Nematicidal and Molecular Docking Investigation of Essential Oils from Pogostemon cablin Ecotypes against Meloidogyne incognita.

Root-knot nematode, Meloidogyne incognita is one of the most destructive nematodes worldwide. Essential oils (EOs) are being extensively utilized as eco-benign bionematicides, although the precise mechanism of action remains unclear. Pogostemon cablin Benth. is well-known as "Patchouli". It is native to South East Asia and known for ethno-pharmacological properties. In this study, chemical composition and potential nematicidal effect of EOs hydrodistilled from the leaves of P. cablin grown at three different locations in India were comprehensively investigated to correlate their mechanism of action for target specific binding affinities toward nematode proteins. Aromatic volatile Pogostemon essential oils (PEO) from Northern India (PEO-NI), Southern India (PEO-SI) and North Eastern India (PEO-NEI) were analyzed by Gas Chromatography-Mass Spectrometry (GC/MS) to characterize forty volatile compounds. Maximum thirty-three components were identified in PEO-NEI. Sesquiterpenes were predominant with higher content of α-guaiene (2.3-24.4 %), patchoulol (6.1-32.7 %) and α-bulnesene (5.9-27.1 %). Patchoulol was the major component in PEO-SI (32.7±1.2 %) and PEO-NEI (29.2±1.1 %), while α-guaiene in PEO-NI (24.4±1.2 %). In vitro nematicidal assay revealed significant nematicidal action (LC50 44.6-87.0 µg mL-1 ) against juveniles of M. incognita within 24 h exposure. Mortality increases with increasing time to 48 h (LC50 33.6-71.6 µg mL-1 ) and 72 h (LC50 27.7-61.2 µg mL-1 ). Molecular modelling and in silico studies revealed multi-modal inhibitive action of α-bulnesene (-22 to -13 kJ mol-1 ) and α-guaiene (-22 to -12 kJ mol-1 ) against three target proteins namely, acetyl cholinesterase (AChE), odorant response gene-1 (ODR1), odorant response gene-3 (ODR3). Most preferable binding mechanism was observed against AChE due to pi-alkyl, pi-sigma, and hydrophobic interactions. Structure nematicidal activity relationship suggested the presence of hydroxy group for nematicidal activity is nonessential, rather highly depends on synergistic composition of sesquiterpene hydrocarbons.

Nematicidal Activity of Essential Oil from Lavandin (Lavandula × intermedia Emeric ex Loisel.) as Related to Chemical Profile.

Essential oils (EOs) from lavandin are known for a large spectrum of biological properties but poorly and contrastingly documented for their activity against phytoparasitic nematodes. This study investigated the toxicity of EOs from three different lavandin cultivars, Abrialis, Rinaldi Cerioni, and Sumiens, either to juveniles (J2) and eggs of the root-knot nematode Meloidogyne incognita and to infective stages of the lesion nematode Pratylenchus vulnus. The suppressive activity of treatments with EOs from the three lavandin cultivars in soil infested by M. incognita was also investigated in a greenhouse experiment on potted tomato. The compositional profiles of tested EOs were also analyzed by GC-FID and GC-MS. Linalool was the major component of all the three EOs, as accounting for about 66%, 48%, and 40% of total EO from cv Rinaldi Cerioni, Sumiens, and Abrialis, respectively. Linalool acetate was the second most abundant compound in the EOs from cv Abrialis (18.3%) and Sumiens (14.9%), while significant amounts of camphor (11.5%) and 1,8-cineole (12.1%) were detected in cv Rinaldi Cerioni and Sumiens EOs, respectively. The mortality of M. incognita J2 peaked 82.0%, 95.8%, and 89.8% after a 24 h treatment with 100 mg·mL-1 solutions of cv Abrialis, Rinaldi Cerioni, and Sumiens EOs, respectively. Infective specimens of P. vulnus were largely more sensitive than M. incognita J2, as there were peak mortality rates of 65.5%, 67.7%, and 75.7% after 4 h of exposure to Abrialis, Rinaldi Cerioni, and Sumiens EO, respectively. All three lavandin EOs significantly affected also M. incognita egg hatchability, which reduced to 43.6% after a 48 h egg mass exposure to a 100 µg·mL-1 solution of cv Rinaldi Cerioni EO. Soil treatments with the three lavandin EOs strongly reduced, according to a dose-effect relationship, density of M. incognita eggs, and J2 both on tomato roots and in soil, as well as significantly reduced gall formation on tomato roots. Finally, almost all soil treatments with the lavandin EOs also resulted in a positive impact on tomato plant growth.

Identification and Characterization of Nematicidal Volatile Organic Compounds from Deep-Sea Virgibacillus dokdonensis MCCC 1A00493.

Root-knot nematode diseases cause severe yield and economic losses each year in global agricultural production. Virgibacillus dokdonensis MCCC 1A00493, a deep-sea bacterium, shows a significant nematicidal activity against Meloidogyne incognita in vitro. However, information about the active substances of V. dokdonensis MCCC 1A00493 is limited. In this study, volatile organic compounds (VOCs) from V. dokdonensis MCCC 1A00493 were isolated and analyzed through solid-phase microextraction and gas chromatography-mass spectrometry. Four VOCs, namely, acetaldehyde, dimethyl disulfide, ethylbenzene, and 2-butanone, were identified, and their nematicidal activities were evaluated. The four VOCs had a variety of active modes on M. incognita juveniles. Acetaldehyde had direct contact killing, fumigation, and attraction activities; dimethyl disulfide had direct contact killing and attraction activities; ethylbenzene had an attraction activity; and 2-butanone had a repellent activity. Only acetaldehyde had a fumigant activity to inhibit egg hatching. Combining this fumigant activity against eggs and juveniles could be an effective strategy to control the different developmental stages of M. incognita. The combination of direct contact and attraction activities could also establish trapping and killing strategies against root-knot nematodes. Considering all nematicidal modes or strategies, we could use V. dokdonensis MCCC 1A00493 to set up an integrated strategy to control root-knot nematodes.

Phomaketide A Inhibits Lymphangiogenesis in Human Lymphatic Endothelial Cells.

Lymphangiogenesis is an important biological process associated with cancer metastasis. The development of new drugs that block lymphangiogenesis represents a promising therapeutic strategy. Marine fungus-derived compound phomaketide A, isolated from the fermented broth of Phoma sp. NTOU4195, has been reported to exhibit anti-angiogenic and anti-inflammatory effects. However, its anti-lymphangiogenic activity has not been clarified to date. In this study, we showed that phomaketide A inhibited cell growth, migration, and tube formation of lymphatic endothelial cells (LECs) without an evidence of cytotoxicity. Mechanistic investigations revealed that phomaketide A reduced LECs-induced lymphangiogenesis via vascular endothelial growth factor receptor-3 (VEGFR-3), protein kinase Cδ (PKCδ), and endothelial nitric oxide synthase (eNOS) signalings. Furthermore, human proteome array analysis indicated that phomaketide A significantly enhanced the protein levels of various protease inhibitors, including cystatin A, serpin B6, tissue factor pathway inhibitor (TFPI), and tissue inhibitor matrix metalloproteinase 1 (TIMP-1). Importantly, phomaketide A impeded tumor growth and lymphangiogenesis by decreasing the expression of LYVE-1, a specific marker for lymphatic vessels, in tumor xenograft animal model. These results suggest that phomaketide A may impair lymphangiogenesis by suppressing VEGFR-3, PKCδ, and eNOS signaling cascades, while simultaneously activating protease inhibitors in human LECs. We document for the first time that phomaketide A inhibits lymphangiogenesis both in vitro and in vivo, which suggests that this natural product could potentially treat cancer metastasis.

Isolation of Ceramides from Tagetes patula L. Yellow Flowers and Nematicidal Activity of the Fractions and Pure Compounds against Cyst Nematode, Heterodera zeae.

Investigation of yellow flower extract of Tagetes patula L. led to the identification of an aggregate of five phytoceramides. Among them, (2R)-2-hydroxy-N-[(2S,3S,4R,8E)-1,3,4-trihydroxyicos-8-en-2-yl]icosanamide, (2R)-2-hydroxy-N-[(2S,3S,4R,8E)-1,3,4-trihydroxyicos-8-en-2-yl]heneicosanamide, (2R)-2-hydroxy-N-[(2S,3S,4R,8E)-1,3,4-trihydroxyicos-8-en-2-yl]docosanamide, and (2R)-2-hydroxy-N-[(2S,3S,4R,8E)-1,3,4-trihydroxyicos-8-en-2-yl]tricosanamide were identified as new compounds and termed as tagetceramides, whereas (2R)-2-hydroxy-N-[(2S,3S,4R,8E)-1,3,4-trihydroxyicos-8-en-2-yl]tetracosanamide was a known ceramide. A steroid (ß-sitosterol glucoside) was also isolated from the subsequent fraction. The structures of these compounds were determined on the basis of spectroscopic analyses, as well as chemical method. Several other compounds were also identified by GC/MS analysis. The fractions and some commercial products, a ceramide HFA, ß-sitosterol, and stigmasterol were evaluated against an economically important cyst nematode, Heterodera zeae. Ceramide HFA showed 100 % mortality, whereas, ß-sitosterol and stigmasterol were 40-50 % active, at 1 % concentration after 24 h of exposure time, while ß-sitosterol glucoside revealed no activity against the nematode.

Cyclo(l-Pro⁻l-Leu) of Pseudomonas putida MCCC 1A00316 Isolated from Antarctic Soil: Identification and Characterization of Activity against Meloidogyne incognita.

Pseudomonas putida MCCC 1A00316 was originally isolated from an Antarctic soil and has demonstrated potential nematicidal activity. Thus, it has promising applications for the biological control of Meloidogyne incognita. The larval mortality and egg-hatching inhibition rates of M. incognita will increase with the rising concentration of culture filtrates of P. putida MCCC 1A00316 and the duration of exposure. Thus, this study aimed to separate, purify, and identify nematicidal compounds from P. putida MCCC 1A00316 and to validate their anti-M. incognita activities. Compounds were purified through silica gel column chromatography and thin-layer chromatography combined with high-performance liquid chromatography (HPLC). Structural identification was conducted through liquid chromatography time-of-flight mass spectrometry, ¹H nuclear magnetic resonance (NMR) spectroscopy, 13C-NMR, and Marfey's method. The isolated compounds were identified as cyclo(l-Pro⁻l-Leu) on the basis of the results of the above analyses and previously reported data. The effects of various concentrations of cyclo(l-Pro⁻l-Leu) on the mortality rates of second-stage juveniles (J2) of M. incognita were investigated. Results showed that HPLC-purified cyclo(l-Pro⁻l-Leu) displayed nematicidal activities. The mortality rate of M. incognita J2 reached 84.3% after 72 h of exposure to 67.5 mg/L cyclo(l-Pro⁻l-Leu). The lowest egg-hatching rate (9.74%) was observed after 8 days of incubation with 2000 mg/L cyclo(l-Pro⁻l-Leu). An egg-hatching rate of 53.11% was obtained under the control treatment (sterile distilled water). However, cyclo(l-Pro⁻l-Leu) did not elicit chemotaxis activity to M. incognita. This is the first work to investigate the anti-M. incognita characteristics of cyclo(l-Pro⁻l-Leu).

Nematicidal protease genes screened from a soil metagenomic library to control Radopholus similis mediated by Pseudomonas fluorescens pf36.

Controlling Radopholus similis, an important phytopathogenic nematode, is a challenge worldwide. Herein, we constructed a metagenomic fosmid library from the rhizosphere soil of banana plants, and six clones with protease activity were obtained by functionally screening the library. Furthermore, subclones were constructed using the six clones, and three protease genes with nematicidal activity were identified: pase1, pase4, and pase6. The pase4 gene was successfully cloned and expressed, demonstrating that the protease PASE4 could effectively degrade R. similis tissues and result in nematode death. Additionally, we isolated a predominant R. similis-associated bacterium, Pseudomonas fluorescens (pf36), from 10 R. similis populations with different hosts. The pase4 gene was successfully introduced into the pf36 strain by vector transformation and conjugative transposition, and two genetically modified strains were obtained: p4MCS-pf36 and p4Tn5-pf36. p4MCS-pf36 had significantly higher protease expression and nematicidal activity (p < 0.05) than p4Tn5-pf36 in a microtiter plate assay, whereas p4Tn5-pf36 was superior to p4MCS-pf36 in terms of genetic stability and controlling R. similis in growth pot tests. This study confirmed that R. similis is inhibited by the associated bacterium pf36-mediated expression of nematicidal proteases. Herein, a novel approach is provided for the study and development of efficient, environmentally friendly, and sustainable biocontrol techniques against phytonematodes.

Plant Volatiles Reduce the Viability of the Root-Knot Nematode Meloidogyne incognita Either Directly or When Retained in Water.

Volatile organic compounds (VOC) produced by green residues for the management of plant-parasitic nematodes are poorly studied for oilseed plants and some Brassica spp. To investigate the activity of VOC in vitro and as biofumigants, dry and aqueous macerates of broccoli (Brassica oleracea var. italica) shoots and sunflower (Helianthus annuus) seed were used against the root-knot nematode Meloidogyne incognita. VOC produced by sunflower seed caused higher mortality of M. incognita second-stage juveniles (J2) than VOC produced by broccoli shoots but both plant species were equally effective in decreasing the infectivity and reproduction of this nematode. The number of galls and eggs produced by the nematode in tomato roots was reduced by 89 and 95%, respectively, on average, at the highest concentrations of broccoli and sunflower seed macerates tested as biofumigants. When nematodes were placed in water exposed to broccoli VOC, J2 immobility increased and the number of galls and eggs produced by the nematode in tomato roots decreased 80 and 96%, respectively. Water exposed to sunflower seed VOC had no effect on the viability of the nematode. Gas chromatography was used to identify five and six chemical groups in broccoli and in sunflower seed macerates, respectively, but only alcohols, sulfurated VOC, and terpenes were detected in the water exposed to these plant macerates. Sulfurated VOC from the water exposed to broccoli macerates were found to be involved in its activity against M. incognita. The purified VOC dimethyl disulfide (DMDS) and 3-pentanol were tested directly against J2 and showed a lethal concentration of 176 and 918 µg/ml (ppm), respectively, whereas dimethyl sulfide had no effect against M. incognita. Furthermore, DMDS and 3-pentanol retained in water killed J2 and reduced gall formation and the number of eggs of M. incognita on tomato roots. Both these plant species produced toxic VOC to M. incognita, whereas only VOC retained in water exposed to broccoli had activity against M. incognita.

[Chemical constituents from fruits of Aristolochia mollissima and their nematicidal activity against root-knot nematode].

In the present study, in vitro nematicidal activity of chemical compositions from the methanol extract of Aristolochia mollissima fruits against the second stage juvenile (J2) of Meloidogyne javanica have been investigated. By using silica gel column chromatography, Sephadex LH-20 gel column chromatography methods, fourteen compounds were isolated from methanol extract of A. mollissima fruits. On the basis of spectral data, their structures were identified as aristolochic acid I (1), aristololactam I (2), aristololactam W (3), manshurolide (4), aristolactone (5), saropeptate (6), 2-(1-oxononadecyl)aminobenzoic acid (7), ß-sitosterol (8), sitostanetriol (9), daucosterol (10), formosolic acid (11), 5-ethyl-8,8-dimethyl nonanal (12), tetracosanoic acid,2,3-dihydroxypropyl ester (13) and tetracosanoic acid (14), respectively. It is the first time that compounds 2-4, 6-7, 9-14 are separated from A. mollissima. Furthermore, nematicidal activity of fourteen monomer compounds against J2 Meloidogyne javanica in vitro were analyzed. The compounds 1-3, 6-7 exhibited different degrees toxic effects on J2 M. javanica in vitro, especially for aristolochic acid I (1), aristololactam I (2), aristololactam W (3) with the LC50 values of 45.25, 36.56, 119.46 mg·L⁻¹ after 96 h. So, A. mollissima have the potential value of developing new plant source to control root nematodes.

Natural Products of Picea Endophytes from the Acadian Forest.

Endophytes of healthy needles were collected from Picea rubens (red spruce) and P. mariana (black spruce) in a survey of southeastern New Brunswick, Canada. Four endophyte strains were selected for further investigation based on the production of biologically active extracts from culture filtrates during screening as well as phylogenetic relationship to species known to produce natural products or taxonomic novelty. A novel endophyte within the family Rhytismataceae produced two new dihydropyrones (1 and 2) as major metabolites together with phthalides (3 and 4), isocoumarins (5 and 6), and tyrosol (7). Lachnum cf. pygmaeum synthesized a new chlorinated para-quinone, chloromycorrhizinone A (8), and the nematicidal compounds (1'Z)-dechloromycorrhizin A (9), mycorrhizin A (10), and chloromycorrhizin A (11). A new isocoumarin (12) and four related structures (13-16) were isolated from an undescribed taxon in the Mycosphaerellaceae. The known antifungal metabolites cryptosporiopsin (17), 5-hydroxycryptosporiopsin (18), (+)-cryptosporiopsinol (19), and mellein (20) were produced by Pezicula sporulosa. Phylogenetically diverse conifer endophytes from the Acadian forest continue to be a productive source of new biologically active natural products.

Two new tenvermectins from a genetically engineered strain Streptomyces avermitilis MHJ1011.

Two new tenvermectins, tenvermectins C (1) and D (2), were isolated from Streptomyces avermitilis MHJ1011. Their structures were determined by extensive spectroscopic analysis and by comparison with a related known compound, tenvermectin A. Compounds 1 and 2 exhibited potent nematocidal and acaricidal activities against Bursaphelenchus xylophilus and Tetranychus cinnabarinus.

New macrocyclic lactones with acaricidal and nematocidal activities from a genetically engineered strain Streptomyces bingchenggensis BCJ60.

Two new macrocyclic lactones, 4,25-diethyl-4,25-demethyl-milbemycin ß3 (1) and 27-formaldehyde-milbemycin ß14 (2), were isolated from a genetically engineered strain Streptomyces bingchenggensis BCJ60. Their structures were determined on the basis of spectroscopic analysis, including 1D and 2D NMR techniques as well as ESI-MS and comparison with data from the literature. The acaricidal and nematocidal capacities of compounds 1 and 2 were evaluated against Tetranychus cinnabarinus and Bursaphelenchus xylophilus, respectively. The results showed that the two new macrocyclic lactones 1 and 2 possessed potent acaricidal and nematocidal activities.

Identification for the First Time of Cyclo(d-Pro-l-Leu) Produced by Bacillus amyloliquefaciens Y1 as a Nematocide for Control of Meloidogyne incognita.

The aim of the current study was to describe the role and mechanism of Bacillus amyloliquefaciens Y1 against the root-knot nematode, Meloidogyne incognita, under in vitro and in vivo conditions. Initially, the exposure of the bacterial culture supernatant and crude extract of Y1 to M. incognita significantly inhibited the hatching of eggs and caused the mortality of second-stage juveniles (J2), with these inhibitory effects depending on the length of incubation time and concentration of the treatment. The dipeptide cyclo(d-Pro-l-Leu) was identified in B. amyloliquefaciens culture for the first time using chromatographic techniques and nuclear magnetic resonance (NMR ¹H, 13C, H-H COSY, HSQC, and HMBC) and recognized to have nematocidal activity. Various concentrations of cyclo(d-Pro-l-Leu) were investigated for their effect on the hatching of eggs and J2 mortality. Moreover, the in vivo nematocidal activity of the Y1 strain was investigated by conducting pot experiments in which tomato plants were inoculated with M. incognita. Each and every pot was amended 50 mL of fertilizer media (F), or Y1 culture, or nematicide (N) (only once), or fertilizer media with N (FN) at 1, 2, 3, 4 and 5 weeks after transplantation. The results of the pot experiments demonstrated the antagonistic effect of B. amyloliquefaciens Y1 against M. incognita as it significantly decreases the count of eggs and galls per root of the tomato plant as well as the population of J2 in the soil. Besides, the investigation into the growth parameters, such as the length of shoot, shoot fresh and dry weights of the tomato plants, showed that they were significantly higher in the Y1 strain Y1-treated plants compared to F-, FN- and N-treated plants. Therefore, the biocontrol repertoire of this bacterium opens a new insight into the applications in crop pest control.

Five Unprecedented Secondary Metabolites from the Spider Parasitic Fungus Akanthomyces novoguineensis.

Five new compounds including the glycosylated ß-naphthol (1, akanthol), a glycosylated pyrazine (2, akanthozine), and three amide derivatives including a hydroxamic acid derivative (3-5) were isolated from the spider-associated fungus Akanthomyces novoguineensis (Cordycipitaceae, Ascomycota). Their structures were elucidated by using high resolution mass spectrometry (HRMS) and NMR spectroscopy. In this study, the antimicrobial, cytotoxic, anti-biofilm, and nematicidal activities of the new compounds were evaluated. The distribution pattern of secondary metabolites in the species was also revealed in which more isolates of A. novoguineensis were encountered and their secondary metabolite profiles were examined using analytical HPLC with diode array and mass spectrometric detection (HPLC-DAD/MS). Remarkably, all isolated compounds are specifically produced by A. novoguineensis.

Evaluation of different Mediterranean essential oils as prophylactic agents in anisakidosis.

CONTEXT: Anisakis Dujardin 1845 (Anisakidae) nematodes can cause gastrointestinal and allergic diseases when humans eat raw or undercooked seafood containing larvae. There is currently no drug available in the market against this parasitic disease, and the study of plant-derived molecules could be useful in the discovery of effective compounds. OBJECTIVE: This research assesses the biocidal activity of a range of essential oils (EOs) from some Mediterranean plants against larvae found in the musculature of fresh fish. MATERIALS AND METHODS: EOs composition was analyzed by gas chromatography-mass spectroscopy. All the EOs were diluted at 5% v/v in olive oil to cover the fish with the solutions for 24 h. The larvae that abandoned the muscle and the larvae obtained from the artificial digestion of the fish were collected. Controls were carried out in parallel. Furthermore, Wistar rats were infected with the live larvae collected from the in vitro trials in order to find any larvae that may have penetrated the gastrointestinal wall. RESULTS: Between 60.8% and 87.6% of parasites treated with EOs abandoned the fish muscle, and the highest in vitro mortality rate was achieved with oregano EO (53.9%). Rats previously treated with oregano, cumin and Spanish lavender EOs showed no detectable lesions in the digestive tract due to the infection with larvae. CONCLUSIONS: Oregano (Origanum vulgare L. Lamiaceae), cumin (Cuminum cyminum L. Apiaceae) and Spanish lavender (Lavender stoechas L. Lamiaceae) EOs could be used as promising ingredients in the development of products for the control of anisakiasis.

[A new sesquiterpene from Chinese agarwood induced by artificial holing].

In order to study the chemical constituents of n-butanol fraction of ethanol extract from Chinese agarwood induced by artificial holing, various chromatographic techniques were carried out to isolate compounds, and the structures of compounds were determined through a combined analysis of physicochemical properties and spectroscopic evidence. Seven compounds were obtained and identified as selina-3,11-dien-9,15-diol (1), aquilarone D (2), 5α,6ß,7α,8ß-tetrahydroxy-2-[2-(2-hydroxyphenyl)ethyl]-5,6,7,8-tetrahydrochromone (3), 6,7-dimethoxy-2-[2-(4-methoxyphenyl)ethyl]chromone (4), syringin (5), methyl (Z)-p-coumarate (6), and 4'-methoxycinnamic acid (7), among which compound 1 was a new compound and compounds 5-7 were isolated from agarwood for the first time. The bioactivity assay results concluded that compounds 6 and 7 showed certain nematicidal activity against Panagrellus redivivus, and compounds 4, 6 and 7 exhibited cytotoxicity against BEL-7402, SGC-7901 and A549 carcinoma cell lines.

Practical and low cost whole-organism motility assay: A step-by-step protocol.

Here, we provide a step-by-step protocol for a practical and low cost whole-organism assay for the screening of chemical compounds for activity against parasitic worms. This assay has considerable advantages over conventional methods, mainly in relation to ease of use, throughput, time and cost. It is readily suited to the screening of hundreds to thousands of compounds for subsequent hit-to-lead optimisation, and should be applicable to many different parasites and other organisms commensurate with the size of wells in the microtiter plates used for phenotypic screening.

Nematicidal Stemona Alkaloids from Stemona parviflora.

Eight new alkaloids, 3ß-n-butylstemonamine (1), 8-oxo-3ß-n-butylstemonamine (2), 3-n-butylneostemonine (3), 10-epi-3-n-butylneostemonine (4), 8-oxo-oxymaistemonine (5) protostemonine N4-oxide (6), (19S)-hydroxy-21-methoxystemofoline (7), and parvistemonine A (8), were isolated from the roots of Stemona parviflora, together with 17 known alkaloids. The structures of the new alkaloids were elucidated based on a comprehensive spectroscopic data analysis. The absolute configurations of 1-4 were determined by the ECD exciton chirality method and quantum ECD calculations. Protostemonine (10) and stemofoline (12) showed strong nematicidal activity against Panagrellus redivevus, with IC50 values of 0.10 and 0.46 µM, respectively.

Phytotoxic and Nematicidal Components of Lavandula luisieri.

Several preparations were obtained from the aerial parts of predomesticated Lavandula luisieri, including the essential oil and ethanolic, hexane, and ethyl acetate extractives. Additionally, pilot plant vapor pressure extraction was carried out at a pressure range of 0.5-1.0 bar to give a vapor pressure oil and an aqueous residue. A chemical study of the hexane extract led to the isolation of six necrodane derivatives (1, 2, and 4-7), with four of these (1, 2, 5, and 7) being new, as well as camphor, a cadinane sesquiterpene (9), tormentic acid, and ursolic acid. The EtOAc and EtOH extracts contained a mixture of phenolic compounds with rosmarinic acid being the major component. Workup of the aqueous residue resulted in the isolation of the necrodane 3 and (1R*,2S*,4R*)-p-menth-5-ene-1,2,8-triol (8), both new natural compounds. The structures of the new compounds were established based on their spectroscopic data. The phytotoxic and nematicidal activities of these compounds were evaluated.

Labdane Diterpenes from the Fruits of Sinopodophyllum emodi.

Two new labdane diterpenes, sinoditerpene A (1) and B (2), were isolated from the fruits of Sinopodophyllum emodi, along with two known analogues 3 and 4. Their structures were established on the basis of extensive spectroscopic analysis. The isolation of compounds 1-4 represents the first report of diterpenes from the genus Sinopodophyllum. The cytotoxic activities of all isolated compounds were evaluated in comparison with 5-fluorouracil against the MCF-7 and HepG2 cell lines, towards which 3 showed more potent cytotoxicity.