Two Toxic Kaurene Glycosides from the Burrs of Xanthium pungens

MacLeod, John K.; Moeller, P.; Franke, Fritz P.

doi:10.1021/np50068a025

Cited by 23 publications

(13 citation statements)

References 4 publications

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“…The anti-nociceptive activities shown by MEXS in these models indicate that it may possess peripherally and centrally mediated anti-nociceptive properties. Although the toxicity of Xanthium strumarium has been reported to the animals which might be either due to a mixture of unidentified alkaloids present in the aerial parts of the plant 40) or due to poisonous water soluble toxic kaurene glycosides, 41) we did not find any toxic syndromes based on the body weight change during MEXS treatment. Further studies to fractionate the toxic and anti-inflammatory fractions are, therefore, required to be undertaken.…”

Section: Discussioncontrasting

confidence: 71%

Methanol Extract of <i>Xanthium strumarium</i> L. Possesses Anti-inflammatory and Anti-nociceptive Activities

Kim

Park

Won

et al. 2005

Biological & Pharmaceutical Bulletin

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Nitric oxides (NOs) and prostaglandins (PGs) are wellknown proinflammatory mediators in the pathogenesis of inflammation.1) NO plays a major role in the regulation of vascular tone, neurotransmission, platelet aggregation, and other homeostatic mechanisms.2) NO is synthesized by the three isoforms of nitric oxide synthase (NOS); neuronal NOS (nNOS), endothelial NOS (eNOS), and inducible NOS (iNOS). Although nNOS and eNOS are constitutively expressed, iNOS is expressed in response to interferon-g, lipopolysccharide (LPS), and a variety of proinflammatory cytokines. [3][4][5] The proinflammatory properties of NO are attributed to the excessive production of NO by iNOS and are influenced by factors such as interactions between NO and other oxidants (e.g., peroxynitrite formation with the superoxide anion), the duration of NO production, and substrate availability. A number of studies have shown that the chronic phase of inflammation in particular, is correlated with an increase in iNOS activity. 6) Moreover, elevated levels of NO have been detected in a variety of pathophysiological processes, including circulatory shock, inflammation, and cancer. 5,7,8) Cyclooxygenase (COX) is involved in the inflammatory process and catalyzes the rate-limiting step in the synthesis of prostaglandins from arachidonic acid. COX exists in two isoforms; COX-1 and COX-2. 9) Like nNOS and eNOS, COX-1 is expressed constitutively in most tissues and appears to be responsible for maintaining normal physiological functions. On the other hand, COX-2 is detected in only certain types of tissues and is induced transiently by growth factors, proinflammatory cytokines, tumor promoters, and bacterial toxins. 10,11) LPS is a major inflammatory molecule that triggers the production of proinflammatory cytokines such as TNF-a in various cell types.12,13) TNF-a plays a key role in the induction and perpetuation of inflammation in autoimmune reactions by activating T cells and macrophages, and by up-regulating other proinflammatory cytokines and endothelial adhesion molecules, such as intercellular adhesion molecule 1 and vascular cell adhesion molecule 1, which enhance the recruitment of leukocytes to sites of inflammation. 14)Like a TNF-a, LPS is known to activate transcription factors such as nuclear factor-kappa B (NF-kB)/Rel, activator protein (AP)-1, NF-IL6 and CREB/ATF. These nuclear factors are important for the expressions of numerous genes, which include IL-1b in macrophages. 15,16) Transcription factors belonging to the NF-kB family regulate a range of genes that mediate inflammation and cell survival.17) NF-kB exists in most cells as homodimeric or heterodimeric complexes containing p50 and p65 subunits, and remains inactive in the cytoplasm in association with the NF-kB inhibitory protein Ik B. Moreover, the activation of NF-kB is tightly controlled by a series of inhibitory proteins (IkB-a, IkB-b, and IkB-e) that sequester the NF-kB complex in the cytoplasm and prevent it from binding to nuclear DNA. The pathway of NF-kB induction in res...

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Section: Discussioncontrasting

confidence: 71%

Methanol Extract of <i>Xanthium strumarium</i> L. Possesses Anti-inflammatory and Anti-nociceptive Activities

Kim

Park

Won

et al. 2005

Biological & Pharmaceutical Bulletin

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“…Xanthium is defined as a toxic herb in Chinese Pharmacopoeia. The main toxic compound isolated from this plant has been identified as carboxyatractyloside, which is a kaurene glycoside (Macleod et al 1990). Thus, the use of this plant required special attention as it can cause toxicity.…”

Section: Resultsmentioning

confidence: 99%

Antiplasmodial activity of Xanthium strumarium against Plasmodium berghei-infected BALB/c mice

2011

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The present work was undertaken to evaluate the antiplasmodial activity of ethanolic leaves extract of traditional medicinal plant Xanthium strumarium in Plasmodium berghei-infected BALB/c mice along with phytochemical screening and acute toxicity test to support its traditional medicinal use as a malaria remedy. The ethanolic leaves extract of X. strumarium (ELEXS) 150, 250, 350 and 500 mg/kg/day demonstrated dose-dependent chemosuppression during early and established infection long with significant (p < 0.001) repository activity. The oral administration of 500 mg/kg/day concentration showed a maximum of 88.6% chemosuppression during early infection, which was more than that of the standard drug chloroquine (5 mg/kg/day) with 88.3% chemosuppression. However, 60% mortality has been found in this group. The LD(50) of ELEXS was found to be 1.5 g/kg/mouse. The administration of 350 mg/kg/day concentration of extract have been found to exert 90.40% chemosuppression during repository infection, which was well comparable to standard drug pyrimethamine (1.2 mg/kg/day) exerting 92.91% chemosuppression. The extract has been found to enhance mean survival time of mice from 21 to 26 days with 250 and 350 mg/kg/day concentrations, while 150 mg/kg/day concentration has been found to sustain all the mice up to 29 days which was similar to the employed standard drug chloroquine (5 mg/kg/day). All these findings support the ethanopharmacological use of X. strumarium as malarial remedy and indicate the potential of plant for active antiplasmodial components.

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“…The chemistry of this genus is quite homogenous, with sesquiterpene lactones being detected in all cases (3)(4)(5)(6). The occurrence of some toxic kaurene glycosides has been reported (7)(8). The composition of oil of X. pennsylvanicum has been reported earlier (9).…”

Section: Previous Workmentioning

confidence: 85%

Composition of the Essential Oil ofXanthium brasilicumVellozo from Iran

Habibi

Laleh

Masoudi

et al. 2004

Journal of Essential Oil Research

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Two Toxic Kaurene Glycosides from the Burrs of Xanthium pungens

Abstract: Two H2O-soluble toxic kaurene glycosides 3 and 4 responsible in part for the poisonous properties of the burr of Xanthium pungens have been isolated and identified. The structures of the compounds were elucidated using high resolution 2D nmr and mass spectral techniques.

Cited by 23 publications

References 4 publications

Methanol Extract of <i>Xanthium strumarium</i> L. Possesses Anti-inflammatory and Anti-nociceptive Activities

Methanol Extract of <i>Xanthium strumarium</i> L. Possesses Anti-inflammatory and Anti-nociceptive Activities

Antiplasmodial activity of Xanthium strumarium against Plasmodium berghei-infected BALB/c mice

Composition of the Essential Oil ofXanthium brasilicumVellozo from Iran

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