A new benzophenanthridine alkaloid and other bioactive constituents from the stem bark of Zanthoxylum heitzii

Wangensteen, Helle; Ho, Giang Thanh Thi; Tadesse, Margey; Miles, Christopher O.; Moussavi, Nastaran; Mikolo, Bertin; Malterud, Karl Egil

doi:10.1016/j.fitote.2016.01.012

Cited by 25 publications

(25 citation statements)

References 18 publications

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“…Chelerythrin, 6hydroxy-dihydrochelerythrine, trans-fagaramide, γ-fagarine, scoparone, pellitorine, and sesamin were moderately toxic (LC 50 between 10 and 100 µg/mL), while arnottianamide, burkinabin B, cis-fagaramide, hesperidin, chlorogenic acid, neochlorogenic acid, 6,7,8-trimethoxycoumarin, skimmianine, and synephrine showed low toxicity or were nontoxic to brine shrimp nauplii (LC 50 > 100 µg/mL). Although literature values for toxicity in this assay system vary widely, our data for chlorogenic acid [36], scoparone [37], pellitorine [38], and sesamin [38] are in reasonable accord with previously reported values. To our knowledge, no toxicity data for brine shrimp nauplii have been reported previously for arnottianamide, burkinabin B, chelerythrine, 6-hydroxy-dihydrochelerythrine, bis-dihydrochelerythrinyl ether, cis-fagaramide, trans-fagaramide, γ-fagarine, hesperidin, neochlorogenic acid, 6,7,8-trimethoxycoumarin, skimmianine, and synephrine.…”

Section: Resultssupporting

confidence: 92%

“…Extracts and isolated compounds were dissolved in DMSO and the assay was carried out as previously described in 5 mL test tubes for extracts (6-9 concentrations) [38] or in 96-well microplates for isolated compounds (1, 10, and 100 µg/mL) [42]. Podophyllotoxin, 100 µg/mL, (purity ≥ 98 %; Sigma-Aldrich) was used as a positive control.…”

Section: Toxicity Against Artemia Salina Naupliimentioning

confidence: 99%

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Anti-plasmodial Effects of Zanthoxylum zanthoxyloides

et al. 2019

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Zanthoxylum zanthoxyloides, syn. Fagara zanthoxyloides, is a tree growing in West Africa and is used in traditional medicine against a variety of diseases, including malaria. In the work reported here, root bark and stem bark extracts of this tree, as well as compounds isolated from the extracts, have been investigated for activity in vitro against chloroquine-sensitive and chloroquine-resistant strains of Plasmodium falciparum. In addition, toxicity against nauplii of the brine shrimp Artemia salina has been studied. Dichloromethane extracts of the root bark and stem bark, and a methanol extract of the stem bark, showed anti-parasitic activity towards chloroquine-sensitive as well as chloroquine-resistant P. falciparum, with IC50 values between 1 and 10 µg/mL. Among the isolated compounds, bis-dihydrochelerythrinyl ether, buesgenine, chelerythrine, γ-fagarine, skimmianine, and pellitorine were the most active, with IC50 values of less than 5 µg/mL. The dichloromethane extracts were toxic to brine shrimp nauplii, with LC50 values of less than 1 µg/mL. Methanol extracts were much less toxic (LC50 between 50 and 100 µg/mL). Among the isolated substances, bis-dihydrochelethrinyl ether was the most toxic (LC50 ca. 2 µg/mL).

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Section: Resultssupporting

confidence: 92%

Section: Toxicity Against Artemia Salina Naupliimentioning

confidence: 99%

Anti-plasmodial Effects of Zanthoxylum zanthoxyloides

et al. 2019

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“…Chelidonine 300 heitzii stem bark. 72 Furthermore, dihydrocheleryhtrine (312) was isolated from Z. tingoassuiba 78 and decarine (313) was identified from Zanthoxylum myriacanthum var. pubescens bark.…”

Section: Naphthylisoquinoline Alkaloidsmentioning

confidence: 99%

“…Hence, the alkaloids induced antifeeding and larval lethality on L. dispar larvae 92. Heitziquinone (308) from Z. heitzii presented the weak or inactive toxicity against brine shrimp (Artemia salina) 72. Cis-and trans-protopinium (187, 188) from F. parviflora showed nematicidal activity against the southern rootknot nematode Meloidogyne incognita.…”

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confidence: 99%

Biologically active isoquinoline alkaloids covering 2014–2018

Shang

Yang

Morris‐Natschke

et al. 2020

Medicinal Research Reviews

146

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Isoquinoline alkaloids, an important class of N-based heterocyclic compounds, have attracted considerable attention from researchers worldwide since the early 19th century. Over the past 200 years, many compounds from this class were isolated, and most of them and their analogs possess various bioactivities. In this review, we survey the updated literature on bioactive alkaloids and highlight research achievements of this alkaloid class during the period of 2014-2018. We reviewed over 400 molecules with a broad range of bioactivities, including antitumor, antidiabetic and its complications, antibacterial, antifungal, antiviral, antiparasitic, insecticidal, anti-inflammatory, antioxidant, neuroprotective, and other activities. This review should provide new indications or directions for the discovery of new and better drugs from the original naturally occurring isoquinoline alkaloids.

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“…Previous investigations have reported the antimicrobial activities of the bark of Z. heitzii ; its fruits have also been reported to have beneficial effects against sickle cell diseases [ 15 ]. Chemical studies also had isolated and characterized a variety of active compounds from the bark of Z. heitzii [ 18 ]. Recently, meso-2,3-bis(3,4,5-trimethoxybenzyl)-1,4-butanediol and 4-acetoxy-2,3-bis(3,4,5-trimethoxybenzyl)-1-butanol, two alkaloids, and triterpenes were isolated from the bark of Z. heitzii and characterized [ 17 ].…”

Section: Introductionmentioning

confidence: 99%

Zanthoxylum heitzii Modulates Ferric Nitrilotriacetate‐Dependent Oxidative Alterations in Four Vital Organs: An In Vitro Organoprotective Model

Essogo

Moukette

Tankeu

et al. 2017

Evidence-Based Complementary and Alternative Medicine

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Ferric nitrilotriacetate (Fe-NTA) is a highly reactive compound used to induce degenerative disorders through oxidative stress (OS). Zanthoxylum heitzii (Z. heitzii) is a spice used as a medicinal plant to treat a variety of illnesses. This study investigated the ability of extracts from the leaves, fruits, roots, and barks of Z. Heitzii to inhibit Fe-NTA mediated oxidative damage in rats. The supernatant of rat liver homogenates was pretreated with the extracts for one hour before the induction of oxidative damage using a solution of Fe-NTA (400 mM). The activities of superoxide dismutase (SOD), catalase, and peroxidases were measured together with the marker of lipid peroxidation and the level of glutathione. The pretreated groups showed a significant increase in the activity of SOD, catalase, and peroxidases. The methanolic extract from the leaves of Z. heitzii (36.78 ± 3.30) and aqueous extract from the fruits (37.01 ± 2.52) showed the highest activities of SOD in the liver. The lowest concentration of MDA was found in the liver, and the glutathione was greater in the brain. Conclusively, these results suggest that Z. heitzii might be a chemoprotector which may be used in for prevention of distinct types of diseases induced by oxidative stress.

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A new benzophenanthridine alkaloid and other bioactive constituents from the stem bark of Zanthoxylum heitzii

Cited by 25 publications

References 18 publications

Anti-plasmodial Effects of Zanthoxylum zanthoxyloides

Anti-plasmodial Effects of Zanthoxylum zanthoxyloides

Biologically active isoquinoline alkaloids covering 2014–2018

Zanthoxylum heitzii Modulates Ferric Nitrilotriacetate‐Dependent Oxidative Alterations in Four Vital Organs: An In Vitro Organoprotective Model

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