Enantiomeric β-carboline dimers from Picrasma quassioides and their anti-hepatoma potential.

Abstract:

:Four pairs of enantiomeric β-carboline alkaloids, (+/-)-kumudine A-D, along with their biosynthesis-related compound kumudine E, were obtained from the stems of Picrasma quassioides. Their structures, including the absolute configurations, were determined via extensive spectroscopic data combined with electronic circular dichroism (ECD) spectroscopic analyses and quantum mechanical ECD calculations. (+/-)-Kumudine A possessed a scaffold of β-carboline-phenylpropanoid adduct, which were the first examples of this type of β-carboline alkaloid from nature. The cytotoxicity assay against hepatocellular carcinoma Hep3B and HepG2 cells was evaluated by SRB assay, which showed that (-)-Kumudine B had stronger effect than its enantiomer (+)-Kumudine B in Hep3B cells. Moreover, further flow cytometry analysis also supported the enantioselectivity between (+)-Kumudine B and (-)-Kumudine B, suggesting that the compounds caused death of hepatoma cells through apoptosis induction.

journal_name

Phytochemistry

journal_title

Phytochemistry

authors

Zhao WY,Zhou WY,Chen JJ,Yao GD,Lin B,Wang XB,Huang XX,Song SJ

doi

10.1016/j.phytochem.2018.12.002

subject

Has Abstract

pub_date

2019-03-01 00:00:00

pages

39-45

eissn

0031-9422

issn

1873-3700

pii

S0031-9422(18)30693-9

journal_volume

159

pub_type

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