Peroxy natural products

Casteel, Dee Ann

doi:10.1039/np9920900289

Cited by 152 publications

(91 citation statements)

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“…In the past several decades, natural peroxides have been isolated from a wide variety of plants, and marine organisms 1,2 . Extensive pharmacological screening performed on microorganisms and other species resulted in discovery of novel peroxides with antitumor, antibacterial, antimalarial, and antiviral agents 1,3 .…”

Section: Introductionmentioning

confidence: 99%

Ascaridole and Related Peroxides From the Genus Chenopodium

Dembitsky¹,

Shkrob²,

Hanŭs³

2008

Biomed Pap Med Fac Univ Palacky Olomouc Czech Repub

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Aim: Detection of monoterpenoid ascaridole and other terpenoids in the genus Chenopodium from the East Mediterranean.Method: Distribution of ascaridole in leaves of 13 species medicinal plant belonging to the genus Chenopodium was examined with the help of the GC-MS method.Results: cis-Ascaridole was found as a major peroxy monoterpenoid (up to 46.9 %) in the oil. Three minor isomers: cis-isoascaridole (1.1-6.4 %), trans-ascaridole (1-2 %), and trans-isoascaridole (1-2 %) were also detected. The biological activities and biosynthesis of ascaridole are further discussed. Conclusions:The results on Ascaridol and the major volatiles and semi-volatiles of wild species belonging to the genus Chenopodium provide important information on biologically active monoterpenoid compounds and volatile metabolites biosynthesized in wild medicinal plants growing in the East Mediterranean.

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Section: Introductionmentioning

confidence: 99%

Ascaridole and Related Peroxides From the Genus Chenopodium

Dembitsky¹,

Shkrob²,

Hanŭs³

2008

Biomed Pap Med Fac Univ Palacky Olomouc Czech Repub

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“…So far, a lot of peroxy compounds were isolated from natural products. The chemistry of mono-and polycyclic peroxides has attracted considerable recent attention since a significant number of peroxidic natural products with interesting pharmacological properties have been isolated [25,26]. In our experiment, NaBH 4 was used to reduce compound 1 to get the monomers, but all attempts were unsuccessful.…”

Section: Resultsmentioning

confidence: 98%

Inhibition of lipid peroxidation, cyclooxygenase enzyme and human tumor cell proliferation by compounds in herbal water

Liu

Mulabagal

Bowen‐Forbes

et al. 2009

Molecular Nutrition Food Res

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A powdered mixture of dried herbs, "Panamrutham", is sold in India for the preparation of "herbal drinking water". The hot water extract of this herbal mixture gave lipid peroxidation (LPO), cyclo-oxygenase (COX-1 and -2) enzyme and human tumor cell proliferation inhibitory activities between 25 and 250 microg/mL. The bioassay-guided purification of the water extract afforded a novel compound (1), along with phenolics (2, 4, 6, and 7) and sesquiterpenoids (3 and 5). The isolates were evaluated for LPO, COX-1 and -2 enzyme and human tumor cell proliferation inhibitory activities. At 25 microg/mL, compounds 1-7 inhibited LPO by 22-73% and COX-1 and -2 enzymes by 3-14% and 14-74%, respectively. Compounds 5 and 6 at 25 microg/mL showed growth inhibition of colon, gastric, lung, breast and central nervous system human tumor cell lines by 60 and 67, 43 and 60, 24 and 64, 34 and 65, 6 and 27%, respectively. Compounds 2, 4 and 7 displayed weak or moderate growth inhibition of colon, gastric and breast human tumor cell lines. This is the first report on the LPO inhibitory activities of compounds 1 and 3-7 and the COX and tumor cell proliferation inhibitory activities of compounds 1, 3-5 and 7.

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“…In the meantime, as much as 320 peroxides have been isolated from natural material (Casteel, 1992). They occur mainly as terpene derivatives, although cumarine, fatty acids and alkaloids peroxides derivatives have also been isolated.…”

Section: Introductionmentioning

confidence: 99%

“…This oil was utilized as anthelmintic and ascaridole was identified as responsible for its activity (Gessner, 1953;Hope, 1958). In the following decades, compounds with a similar structure were not isolated; peroxides were considered to be too unstable and ascaridole was thought to be an exception.In the meantime, as much as 320 peroxides have been isolated from natural material (Casteel, 1992). They occur mainly as terpene derivatives, although cumarine, fatty acids and alkaloids peroxides derivatives have also been isolated.…”

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confidence: 99%

“…Beside plants, many species of fungi and marine organisms produce metabolites containing a peroxide group. The peroxide function has been detected in different classes of natural compounds that are mentioned in Table I, based on the review published by Casteel (1992). The occurrence in vascular plant families according the literature published until 1999 is summarized by Table II. Many biological activities were described for the peroxides.…”

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confidence: 99%

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Screening of brazilian plants for the presence of peroxides

Schenkel¹,

Rüċker²,

Manns³

et al. 2002

Rev. Bras. Cienc. Farm.

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Uniterms:• Peroxides• Antimalarial activity• Asteraceae INTRODUCTIONThe occurrence of natural products which contain a peroxide group has been known since 1911, when ascaridole was isolated from the essential oil of Chenopodium ambrosioides (Chenopodiaceae). This oil was utilized as anthelmintic and ascaridole was identified as responsible for its activity (Gessner, 1953;Hope, 1958). In the following decades, compounds with a similar structure were not isolated; peroxides were considered to be too unstable and ascaridole was thought to be an exception.In the meantime, as much as 320 peroxides have been isolated from natural material (Casteel, 1992). They occur mainly as terpene derivatives, although cumarine, fatty acids and alkaloids peroxides derivatives have also been isolated. Beside plants, many species of fungi and marine organisms produce metabolites containing a peroxide group. The peroxide function has been detected in different classes of natural compounds that are mentioned in Table I, based on the review published by Casteel (1992). The occurrence in vascular plant families according the literature published until 1999 is summarized by Table II. Many biological activities were described for the peroxides. They show ichthyotoxic and antimicrobial activity, fungicide, anthelmintic and cytotoxic activity. At the moment, the most important activity exhibited by peroxides is the antimalarial activity (Vennerstrom, Easton, 1988;Rücker, 1994). The prevention and cure of malaria depends on a limited number of drugs. Resistance of the malaria parasites Plasmodium ssp. to drugs such as quinine (and more lately chloroquine) occurs with increasing frequency and emphasize the necessity to develop new agents for malaria chemotherapy (Kirby, 1996). Quinghaosu (artemisinin), a sesquiterpene isolated from Artemisia annua, is the best known plant derivative as an antimalarial drug after quinine (Klayman, 1985). Another sesquiterpene peroxide, named yingzhaosu, was isolated from Artabotrys uncinatus (Annonaceae) and also possesses a significant antimalarial activity. Both compounds contain an endoperoxid group, which is responsible for their activity (Klayman, 1985) and have opened a new chapter in the chemotherapy of malaria. The majority of drugs active against malaria are in fact derived from natural products or from structures suggested by natural products prototypes, but, as a source of novel drugs, plants remain largely understudied (Kirby, 1996). Falkenberg et al. 192 Herewith we report the screening for detection of peroxides in extracts from higher plants from the states of Rio Grande do Sul and Santa Catarina, Brazil, based on Huber & Fröhlke's chromatographic test. The screening was developed to select promising plants for detailed investigation, aiming the isolation and structure elucidation of new peroxides. Fresh plant material (10-20 g) was crushed and extracted with CH 2 Cl 2 or CHCl 3 (10-20 mL) previously tested for peroxides. The extraction procedures were performed at the same day of the plant c...

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Peroxy natural products

Cited by 152 publications

References 318 publications

Ascaridole and Related Peroxides From the Genus Chenopodium

Ascaridole and Related Peroxides From the Genus Chenopodium

Inhibition of lipid peroxidation, cyclooxygenase enzyme and human tumor cell proliferation by compounds in herbal water

Screening of brazilian plants for the presence of peroxides

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