Alkaloids of Boehmeria cylindrica (family Urticaceae): Identification of a cytotoxic agent, highly active against Eagle's 9KB carcinoma of the nasopharynx in cell culture, as crytopleurine

Farnsworth, N. R.; Hart, NK; Johns, SR; Lamberton, JA; Messmer, W M

doi:10.1071/ch9691805

Cited by 26 publications

(9 citation statements)

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“…Despite the traditional usage, there is only one study aiming at the investigation of the pharmacological potential of B. caudata that describes the cytotoxic activity of B. caudata stem wood ethanolic extract upon human epidermoid carcinoma of the nasopharynx [8]. Considering the Boehmeria genus, there is evidence of anti-inflammatory and antitumor effects in addition to the presence of phenanthroquinolizidine alkaloids, such as cryptopleurine, in some extracts [9][10][11][12][13][14]. Therefore, the present study prompted the in vitro and in vivo evaluation of anti-inflammatory and antitumor effects of the ethanolic extract of B. caudata aerial parts.…”

Section: Introductionmentioning

confidence: 99%

An Ethanolic Extract of Boehmeria caudata Aerial Parts Displays Anti-inflammatory and Anti-tumor Activities

Paiva

Nonato

Ruiz

et al. 2020

PMIO

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The tumor microenvironment presents several therapeutic targets, with inflammation being one of them. In search of new drugs, plants have shown to be an effective source of potent anti-inflammatory and anticancer agents. This study aimed to evaluate the antitumoral and inflammatory activities of Boehmeria caudata aerial parts extract. Bioguided in vitro antiproliferative screening showed that phenanthroquinolizidine obtained from the aerial B. caudata ethanolic extract had a straight relationship with activity. Moreover, the orally administered ethanolic extract reduced Ehrlich solid tumor growth and displayed an anti-inflammatory effect in both evaluated experimental models (carrageenan-induced paw edema and croton oil-induced ear edema). These results suggest that the antitumor activity of the ethanolic extract could be explained by antiproliferative effects associated with anti-inflammatory action.

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Section: Introductionmentioning

confidence: 99%

An Ethanolic Extract of Boehmeria caudata Aerial Parts Displays Anti-inflammatory and Anti-tumor Activities

Paiva

Nonato

Ruiz

et al. 2020

PMIO

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“…The residue was washed with ethanol (10 mL) and ether (10 mL) to give compounds 5-8. General synthetic procedure for compounds [11][12][13][14][15][16][17][18][19][20][21][22][23] The solution of compound 1 (1 mmol) and corresponding acid (1.1 mmol) in CH 2 Cl 2 (30 mL) and ethanol (30 mL) was refluxed for 6 h under N 2 and then concentrated in vacuo. The residue was washed with ethanol (10 mL) to give compounds 11-23.…”

Section: 367-tetrahydroxyphenanthroquinolizidine (4)mentioning

confidence: 99%

Design, Synthesis, Anti‐Tobacco Mosaic Virus (TMV) Activity, and SARs of 7‐Methoxycryptopleurine Derivatives

et al. 2014

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A series of 7-methoxycryptopleurine derivatives 2-23 were prepared and evaluated for their antiviral activity against tobacco mosaic virus (TMV) for the first time. The bioassay results showed that most of these compounds exhibited excellent in vivo anti-TMV activity, of which 7-methoxycryptopleurine salt derivatives 16, 19, and 23 displayed significantly higher activity than 7-methoxycryptopleurine (1) and commercial ribavirin and ningnanmycin. Salification, the most commonly employed method for modifying physical-chemical properties, did significantly increase antiviral activity, and different salt forms displayed different antiviral effect. This study provides fundamental support for development and optimization of phenanthroquinolizidine alkaloids as potential inhibitors of plant virus.

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“…Synthesis of 6-Cyclopropylmethoxy-2,3dimethoxyphenanthro[9,10-b]quinolizidine (17) Compound 17 was synthesized from 42 (3 mmol) by using a similar procedure for the synthesis of alkaloids 10-14, white powder (0.87 g, 80%).…”

Section: Synthesis Of 2-[(3-cyclopropylmethoxy-67dimethoxyphenanthrementioning

confidence: 99%

“…Phenanthroquinolizidine alkaloids are a small group of alkaloids existing in the Lauraceae, Vitaceae and Urticaceae family of plants. Only five of these alkaloids ((R)-cryptopleurine (2), (R)-boehmeriasin A (5), boehmeriasin B (18), cryptopleuridine and (14aR,15R)-15-hydroxycryptopleurine (19), Figure 1) have been isolated by now [15][16][17][18]. It has been reported that these alkaloids possess unique and interesting biological properties including vesicant [15], antimicrobial [19], antiviral [20,21] and anti-tumor [22][23][24] activities.…”

Section: Introductionmentioning

confidence: 99%

First Discovery and Stucture-Activity Relationship Study of Phenanthroquinolizidines as Novel Antiviral Agents against Tobacco Mosaic Virus (TMV)

et al. 2012

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A series of phenanthroquinolizidine alkaloids 1–24 were prepared and first evaluated for their antiviral activity against tobacco mosaic virus (TMV). The bioassay results showed that most of these compounds exhibited good to excellent in vivo anti-TMV activity, of which compounds 1, 2, 15 and 16 displayed significantly higher activity than (R)-antofine and commercial Ningnanmycin at the same test condition. The substituents on the phenanthrene moiety play an important role for maintaining high in vivo antiviral activity. The introduction of 6-hydroxyl, which is proposed to interact with TMV RNA, did increased anti-TMV activity. The 14aR-configuration was confirmed to be the preferred antiviral configuration for phenanthroquinolizidine alkaloids. Introduction of hydroxy group at 15-position of phenanthroquinolizidine alkaloids increased activity for S-configuration but decreased activity for R-configuration. Present study provides fundamental support for development and optimization of phenanthroquinolizidine alkaloids as potential inhibitors of plant virus.

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Alkaloids of Boehmeria cylindrica (family Urticaceae): Identification of a cytotoxic agent, highly active against Eagle's 9KB carcinoma of the nasopharynx in cell culture, as crytopleurine

Cited by 26 publications

References 0 publications

An Ethanolic Extract of Boehmeria caudata Aerial Parts Displays Anti-inflammatory and Anti-tumor Activities

An Ethanolic Extract of Boehmeria caudata Aerial Parts Displays Anti-inflammatory and Anti-tumor Activities

Design, Synthesis, Anti‐Tobacco Mosaic Virus (TMV) Activity, and SARs of 7‐Methoxycryptopleurine Derivatives

First Discovery and Stucture-Activity Relationship Study of Phenanthroquinolizidines as Novel Antiviral Agents against Tobacco Mosaic Virus (TMV)

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