Planta Med 2013; 79 - PI24
DOI: 10.1055/s-0033-1352114

Bioactive constituents from the twigs of Zanthoxylum ailanthoides

JJ Chen 1, CY Chung 2, MI Chung 2, TL Hwang 3
  • 1Graduate Institute of Pharmaceutical Technology & Department of Pharmacy, Tajen University, Pingtung 907, Taiwan
  • 2Faculty of Pharmacy, Kaohsiung Medical University, Kaohsiung 807, Taiwan
  • 3Graduate Institute of Natural Products, Chang Gung University, Taoyuan 333, Taiwan

Zanthoxylum ailanthoides Sieb. & Zucc. (Rutaceae) is a medium-to-large-sized tree, found at low altitude in forests of China, Japan, Korea, Philippines, and Taiwan. Various benzo[c]phenanthridines, coumarins, lignans, flavonoids, quinolines, benzenoids, and triterpenoids are widely distributed in this plant. Many of these compounds exhibit anti-platelet aggregation, anti-HIV, and anti-inflammatory activities. Investigation on EtOAc-soluble fraction of the twigs of Z. ailanthoides has led to the isolation of a new benzo[c]phenanthridine, oxynorchlerythrine (1), and a new benzenoid, methyl 4-(2-hydroxy-4-methoxy-3-methyl-4-oxobutoxy)benzoate (2), together with 5 known compounds, including, two benzo[c]phenanthridines, decarine and 6-acetonyldihydrochelerythrine, and three lignans, (-)-syringaresinol, 5′,5′′-didemethoxypinoresinol, and (+)-episesamin. The structure of new compound 1 and 2 were determined through spectral analyses including extensive 2D NMR data. Among the isolated compounds, decarine, (-)-syringaresinol, and xanthyletin exhibited potent inhibition (IC50 values ≤4.79 µg/ml) of superoxide generation by human nutrophils in response to N-formyl-L-methionyl-L-leucyl-L-phenylalanine/cytochalasin B (fMLP/CB).

Fig. 1

Acknowledgement: This research was supported by grants from the National Science Council (NSC, Taiwan) (No. NSC 98 – 2320-B-127 – 001-MY3 and NSC 101 – 2320-B-127 – 001-MY3), awarded to Prof. J.-J. Chen.