Secondary metabolites and cytotoxic activities from the stem bark of Zanthoxylum nitidum

Abstract

A dihydrobenzo [c]phenanthridine alkaloid, epizanthocadinanine A (1), together with 27 known compounds, including eight benzo[c]phenanthridines, i.e., oxynitidine (2), oxyavicine (3), oxychelerythrine (4), dihydrochelerythrine (5), 6-acetonyldihydrochelerythrine (6), norchelerythrine (7), decarine (8), and arnottianamide (9); two 2-quinolones, i.e., flindersine (10) and 4-methoxy-1-methyl-2-quinolone (11); two furoquinolines, i.e., skimmianine (12) and g-fagarine (13); three aporphines, i.e., liriodenine (14), N-acetyldehydroanonaine (15), and N-acetylanonaine (16); six lignans, i.e., sesamin (17), episesamin (18), piperitol-3,3-dimethylallyl ether (19), xanthoxylol-3,3-dimethylallyl ether (20), savinin (21), and 2,3-bis(3,4-methylenedioxybenzyl)but-2-en-4-olide (22); three terpenoids, i.e., acadinol (23), anticopalol (24), and spathulenol (25); one coumarin, i.e., aesculetin dimethyl ether (26); and two steroids, i.e., b-sitosterol (27) and b-sitostenone (28) were isolated from the stem bark of Zanthoxylum nitidum. Their structures were elucidated on the basis of extensive 1D-and 2D-NMR as well as MS analyses. Moreover, the recently reported structures 2' -4' of rhoifolines B and A, and 8-methoxynorchelerythrine, resp., isolated as new compounds from Z. rhoifolium and Z. nitidum, resp., could be assigned the revised structures 2 -4 by reinvestigation of the spectroscopic data. In addition, the cytotoxicity of the isolates was evaluated on the MCF-7, NCI-H460, and SF-268 cell lines. Among these isolates, liriodenine (14) was the most active compound against the MCF-7, NCI-H460, and SF-268 cell lines with IC 50 values of 2.19, 2.38, and 3.19 mg/ml, resp.

Identification of spathulenol in Salvia mirzayanii and the immunomodulatory effects

“…The presence of spathulenol has been shown previously in a few other species including Salvia yosgadensis (Topcu et al ., 1996), Salvia rhytidea Benth (Sajjadi and Ghannadi, 2005) and Salvia sclarea (Ulubelen et al ., 1994) as well. Apart from Salvia species, the presence of spathulenol in essential oils from various other plants has been reported (Chao et al ., 2005; Yang et al ., 2009; Martins et al ., 2008; Aguilar‐Guadarrama and Rios, 2004). Essential oils of a few of these plants have shown antiinflammatory effects, e.g.…”

Candelariella vitellina extract triggers in vitro and in vivo cell death through induction of apoptosis: A novel anticancer agent

“…Numerous studies have reported the inhibitory effects of the following terpenes as secondary metabolites of C. vitellina; Hericenone A (Rama Rao and Reddy, 1992), Ovellin B (Belofsky et al, 1998), Ganoderol A and Ganoderiol F (Chen et al, 2017), Ganodermatriol (Liu et al, 2012), and Fomefficinic acid A (Shen et al, 2013). In contrast, cytotoxicity was attributed to compounds with a polyketides structure such as Hormothamnione (Gerwick et al, 1986), Arnottianamide (Yang et al, 2009), and Comazaphilone C (Gao et al, 2011) (Table 1). Chen, S., Li, X., Yong, T., Wang, Z., Su, J., Jiao, C., Xie, Y., Yang, B.B., 2017…”

Alkaloids From Zanthoxylum nitidum and Their Cytotoxic Activity

“…In folk medicine, its roots have been used to promote blood circulation, dissipate blood stasis, and cure snake bite; leaves and stems have been used to treat toothache, sore throat, cough, and fever. Previous phytochemical investigations of this plant led to the isolation of phenanthridine alkaloids, [1][2][3] quinolines, 4 phenylpropanoids, 5 lignans, and coumarins. [4][5][6] These compounds exhibited anti-virus, 7 anti-inflammatory, 8,9 and anti-cancer activities.…”

“…Previous phytochemical investigations of this plant led to the isolation of phenanthridine alkaloids, [1][2][3] quinolines, 4 phenylpropanoids, 5 lignans, and coumarins. [4][5][6] These compounds exhibited anti-virus, 7 anti-inflammatory, 8,9 and anti-cancer activities. [4][5][6][7][8][9][10] This paper reports three new alkaloids from Z. nitidum.…”