A New C22‐Quassinoid with Anti‐Pancreatic Adenocarcinoma Activity from Seeds of Brucea javanica

An undescribed C22‐quassinoid named sergeolide A (1) and fifteen known quassinoids (2–16) were obtained from the seeds of Brucea javanica (Simaroubaceae). All chemical structures were established based on spectroscopic data and X‐ray diffraction analysis. Sergeolide A (1) is the first example of a n...

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Bibliographic Details
Published in:Chemistry & biodiversity 2022-06, Vol.19 (6), p.e202101004-n/a
Main Authors: Yang, Cheng‐Bin, Lu, Si‐Nan, Lu, Cai, Xu, Ming‐Ming, Duan, Jin‐Ao, Che, Chun‐Tao, Zhou, Junfei, Zhao, Ming
Format: Article
Language:English
Subjects:
Adenocarcinoma
anti-pancreatic cancer
Brucea javanica
Crystal structure
NMR
Nuclear magnetic resonance
Pancreatic cancer
quassinoid
Quassinoids
Rings (mathematics)
Seeds
sergeolide A
Simaroubaceae
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Summary:An undescribed C22‐quassinoid named sergeolide A (1) and fifteen known quassinoids (2–16) were obtained from the seeds of Brucea javanica (Simaroubaceae). All chemical structures were established based on spectroscopic data and X‐ray diffraction analysis. Sergeolide A (1) is the first example of a naturally occurring C22‐quassinoid bearing a butenolide group fused the A ring of the bruceolide skeleton from Brucea genus. And this is the first report of the NMR data for desmethyl‐bruceines B (2) and C (3) and the crystal structure for bruceolide (11). In addition, all isolates were evaluated for their anti‐pancreatic adenocarcinoma activity by measuring the growth inhibitory of the MIA PaCa‐2 cell lines. Consequently, compounds 1, 7–10, and 12–16 exhibited potent anti‐pancreatic cancer activity in vitro (IC50=0.054∼0.357 μM).
ISSN:1612-1872
1612-1880
DOI:10.1002/cbdv.202101004