Aristolene

Volatiles Profiling, Allelopathic Activity, and Antioxidant Potentiality of Xanthium Strumarium Leaves Essential Oil from Egypt: Evidence from Chemometrics Analysis.[Pubmed:30736389]

Molecules. 2019 Feb 7;24(3). pii: molecules24030584.

The essential oil (EO) of Xanthium strumarium L. leaves (family: Asteraceae) was extracted by hydrodistillation, and then analyzed by gas chromatography-mass spectrometry (GC-MS). Forty-three essential compounds were identified. The sesquiterpenoids represented the major constituents (72.4%), including oxygenated (61.78%) and non-oxygenated (10.62%) sesquiterpenes, followed by monoterpenes (25.19%). The diterpenoids and oxygenated hydrocarbons were determined as minor compounds. The main constituents of the EO were 1,5-dimethyltetralin (14.27%), eudesmol (10.60%), l-borneol (6.59%), ledene alcohol (6.46%), (-)-caryophyllene oxide (5.36%), isolongifolene, 7,8-dehydro-8a-hydroxy (5.06%), L-bornyl acetate (3.77%), and Aristolene epoxide (3.58%). A comparative analysis was stated here between the EO of Egyptian X. strumarium and those previously reported from Pakistan, Iran, and Brazil based on chemometic tools such as principal components analysis (PCA) and agglomerative hierarchical clustering (AHC). The EO of X. strumarium showed weak 1, 1-diphenyl-2-picryl hydrazyl (DPPH) radical scavenging activity with IC50 321.93 microL/L(-1), which was comparable to ascorbic acid as a reference. However, the EO exhibited significant allelopathic potential regarding the germination and growth of the noxious weed Bidens pilosa in a concentration-dependent manner. Therefore, further study is recommended to characterize the EO from X. strumarium as an eco-friendly green bioherbicide against weeds, as well as determine their mode of actions.

Organ-Specific Phytochemical Profiling and Antioxidant Analysis of Parthenium hysterophorus L.[Pubmed:30027101]

Biomed Res Int. 2018 Jun 20;2018:9535232.

Parthenium hysterophorus is a weed of global concern with high threshold of tolerance against most of biotic and abiotic stresses. Phytochemical profile and in vitro antioxidant analysis may help in understanding its tolerance to stresses. Root, stem, leaf, phyllary, and receptacle (including disc and ray florets) were chemotyped employing GC tof-MS and assessed for antioxidant activity by DPPH, FRAP, HRSA, and TAC assays. Phytochemicals identified were terpenes, fatty acids, hydrocarbons, phytosterols, and compounds of miscellaneous chemical nature. Organ-specific maximum concentration of metabolite was beta-vatirenene (root), hexadecanoic acid methylester (stem), Aristolene epoxide (leaf), hexadecanoic acid methylester (phyllary), and hexadecanoic acid methylester (receptacle). Identified metabolites could be associated with stress tolerance mechanisms, basic metabolism, and allelopathy, etc. Root extracts showed highest antioxidant potential followed by receptacle. It can be concluded that diverse and unique phytochemical profile and great antioxidant potential make P. hysterophorus stress-tolerant, hence a weed of global habitat.

Fungus-Farming Termites Selectively Bury Weedy Fungi that Smell Different from Crop Fungi.[Pubmed:29124530]

J Chem Ecol. 2017 Oct;43(10):986-995.

Mutualistic associations such as the fungal farms of insects are prone to parasitism and are consequently vulnerable to attack by weeds and pests. Therefore, efficient farm management requires quick detection of weeds for their elimination. Furthermore, if the available weedicides are non-specific, then the ability of insects to discriminate between crop and weeds becomes essential for targeted application of such compounds. Here, we demonstrate for the first time in fungus-farming insects, that worker castes of the fungus-growing termite Odontotermes obesus discriminate between their crop (Termitomyces) and the weedy (Pseudoxylaria) fungi, even if exposed to only fungal scents. Termites respond to the presence of fungal mycelium or scent alone, by burying the weed with the offered material such as soil or agar, possibly anointing the weed with chemicals in the process. The scent profiles of crop and weedy fungi are distinct and the differences are likely exploited by termites to selectively mount their defences. Sesquiterpene compounds such as Aristolene and viridiflorol, which are absent from crop odours, may constitute the "weedy scent". Our results provide a general mechanism of how other fungus-farming insects could avoid indiscriminate application of non-specific fungicides which could lead to poisoning their crops, and have bearing on the stability of the mutualism between termites and their crop fungus in the face of parasitism by weedy fungi.

Composition and Antimicrobial Activity of the Essential Oils of Three Plant Species from the Sabana of Bogota (Colombia): Myrcianthes leucoxyla, Vallea stipularis and Phyllanthus salviifolius.[Pubmed:30508364]

Nat Prod Commun. 2016 Dec;11(12):1913-1918.

In recent decades, essential oils (EOs) have become an important alternative source of antimicrobial agents. The objective of this study was to evaluate the antimicrobial activity of EOs obtained from the leaves of Myrcianthes leucoxyla Mc. Vaughn., Vallea stipularis L.f and Phyllanthus salviioius Kunth for prevalent microbial strains and also to contribute to the knowledge of their chemical composition. EOs were obtained by hydrodistillation and analyzed by GC-MS. The main compounds for V. stipularis EO were alpha-tujene (6.6%) and cedrene epoxide (12.0%), for M leucoxila EO 1,8 cineole (6.3%) and caryophyllene oxide (21.7%), and for P. salviifolius Aristolene (17.3%) and geranyl tiglate (15.9%). Antimicrobial tests showed that M leucoxyla EO was the most active, showing zones of inhibition against all strains used, specifically against Pseudomonas aenginosa and Salmonella typhimurium with percentages of inhibition higher than 50%. Compared with positive controls, this activity may be related to the presence of 1,8 cineole.

Protective antifungal activity of essential oils extracted from Buddleja perfoliata and Pelargonium graveolens against fungi isolated from stored grains.[Pubmed:26854645]

J Appl Microbiol. 2016 May;120(5):1264-70.

AIMS: The chemical composition and antifungal activity of essential oils extracted from Buddleja perfoliata and Pelargonium graveolens were analysed to assess their efficacy as a potential alternative to synthetic chemical fungicides to protect stored grain. METHODS AND RESULTS: Essential oils were obtained by hydrodistillation, while GC-MS were used to characterize the components of theses oils. The main components identified from the essential oil of B. perfoliata were cubenol, eudesmol, germacrene D-4-ol and cis-verbenol; whereas (-)-Aristolene, beta-citronellol and geraniol, were identified in P. graveolens. These essential oils were tested against a panel of fungal strains isolated from stored grains. Toxicity of the essential oils was assessed using two models represented by human-derived macrophages and the brine shrimp assay. Moreover, inflammatory response of the oils was assessed by measuring secretion of the pro-inflammatory cytokines IL-6 and TNF-alpha using a human-derived macrophage cell line. Results show potent antifungal activity against a collection of fungi, with minimal inhibitory concentrations ranging from 0.3 to 50 mug ml(-1) for both plants. A moderated cytotoxicity was observed, but no inflammatory responses. CONCLUSIONS: These oils can be used as an alternative for synthetic chemical fungicides used to protect stored grains. SIGNIFICANCE AND IMPACT OF THE STUDY: Synthetic chemical fungicides are used to protect stored grains, but their broad use raises concerns about effects on the environment and human health. The impact of the present report is that the use of essential oils is an eco-friendly alternative for fungal control in postharvest grains with a low impact to the environment.

Effect of gibberellic acid (GA), indole acetic acid (IAA) and benzylaminopurine (BAP) on the synthesis of essential oils and the isomerization of methyl chavicol and trans-anethole in Ocimum gratissimum L.[Pubmed:25045609]

Springerplus. 2014 Jun 26;3:321.

Basil (O. gratissimum L) is a aromatic and medicinal plant widely used in traditional medicine in Morocco. The aim of this work was to study the effect of three plant growth regulators gibberellic acid (GA), indole 3-acetic acid (IAA) and benzylaminopurine (BAP) on the content and composition of essential oils of this plant, especially on the main compound (methyl chavicol) and its isomer (the trans-anethole). The results showed a wide variation on yield, content and range of the molecule constituent of oil, with a balance of appearances and/or disappearances of a few molecules. GA caused a slight decrease in the oil yield (0.2%), but it increased the diversity of compounds (17 molecules) with the appearance of four new compounds (naphthalene, camphor, germacrene-D, and ledene) and disappearance of (beta cedrene, azulene). This variation also caused a very important decrease in the main compound (methyl chavicol) and increases its isomer (trans-anethole). IAA and BAP caused an increase in the yield of essential oil (0.30% and 0.32% respectively) without much influence on the main compounds, but with some change in the composition such as the appearance of (germacrene-D) and the disappearance of (Aristolene).

Volatile organic compounds of six French Dryopteris species: natural odorous and bioactive resources.[Pubmed:24660483]

Nat Prod Commun. 2014 Jan;9(1):137-40.

Aerial parts of six Dryopteris species collected in France were investigated for volatile organic compounds (VOC) for the first time. Fifty-three biosynthesized VOC from the shikimic, lipidic and terpenic pathways were identified using gas chromatography/mass spectrometry. Many bioactive polyketide compounds as filicinic derivatives (from 8.5 to 23.5%) and phloroglucinol derivatives (from 8.2 to 53.8%) with various pharmacological activities were detected in high amount from five analysed Dryopteris species, in particular D. oreades and D. borreri, i.e., propionylfilicinic acid (> 10% in D. affinis and D. ardechensis) and 2,6-dihydroxy-4-methoxy-3-methylbutyrophenone (aspidinol) (19.1% and 14.6% in D. oreades and D. borreri, respectively). Several terpenic derivatives with a low odor threshold were identified, i.e., carota-5,8-diene (from 2.5 to 18.4%: floral, woody or fresh bark note), (E)-nerolidol (> 10% for D. borreri and D. cambrensis; floral or woody odor), alpha-selinene (> 7% for D. ardechensis; woody-spicy odor), and Aristolene (12.8% in D. affinis; flower, sweet odor). The main isoprenoid derivatives were 4-hydroxy-5,6-epoxyionol, 3-oxo-alpha-ionol and 4-oxo-7,8-dihydro-beta-ionone (essentially in D. remota), whereas the main aromatic compound was 4-hydroxy-3-methoxyacetophenone (20.6% and 12.6% in D. cambrensis and D. borreri, respectively) and the main lipid derivative was 1-octen-3-ol with a mushroom-like odor (from 0.4 to 8.3%). Dryopteris species resources are of great interest as a reservoir of odorous and bioactive compounds.

Increases of 2-furanmethanol and maltol in Korean red ginseng during explosive puffing process.[Pubmed:20492218]

J Food Sci. 2010 Mar;75(2):C147-51.

The explosive puffing process may provide characteristic physicochemical properties in red ginseng. The effects of explosive puffing on the changes of volatiles in red ginseng were investigated using headspace-solid phase microextraction (HS-SPME)-gas chromatograph (GC) with a mass selective detector (MS). Formation of porous structures and smaller pieces were clearly observed on the surface of puffed red ginseng by scanning electron microscopy. Total volatiles in puffed red ginseng increased by 87% compared to those in red ginseng. Hexanal, Delta-selinene, and beta-panasinsene were major volatiles in red ginseng, whereas Aristolene, beta-panasinsene, and calarene were main volatiles in puffed red ginseng. Puffing process decreased volatiles from lipid oxidation including aldehydes, ketones, and 2-pentylfuran and increased terpenoids in red ginseng. Selective ion monitoring (SIM) mode for GC/MS results showed that 2-furanmethanol and maltol were present at the concentrations of 0.20% and 0.24%, respectively, in red ginseng and 5.86% and 3.99%, respectively, in puffed red ginseng. The explosive puffing process increased 2-furanmethanol and maltol in puffed red ginseng significantly (P < 0.05) with the changes of microstructures.

Insecticidal activity of Valeriana jatamansi (Valerianaceae) against mosquitoes.[Pubmed:18666542]

J Am Mosq Control Assoc. 2008 Jun;24(2):315-8.

A root extract of Valeriana jatamansi (code BAL-O) exhibited larvicidal and adulticidal activity against different mosquito species. The median lethal concentration (LC50) of BAL-O against larvae of Anopheles stephensi, Anopheles culicifacies, Aedes aegypti, Aedes albopictus, and Culex quinquefasciatus were 68.1, 42.8, 51.2, 53.8, and 80.6 mg/liter, respectively. The LC50 and the 90% lethal concentration against adult An. stephensi, An. culicifacies, Ae. aegypti, Ae. albopictus, and Cx. quinquefasciatus were 0.14, 0.16, 0.09, 0.08, and 0.17 and 0.24, 0.34, 0.25, 0.21, and 0.28 mg/cm2, respectively. The median knock-down time and 90% knock-down time of the fraction were 13, 13, 12, 13, and 18 and 24, 25, 21, 20, and 42 min against An. stephensi, An. culicifacies, Ae. aegypti, An. albopictus and Cx. quinquefasciatus, respectively, using 0.28 mg/cm2 impregnated papers. The median effective time and 90% effective time against An. stephensi at 4 degrees C were 46.6 and 8.7 days, and at 29 degrees C, 25.5 and 5.6 days, respectively. Gas chromatographic-mass spectrometric analysis of BAL-O showed 2-butanone,4-(2,6,6-trimethyl-2-cyclohexen-l-yl) (10.11%), patchouli alcohol (8.55%), cubenol (5.97%), caryophyllene oxide (5.46%), cadinol (5.23%), and Aristolene (5.19%).

Comparative study on volatile components of Nardostachys rhizome.[Pubmed:18404355]

J Nat Med. 2008 Jan;62(1):112-6.

Volatile components in 13 crude drug samples derived from Nardostachys chinensis or Nardostachys grandiflora were studied by solid phase micro extraction (SPME)-GC and SPME-GC-MS. Twenty-three compounds accounting for 81.3 and 70.0% of volatile components in newly collected samples of two species were identified. beta-Maaliene, 9-Aristolene, calarene and patchouli alcohol were identified as the major volatile constituents of N. chinensis, whereas aromadendrene, cube-11-ene, epi-alpha-selinene, spirojatamol and valeranone were identified as those of N. grandiflora. Using the peaks of beta-maaliene and 9-Aristolene in GC profiles as the marker, two Nardostachys species were clearly distinguished among the samples examined.

Analytical discrimination of poisonous and nonpoisonous chemotypes of giant fennel (Ferula communis L.) through their biologically active and volatile fractions.[Pubmed:17002421]

J Agric Food Chem. 2006 Oct 4;54(20):7556-63.

Giant fennel (Ferula communis L.) from Sardinia is characterized by two chemotypes with different biological activities. One chemotype is poisonous, due to prenylcoumarins, and responsible for ferulosis, which mainly affects sheep and goats, cattle, and horses; the other chemotype is nonpoisonous and contains daucane esters. The two chemotypes cannot be distinguished botanically. High-performance liquid chromatography-diode array-ultraviolet detection-mass spectrometry (HPLC-DAD-UV-MS) analysis of the composition of the fractions containing the biologically active metabolites and of the volatile fractions, by gas chromatography-mass spectrometry (GC-MS), of both essential oil and headspace sampled by headspace solid-phase microextraction (HS-SPME) are here shown to be effective in discriminating the poisonous and nonpoisonous chemotypes. HS-SPME with CAR/PDMS/DVB in combination with GC-MS has also been found to be a successful, fully automated one-step method for rapid and unequivocal discrimination of the two chemotypes, using Aristolene and allohedycaryol as markers of the poisonous and nonpoisonous chemotypes, respectively.

Biotransformation of aristolane- and 2,3-secoaromadendrane-type sesquiterpenoids having a 1,1-dimethylcyclopropane ring by Chlorella fusca var. vacuolata, mucor species, and Aspergillus niger.[Pubmed:16755059]

Chem Pharm Bull (Tokyo). 2006 Jun;54(6):861-8.

Biotransformation of the aristolane-type sesquiterpene hydrocarbon (+)-1(10)-Aristolene (1) from the crude drug Nardostachys chinensis and of the 2,3-secoaromadendrane-type sesquiterpene lactone plagiochilide (2) from the liverwort Plagiochila fruticosa by three microorganisms, Chlorella fusca var. vacuolata, Mucor species, and Aspergillus niger was investigated. C. fusca var. vacuolata and Mucor sp. introduced oxygen function into the cyclohexane ring of Aristolene while A. niger oxidized stereoselectively one methyl of the 1,1-dimethyl group on the cyclopropane ring of aristolanes and 2,3-secoaromadendrane to give C-12 primary alcohol and C-12 carboxylic acid. The possible metabolic pathway of the formation of new metabolites is discussed. The stereostructures of new metabolites were established by a combination of NMR spectroscopy including HMBC and NOESY, X-ray crystallographic analysis, and chemical reaction.

Terpenoids from the roots and rhizomes of Nardostachys chinensis.[Pubmed:16038567]

J Nat Prod. 2005 Jul;68(7):1131-3.

A new diterpene, 10-isopropyl-2,2,6-trimethyl-2,3,4,5-tetrahydronaphtha[1,8-bc]oxocine-5,11-diol (1), and a new monoterpene, 6-hydroxy-7-(hydroxymethyl)-4-methylenehexahydrocyclopenta[c]pyran-1(3H)-one, together with four known sesquiterpenes, delta1(10)-Aristolene-9beta-ol, debilon, nardosinone, and kanshone A, were isolated from the roots of Nardostachys chinensis. The structures of the new compounds were established on the basis of their spectroscopic data, and the structure of 1 was confirmed by X-ray crystallographic analysis.

Gansongon, a New Aristolane Ketone from Nardostachys chinesis Batalin and Structure Revision of an Aristolenol.[Pubmed:17269099]

Planta Med. 1987 Dec;53(6):556-8.

A new instable aristolane type sesquiterpene ketone, gansongone ( 1), was isolated from the fresh underground parts of NARDOSTACHYS CHINESIS Batalin (Valerianaceae), growing in the province Sichuan (China). The structure of 1 was elucidated by spectroscopic and chemical methods. The structure of the corresponding alcohol 2, which was also found in N. CHINENSIS and formerly regarded as 9-Aristolene-1alpha-ol ( 5) has to be revised to l(10)-Aristolene-9beta-ol ( 2) from results of 2D-NMR-spectroscopy and oxidation to 1. Besides 1 and 2, the following compounds have been identified in the ethanol extract of the fresh plant material of N. CHINENSIS: nardosinone, nardosinondiol, deoxonarchinol A, beta-sitosterol, oleanolic acid, ethyl beta- D-glucopyranoside.