Acetylated pseudoguaianolides from Parthenium hysterophorus and their cytotoxic activity

Das, Biswanath; Reddy, V. Krishna; Krishnaiah, Maddeboina; Sharma, Ashish; Kumar, K. Ravi; Rao, J. Venkateswara; Sridhar, V.

doi:10.1016/j.phytochem.2007.05.002

Cited by 37 publications

(26 citation statements)

References 11 publications

(10 reference statements)

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“…Presence of terpenoides, streroides, flavonoids, tannins and alkaloids in the ethylacetate and methanol elutes are in agreement with the findings of [24][25][26][27][28][29][30][31][32][33][34][35]. Gross allelopathic potential of P. hysterophorus, revealed from the seed germination bioassay.…”

Section: Discussionsupporting

confidence: 86%

Study of <i>Parthenium hysterophorus</i> L. Extracts (First Clean-Up Fractions) on Seed Germination Behaviour in Search of Bioactive Fractions for Preparation of Bioherbicide Formulations

Pati

Chowdhury

2015

ILNS

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Increase in productivity is directly related with increase pesticide consumption. So there is a strong desire to use "greener" chemistry to produce more toxicologically and environmentally benign pesticides and natural products. In this present study, a comparison was made to evaluate the phytotoxicity potential of first cleanup fractions obtained from sequentially extracted solvent (ethyl-acetate, methanol) extracts of Parthenium hysterophorus L. (aerial parts) in vitro through bench-top seed germination assay (Vigna radiata L.). One-way analysis of variance (ANOVA) followed by Duncan's multiple range test (DMRT) were done for statistical analysis of the data. The study reveals that germination, growth and vigour was significantly (P<0.05) reduced by ethyl-acetate and methanol fractions. A significant changes in soluble and insoluble sugar content, protein, amino acid content and cellular metabolic activity was aslo observed by 1F3, 1F4, 1F6, and 1F9 fractions. The present study concluded that phytotoxicity of four fractions (1F3, 1F4, 1F6, and 1F9) from ethylacetate and methanolic crude extracts of Parthenium hysterophorus could be exploited as potential bioherbicide for future weed management programme and the development of bioherbicide for commercial use.

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Section: Discussionsupporting

confidence: 86%

Study of <i>Parthenium hysterophorus</i> L. Extracts (First Clean-Up Fractions) on Seed Germination Behaviour in Search of Bioactive Fractions for Preparation of Bioherbicide Formulations

Pati

Chowdhury

2015

ILNS

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“…Another study shows that, isolated 8b-acetoxyparthenin from the aerial part, a new epoxy-sesquiterpenoid parthoxynol 18 and a highly oxygenated pseudoguaianolide 8b-acetoxyhysterone C, 19 from flower, two minor pseudoguaianolides parthenin-8b-isopentanoate and parthenin-8b-isopentenoate from whole plant of P. hysterophorus 20 Two new pseudoguaianolide type sesquiterpene lactones, named deacetyltetraneurin A (8) and hysterone E (9), along with scopoletin (10), 8b-hydroxycoronopilin, and conchasin A (11) were also isolated from flower 21,22 . One report shows that leaves of P. hysterophorus contained dihydroparthenin and 13-methoxydihydrocoronopilin 23 .…”

Section: Phytochemistrymentioning

confidence: 99%

“…Sesquiterpenoid, charminarone (16), the first seco-pseudoguaianolide, was isolated along with other well-known compounds from the whole plant of P. hysterophorus 26 . Along with above mentioned compounds ambrosin, flavonoids (quercelagetin 3, 7-dimethylether; 6 hydroxyl kaempferol 3-0) fumaric acid (17), p-hydroxybenzoin (18), vanillic acid (19), caffeic acid (20), p-courmaric acid (21), p-anisic acid (22), chlorogenic acid (23), ferulic acid (24), sitosterol and some unidentified alcohols were also isolated. The chemical compound of the oil of P. hysterophorus.…”

Section: Phytochemistrymentioning

confidence: 99%

Parthenium Hysterophorus. L. (Asteraceae) : A Boon or Curse? (A Review)

Joshi¹,

Bachheti²,

Sharma³

et al. 2016

Orient. J. Chem

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Parthenium hysterophorus (Linn.) is violent every where annual, herbivorous weed, commonly found in America but presently invaded in four continents. It shows hazardous effect on human health, livestock as well as it reduces the crop production due to its allelopathic effect. Partheniun with other constituents discussed are the cause behind the intimidating role of this weed. Inspite of these drawbacks the weed is traditionally known for the treatment of wounds, fever, ulcerated sores and malaria. It can also be used to increase the agricultural productivity and for the elimination of heavy metals from soil as well as from water to reduce pollution. The main aim of this review article is to summarise the main positive and negative effects of the Parthenium hysterophorus.

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“…General cytotoxicity of parthenin remains a concern, but its activity varies greatly among different cell lines, as illustrated by 50% inhibitory concentrations (IC 50 s) of 0.061 M and 594 M against Jurkat cells and HeLa cells, respectively (26). Less toxic, synthetic parthenin derivatives show promise when tested across a number of human cell lines (17,19,26). As mentioned above, parthenin belongs to a class of compounds (SQLs) that also includes artemisinin.…”

mentioning

confidence: 99%

“…Parthenin may act through a variety of mechanisms, including directly damaging DNA, inhibiting oxidative phosphorylation, inducing formation of nitric oxide, and promoting apoptotic signaling (18,19,(22)(23)(24)(25). General cytotoxicity of parthenin remains a concern, but its activity varies greatly among different cell lines, as illustrated by 50% inhibitory concentrations (IC 50 s) of 0.061 M and 594 M against Jurkat cells and HeLa cells, respectively (26). Less toxic, synthetic parthenin derivatives show promise when tested across a number of human cell lines (17,19,26).…”

mentioning

confidence: 99%

The Nonartemisinin Sesquiterpene Lactones Parthenin and Parthenolide Block Plasmodium falciparum Sexual Stage Transmission

Balaich

Mathias

Torto

et al. 2016

Antimicrob Agents Chemother

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f Parthenin and parthenolide are natural products that are closely related in structure to artemisinin, which is also a sesquiterpene lactone (SQL) and one of the most important antimalarial drugs available. Parthenin, like artemisinin, has an effect on Plasmodium blood stage development. We extended the evaluation of parthenin as a potential therapeutic for the transmissible stages of Plasmodium falciparum as it transitions between human and mosquito, with the aim of gaining potential mechanistic insight into the inhibitory activity of this compound. We posited that if parthenin targets different biological pathways in the parasite, this in turn could pave the way for the development of druggable compounds that could prevent the spread of artemisinin-resistant parasites. We examined parthenin's effect on male gamete activation and the ookinete-to-oocyst transition in the mosquito as well as on stage V gametocytes that are present in peripheral blood. Parthenin arrested parasite development for each of the stages tested. The broad inhibitory properties of parthenin on the evaluated parasite stages may suggest different mechanisms of action between parthenin and artemisinin. Parthenin's cytotoxicity notwithstanding, its demonstrated activity in this study suggests that structurally related SQLs with a better safety profile deserve further exploration. We used our battery of assays to test parthenolide, which has a more compelling safety profile. Parthenolide demonstrated activity nearly identical to that of parthenin against P. falciparum, highlighting its potential as a possible transmission-blocking drug scaffold. We discuss the context of the evidence with respect to the next steps toward expanding the current antimalarial arsenal.A n estimated 198 million cases of malaria and 584,000 deaths, mostly among young children, were reported worldwide in 2013 (1). However, as a result of concerted control efforts since 2000, including antimalarial drugs, mortality has declined by 47%, resulting in an estimated 4.3 million lives saved (1). Artemisinin, delivered with a partnered drug, is one of the fastest acting antimalarial therapies available (2, 3). However, antimalarial resistance in Plasmodium falciparum has been described recently in Southeast Asia (4). This discovery emphasizes the need for novel compounds that are effective against resistant strains, presumably because they act on the parasite differently from artemisinin. Artemisinin was originally isolated from Artemisia annua, or sweet wormwood, a member of the Asteraceae family. We hypothesized that natural product compounds derived from related family members might retain potent activities against Plasmodium while targeting different biological pathways.Parthenin is a sesquiterpene lactone (SQL) derived from Parthenium hysterophorus, which is an invasive, flowering annual weed in the Asteraceae family; it grows to 2 m in height, with small white flowers, and has spread throughout much of the world (5). P. hysterophorus causes millions of dollars in damag...

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Acetylated pseudoguaianolides from Parthenium hysterophorus and their cytotoxic activity

Cited by 37 publications

References 11 publications

Study of <i>Parthenium hysterophorus</i> L. Extracts (First Clean-Up Fractions) on Seed Germination Behaviour in Search of Bioactive Fractions for Preparation of Bioherbicide Formulations

Study of <i>Parthenium hysterophorus</i> L. Extracts (First Clean-Up Fractions) on Seed Germination Behaviour in Search of Bioactive Fractions for Preparation of Bioherbicide Formulations

Parthenium Hysterophorus. L. (Asteraceae) : A Boon or Curse? (A Review)

The Nonartemisinin Sesquiterpene Lactones Parthenin and Parthenolide Block Plasmodium falciparum Sexual Stage Transmission

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