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Sesquiterpen*

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https://read.qxmd.com/read/30901154/the-furan-shuffling-hypothesis-a-biogenetic-proposal-for-eremophilane-sesquiterpenoids
#1
Raphael Liffert, Nicolas Lardon, Anthony Linden, Karl Gademann
Based on the structural similarities of the recently isolated eremophilane-type sesquiterpenoids microsphaeropsisin B and C and the iso-eremophilane periconianone C, we suggest a revised biogenetic hypothesis for C8-C11 connected iso-eremophilanes. In this communication, we provide strong experimental evidence corroborating our biogenetic proposal. The first enantioselective total syntheses of microsphaeropsisin B and C have been achieved starting from a known intermediate, whose synthesis has been elaborated in the course of the total synthesis of periconianone A in our group, and in a total of 15 steps starting from γ-hydroxy carvone...
March 22, 2019: Angewandte Chemie
https://read.qxmd.com/read/30901009/divergent-total-syntheses-of-five-illudalane-sesquiterpenes-and-assignment-of-the-absolute-configuration
#2
Zhixiong Zeng, Yifan Zhao, Yandong Zhang
Concise, divergent total syntheses of five bioactive illudalane sesquiterpenes have been achieved. Our synthesis features an intermolecular [2+2+2] cycloaddition, and a lactone-directed aromatic C-H oxygenation to generate a temporary phenolic hydroxyl group which enables regioselective methylation. Furthermore, the absolute configuration of radulactone was assigned by chemical synthesis.
March 22, 2019: Chemical Communications: Chem Comm
https://read.qxmd.com/read/30897836/preparation-of-sesquiterpene-lactone-derivatives-cytotoxic-activity-and-selectivity-of-action
#3
María F Beer, Augusto E Bivona, Andrés Sánchez Alberti, Natacha Cerny, Guillermo F Reta, Víctor S Martín, José M Padrón, Emilio L Malchiodi, Valeria P Sülsen, Osvaldo J Donadel
Cancer is one of the most important causes of death worldwide. Solid tumors represent the great majority of cancers (>90%) and the chemotherapeutic agents used for their treatment are still characterized by variable efficacy and toxicity. Sesquiterpene lactones are a group of naturally occurring compounds that have displayed a diverse range of biological activities including cytotoxic activity. A series of oxygenated and oxy-nitrogenated derivatives ( 4 ⁻ 15 ) from the sesquiterpene lactones cumanin ( 1 ), helenalin ( 2 ), and hymenin ( 3 ) were synthesized...
March 20, 2019: Molecules: a Journal of Synthetic Chemistry and Natural Product Chemistry
https://read.qxmd.com/read/30897708/cle-10-from-carpesium-abrotanoides-l-suppresses-the-growth-of-human-breast-cancer-cells-mda-mb-231-in-vitro-by-inducing-apoptosis-and-pro-death-autophagy-via-the-pi3k-akt-mtor-signaling-pathway
#4
Li Tian, Fan Cheng, Lei Wang, Wen Qin, Kun Zou, Jianfeng Chen
BACKGROUND: The antitumor activity of CLE-10 (4-epi-isoinuviscolide), a sesquiterpene lactone compound, isolated from Carpesium abrotanoides L. has rarely been reported. The aim of this study is to investigate the antitumor activity of CLE-10 and give a greater explanation of its underlying mechanisms. METHODS: The cytotoxicity of CLE-10 was evaluated using MTT assay. Autophagy was detected by the formation of mRFP-GFP-LC3 fluorescence puncta and observed using transmission electron microscopy, while flow cytometry was employed to detect apoptosis...
March 20, 2019: Molecules: a Journal of Synthetic Chemistry and Natural Product Chemistry
https://read.qxmd.com/read/30890467/in-vitro-antileishmanial-and-cytotoxic-activities-of-nerolidol-are-associated-with-changes-in-plasma-membrane-dynamics
#5
Lais Alonso, Kelly de Souza Fernandes, Sebastião Antônio Mendanha Neto, Pablo José Gonçalves, Rodrigo Saar Gomes, Miriam Leandro Dorta, Antonio Alonso
The sesquiterpene nerolidol is a membrane-active compound that has demonstrated antitumor, antibacterial, antifungal and antiparasitic activities. In this study, we used electron paramagnetic resonance (EPR) spectroscopy and biophysical parameters determined via cell culture assays to study the mechanisms underlying the in vitro antileishmanial activity of nerolidol. The EPR spectra of a spin-labeled stearic acid indicated notable interactions of nerolidol with the cell membrane of Leishmania amazonensis amastigotes...
March 16, 2019: Biochimica et Biophysica Acta. Biomembranes
https://read.qxmd.com/read/30890423/commipholactam-a-a-cytotoxic-sesquiterpenoidal-lactam-from-resina-commiphora
#6
Si-Si Zhu, Da-Peng Qin, Shao-Xiang Wang, Cui Yang, Gan-Peng Li, Yong-Xian Cheng
Diverse terpenoids including a novel sesquiterpenoidal lactam, commipholactam A (1), and a structurally related new cadinane sesquiterpenoid, commiphorane H (2), a new eudesmane sesquiterpenoid, commiphorane I (4), a new guaiane sesquiterpenoid, commiphorane J (5), and two new nor-abietane diterpenoids, commiphoranes K1 and K2 (6 and 7) along with two known terpenoids (3 and 8), were isolated from Resina Commiphora. Their structures with absolute configurations were characterized by spectroscopic methods and calculated electronic circular dichroism (ECD)...
March 16, 2019: Fitoterapia
https://read.qxmd.com/read/30889936/antitrypanosomal-activity-of-sesquiterpene-lactones-from-helianthus-tuberosus-l-including-a-new-furanoheliangolide-with-an-unusual-structure
#7
Anna Galkina, Nico Krause, Mairin Lenz, Constantin G Daniliuc, Marcel Kaiser, Thomas J Schmidt
As part of our efforts to exploit the antitrypanosomal potential of sesquiterpene lactones (STL) from Helianthus tuberosus L. (Asteraceae), besides the known 4,15- iso -atriplicolide tiglate, -methacrylate and -isobutyrate, a hitherto unknown STL was isolated. Its structure was solved by extensive NMR measurements and confirmed by single crystal X-ray crystallography. This novel compound is a structural analog 4,15- iso -atriplicolide tiglate that possesses the same basic furanoheliangolide skeleton but differs in the position of the oxo function which is at C-2 instead of C-1, as well as in the fact that the oxygen atom of the furanoid ring is part of a hemiketal structure at C-3 and a double bond between C-5 and C-6...
March 18, 2019: Molecules: a Journal of Synthetic Chemistry and Natural Product Chemistry
https://read.qxmd.com/read/30888525/identification-of-spontaneous-mutation-for-broad-spectrum-brown-planthopper-resistance-in-a-large-long-term-fast-neutron-mutagenized-rice-population
#8
Wintai Kamolsukyeunyong, Siriphat Ruengphayak, Pantharika Chumwong, Lucia Kusumawati, Ekawat Chaichoompu, Watchareewan Jamboonsri, Chatree Saensuk, Kunyakarn Phoonsiri, Theerayut Toojinda, Apichart Vanavichit
BACKGROUND: The development of rice varieties with broad-spectrum resistance to insect pests is the most promising approach for controlling a fast evolving insect pest such as the brown planthopper (BPH). To cope with rapid evolution, discovering new sources of broad-spectrum resistance genes is the ultimate goal. RESULTS: We used a forward genetics approach to identify BPH resistance genes in rice (Oryza sativa L.) using double digest restriction site-associated DNA sequencing (ddRADseq) for quantitative trait loci (QTL)-seq of the backcross inbred lines (BILs) derived from a cross between the BPH-susceptible cultivar KDML105 and BPH-resistant cultivar Rathu Heenati (RH)...
March 19, 2019: Rice
https://read.qxmd.com/read/30887855/one-new-sterpurane-sesquiterpene-from-cultures-of-the-basidiomycete-pholiota-nameko
#9
Wan-Rong Niu, Cong-Liang Guo, Deng-Ji Lou, Rui-Ting Li, Qiao Xiang, Yu-Lin Zou, Xiu-Ming Cui, Xiao-Yan Yang
One new sterpurane sesquiterpene (1), named (3R,6S,7S,8R,10S)-3,7,14-trihydroxy-1-sterpurene was isolated from cultures of the basidiomycete Pholiota nameko. The structure of new compound was elucidated by extensive spectroscopic. Additionally, a single crystal X-ray diffraction not only confirmed the structure, but also determined the absolute configuration of the new compound. The compound was evaluated for cytotoxicity against five human cancer cell lines, but no significant cytotoxicity were found (IC50 values > 40 μM)...
March 19, 2019: Natural Product Research
https://read.qxmd.com/read/30887848/new-cadinane-sesquiterpenoids-from-mikania-micrantha
#10
Yao Zhang, You-Mei Zeng, You-Kai Xu, Shu-Qi Wu, Shen Li, Hai-Yan Tian, Yin Sheng
Chemical investigation of the aerial parts of Mikania micrantha led to the isolation of eight sesquiterpenoids and ten diterpenoids, including five cadinane sesquiterpenoids (1-5), three bisabolene sesquiterpenoids (6 - 8), nine ent-kaurane diterpenoids (9-17), and an abietane diterpenoid (18). Among them, 1 - 3 are new and feature a rare lactone or furan ring derived from C-6 isopropyl group side chain. Compound 18 was isolated from genus Mikania for the first time, and was also the first example of abietane-type diterpenoids from this plant...
March 19, 2019: Natural Product Research
https://read.qxmd.com/read/30884696/wild-edible-swiss-chard-leaves-beta-vulgaris-l-var-cicla-nutritional-phytochemical-composition-and-biological-activities
#11
Zeineb Mzoughi, Hassiba Chahdoura, Yasmine Chakroun, Montaña Cámara, Virginia Fernández-Ruiz, Patricia Morales, Habib Mosbah, Guido Flamini, Mejdi Snoussi, Hatem Majdoub
Nutritional, soluble carbohydrates and aroma volatile profiles of Tunisian wild Swiss chard leaves (Beta vulgaris L. var. cicla) have been characterized. The chemical composition of an ethanol chard leaves extract, as well as its in vitro antioxidant, α-amylase and α-glucosidase inhibition activities were carefully evaluated. The results of the proximate composition showed that total carbohydrate fraction, mainly as dietary fiber were the major macronutrient (2.43 g/100 g fw), being the insoluble dietary fiber the predominant fraction (2...
May 2019: Food Research International
https://read.qxmd.com/read/30884667/fixed-oil-from-seeds-of-narrow-leaved-ash-f-angustifolia-subsp-angustifolia-chemical-profile-antioxidant-and-antiproliferative-activities
#12
Alessandra Giardinieri, Rosario Schicchi, Anna Geraci, Sergio Rosselli, Filippo Maggi, Dennis Fiorini, Massimo Ricciutelli, Monica Rosa Loizzo, Maurizio Bruno, Deborah Pacetti
Fraxinus angustifolia subsp. angustifolia is a plant with an age-old use for the production of manna. However, it is also a valuable source of fixed oil rich-seeds. In the present study we examined the chemical and biological properties of this oil in order to support a possible application in foodstuffs, nutraceuticals and cosmetics. Fatty acid composition, volatile and phenolic substances were evaluated. Oleic and linoleic acid represented 45.5% and 50.0%, respectively, of the total fatty acid composition...
May 2019: Food Research International
https://read.qxmd.com/read/30877435/methylobacterium-oryzae-cbmb20-influences-photosynthetic-traits-volatile-emission-and-ethylene-metabolism-in-oryza-sativa-genotypes-grown-in-salt-stress-conditions
#13
Poulami Chatterjee, Arooran Kanagendran, Sandipan Samaddar, Leila Pazouki, Tong-Min Sa, Ülo Niinemets
Inoculation of endophytic Methylobacterium oryzae CBMB20 in salt-stressed rice plants improves photosynthesis and reduces stress volatile emissions due to mellowing of ethylene-dependent responses and activating vacuolar H+ -ATPase. The objective of this study was to analyze the impact of ACC (1-aminocyclopropane-1-carboxylate) deaminase-producing Methylobacterium oryzae CBMB20 in acclimation of plant to salt stress by controlling photosynthetic characteristics and volatile emission in salt-sensitive (IR29) and moderately salt-resistant (FL478) rice (Oryza sativa L...
March 15, 2019: Planta
https://read.qxmd.com/read/30875445/chemical-characterization-of-euphorbia-heterophylla-l-essential-oils-and-their-antioxidant-activity-and-allelopathic-potential-on-cenchrus-echinatus-l
#14
Abdelsamed I Elshamy, Ahmed M Abd El-Gawad, Abd El-Nasser G El Gendy, Abdulaziz M Assaeed
The genus Euphorbia attracted the attention of many researchers worldwide, from natural products, bioactivity, and ecological perspective. The essential oils (EOs) of Euphorbia heterophylla are poorly studied. Therefore the present study aimed to provide a detailed profile of the E. heterophylla EOs as well as determine thier antioxidant and allelopathic activities. The EOs from aerial parts of E. heterophylla were extracted using hydrodistillation and analyzed via GC-MS. The antioxidant activity was determined based on scavenging of the free radicle, 1,1-Diphenyl-2-picrylhydrazyl and H2O2...
March 15, 2019: Chemistry & Biodiversity
https://read.qxmd.com/read/30874370/isocostic-acid-a-promising-bioactive-agent-from-the-essential-oil-of-inula-viscosa-l-insights-from-drug-likeness-properties-molecular-docking-and-sar-analysis
#15
Ibrahim Aissa, Vijaykumar D Nimbarte, Afifa Zardi-Bergaoui, Mansour Znati, Guido Flamini, Roberta Ascrizzi, Hichem Ben Jannet
The chemical composition of the essential oil (LEO) and its volatile fractions (V1 -V10 ) collected during the hydrodistillation process every 15 min from the fresh leaves of I. viscosa (L.), growing in Tunisia, were analyzed by GC-FID and GC/MS. Eighty-two compounds, representing 90.9-99.4 % of the total samples, were identified. The crude essential oil (LEO) and its fractions (V1 -V10 ) were characterized by the presence of a high amount of oxygenated sesquiterpenes (82.7-95.8 %). Isocostic acid (1) was found to be the most abundant component (37...
March 15, 2019: Chemistry & Biodiversity
https://read.qxmd.com/read/30869892/cytotoxic-germacrane-type-sesquiterpene-lactones-from-the-whole-plant-of-carpesium-lipskyi
#16
Nan-Lin Zhu, Chunping Tang, Chenghui Xu, Chang-Qiang Ke, Ge Lin, Janar Jenis, Sheng Yao, Hongchun Liu, Yang Ye
Ten new sesquiterpene lactones, carlipsines A-J (1-10), and 12 known analogues (11-22) were isolated from the whole plant of Carpesium lipskyi. Their structures were elucidated by using 1D and 2D NMR and HRESIMS analyses, and their absolute configurations were confirmed by X-ray diffraction studies. All compounds were identified as germacranolides with diverse substructural features. Compounds 1-4 are 2,5-hemiacetal-linked germacranolides. Compounds 5 and 6 possess a 1,2-epoxy moiety. Compounds 7 and 8 represent unusual 1,5-hemiacetal-linked germacranolides...
March 14, 2019: Journal of Natural Products
https://read.qxmd.com/read/30868818/-a-new-eudesmane-type-sesquiterpene-from-cultivated-clerodendranthus-spicatus-in-hainan
#17
Hui-Qin Chen, Rong-Rong Zhang, Wen-Li Mei, Cai-Hong Cai, Cui-Juan Gai, Xu-Dong Yu, Hao-Fu Dai
Six compounds were isolated from the aerial part of cultivated Clerodendranthus spicatus in Hainan with various chromatographic techniques,and their structures were determined as:1-dehydroxy-1-oxo-rupestrinol(1),N-trans-feruloyltyramine(2),methyl 3,4-dihydroxyphenyllactate(3),caffein acid(4),methyl caffeate(5) and ethyl caffeate(6),via analysis of physicochemical properties and spectroscopic evidence.Compound 1 was a new compound,while compounds 2 and 3 were isolated from C.spicatus for the first time.Biological activity results showed that compounds 2-4 exhibited α-glucosidase inhibitory activity with different inhibition ratio...
January 2019: Zhongguo Zhong Yao za Zhi, Zhongguo Zhongyao Zazhi, China Journal of Chinese Materia Medica
https://read.qxmd.com/read/30868670/dietary-zerumbone-a-sesquiterpene-ameliorates-hepatotoxin-mediated-acute-and-chronic-liver-injury-in-mice
#18
Jong-Won Kim, Daram Yang, Hyeneui Jeong, Il Song Park, Min-Ho Lee, Chae Woong Lim, Bumseok Kim
Acute liver injury (ALI) is a life-threatening clinical syndrome. Long-lasting liver injury can lead to chronic hepatic inflammation and fibrogenic responses. Zerumbone (ZER), the main constituent of rhizomes of Zingiber zerumbet Smith, has a variety of functions including anticancer activity. We investigated the role of ZER on the progression of hepatotoxin-induced liver injury. Single or repeated injection of CCl4 was used to induce acute or chronic liver injury, respectively. Mice were orally administered with ZER (10, 50 mg/kg) during the experimental period...
March 14, 2019: Phytotherapy Research: PTR
https://read.qxmd.com/read/30866831/deficiency-of-valencene-in-mandarin-hybrids-is-associated-with-a-deletion-in-the-promoter-region-of-the-valencene-synthase-gene
#19
Qibin Yu, Ming Huang, Hongge Jia, Yuan Yu, Anne Plotto, Elizabeth A Baldwin, Jinhe Bai, Nian Wang, Frederick G Gmitter
BACKGROUND: Valencene is a major sesquiterpene in citrus oil and biosynthesized by valencene synthase (Cstps1; EC: 4.2.3.73) from the 15-carbon substrate farnesyl diphosphate. It is abundant in juice of some mandarins (e.g. Citrus reticulata Blanco cv. Fortune), however, it is undetectable in others (e.g. C. reticulata Blanco cv. Murcott), We have discovered that the Murcott mandarin Cstps1 gene expression is severely reduced. A previous genetic mapping study using an F1 population of Fortune × Murcott found that the segregation of valencene production in fruit exhibited a Mendelian inheritance ratio of 1:1...
March 13, 2019: BMC Plant Biology
https://read.qxmd.com/read/30864870/%C3%AE-caryophyllene-a-natural-sesquiterpene-attenuates-neuropathic-pain-and-depressive-like-behavior-in-experimental-diabetic-mice
#20
Dalia Samanta Aguilar-Ávila, Mario Eduardo Flores-Soto, Carolina Tapia-Vázquez, Omar Alonso Pastor-Zarandona, Rocío Ivette López-Roa, Juan Manuel Viveros-Paredes
Neuropathic pain (NP) is associated with chronic hyperglycemia and emotional disorders such as depression in diabetic patients, complicating the course of treatment. Drugs currently used to treat NP have undesirable side effects, so research on other natural sources has been required. β-caryophyllene (BCP), a natural sesquiterpene found in some food condiments and considered an agonist to cannabinoid receptor type 2, could have potential therapeutic effects to treat conditions such as NP and emotional disorders...
March 13, 2019: Journal of Medicinal Food
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