Naturally Occurring Aristolactams, Aristolochic Acids and Dioxoaporphines and Their Biological Activities

Kumar, Vineet; Poonam, Poonam; Prasad, Ashok K.; Parmar, Virinder S.

doi:10.1002/chin.200411269

Cited by 7 publications

(8 citation statements)

References 1 publication

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“…34 Importantly, all species of Aristolochia contain aristolochic acid. 35 Nortier (Brussels, Belgium) provided a clinical and epidemiologic update to SPECIAL ARTICLE www.jasn.org her original case study report, based on 112 patients with a diagnosis of Chinese herb nephropathy, 53 with renal failure. Among the latter, removal of the native kidneys and ureters revealed a high prevalence (Ͼ40%) of urothelial cancer.…”

Section: Endemic (Balkan) Nephropathy ‫؍‬ Chinese Herbal Nephropathy mentioning

confidence: 99%

Role of Environmental Toxins in Endemic (Balkan) Nephropathy

Grollman¹,

Jelaković²

2007

Journal of the American Society of Nephrology

137

100

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Section: Endemic (Balkan) Nephropathy ‫؍‬ Chinese Herbal Nephropathy mentioning

confidence: 99%

Role of Environmental Toxins in Endemic (Balkan) Nephropathy

Grollman¹,

Jelaković²

2007

Journal of the American Society of Nephrology

137

100

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“…(Benzo-fused) oxindoles (indolin-2-ones) are important structural motifs frequently found in pharmaceuticals, natural products and biologically active molecules (for example, antitumor, antibacterial, insecticidal and anthelmintic properties), and are also versatile building blocks for the preparation of structurally complex compounds [21][22][23][24][25] . Therefore, the development of new strategies for the facile synthesis of the indolin-2-one scaffolds from easily available starting materials has been an active research area [26][27][28][29] .…”

mentioning

confidence: 99%

Unexpected regioselective carbon–hydrogen bond activation/cyclization of indolyl aldehydes or ketones with alkynes to benzo-fused oxindoles

Liu

Song

et al. 2014

Nat Commun

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Rhodium-catalyzed carbon-hydrogen bond activation has attracted great interest in the construction of carbon-carbon and carbon-heteroatom bonds. In recent years, transition metal-mediated oxygen transposition through a 'dehydration-rehydration' process has been considered as a promising strategy towards oxygen-functionalized compounds. Here we describe an unexpected rhodium-catalyzed regioselective carbon-hydrogen bond activation/ cyclization of easily available indolyl aldehydes or ketones with alkynes to afford benzo-fused oxindoles, involving the sequential carbonyl-assisted carbon-hydrogen activation of the indole ring at the 4-position, [4 þ 2] cyclization, aromatization via dehydration, nucleophilic addition of water to iminium and oxidation. Isotopic labelling experiments disclose the occurrence of apparent oxygen transposition via dehydration-rehydration from the indolyl-3-carbonyl group to the 2-position of pyrrole to forge a new carbonyl bond. The tandem reaction has been used as the key step for the concise synthesis of priolines, a type of alkaloid isolated from the roots of Salvia prionitis.

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“…AA refers to a mixture of structurally related nitrophenanthrene carboxylic acids whose major constituents include 8-methoxy-6-nitrophenanthro-(3,4-D)-1,3-dioxolo-5-carboxylic acid (aristolochic acid I, AA-I) and its 8-demethoxylated form (aristolochic acid II, AA-II) (Kumar et al, 2003). Despite the global use of AA in herbal remedies, only limited data are available regarding the metabolic fate of AA-I and AA-II in experimental animals and humans (Krumbiegel et al, 1987).…”

mentioning

confidence: 99%

Selective Toxicity of Aristolochic Acids I and II

Shibutani

Dong²,

Suzuki³

et al. 2007

Drug Metab Dispos

138

124

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ABSTRACT:Ingestion of herbal remedies containing aristolochic acids (AAs) is associated with the development of a syndrome, designated aristolochic acid nephropathy (AAN), which is characterized by chronic renal failure, tubulointerstitial fibrosis, and urothelial cancer. To distinguish the component(s) of AA responsible for these varied toxic effects, we administered 2.5 mg/kg/day of AA-I or AA-II for 9 days, either i.p. or p.o., to male C3H/He mice. Tissues were then collected and subjected to biochemical and histopathologic examination. Genotoxicity was assessed by determining quantitatively the level of aristolactam-DNA adducts in various tissues using 32 P-postlabeling/polyacrylamide gel electrophoresis and an internal standard. In the primary target tissues, represented by the renal cortex, medulla, and bladder, we found similar levels of DNA adducts derived from AA-I and AA-II. However, in nontarget tissues, the liver, stomach, intestine, and lung, the levels of aristolactam-DNA adducts derived from AA-I were significantly higher than those derived from AA-II. Histopathologic analysis revealed tubular cell necrosis and interstitial fibrosis in the renal cortex of AA-I-treated mice but only minimal changes in the renal cortex of mice treated with AA-II. We conclude that AA-I and AA-II have similar genotoxic and carcinogenic potential, and, although both compounds are cytotoxic, AA-I is solely responsible for the nephrotoxicity associated with AAN.

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Naturally Occurring Aristolactams, Aristolochic Acids and Dioxoaporphines and Their Biological Activities

Abstract: For Abstract see ChemInform Abstract in Full Text.

Cited by 7 publications

References 1 publication

Role of Environmental Toxins in Endemic (Balkan) Nephropathy

Role of Environmental Toxins in Endemic (Balkan) Nephropathy

Unexpected regioselective carbon–hydrogen bond activation/cyclization of indolyl aldehydes or ketones with alkynes to benzo-fused oxindoles

Selective Toxicity of Aristolochic Acids I and II

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