Zanthoamides G-I: Three new alkamides from Zanthoxylum zanthoxyloides

Guetchueng, Stéphanie Tamdem; Nahar, Lutfun; Ritchie, Kenneth J.; Ismail, Fyaz M.D.; Evans, Andrew R.; Sarker, Satyajit D.

doi:10.1016/j.phytol.2018.05.031

Cited by 22 publications

(12 citation statements)

References 28 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…It is endowed with pharmacologically useful phytochemicals, some of which are responsible for their previously reported antitrypanosomal effects [ 14 ]. Even though compound 1 has previously been isolated from Z. zanthoxyloides [ 27 , 28 ], as well as shown to possess antitrypanosomal activity against T. b. rhodesiense and T. cruzi in a separate study [ 29 ], the complete structures and mechanisms of antitrypanosomal action for the phytochemicals of Z. zanthoxyloides have received little attention. In this study, two major phytochemicals, compound 1 (skimmianine) and compound 2 (9-oxo-10,12-octadecadienoic acid (9-oxo-ODA)) were isolated from the root of Z. zanthoxyloides and subsequently investigated for mechanisms by which they alter the cell viability, cell cycle, and cell morphology of T. brucei.…”

Section: Discussionmentioning

confidence: 99%

Isolation and Antitrypanosomal Characterization of Furoquinoline and Oxylipin from Zanthoxylum zanthoxyloides

et al. 2020

View full text Add to dashboard Cite

In the absence of vaccines, there is a need for alternative sources of effective chemotherapy for African trypanosomiasis (AT). The increasing rate of resistance and toxicity of commercially available antitrypanosomal drugs also necessitates an investigation into the mode of action of new antitrypanosomals for AT. In this study, furoquinoline 4, 7, 8-trimethoxyfuro (2, 3-b) quinoline (compound 1) and oxylipin 9-oxo-10, 12-octadecadienoic acid (compound 2) were isolated from the plant species Zanthoxylum zanthoxyloides (Lam) Zepern and Timler (root), and their in vitro efficacy and mechanisms of action investigated in Trypanosoma brucei (T. brucei), the species responsible for AT. Both compounds resulted in a selectively significant growth inhibition of T. brucei (compound 1, half-maximal effective concentration EC50 = 1.7 μM, selectivity indices SI = 74.9; compound 2, EC50 = 1.2 μM, SI = 107.3). With regards to effect on the cell cycle phases of T. brucei, only compound 1 significantly arrested the second growth-mitotic (G2-M) phase progression even though G2-M and DNA replication (S) phase arrest resulted in the overall reduction of T. brucei cells in G0-G1 for both compounds. Moreover, both compounds resulted in the aggregation and distortion of the elongated slender morphology of T. brucei. Analysis of antioxidant potential revealed that at their minimum and maximum concentrations, the compounds exhibited significant oxidative activities in T. brucei (compound 1, 22.7 μM Trolox equivalent (TE), 221.2 μM TE; compound 2, 15.0 μM TE, 297.7 μM TE). Analysis of growth kinetics also showed that compound 1 exhibited a relatively consistent growth inhibition of T. brucei at different concentrations as compared to compound 2. The results suggest that compounds 1 and 2 are promising antitrypanosomals with the potential for further development into novel AT chemotherapy.

show abstract

Section: Discussionmentioning

confidence: 99%

Isolation and Antitrypanosomal Characterization of Furoquinoline and Oxylipin from Zanthoxylum zanthoxyloides

et al. 2020

View full text Add to dashboard Cite

show abstract

“…The IR spectrum of 1 shows typical absorptions of hydroxyl and C=C double bond groups. [15]. The hydrogen signal at δH 4.28 (1H, d, J = 7.7 Hz, H-1`) exhibits besides the characteristic chemical shift expected for β anomeric hydrogens, a significantly larger J value, which is consistent with the axial-axial coupling [15,16] The relative stereochemistry of the diterpene moiety was based on 1D NOE NMR experiments, obtained in CDCl3.…”

Section: Antileishmanialmentioning

confidence: 84%

“…[15]. The hydrogen signal at δH 4.28 (1H, d, J = 7.7 Hz, H-1`) exhibits besides the characteristic chemical shift expected for β anomeric hydrogens, a significantly larger J value, which is consistent with the axial-axial coupling [15,16] The relative stereochemistry of the diterpene moiety was based on 1D NOE NMR experiments, obtained in CDCl3. The selective irradiation of the resonance frequency of the methyl hydrogen at δH 1.02 (H-20ax) shows mainly NOE enhancement on the signals at δH 1.90 (H-14ax), 1.71 (H-12ax) and 0.81 (H-19ax), which is compatible with ent-kaurane skeleton.…”

Section: Antileishmanialmentioning

confidence: 84%

Antileishmanial Activity of a New ent-Kaurene Diterpene Glucoside Isolated from Leaves of Xylopia excellens R.E.Fr. (Annonaceae)

Alencar¹,

Silva²,

Almeida³

et al. 2018

Rec.Nat.Prod.

View full text Add to dashboard Cite

show abstract

“…Another compound Tambulin, a flavonoid isolated from the fruit exhibited antiproliferative action on certain cancer cell lines like MCF-7, WRL-68, COLO-205, MDAMB-231, with an IC 50 ranging from 37.96 to 48.7 μg/mL [45]. Three compounds isolated from Z. zanthoxyloides fruits ME, hesperidin, skimmianine, and sesamine, possess anticancerous activity up to some level against A549, MCF7, and PC3 cell lines [47]. Pang et al [48] confirms the anti-proliferative activity of seed oil of Z. bungeanum Maxim.…”

Section: Zanthoxylum As Herbal Medicine In Modern Pharmacology 41 Anmentioning

confidence: 99%

An Overview of Genus Zanthoxylum with Special Reference to Its Herbal Significance and Application

Ekka¹,

Jadhav²,

Quraishi³

2020

Herbs and Spices

View full text Add to dashboard Cite

The plants of genus Zanthoxylum are effectually utilized in conventional and present-day medicine system to fight many diseases and disorders like pain, seizures, inflammation, cancer, liver and heart malady. Many of its plants-trees and shrubs, are citrus in nature, with curative antimicrobial, antihelminthic, antipyretic, and antiviral activities. More than 100 of its plant species have been identified and recorded for their potential as an herb in modern pharmacopeia. The species of this genus also have potent ethno-pharmacological significance. Many medicinal secondary metabolites like terpenoids, flavonoids, and alkaloids have also been profiled in many Zanthoxylum species. Additionally, fruit of many of the species is also significantly utilized as a major spice under the name "Sichuan pepper" in many countries like China and India. Thus, this unique blend of herb and spice characteristic of the genus needs a detailed description. This chapter highlights the major significant discoveries in the recent decade in this genus, which can add a step in the way of development of herbal medicines. Documentation of such medicinal plants may aid in derivation of plant-based medicines, which is the demand of the hour.

show abstract

Zanthoamides G-I: Three new alkamides from Zanthoxylum zanthoxyloides

Cited by 22 publications

References 28 publications

Isolation and Antitrypanosomal Characterization of Furoquinoline and Oxylipin from Zanthoxylum zanthoxyloides

Isolation and Antitrypanosomal Characterization of Furoquinoline and Oxylipin from Zanthoxylum zanthoxyloides

Antileishmanial Activity of a New ent-Kaurene Diterpene Glucoside Isolated from Leaves of Xylopia excellens R.E.Fr. (Annonaceae)

An Overview of Genus Zanthoxylum with Special Reference to Its Herbal Significance and Application

Contact Info

Product

Resources

About