts (Anthocerotae) and liverworts (Hepaticae)—to be used as a sources of interesting bioactive constituents for both pharmaceutical and agricultural areas, providing an updated overview of the latest relevant insights.

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The first identification of isoflavones from a bryophyte

Cited by 42 publications

References 6 publications

Antarctic Moss Biflavonoids Show High Antioxidant and Ultraviolet-Screening Activity

Antarctic Moss Biflavonoids Show High Antioxidant and Ultraviolet-Screening Activity

Inhibitory effects of orobol 7-O-d-glucoside from banaba (Lagerstroemia speciosa L.) on human rhinoviruses replication

Bryo-Activities: A Review on How Bryophytes Are Contributing to the Arsenal of Natural Bioactive Compounds against Fungi

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