The Biflavonoid Pattern of Anacolia webbii

Seeger, Tassilo; Geiger, Hans; Mues, Rüdiger; Zinsmeister, Hans Dietmar

doi:10.1515/znc-1993-5-621

Cited by 5 publications

(7 citation statements)

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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%

“…The molecular formula of C 30 H 18 O 12 of compound 1 was confirmed by HRESIMS with an assigned [M – H] − peak at m / z 569.0732. Compound 1 was identified as the known biflavone 8-[5-(5,7-dihydroxy-4-oxo-4 H -chromen-2-yl)-2,3-dihydroxyphenyl]-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4 H -chromen-4-one (5′,8″-biluteolin or 5′,3‴-dihydroxyamentaflavone), previously identified in other moss species. − According to Seeger et al 1990, the most common methanol-soluble moss biflavonoids are dimers of luteolin and their 2,3- or 2″,3″-dihydro derivatives.…”

Section: Results and Discussionmentioning

confidence: 99%

“…The 1 H and 13 C NMR spectra of compound 2 showed some duplication of resonances. This may result from the presence of diastereomers, arising from the C-2 stereogenic center in combination with the likely C-5′−C-8″ stereogenic axis.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

“…collected at retention times of 38,26,19, and 40 min, respectively. These isolates were characterized by 1 H NMR, 13 C NMR, gCOSY, and gHMBC spectroscopic analyses and/or EIDI mass spectrometry then compared with commercial standards. µL) was added and thoroughly mixed, allowing the last row to be used to correct for background absorbance (Abs blank).…”

Section: And the Antarctic Speciesmentioning

confidence: 99%

“…1 H and13 C NMR Spectroscopic Data for Compounds 1 and 2 (in acetone-d 6 ). Two diasteromers are apparent in the spectra of compound 2, presumably due to one chiral centre being present at C2 combined with atropisomerism associated with restricted rotation around the C5'-C8'' axis.S1 Where separate resonances have been resolved, both chemical shifts are given in the table.…”

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confidence: 99%

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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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