The Crystal Structure of Scopadulcic Acid A from Paraguayan Crude Drug "Typychá Kuratú" (Scoparia dulcis)

Hayashi, Toshimitsu; Kishi, Mieko; Kawasaki, M.; Arisawa, Munehisa; Morita, Naokata; Berganza, Luis H.

doi:10.1021/np50056a034

Cited by 20 publications

(12 citation statements)

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“…[120] Subsequent studies showed that scopadulcic acid B is a powerful inhibitor of H + ,K + -ATPase, the proton pump for gastric acid secretion, as well as an inhibitor of herpes simplex virus type 1 and of bone resorption by osteoclast cells. [121] The structure of scopadulcic acid A was established by X-ray crystallography, [122] whereas the absolute configuration of these diterpenoid acids was suggested on the basis of CD measurements and later confirmed by enantioselective synthesis. [123] The bicyclo[3.2.1]octane subunit of scopadulcic acids A and B is also found in tetracyclic diterpenes such as aphidicolin and stemarin.…”

Section: Scopadulcic Acids a And Bmentioning

confidence: 99%

“…in 1987 from Scoparia dul cis L . This flowering plant is widely distributed in the tropics and subtropics and is considered by several native populations to possess various medicinal properties . Subsequent studies showed that scopadulcic acid B is a powerful inhibitor of H + ,K + ‐ATPase (the proton pump for gastric acid secretion) as well as an inhibitor of herpes simplex virus type 1 and of bone resorption by osteoclast cells .…”

Section: Scopadulcic Acids a And Bmentioning

confidence: 99%

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Synthetic Strategies toward Natural Products Containing Contiguous Stereogenic Quaternary Carbon Atoms

et al. 2016

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Strategies for the total synthesis of complex natural products that contain two or more contiguous stereogenic quarternary carbon atoms in their intricate structures are reviewed with twelve representative examples. Emphasis has been put on the methods to create quarternary carbon stereocenters, including syntheses of the same natural product from different groups, thereby showcasing diversity of thought and individual creativity. A compendium of selected natural products containing two or more contiguous stereogenic quarternary carbon atoms and key reactions in their total or partial syntheses is provided in the Supporting Information section.

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Section: Scopadulcic Acids a And Bmentioning

confidence: 99%

Section: Scopadulcic Acids a And Bmentioning

confidence: 99%

Synthetic Strategies toward Natural Products Containing Contiguous Stereogenic Quaternary Carbon Atoms

et al. 2016

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“…berichteten Hayashi et al. 1987 . Diese Blütenpflanze ist in den Tropen und Subtropen weit verbreitet.…”

Section: Die Scopadulcinsäuren a Und Bunclassified

“…Wissenschaftliche Untersuchungen haben ergeben, dass Scopadulcinsäure B ein potenter Inhibitor der H + ,K + ‐ATPase (der für die Magensäurebildung verantwortlichen Protonenpumpe in Zellen der Magenschleimhaut) ist und auch hemmend auf die Vermehrung von Herpes‐simplex‐Viren vom Typ 1 sowie die Knochenresorption durch Osteoklasten wirkt . Die Struktur von Scopadulcinsäure A wurde röntgenkristallographisch aufgeklärt; die absolute Konfiguration dieser Diterpenoidsäuren wurde durch Circulardichroismus(CD)‐Messungen abgeleitet und später durch enantioselektive Synthesen bestätigt . Die Bicyclo[3.2.1]octan‐Untereinheit der Scopadulcinsäuren A und B findet sich auch in tetracyclischen Diterpenen wie Aphidicolin und Stemarin.…”

Section: Die Scopadulcinsäuren a Und Bunclassified

Strategien für die Synthese von Naturstoffen mit benachbarten stereogenen quartären Kohlenstoffatomen

et al. 2016

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Anhand zwölf repräsentativer Beispiele stellen wir in diesem Aufsatz Strategien für die Totalsynthese komplexer Naturstoffe vor, die zwei oder mehr benachbarte stereogene quartäre Kohlenstoffatomen in ihren komplexen Molekülstrukturen enthalten. Das Hauptaugenmerk liegt dabei auf den Methoden zur Konstruktion quartärer stereogener Kohlenstoffzentren, einschließlich der Synthese desselben Naturstoffs auf verschiedenen Wegen durch unterschiedliche Forschergruppen; dies soll die Vielfalt der Gedankengänge sowie die Individualität kreativer Leistungen verdeutlichen. Ein Kompendium von ausgewählten Naturstoffen mit zwei oder mehr benachbarten stereogenen quartären Kohlenstoffatomen sowie von Schlüsselreaktionen ihrer jeweiligen Total‐ oder Partialsynthesen findet sich in den Hintergrundinformationen.

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“…S. dulcis has been extensively studied for its chemical constituents like triterpenes, 2,4,7,8 diterpenes, 4,7,9–15 benzoxazinoid, flavonoids, iridoid and iridoid glycosides compounds 3,16 and other constituents coixol, glutinol, glutinone, friedelin, betulinic acid, and tetratriacontan-1-ol 17 are also reported.…”

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confidence: 99%

Isolation and characterization of cytotoxic and anti-inflammatory constituents fromScoparia dulcisL

Nur‐e‐Alam

Ahmed

Yousaf

et al. 2020

Journal of Chemical Research

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Scoparia dulcis L. is one of the edible widely distributed Scropholariaceae species in Asia, Africa and America. It is used in the treatment of respiratory and inflammatory diseases, diabetes, hypertension, cancer, hepatitis and tuberculosis. A phytochemical investigation on S. dulcis led to the isolation of two new acyclic diterpenes Acetic acid 6-hydroxy-2-(6-hydroxy-4-methyl-hex-4-enylidene)-4,8-dimethyl-undeca-4,8-dienyl ester (1) and Acetic acid 8-hydroxy-2-(6-hydroxy-4-methyl-hex-4-enylidene)-6,10-dimethyl-undeca-5,9-dienyl ester (2) in addition to eight known compounds (3–10), namely scopadulciol (3), 4- epi-scopadulcic acid B (4), dulcidiol (5), scopadulcic acid B (6), hymenoxin (7), glutinol (8), eupatilin (9) and 5-demethylnobiletin (10). The structures elucidation was performed using spectroscopic means, including 1D and 2D nuclear magnetic resonance and high-resolution electrospray ionization mass spectrum spectrometric analysis. Furthermore, the isolated compounds were investigated for their anti-inflammatory activity through the determination of inhibition of nuclear factor-kappa B activity in human chondrosarcoma (SW1353) cells, the inhibition of inducible nitric oxide synthase mouse macrophages (RAW264.7) and the decrease in cellular oxidative stress in HepG2 cells. Moreover, the cytotoxic activity was investigated against four cancer and two kidney cell lines. Among the isolates, 3, 5 and 10 showed anti-inflammatory activity in terms of inhibiting nuclear factor-kappa B and inducible nitric oxide synthase. Compounds 3–5 were the most cytotoxic towards cancer cell lines (IC50: 3.8 µM to 42.3 µM) followed by 10 (IC50: 30.9- > 64.4 µM). Cytotoxicity of compounds 3–5 was comparable to the activity of doxorubicin.

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The Crystal Structure of Scopadulcic Acid A from Paraguayan Crude Drug "Typychá Kuratú" (Scoparia dulcis)

Cited by 20 publications

References 1 publication

Synthetic Strategies toward Natural Products Containing Contiguous Stereogenic Quaternary Carbon Atoms

Synthetic Strategies toward Natural Products Containing Contiguous Stereogenic Quaternary Carbon Atoms

Strategien für die Synthese von Naturstoffen mit benachbarten stereogenen quartären Kohlenstoffatomen

Isolation and characterization of cytotoxic and anti-inflammatory constituents fromScoparia dulcisL

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