Synthesis of melampolides and cis,cis-germacranolides as natural herbicide models

Macías, Francisco A.; Velasco, Raul F.; Álvarez, José Ángel Pérez; Castellano, Diego; Galindo, Juan C. G.

doi:10.1016/j.tet.2004.06.128

Cited by 20 publications

(10 citation statements)

References 29 publications

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“…The activities of these compounds have been related to the presence of the α-methylene-γ-lactone moiety, the presence of an oxygenated group (mainly an angelate ester) at C-8, and/or the different special arrangements that the molecule can adopt. 38 It seems that the accessibility of groups that can be alkylated plays an important role in the activity of these compounds. Moreover, these compounds have shown a wide spectrum of activities: allelopathic, deterrent, cytotoxic, bacteriacidal, fungicicidal, etc.…”

Section: Journal Of Agricultural and Food Chemistrymentioning

confidence: 99%

Isolation of Bioactive Compounds from Sunflower Leaves (Helianthus annuusL.) Extracted with Supercritical Carbon Dioxide

Marsni

Torres

Varela

et al. 2015

J. Agric. Food Chem.

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ABSTRACT:The work described herein is a continuation of our initial studies on the supercritical fluid extraction (SFE) with CO 2 of bioactive substances from Helianthus annuus L. var. Arianna. The selected SFE extract showed high activity in the wheat coleoptile bioassay, in Petri dish phytotoxicity bioassays, and in the hydroponic culture of tomato seeds. Chromatographic fractionations of the extracts and a spectroscopic analysis of the isolated compounds showed 52 substances belonging to 10 different chemical classes, which were mainly sesquiterpene lactones, diterpenes, and flavonoids. Heliannuol M (31), helivypolides K and L (36, 37), and helieudesmanolide B (38) are described for the first time in the literature. Metabolites have been tested in the etiolated wheat coleoptile bioassay with good results in a noteworthy effect on germination. The most active compounds were also tested on tomato seeds, heliannuol A (30) and leptocarpin (45) being the most active, with values similar to those of the commercial herbicide.

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Section: Journal Of Agricultural and Food Chemistrymentioning

confidence: 99%

Isolation of Bioactive Compounds from Sunflower Leaves (Helianthus annuusL.) Extracted with Supercritical Carbon Dioxide

Marsni

Torres

Varela

et al. 2015

J. Agric. Food Chem.

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“…Sesquiterpene lactones are known to possess allelopathic activities against many plants (Baruah et al 1994;Dayan et al 1999;Macías et al 1999Macías et al , 2004Vyvyan 2002). However, few studies have reported the phytotoxic effects of sesquiterpene lactones against economic weeds (Batish et al 1997(Batish et al , 2002Pandey 1996).…”

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confidence: 99%

Herbicidal Activity of Three Sesquiterpene Lactones on Wild Oat (Avena fatua) and Their Possible Mode of Action

2009

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Inhibitory effects of two sesquiterpene lactones, costunolide and parthenolide, isolated from dichloromethane extract of the stem bark of southern magnolia and a parthenolide derivative, 1,10-epoxyparthenolide, were evaluated on germination and seedling growth of wild oat. The sesquiterpene lactones effected a significant reduction of seed germination, particularly at the highest concentrations of 200, 400, and 600 mg L 21 , with costunolide being the most active one. Furthermore, the three sesquiterpenes strongly inhibited root and shoot growth of the weed. However, the inhibition of root growth by all compounds was greater than that of shoot growth. Parthenolide inhibited growth of both root and shoot more strongly than the other compounds and a reference herbicide imazamethabenz. At a concentration of 100 mg L 21 , parthenolide caused 87 and 41% growth inhibition of root and shoot, respectively. Parthenolide was tested for its effect on acetolactate synthase (ALS) activity. The compound inhibited the enzyme in a concentration-dependent manner, with 50% inhibition of 51.44 mM. The results of this study indicated that the herbicidal activity of the isolated sesquiterpene may be attributed to inhibition of ALS. The promising phytotoxic activity of sesquitepene lactones reported here could be considered a starting point for developing environmentally safer herbicides. Nomenclature: Costunolide; parthenolide; 1,10-epoxyparthenolide; imazamethabenz; wild oat, Avena fatua L.; southern magnolia, Magnolia grandiflora L. (Magnoliaceae). Figure 2. In vitro effect of parthenolide and imazamethabenz-methyl on acetolactate synthase activity extracted from wild oat. Values are the mean of three replicates from two runs. I 50 5 51.44 mM for parthenolide. I 50 5 12.62 mM for imazamethabenz.

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“…To prepare a highly diverse library of O -benzyl aminotriols, 3 was oxidized to 10 using SeO 2 / t -BuOOH (TBHP) as oxidant [ 85 ]. The epoxidation of 10 with m -CPBA delivered a 4:1 mixture of epoxides 11a and 11b .…”

Section: Resultsmentioning

confidence: 99%

Novel (+)-Neoisopulegol-Based O-Benzyl Derivatives as Antimicrobial Agents

Lê

Huỳnh

Bamou

et al. 2021

IJMS

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Discovery of novel antibacterial agents with new structures, which combat pathogens is an urgent task. In this study, a new library of (+)-neoisopulegol-based O-benzyl derivatives of aminodiols and aminotriols was designed and synthesized, and their antimicrobial activity against different bacterial and fungal strains were evaluated. The results showed that this new series of synthetic O-benzyl compounds exhibit potent antimicrobial activity. Di-O-benzyl derivatives showed high activity against Gram-positive bacteria and fungi, but moderate activity against Gram-negative bacteria. Therefore, these compounds may serve a good basis for antibacterial and antifungal drug discovery. Structure–activity relationships were also studied from the aspects of stereochemistry of the O-benzyl group on cyclohexane ring and the substituent effects on the ring system.

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Synthesis of melampolides and cis,cis-germacranolides as natural herbicide models

Cited by 20 publications

References 29 publications

Isolation of Bioactive Compounds from Sunflower Leaves (Helianthus annuusL.) Extracted with Supercritical Carbon Dioxide

Isolation of Bioactive Compounds from Sunflower Leaves (Helianthus annuusL.) Extracted with Supercritical Carbon Dioxide

Herbicidal Activity of Three Sesquiterpene Lactones on Wild Oat (Avena fatua) and Their Possible Mode of Action

Novel (+)-Neoisopulegol-Based O-Benzyl Derivatives as Antimicrobial Agents

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