6-Carboxydihydroresveratrol 3-O-β-glucopyranoside — A novel natural product from the Cretaceous relict Metasequoia glyptostroboides

Nguyen, Xuan Hong Thy; Juvik, Ole Johan; Øvstedal, Dag Olav; Fossen, Torgils

doi:10.1016/j.fitote.2014.03.001

Cited by 8 publications

(20 citation statements)

References 31 publications

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“…The natural products isolated from M. glyptostroboides grown in Norway were mainly different from those reported from the tree grown at other localities (Nguyen et al 2014). This may be accounted for by the fact that the sunlight conditions (particularly the day length) in the growth season in Norway are quite different from that of other locations from which plant material has been analyzed.…”

Section: Temperature and Sunlight Conditions –Potential Influential Fcontrasting

confidence: 73%

“…6) isolated from branches and stems of M. glyptostroboides exhibited mild cytotoxic activity against A549 and Colo 205 cell lines (Zeng et al 2012). 6-Carboxydihydroresveratrol-3-glucoside ( 31 ) is the only stilbenoid (bibenzyl) derivative hitherto reported from M. glyptostroboides (Nguyen et al 2014). Bibenzyl aglycones with carboxylic substituents have a restricted occurrence in nature.…”

Section: Other Aromatic Compounds Specific To M Glyptostroboidesmentioning

confidence: 99%

“…Bibenzyl aglycones with carboxylic substituents have a restricted occurrence in nature. The fact that these compounds have mainly been found in species belonging to the oldest lineages of plant families like the fern Hicriopteris glauca (Fang et al 2012), Liverworts (Pryce 1971; Pryce 1972; Valio et al 1969) and algae (Huneck and Pryce 1971) indicate that these compounds may be biogenetic precursors of modern plant stilbenoids, with the COOH group being a biogenetic archaicism (Nguyen et al 2014). …”

Section: Other Aromatic Compounds Specific To M Glyptostroboidesmentioning

confidence: 99%

“…Reports on natural products from M. glyptostroboides available in current literature have been conducted on trees growing at quite a few rather different localities, including several European and Asian countries, including China (Dong et al 2011), South Korea (Bajpai and Kang 2010a, 2011a, b; Bajpai et al 2007a, b, 2009, 2010, 2014a; Duan et al 2009), Japan (Fujita 1990; Hayashi et al 1969; Ida 1981a, b; Nakatani et al 1991), Poland (Czeczuga 1987; Krauze-Baranowska 2004), Germany (Beckmann and Geiger 1968; Beckmann et al 1971; Beckmann and Schuhle 1968; Braun and Breitenbach 1977), France (Mongrand et al 2001) and Norway (Nguyen et al 2014). The natural products isolated from M. glyptostroboides grown in Norway were mainly different from those reported from the tree grown at other localities (Nguyen et al 2014).…”

Section: Temperature and Sunlight Conditions –Potential Influential Fmentioning

confidence: 99%

“…Flavones77 ApigeninLeavesTLC, UV, MS, NMRKrauze-Baranowska (2004)78 Apigenin-7-glucosid (Cosmosiin)LeavesTLC, PCBeckmann and Geiger (1968)79 LuteolinLeavesTLC, UV, MS, NMRKrauze-Baranowska (2004)80 Luteolin-7-glucosidLeavesTLC, PCBeckmann and Geiger (1968)81 TricetinLeavesTLC, PCBeckmann and Geiger (1968)82 Tricetin-7-glucosidLeavesTLC, PCBeckmann and Geiger (1968)83 Tricetin 3′-O-glucosideLeavesTLC, UV, MS, NMRKrauze-Baranowska (2004)III. Dihydroflavonols84 Aromadendrin-7-O-β-glucopyranosideLeavesNMR, MSNguyen et al (2014)85 Aromadendrin oxideLeavesGC–MSBajpai et al (2009)LeavesGC–MSBajpai and Kang (2011b)IV. Flavonols86 KaempferolN/APCTakahashi et al (1960b)…”

Section: Introductionmentioning

confidence: 99%

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Growing with dinosaurs: natural products from the Cretaceous relict Metasequoia glyptostroboides Hu & Cheng—a molecular reservoir from the ancient world with potential in modern medicine

et al. 2015

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After the sensational rediscovery of living exemplars of the Cretaceous relict Metasequoia glyptostroboides—a tree previously known exclusively from fossils from various locations in the northern hemisphere, there has been an increasing interest in discovery of novel natural products from this unique plant source. This article includes the first complete compilation of natural products reported from M. glyptostroboides during the entire period in which the tree has been investigated (1954–2014) with main focus on the compounds specific to this plant source. Studies on the biological activity of pure compounds and extracts derived from M. glyptostroboides are reviewed for the first time. The unique potential of M. glyptostroboides as a source of bioactive constituents is founded on the fact that the tree seems to have survived unchanged since the Cretaceous era. Since then, its molecular defense system has resisted the attacks of millions of generations of pathogens. In line with this, some recent landmarks in Metasequoia paleobotany are covered. Initial spectral analysis of recently discovered intact 53 million year old wood and amber of Metasequoia strongly indicate that the tree has remained unchanged for millions of years at the molecular level.

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Section: Temperature and Sunlight Conditions –Potential Influential Fcontrasting

confidence: 73%

Section: Other Aromatic Compounds Specific To M Glyptostroboidesmentioning

confidence: 99%