Total synthesis of the pyranocoumaronochromone lupinalbin H

Selepe, Mamoalosi A.; Drewes, Siegfried E.; Heerden, Fanie R. van

doi:10.1016/j.tet.2011.09.042

Cited by 18 publications

(15 citation statements)

References 33 publications

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“…The 1 H- and 13 C-NMR data of lupinalbin A and 2′-hydroxygenistein are shown in Table 1 and the MS data for all three compounds are given below. The spectroscopic data were in good correlation to published data (see Table 1 ) [ 13 , 14 ].…”

Section: Methodssupporting

confidence: 84%

Lupinalbin A as the most potent estrogen receptor α- and aryl hydrocarbon receptor agonist in Eriosema laurentii de Wild. (Leguminosae)

Ateba

Njamen

Medjakovic

et al. 2014

BMC Complement Altern Med

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BackgroundEriosema laurentii De Wild. (Leguminosae) is a plant used in Cameroon against infertility and gynecological or menopausal complaints. In our previous report, a methanol extract of its aerial parts was shown to exhibit estrogenic and aryl hydrocarbon receptor agonistic activities in vitro and to prevent menopausal symptoms in ovariectomized Wistar rats.MethodsIn order to determine the major estrogen receptor α (ERα) agonists in the extract, an activity-guided fractionation was performed using the ERα yeast screen. To check whether the ERα active fractions/compounds also accounted for the aryl hydrocarbon receptor (AhR) agonistic activity of the crude methanol extract, they were further tested on the AhR yeast screen.ResultsThis study led to the identification of 2′-hydroxygenistein, lupinalbin A and genistein as major estrogenic principles of the extract. 2′-hydroxygenistein and lupinalbin A were, for the first time, also shown to possess an AhR agonistic activity, whereas genistein was not active in this assay. In addition, it was possible to deduce structure-activity relationships.ConclusionsThese results suggest that the identified compounds are the major active principles responsible for the estrogenic and AhR agonistic activities of the crude methanol extract of the aerial parts of Eriosema laurentii.

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Section: Methodssupporting

confidence: 84%

Lupinalbin A as the most potent estrogen receptor α- and aryl hydrocarbon receptor agonist in Eriosema laurentii de Wild. (Leguminosae)

Ateba

Njamen

Medjakovic

et al. 2014

BMC Complement Altern Med

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“…van Heerden and co-workers demonstrated a highly convergent route for the synthesis of naturally occurring phytoestrogen, Lupinalbin A ( Selepe et al., 2011 ), starting from resorcinol and trihydroxyacetophenone, in two major steps that involve the preparation of 2′-hydroxygenistein by the Suzuki-Miyaura reaction, followed by oxidative cyclodehydrogenation ( Scheme 1 B).…”

Section: Construction Of Natural Products From Potentially Lignin-dermentioning

confidence: 99%

Pharmaceutically relevant (hetero)cyclic compounds and natural products from lignin-derived monomers: Present and perspectives

Afanasenko

Barta

2021

iScience

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Summary Lignin, the richest source of renewable aromatics on the planet, is an intriguing raw material for the construction of value-added aromatics. In the past decade, much progress has been made regarding the development of efficient lignin depolymerization methods, able to produce specific monophenol derivatives in high-enough selectivity and yields. This now serves as an excellent basis for developing powerful downstream conversion strategies toward a wide range of products, including fine chemical building blocks. The inherent structural features of lignin-derived platform chemicals undoubtedly inspire the development of novel, creative, atom-economic synthetic routes toward biologically active molecules or natural products. In this perspective we attempt to bridge the structural features of lignin-derived platform chemicals with existing synthetic strategies toward the construction of heterocycles and provide a summary of efforts for the production of natural products from aromatics that can be, in principle, obtained from lignin. Last, we comment on the latest efforts that present entire value-chains from wood to valuable pharmaceutically relevant compounds.

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“…An account of natural products in which at least one step involved a SMR is depicted in Figure 9 [126,127,128,129,130,131,132,133,134,135,136,137,138] and Figure 10 [139,140,141,142,143,144,145,146,147,148,149,150]. For each compound, the corresponding authors, the year and the bond constructed using a SMR are showed.…”

Section: Applicationsmentioning

confidence: 99%

Recent Developments in the Suzuki-Miyaura Reaction: 2010–2014

2015

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Abstract:The Suzuki-Miyaura reaction (SMR), involving the coupling of an organoboron reagent and an organic halide or pseudo-halide in the presence of a palladium or nickel catalyst and a base, has arguably become one of most utilized tools for the construction of a C-C bond. This review intends to be general account of all types of catalytic systems, new coupling partners and applications, including the

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Total synthesis of the pyranocoumaronochromone lupinalbin H

Cited by 18 publications

References 33 publications

Lupinalbin A as the most potent estrogen receptor α- and aryl hydrocarbon receptor agonist in Eriosema laurentii de Wild. (Leguminosae)

Lupinalbin A as the most potent estrogen receptor α- and aryl hydrocarbon receptor agonist in Eriosema laurentii de Wild. (Leguminosae)

Pharmaceutically relevant (hetero)cyclic compounds and natural products from lignin-derived monomers: Present and perspectives

Recent Developments in the Suzuki-Miyaura Reaction: 2010–2014

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