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Meng Jin, Zhixin Xiao, Shanshan Zhang, Xiao Men, Xia Li, Baoyue Zhang, Tianxia Zhou, Chung-Der Hsiao, Kechun Liu
α-Bisabolol, an unsaturated monocyclic sesquiterpene alcohol, is a common ingredient in many pharmaceuticals and personal care products (PPCPs). Despite being widely used, little is known about its toxic effects on organisms and aquatic environment. In this study, we investigated the developmental toxicity of α-Bisabolol, especially its effects on the cardiac development using zebrafish embryos as a model. Embryos at 4 h post-fertilization (hpf) were exposed to 10, 30, 50, 70, 90, and 100 μM α-Bisabolol until 144 hpf...
December 8, 2018: Chemosphere
Marcela Nouzova, Crisalejandra Rivera-Pérez, Fernando G Noriega
The juvenile hormones (JHs) are a family of insect acyclic sesquiterpenoids produced by the corpora allata (CA), a pair of endocrine glands connected to the brain. They are involved in the regulation of development, reproduction, behavior, caste determination, diapause, stress response, and numerous polyphenisms. In the post-genomics era, comprehensive analyses using functional 'omics' technologies such as transcriptomics, proteomics and metabolomics have increased our understanding of the activity of the minute CA...
October 2018: Current Opinion in Insect Science
Antonella Di Sotto, Patrizia Paolicelli, Martina Nardoni, Lorena Abete, Stefania Garzoli, Silvia Di Giacomo, Gabriela Mazzanti, Maria Antonietta Casadei, Stefania Petralito
The natural sesquiterpene β-caryophyllene (CRY) has been highlighted to possess interesting pharmacological potentials, particularly due to its chemopreventive and analgesic properties. However, the poor solubility of this sesquiterpene in aqueous fluids can hinder its uptake into cells, resulting in inconstant responses of biological systems, thus limiting its application. Therefore, identifying a suitable pharmaceutical form for increasing CRY bioavailability represents an important requirement for exploiting its pharmacological potential...
December 13, 2018: Pharmaceutics
Yong Joo Park, Hailing Zheng, Jong Hwan Kwak, Kyu Hyuck Chung
Estrogenic activity-oriented fractionation and purification of methanol extract from the rhizome of Cyperus rotundus, a well-known traditional herbal medicine, led to the isolation of six sesquiterpenes. 4α,5α-Oxidoeudesm-11-en-3-one (2) and cyper-11-ene-3,4-dione (3) together with four known sesquiterpenes, cyperotundone (1), caryophyllene α-oxide (4), α-cyperone (5), and isocyperol (6) were obtained from the hexane and dichloromethane fractions. Compounds 2 and 3 were newly isolated from natural resources in particular...
January 2019: Biomedicine & Pharmacotherapy, Biomédecine & Pharmacothérapie
Yijun Zhong, Ling Li, Xiaolong Hao, Xueqing Fu, Yanan Ma, Lihui Xie, Qian Shen, Sadaf Kayani, Qifang Pan, Xiaofen Sun, Kexuan Tang
Artemisinin is well known for its irreplaceable curative effect on the devastating parasitic disease, Malaria. This sesquiterpenoid is specifically produced in Chinese traditional herbal plant Artemisia annua. Earlier studies have shown that phytohormone abscisic acid (ABA) plays an important role in increasing the artemisinin content, but how ABA regulates artemisinin biosynthesis is still poorly understood. In this study, we identified that AaABF3 encoded an ABRE (ABA-responsive elements) binding factor. qRT-PCR analysis showed that AaABF3 was induced by ABA and expressed much higher in trichomes where artemisinin is synthesized and accumulated...
2018: Frontiers in Plant Science
Bin-Yuan Hu, Da-Peng Qin, Shao-Xiang Wang, Jing-Jing Qi, Yong-Xian Cheng
A novel sesquiterpene dimer, spirocommiphorfuran A ( 1 ); two new cadinane sesquiterpenoids, commiphorenes A ( 2 ) and B ( 3 ); along with three known terpenoids ( 4 ⁻ 6 ), were isolated from Resina Commiphora . The structures of these new compounds were characterized by NMR, HRESIMS, quantum chemical computation, and X-ray diffraction analysis. Compound 1 features a 7-oxabicyclo[2.2.1]heptane-2-ene core, representing the first example of germacrane-type sesquiterpene dimer fused via a spiro ring system. Compound 2 is a novel sesquiterpene with a completely new carbon skeleton, which is characteristic of an additional carbon attaching to the cadinane backbone via a carbon⁻carbon bond...
December 7, 2018: Molecules: a Journal of Synthetic Chemistry and Natural Product Chemistry
Pablo Luis B Figueiredo, Laine C Pinto, Jamile S da Costa, Alberto Ray C da Silva, Rosa Helena V Mourão, Raquel C Montenegro, Joyce Kelly R da Silva, José Guilherme S Maia
ETHNOPHARMACOLOGICAL RELEVANCE: Oils and extracts of Eugenia uniflora have been reported as antimicrobial, antifungal, antinociceptive, antiprotozoal, antioxidant and cytotoxic. AIM OF THE STUDY: The oils of five specimens (E1 to E5) that occur in the Brazilian Amazon were extracted, analyzed for their chemical composition, and submitted to antioxidant and cytotoxic assays. MATERIAL AND METHODS: Oils were hydrodistilled, analyzed by GC and GC-MS, and submitted to PCA and HCA analyses...
December 10, 2018: Journal of Ethnopharmacology
Xu-Jie Qin, Ling-Yu Jin, Qian Yu, Hui Liu, Afsar Khan, Huan Yan, Xiao-Jiang Hao, Lin-Kun An, Hai-Yang Liu
Ten new formyl-phloroglucinol-terpene meroterpenoids, eucalypglobulusals A-J (1-10), and ten known analogues were isolated from  Eucalyptus globulus fruits. The structures of 1-10 were determined by spectroscopic analysis, while their absolute configurations were established using calculated and experimental electronic circular dichroism (ECD) spectra. Eucalypglobulusal A was assigned as a new formyl-phloroglucinol-terpene meroterpenoid with a rearranged sesquiterpene skeleton, and an aldol condensation between C-3 and C-5 of the germacrene C moiety was proposed to be a key step in its putative biosynthetic pathway...
December 13, 2018: Journal of Natural Products
Wei Chen, Ping Li, Yi Liu, Yu Yang, Xueting Ye, Fangyi Zhang, Hang Huang
BACKGROUND: Prostate cancer is one of the most commonly diagnosed cancers in men worldwide. Currently available therapies for metastatic prostate cancer are only marginally effective. Therefore, new therapeutic agents are urgently needed to improve patient outcome. Isoalantolactone (IATL), an active sesquiterpene naturally present in many vegetables and medicinal plants, is known to induce cell death and apoptosis in various cancer cell lines. Nevertheless, antitumor mechanisms initiated by IATL in cancer cells have not been fully defined...
December 12, 2018: Journal of Experimental & Clinical Cancer Research: CR
Hui-Xiang Yang, Hong-Lian Ai, Tao Feng, Wen-Xuan Wang, Bin Wu, Yong-Sheng Zheng, Huan Sun, Juan He, Zheng-Hui Li, Ji-Kai Liu
Two trichothecene sesquiterpenoids, trichothecrotocins A (1) and B (2), and a merosesquiterpenoid racemate, (±)-trichothecrotocin C (3), were obtained from potato endophytic fungus Trichothecium crotocinigenum by bioguided isolation. Their structures were elucidated by extensive spectroscopic methods, electronic circular dichroism calculations, and single-crystal X-ray diffraction. Compounds 1 and 2 are trichothecenes possessing new ring systems. Compound 3 possesses a novel 6/6-5/5/5 fused ring system. Compounds 1-3 showed antiphytopathogenic activities with MIC values of 8-128 μg/mL...
December 12, 2018: Organic Letters
Guo Wei, Qidong Jia, Xinlu Chen, Tobias G Köllner, Debashish Bhattacharya, Gane Ka-Shu Wong, Jonathan Gershenzon, Feng Chen
Red algae (Rhodophyta) and land plants belong to the monophyletic clade Archaeplastida and taxa of both groups are rich producers of terpene secondary metabolites. The terpene carbon skeletons of land plants are made by two types of terpene synthases: typical plant terpene synthases and microbial-type terpene synthases (MTPSLs); however, terpene biosynthesis in red algae is poorly understood. By systematic sequence analysis of seven genomes and 34 transcriptomes of red algae, MTPSL homologs were identified within one genome and two transcriptomes, whereas no homolog of typical plant terpene synthase genes was found...
December 11, 2018: Plant Physiology
W J F Acton, W Jud, A Ghirardo, G Wohlfahrt, C N Hewitt, J E Taylor, A Hansel
The emissions of BVOCs from oilseed rape (Brassica napus), both when the plant is exposed to clean air and when it is fumigated with ozone at environmentally-relevant mixing ratios (ca. 135 ppbv), were measured under controlled laboratory conditions. Emissions of BVOCs were recorded from combined leaf and root chambers using a recently developed Selective Reagent Ionisation-Time of Flight-Mass Spectrometer (SRI-ToF-MS) enabling BVOC detection with high time and mass resolution, together with the ability to identify certain molecular functionality...
2018: PloS One
Yang He, Fu Peng, Cao Deng, Liang Xiong, Zi-Yan Huang, Ruo-Qi Zhang, Meng-Jia Liu, Cheng Peng
The Lamiales order presents highly varied genome sizes and highly specialized life strategies. Patchouli, Pogostemon cablin (Blanco) Benth. from the Lamiales, has been widely cultivated in tropical and subtropical areas of Asia owing to high demand for its essential oil. Here, we generated ~681 Gb genomic sequences (~355X coverage) for the patchouli, and the assembled genome is ~1.91 Gb and with 110,850 predicted protein-coding genes. Analyses showed clear evidence of whole-genome octuplication (WGO) since the pan-eudicots γ triplication, which is a recent and exclusive polyploidization event and occurred at ~6...
December 11, 2018: Scientific Data
Gui-Min Xue, Dong-Rong Zhu, Chao Han, Xiao-Bing Wang, Jian-Guang Luo, Ling-Yi Kong
Artemisianins A-D (1-4), four stereoisomers of sesquiterpenoid dimers, forming via [4+2] cycloaddition from a 1, 10-seco-guaianolide dienophile and a guaianolide diene, along with two biosynthetically related precurors 5 and 6, were isolated from the famous traditional Chinese medicine Artemisia argyi. The structures of 1-4, including their absolute configurations, were elucidated by extensive spectroscopic data and ECD/TDDFT calculation analysis. Compounds 1-4 exhibited cytotoxicity with IC50 values ranging from 7...
December 1, 2018: Bioorganic Chemistry
Gui-Min Xue, Dong-Rong Zhu, Tian-Yu Zhu, Xiao-Bing Wang, Jian-Guang Luo, Ling-Yi Kong
Investigation into the chemical diversity of Artemisia argyi led to the discovery of four new (1-4) and one known (5) guaianolide sesquitenpenoid dimers linked via ester bond, and five other known mono-sesquiterpenoids (6-10). Their structures were determined via extensive spectroscopic data, and the absolute configurations of these compounds were elucidated by calculated ECD analysis and chemical method. The dimeric sesquiterpenoids exhibited NO production inhibitory activity with IC50 values ranging from 7...
December 4, 2018: Fitoterapia
Tao Yang, Siyi Wang, Hui Zheng, Li Wang, Dan Liu, Xuanqin Chen, Rongtao Li
Multi-drug resistance (MDR) is one of the dominant reasons for the failure of cancer chemotherapy. P-glycoprotein (P-gp) over-expression in the plasma membrane of drug-resistant tumor cells promotes the efflux of chemotherapeutic agents and plays a significant role in MDR. Several investigations have suggested that dihydro-β-agarofuran sesquiterpenes are the potential modulators of MDR. However, their cellular mechanism in regulating P-gp has not been fully explored. Seven dihydro-β-agarofuran sesquiterpenes (1-7) from Tripterygium hypoglaucum was evaluated for the chemoreversal activity of HepG2/Adr cells...
December 6, 2018: Biochemical and Biophysical Research Communications
Payal Gupta, Meenakshi Sharma, Neha Arora, Vikas Pruthi, Krishna Mohan Poluri
BACKGROUND: Farnesol is an acyclic sesquiterpene alcohol, endogenously synthesized via the ergosterol pathway. It is a quorum sensing molecule (QSM) that was first discovered in C. albicans, and is involved in the inhibition of hyphae formation. METHODS: This review focuses on the comprehensive details of occurrence, chemical/biological synthesis of farnesol and its derivatives, and the factors involved in regulation of its production. Further, the review also presents their cellular functions and diversified biomedical applications...
December 10, 2018: Current Topics in Medicinal Chemistry
Matthew L Condakes, Luiz F T Novaes, Thomas J Maimone
Since the elucidation of the structure of anisatin in the late 1960s, sesquiterpene lactones from various Illicium species of plants have captivated synthetic chemists worldwide, resulting in a large body of synthetic work. In particular, Illicium sesquiterpenes containing the seco-prezizaane carbon framework have seen immense interest in recent years owing to desirable structural and medicinal attributes. This synopsis will focus on recently developed synthetic strategies to access these compact, highly oxidized terpenoids...
December 7, 2018: Journal of Organic Chemistry
José Luis Rodríguez-Chávez, Francisco Franco-Navarro, Guillermo Delgado
BACKGROUND: Nacobbus aberrans (Tylenchida: Pratylenchidae) is one of the main plant-parasitic nematodes species that affects crops in Mexico, generating substantial economic losses. Traditionally, the control of the nematodes is carried out using chemical products; however, research efforts are presently focused on the search for new methods for the control of this pest. Natural products derived from plants are an alternative for the control of populations of plant-parasitic nematodes...
December 7, 2018: Pest Management Science
Shabeeba M Ashraf, Jomon Sebastian, Krishnan Rathinasamy
OBJECTIVES: The aim of this study was to elucidate the antimitotic mechanism of zerumbone and to investigate its effect on the HeLa cells in combination with other mitotic blockers. MATERIALS AND METHODS: HeLa cells and fluorescence microscopy were used to analyse the effect of zerumbone on cancer cell lines. Cellular internalization of zerumbone was investigated using FITC-labelled zerumbone. The interaction of zerumbone with tubulin was characterized using fluorescence spectroscopy...
December 7, 2018: Cell Proliferation
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