3,5-dihydroxy-6,7,8-trimethoxyflavon aus Helichrysum graveolens

Hänsel, Rudolf; Çubukçu, B.

doi:10.1016/s0031-9422(00)88566-0

Cited by 15 publications

(8 citation statements)

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“…However, the flavones are not exclusive to these species. Flavone A has been found in Ainsliaea henryi [ 28 ] and in Helichrysum decumbens [ 29 ] while Flavone B has been isolated from Helichrysum graveolens [ 30 ], as well as Helichrysum odoratissimum [ 31 ], and Helichrysum compactum [ 32 ]. Flavones A and B demonstrated a significant cytotoxic effect against highly tumorigenic cell lines, while sparing normal epithelial cells.…”

Section: Discussionmentioning

confidence: 99%

Mechanism of Action of Two Flavone Isomers Targeting Cancer Cells with Varying Cell Differentiation Status

et al. 2015

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Apoptosis can be triggered in two different ways, through the intrinsic or the extrinsic pathway. The intrinsic pathway is mediated by the mitochondria via the release of cytochrome C while the extrinsic pathway is prompted by death receptor signals and bypasses the mitochondria. These two pathways are closely related to cell proliferation and survival signaling cascades, which thereby constitute possible targets for cancer therapy. In previous studies we introduced two plant derived isomeric flavonoids, flavone A and flavone B which induce apoptosis in highly tumorigenic cancer cells of the breast, colon, pancreas, and the prostate. Flavone A displayed potent cytotoxic activity against more differentiated carcinomas of the colon (CaCo-2) and the pancreas (Panc28), whereas flavone B cytotoxic action is observed on poorly differentiated carcinomas of the colon (HCT 116) and pancreas (MIA PaCa). Apoptosis is induced by flavone A in better differentiated colon cancer CaCo-2 and pancreatic cancer Panc 28 cells via the intrinsic pathway by the inhibition of the activated forms of extracellular signal-regulated kinase (ERK) and pS6, and subsequent loss of phosphorylation of Bcl-2 associated death promoter (BAD) protein, while apoptosis is triggered by flavone B in poorly differentiated colon cancer HCT 116 and MIA PaCa pancreatic cancer cells through the extrinsic pathway with the concomitant upregulation of the phosphorylated forms of ERK and c-JUN at serine 73. These changes in protein levels ultimately lead to activation of apoptosis, without the involvement of AKT.

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Section: Discussionmentioning

confidence: 99%

Mechanism of Action of Two Flavone Isomers Targeting Cancer Cells with Varying Cell Differentiation Status

et al. 2015

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“…Flavone A has been isolated from Ainsliaea henryi , native to the southern and western portions of China [23] . Tomas-Lorente et al, has reported that flavone A was extracted from Helichrysum decumbens along with two other methylated flavonoids [24] Flavone B has been found in Helichrysum graveolens [25] , Helichrysum odoratissimum [26] and Helichrysum compactum [27] . The plant extracts of the latter demonstrated to have antibacterial and antioxidant activities.…”

Section: Discussionmentioning

confidence: 99%

Anti-Neoplastic Activity of Two Flavone Isomers Derived from Gnaphalium elegans and Achyrocline bogotensis

et al. 2012

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Over 4000 flavonoids have been identified so far and among these, many are known to have antitumor activities. The basis of the relationships between chemical structures, type and position of substituent groups and the effects these compounds exert specifically on cancer cells are not completely elucidated. Here we report the differential cytotoxic effects of two flavone isomers on human cancer cells from breast (MCF7, SK-BR-3), colon (Caco-2, HCT116), pancreas (MIA PaCa, Panc 28), and prostate (PC3, LNCaP) that vary in differentiation status and tumorigenic potential. These flavones are derived from plants of the family Asteraceae , genera Gnaphalium and Achyrocline reputed to have anti-cancer properties. Our studies indicate that 5,7-dihydroxy-3,6,8-trimethoxy-2-phenyl-4H-chromen-4-one (5,7-dihydroxy-3,6,8-trimethoxy flavone) displays potent activity against more differentiated carcinomas of the colon (Caco-2), and pancreas (Panc28), whereas 3,5-dihydroxy-6,7,8-trimethoxy-2-phenyl-4H-chromen-4-one (3,5-dihydroxy-6,7,8-trimethoxy flavone) cytototoxic action is observed on poorly differentiated carcinomas of the colon (HCT116), pancreas (Mia PaCa), and breast (SK-BR3). Both flavones induced cell death (>50%) as proven by MTT cell viability assay in these cancer cell lines, all of which are regarded as highly tumorigenic. At the concentrations studied (5–80 µM), neither flavone demonstrated activity against the less tumorigenic cell lines, breast cancer MCF-7 cells, androgen-responsive LNCaP human prostate cancer line, and androgen-unresponsive PC3 prostate cancer cells. 5,7-dihydroxy-3,6,8-trimethoxy-2-phenyl-4H-chromen-4-one (5,7-dihydroxy-3,6,8-trimethoxy flavone) displays activity against more differentiated carcinomas of the colon and pancreas, but minimal cytotoxicity on poorly differentiated carcinomas of these organs. On the contrary, 3,5-dihydroxy-6,7,8-trimethoxy-2-phenyl-4H-chromen-4-one (3,5-dihydroxy-6,7,8-trimethoxy flavone) is highly cytotoxic to poorly differentiated carcinomas of the colon, pancreas, and breast with minimal activity against more differentiated carcinomas of the same organs. These differential effects suggest activation of distinct apoptotic pathways. In conclusion, the specific chemical properties of these two flavone isomers dictate mechanistic properties which may be relevant when evaluating biological responses to flavones.

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“…Die gleiche Verbindung konnte später aus Helichrysum graveolens isoliert werden [2], Nunmehr haben vor einiger Zeit X. A. Domingues und E. Cardenas [3] für ein aus Artemisia-Arten isoliertes Flavon die nämliche Konstitution 7 angegeben; doch zeigen die physikalischen Daten der von uns [1,2] und der von X.…”

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“…Unser Konstitutionsbeweis fußte auf dem Vergleich des permethylierten Naturstoffes 2 mit dem auf eindeutigem Wege synthetisierten 3.5.6.7.8-Penta-methoxyflavon (2). Nun wurde von uns beobachtet [4,5], daß das mit dem 3.5.7-Trihydroxyflavon (7) isomere a.4.6-Trihydroxybenzalcumaranon (5) unter den Bedingungen der Methylierung mit Dimethylsulfat K2CO3 in trockenem Aceton nicht das erwartete Methylierungsprodukt (6) Frage offen, ob das aus den genannten HeiichrysumArten isolierte Flavonoid genuin in der Fla vonform 1 oder mit der damit isomeren Benzalcumaranonform 3 vorliegt.…”

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“…Zur Ergänzung früherer spektroskopischer Daten [1,2] wurde von uns nunmehr das 13 C-NMR-Spektrum herangezogen und mit den in der Literatur niedergelegten Daten für Flavone [7] verglichen. Als Modellsubstanz für die mögliche isomere Form 3 wurde zum Vergleich 2-Benzoyl-3-hydroxy-benzofuran eingehend vermessen ( 13 C-NMR, positionelle Isotopenanalyse; alle Kopplungskonstanten [8]).…”

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3.5-Dihydroxy-6.7.8-trimethoxyflavon aus Heiichrysum graveolens: Bestätigung der Konstitution / Confirmation of the Structure of an Extractive from Helichrysum graveolens as 3,5-Dihydroxy-6,7,8-trimethoxyflavone

Hänsel

Khaliefi

Pelter

1981

Zeitschrift Für Naturforschung B

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3,5-dihydroxy-6,7,8-trimethoxyflavon aus Helichrysum graveolens

Cited by 15 publications

References 1 publication

Mechanism of Action of Two Flavone Isomers Targeting Cancer Cells with Varying Cell Differentiation Status

Mechanism of Action of Two Flavone Isomers Targeting Cancer Cells with Varying Cell Differentiation Status

Anti-Neoplastic Activity of Two Flavone Isomers Derived from Gnaphalium elegans and Achyrocline bogotensis

3.5-Dihydroxy-6.7.8-trimethoxyflavon aus Heiichrysum graveolens: Bestätigung der Konstitution / Confirmation of the Structure of an Extractive from Helichrysum graveolens as 3,5-Dihydroxy-6,7,8-trimethoxyflavone

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