365. An examination of the rutaceae of Hong Kong. Part II. The alkaloids, nitidine and oxynitidine, from Zanthoxylum nitidum

Arthur, H. R.; Hui, W. H.; Ng, Y. L.

doi:10.1039/jr9590001840

Cited by 64 publications

(25 citation statements)

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“…Antiproliferative properties of both groups of compounds have already been reported (Creasy, 1979;Simeon et al, 1989), and studies on the action of benzophenanthridine alkaloids against the growth of HaCaT cells revealed potent inhibitory activity (Vavrečková et al, 1996). Thus, chelerythrine chloride, which has been isolated from certain Zanthoxylum species such as Z. simulans (Arthur et al, 1959;Fang et al, 1993;Ko et al, 1990), was used as a reference compound and inhibited the growth of HaCaT cells with an IC 50 value of 1.23 mg/mL.…”

Section: Resultsmentioning

confidence: 99%

Inhibition of keratinocyte growth by different NepaleseZanthoxylum species

Kumar

Müller

1999

Phytother. Res.

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A total of 11 methanol extracts obtained from four different Nepalese Zanthoxylum species were screened for their antiproliferative activity against the growth of human keratinocytes (HaCaT cells). The extract obtained from Z. armatum barks was highly active with an IC50 value of 11 µg/mL. Also, the extracts obtained from Z. oxyphyllum barks and roots with IC50 values of 53 and 57 µg/mL, respectively, showed potent activity. Their antiproliferative activity was not due to cytotoxic effects on cell membranes, as documented by the activity of lactate dehydrogenase released from the cytoplasm of keratinocytes, which did not exceed that of the control value. Rather, they also protected against radical‐induced damage to model membranes stimulated with 2,2′‐azo‐bis(2‐amidinopropane) dihydrochloride. Copyright © 1999 John Wiley & Sons, Ltd.

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Section: Resultsmentioning

confidence: 99%

Inhibition of keratinocyte growth by different NepaleseZanthoxylum species

Kumar

Müller

1999

Phytother. Res.

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“…The latter had been isolated from Zanthoxylum avicennae root bark, Broussonetia papyrifera fruits, and Zanthoxylum nitidum root . Oxynitidine ( 9 d ) possess potent inhibitory activity toward the hepatitis B virus and had been isolated from various species such as Zanthoxylum rhoifolium , Zanthoxylum nitidum root, and Fagara macrophylla bark,Report suggests that, oxysanguinarine ( 9 a ), isolated from the Ranunculaceae (seeds of Coptis), used as an important drug constituents in China and Japan.…”

Section: Isolation and Biological Profiles Of Benzo[c]‐ Phenanthridinmentioning

confidence: 99%

Biosynthetic Relationships and Total Syntheses of Naturally Occurring Benzo[c]Phenanthridine Alkaloids

et al. 2019

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Benzo[c]phenanthridine alkaloids sharing a tetracyclic structural motif, are an important class of nitrogencontaining small molecules and are used for the treatment of a number of diseases. This review presents a comprehensive survey of the occurrence, chemistry, biochemistry, and biological activity of benzophenanthridine alkaloids. Synthetic approaches to a number of benzo[c]phenanthridine are disclosed in this Minireview. Biosynthetic Relationship of Tetrahydroisoquinoline and Benzo[c]phenanthridine AlkaloidsA plausible biogenetic connection between tetrahydroisoquinoline and benzo[c]phenanthridine alkaloids is shown in Scheme 1. Protopine (3 a) can undergo a demethylation followed by reductive amination to generate tetrahydroisoquinoline alkaloid, stylopine (2 a). The latter can further undergo an [a] Dr. oxidative CÀ N bond cleavage leading to intermediate aldehyde 4 a, which can form a new CÀ C bond (see, 4 c) assisted by in-situ prepared enamine. An elimination followed by oxidation leads to the synthesis of norsanguinarine (1 a).

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“…The pyranoquinoline alkaloid Zanthodioline (2) was previously isolated from Zanthoxylum simulans [2]. The benzophenanthridine alkaloids fargaridine (5) and oxynitidine (7) have been reported respectively from Zanthoxylum rhoifolium [3] and Zanthoxylum nitidum [4]. The benzophenanthridine alkaloids are the most commonly found in the genus [5].…”

Section: Chemotaxonomic Significancementioning

confidence: 99%

Quinolone Alkaloids Along with Other Constituents from Zanthoxylum rhetsa and their Chemotaxonomic Significance

Tuz-Zohora¹,

Muhit²,

Hasan³

et al. 2018

Rec.Nat.Prod.

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A total of eight compounds were isolated from the petroleum ether and chloroform extracts of the root bark of Zanthoxylum rhetsa (Roxb.) (D.C). These are a coumarin xanthyletin (1), five quinolone alkaloids zanthodioline (2), arnottianamide (3), skimmianine (4), fagaridine (5), oxynitidine (7), a lignan pluviatilol (6), and a triterpene lupeol (8) were identified. Structures of the isolates were characterized by extensive 1D and 2D NMR analyses and by comparing their spectral data with the published values. The compounds, zanthodioline (2), oxynitidine (7), fagaridine (5), and pluviatilol (6) are the first record from this plant.

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365. An examination of the rutaceae of Hong Kong. Part II. The alkaloids, nitidine and oxynitidine, from Zanthoxylum nitidum

Cited by 64 publications

References 0 publications

Inhibition of keratinocyte growth by different NepaleseZanthoxylum species

Inhibition of keratinocyte growth by different NepaleseZanthoxylum species

Biosynthetic Relationships and Total Syntheses of Naturally Occurring Benzo[c]Phenanthridine Alkaloids

Quinolone Alkaloids Along with Other Constituents from Zanthoxylum rhetsa and their Chemotaxonomic Significance

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