Design and synthesis of spiro derivatives of parthenin as novel anti-cancer agents

Reddy, D. Mahendhar; Ahmed, Qazi Naveed; Sawant, Sanghapal D.; Bandey, Abid H.; Srinivas, Jada; Shankar, Mannepalli; Singh, Shashank; Verma, Monika; Chashoo, Gousia; Ak, Saxena; Mondhe, Dilip M.; Saxena, Ajit Kumar; Sethi, Vijay; Taneja, Subhash C.; Qazi, G. N.; Kumar, Halmuthur M. Sampath

doi:10.1016/j.ejmech.2011.04.030

Cited by 51 publications

(24 citation statements)

References 27 publications

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“…To overcome this problem, several spiro derivatives of parthenin have been synthesized and evaluated, of which some compounds exhibited improved cytotoxicity toward a small panel of human cancer cells [143]. In an in vivo study on non-inbred Swiss mice bearing EAT performed on parthenin ( 20 ) and its spiro derivative, 2t, (both suspended in 1% gum acacia, 10, 25, 50, 100 or 200 mg/kg, i.p., daily for nine days), significant tumor growth inhibition was observed for compound 2t at a dose of 100 mg/kg, whereas a 200 mg/kg dose of this substance induced mortality of all mice by the fourth day of the treatment.…”

Section: Analogues Of Thapsigargin Without Ester Groups Showing Pomentioning

confidence: 99%

“…In an in vivo study on non-inbred Swiss mice bearing EAT performed on parthenin ( 20 ) and its spiro derivative, 2t, (both suspended in 1% gum acacia, 10, 25, 50, 100 or 200 mg/kg, i.p., daily for nine days), significant tumor growth inhibition was observed for compound 2t at a dose of 100 mg/kg, whereas a 200 mg/kg dose of this substance induced mortality of all mice by the fourth day of the treatment. However, a high level of toxicity without significant antitumor activity was recorded with the parthenin ( 20 ) treatments, which caused mortality of all mice by the second and third day of treatment at 25 and 50 mg/kg doses, respectively, suggesting that compound 2t showed more potent antitumor activity and lower toxicity in mammalians than the parent compound [143]. Following this evidence, further modification of parthenin ( 20 ) produced compound P19 ( 21 ) (Scheme 14 ) [144], which showed cytotoxicity toward the HeLa human cervical carcinoma cell line and the HL-60 human myeloid leukemia cell line [145].…”

Section: Analogues Of Thapsigargin Without Ester Groups Showing Pomentioning

confidence: 99%

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Development of Anticancer Agents from Plant-Derived Sesquiterpene Lactones

Ren¹,

Yu²,

Kinghorn

2016

CMC

131

121

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Sesquiterpene lactones are of considerable interest due to their potent bioactivities, including cancer cell cytotoxicity and antineoplastic efficacy in in vivo studies. Among these compounds, artesunate, dimethylaminoparthenolide, and L12ADT peptide prodrug, a derivative of thapsigargin, are being evaluated in current cancer clinical or preclinical trials. Based on the structures of several antitumor sesquiterpene lactones, a number of analogues showing greater potency have been either isolated as natural products or partially synthesized, and some potential anticancer agents that have emerged from this group of lead compounds have been investigated extensively. The present review focuses on artemisinin, parthenolide, thapsigargin, and their naturally occurring or synthetic analogues showing potential anticancer activity. This provides an overview of the advances in the development of these types of sesquiterpene lactones as potential anticancer agents, including their structural characterization, synthesis and synthetic modification, and antitumor potential, with the mechanism of action and structure-activity relationships also discussed. It is hoped that this will be helpful in stimulating the further interest in developing sesquiterpene lactones and their derivatives as new anticancer agents.

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Section: Analogues Of Thapsigargin Without Ester Groups Showing Pomentioning

confidence: 99%

Section: Analogues Of Thapsigargin Without Ester Groups Showing Pomentioning

confidence: 99%

Development of Anticancer Agents from Plant-Derived Sesquiterpene Lactones

Ren¹,

Yu²,

Kinghorn

2016

CMC

131

121

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“…All parts of the plant are used in traditional medicine as bitter tonic, febrifuge, emmenagogue, antidysenteric and treatment of many infectious and degenerative diseases (Kumar et al, 2013;Reddy et al, 2011).…”

Section: Parthenium Hysterophorus Lmentioning

confidence: 99%

Asteraceae species with most prominent bioactivity and their potential applications: A review

Bessada

Barreira

Oliveira

2015

Industrial Crops and Products

117

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a b s t r a c tOxidative stress has a relevant part in the etiology of several diseases and metabolic disorders, being reasonable to expect that antioxidant compounds might have beneficial effects in health maintenance or disease prevention. Antioxidant compounds might be isolated and characterized from different plant constituents, such as roots, stems, bark, leaves, flowers, fruits and seeds, using proper extraction methods. The Asteraceae family has a worldwide distribution, with special relevance in the Mediterranean, Eastern Europe and Asia Minor, being acknowledged about 25 000 species integrated in approximately 1000 genera. In addition to the anti-inflammatory, analgesic and antipyretic potential of some of these species, their high antioxidant power, as proven in research works with extracts (of roots, stems, bark, leaves, flowers, fruits and seeds) should be highlighted. Herein, the Asteraceae species with highest potential as sources of natural antioxidants with potential uses in medicine and in pharmaceutical, cosmetic and food industries were identified. The species were selected based on their botanical representativeness, being identified the 9 most relevant species: Achillea millefolium L., Acmella oleraceae Murr., Artemisia absinthium L., Bidens pilosa L., Carthamus tinctorius L., Inula crithmoides L., Matricaria recutita L., Otanthus maritimus L. and Parthenium hysterophorus L.. With the obtained information, it could be concluded that the bioactivity of the selected Asteraceae species lacks a complete characterization, constituting a research scope with great potential to be exploited in the development of dietary supplements, bioactive food ingredients or pharmaceutical based products with application in food industry, dermocosmetics or medicine.

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“…In Maharashtra and Gujarat (India) the plant is used in the treatment of diabetes mellitus [13]. The plant has also been reported to have antibacterial [14] and anti tumor activity [15]. Therefore, the aim of present study was to evaluate chemical composition, assessment of antioxidant and bio-membrane protective activities of P. hysterophorus flower and root extracts.…”

Section: Introductionmentioning

confidence: 99%

Antioxidant mediated protective effect of Parthenium hysterophorus against oxidative damage using in vitro models

Kumar

Mishra

Pandey

2013

BMC Complement Altern Med

162

102

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BackgroundParthenium hysterophorus L. (Asteraceae) is a common weed occurring throughout the globe. In traditional medicine its decoction has been used for treatment of many infectious and degenerative diseases. This work was therefore designed to assess the phytochemical constitution of P. hysterophorus flower and root extracts and to evaluate their reducing power, radical scavenging activity as well as protective efficacy against membrane lipid damage.MethodsDried flower and root samples were sequentially extracted with non-polar and polar solvents using Soxhlet apparatus. The phytochemical screening was done using standard chemical methods and thin layer chromatography. Total phenolic content was determined spectrophotometrically. Reducing power and hydroxyl radical scavenging activity assays were used to measure antioxidant activity. Protection against membrane damage was evaluated by inhibition of lipid peroxidation (TBARS assay) in rat kidney homogenate.ResultsFlavonoids, terpenoids, alkaloids and cardiac glycosides were present in all the extract. The total phenol contents in flower and root extracts were found to be in the range 86.69-320.17 mg propyl gallate equivalent (PGE)/g and 55.47-253.84 mg PGE/g, respectively. Comparatively better reducing power was observed in hexane fractions of flower (0.405) and root (0.282). Benzene extract of flower and ethyl acetate fraction of root accounted for appreciable hydroxyl radical scavenging activity (75-77%). Maximum protection against membrane lipid peroxidative damage among flower and root extracts was provided by ethanol (55.26%) and ethyl acetate (48.95%) fractions, respectively. Total phenolic content showed positive correlations with reducing power and lipid peroxidation inhibition (LPOI) % in floral extracts as well as with hydroxyl radical scavenging activity and LPOI % in root extracts.ConclusionStudy established that phytochemicals present in P. hysterophorus extracts have considerable antioxidant potential as well as lipo-protective activity against membrane damage.

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Design and synthesis of spiro derivatives of parthenin as novel anti-cancer agents

Cited by 51 publications

References 27 publications

Development of Anticancer Agents from Plant-Derived Sesquiterpene Lactones

Development of Anticancer Agents from Plant-Derived Sesquiterpene Lactones

Asteraceae species with most prominent bioactivity and their potential applications: A review

Antioxidant mediated protective effect of Parthenium hysterophorus against oxidative damage using in vitro models

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