Alkaloids From Zanthoxylum nitidum and Their Cytotoxic Activity

Abstract

Zanthoxylum nitidum (Roxb.) DC (Rutaceae) is a traditional medicine used for the treatment of various diseases like toothache, gingivitis, fever, colic vomiting, diarrhea, and cholera. Three new alkaloids, zanthocadinanine C (1), 7-methoxy-8-demethoxynitidine (2), and zanthonitiside I (3) were isolated from the stems and twigs of Z. nitidum. Their structures were determined on the basis of extensive spectroscopic, including 1-dimensional and 2-dimensional nuclear magnetic resonance and mass spectroscopy data. Compounds 1-3 were evaluated for cytotoxic activity against 5 human cancer cell lines, KB, MCF-7, LNCaP, HepG-2, and LU-1. Compound 2 showed significant cytotoxic activity against all tested human cancer cell lines with IC 50 values ranging from 10.3 to 12.6 µM.

Insights on Antitumor Activity and Mechanism of Natural Benzophenanthridine Alkaloids

“…Zanthocadinanine C (70) and 7-methoxy-8-demethoxynitidine (71) exhibit cytotoxic activity against five human cancer cell lines KB, MCF-7, LNCaP, HepG-2, and lu-1, whereas the alkaloid 7-methoxy-8-demethoxynitidine (71) has high activity with IC50 values from 10.3 to 12.6 µM. Furthermore, zanthocadinanine C ( 70) is less active with IC50 > 100 µM [98]. Dihydronitidine (72) (Figure 23), a benzophenanthridine alkaloid, is isolated from Zanthoxylum.…”

“…Benzophenanthridine alkaloids 8-methoxynorchelerythrine (90), 11-demethylrhoifoline B (91), 8-methoxynitidine (92), 8-acetylnorchelerythrine (93), 8,9,10,12-tetramethoxynorchelerythrine (94), isointegriamide (95), pancorine (96), 8-methoxychelerythrine (97), oxynitidine (98), and oxysanguinarine (99) (Figure 28) are extracted from Toddalia asiatica. Studies have shown that the above compounds could inhibit eight types of human tumor cell lines in vitro, including A549 (human lung cancer), BGC-823 (human gastric cancer), HCT-15 (human colon cancer), Hela (human cervical cancer), HepG2 (human liver cancer), MCF-7 (human breast cancer), SK-MEL-2 (human skin cancer), and SGC-7901 (human gastric cancer).…”

“…natural product oxynitidine (98) after semi synthetic structure modification. W.-L. Tang et al [110] had suggested that the derivatives of oxynidine are capable of inhibiting the growth and proliferation of human cancer cells and inducing apoptosis by inhibiting the activity of DNA topoisomerase IB (TOP1).…”

Spectrum-Effect Relationship Analysis of Bioactive Compounds in Zanthoxylum nitidum (Roxb.) DC. by Ultra-High Performance Liquid Chromatography Mass Spectrometry Coupled With Comprehensive Filtering Approaches

“…In daily life, ZN could be used as toothpaste and hand sanitizer. In a previous study, researchers were mainly focused on the chemical isolation and activity evaluation of ZN ( Yang et al, 2008 ; Zhao et al, 2018 ; Nguyen et al, 2019 ). ZN extracts showed good anti-inflammatory and antioxidant activities ( Xie, 2000 ; Liu et al, 2014 ).…”

The Effect of Balimo (Zanthoxylum nitidum) Immersion Water On The Hematological Profile of White Rats (Rattus norvegicus) That Given Liquor (Ciu)

“…Phytochemical investigations showed the presence of alkaloids, flavonoids, and true amino acids in the bark of Zanthoxylum nitidum (Bhattacharya & Zaman, 2009). These compounds have benefits as anti-viral, antiinflammatory, antioxidant, and anti-cancer activities (Van Nguyen et al, 2019).…”