Demethylenedelpheline ? A new diterpene alkaloid from Delphinium corumbosum

Cytotoxic esterified diterpenoid alkaloid derivatives with increased selectivity against a drug-resistant cancer cell line

“…13,14 Delpheline ( 1 ) was reacted with various acyl chlorides at 80°C in pyridine to give C-6 substituted benzoyl and cinnamoyl derivatives ( 4–22 ). Delpheline ( 1 ) and 6-(3-trifluoromethylbenzoyl)delpheline ( 12 ) were hydrolyzed under acidic conditions to provide the 7,8-demethylene derivatives, 7,8-demethylenedelpheline ( 23 ) 15 and 7,8-demethylene-6-(3-trifluoromethylbenzoyl)delpheline ( 24 ), respectively. Oxidation of delpheline ( 1 ) with KMnO 4 –acetone gave 19-oxodelpheline ( 25 ).…”

Cytotoxic esterified diterpenoid alkaloid derivatives with increase selectivity against a drug-resistant cancer cell line

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C-6 Esterifications of delpheline (1) were carried out to provide 20 new diterpenoid alkaloid derivatives (4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15)(16)(17)(18)(19)(20)(21)(22) 24). Three natural alkaloids (1-3) and all synthesized compounds (4-25) were evaluated for cytotoxic activity against lung (A549), prostate (DU145), nasopharyngeal (KB), and vincristine-resistant nasopharyngeal (KB-VIN) cancer cell lines and interestingly, showed an improved drug resistance profile compared to paclitaxel.

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“…13,14 Delpheline (1) was reacted with various acyl chlorides at 80°C in pyridine to give C-6 substituted benzoyl and cinnamoyl derivatives (4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15)(16)(17)(18)(19)(20)(21)(22). Delpheline (1) and 6-(3trifluoromethylbenzoyl)delpheline (12) were hydrolyzed under acidic conditions to provide the 7,8-demethylene derivatives, 7,8-demethylenedelpheline (23) 15 and 7,8-demethylene-6-(3-trifluoromethylbenzoyl)delpheline (24), respectively. Oxidation of delpheline (1) with KMnO 4 -acetone gave 19-oxodelpheline (25).…”