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Journal articles on the topic 'Polyacetylenes. Organic compounds'

Author: Grafiati

Published: 4 June 2021

Last updated: 15 February 2022

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1

Mi, Cheng-Neng, Hao Wang, Hui-Qin Chen, et al. "Polyacetylenes from the Roots of Swietenia macrophylla King." Molecules 24, no. 7 (2019): 1291. http://dx.doi.org/10.3390/molecules24071291.

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A phytochemical investigation of the roots of Swietenia macrophylla led to the isolation of seven polyacetylenes, including five new compounds (15) and two known ones (67). Their structures were elucidated by extensive spectroscopic analysis and detailed comparison with reported data. All the isolates were tested for their cytotoxicity against the human hepatocellular carcinoma cell line BEL-7402, human myeloid leukemia cell line K562, and human gastric carcinoma cell line SGC-7901. Compounds 1 and 6 showed moderate cytotoxicity against the above three human cancer cell lines with IC50 values

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2

Amegadzie, Albert K., William A. Ayer, and Lynne Sigler. "Unusual polyketides from the wood-decay fungus Sistotrema raduloides." Canadian Journal of Chemistry 73, no. 12 (1995): 2119–25. http://dx.doi.org/10.1139/v95-261.

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The metabolites of the wood rot decay fungus Sistotremaraduloides (P. Karst) Donk have been investigated and a new type of norpentaketide has been discovered. The compounds sistodiolynne (1), sistolynone (5), and sistopyrone (6) represent new carbon skeletons among natural products. The compounds are very unstable and readily polymerize in the presence of air to give black insoluble material. It has been shown by 13C NMR labelling experiments that they arise from five acetate units, and that a methyl carbon of one of the acetate units is lost during the biosynthesis. The structures were determ

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3

Muniyandi, Kasipandi, Blassan George, Thangaraj Parimelazhagan, and Heidi Abrahamse. "Role of Photoactive Phytocompounds in Photodynamic Therapy of Cancer." Molecules 25, no. 18 (2020): 4102. http://dx.doi.org/10.3390/molecules25184102.

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Cancer is one of the greatest life-threatening diseases conventionally treated using chemo- and radio-therapy. Photodynamic therapy (PDT) is a promising approach to eradicate different types of cancers. PDT requires the administration of photosensitisers (PSs) and photoactivation using a specific wavelength of light in the presence of molecular oxygen. This photoactivation exerts an anticancer effect via apoptosis, necrosis, and autophagy of cancer cells. Recently, various natural compounds that exhibit photosensitising potentials have been identified. Photoactive substances derived from medic

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4

Guan, Huanyu, Xiaomei Luo, Xiaoyan Chang, et al. "Identification of the Chemical Constituents of an Anti-Arthritic Chinese Medicine Wen Luo Yin by Liquid Chromatography Coupled with Mass Spectrometry." Molecules 24, no. 2 (2019): 233. http://dx.doi.org/10.3390/molecules24020233.

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Wen Luo Yin (WLY), a well-known traditional Chinese medicine formulation, has been used as a complementary therapy for the treatment of rheumatoid arthritis in clinical settings. However, the chemical constituents of WLY remain unclear. In this study, a high-performance liquid chromatography coupled with tandem mass spectrometry method was established to separate and comprehensively identify the chemical constituents of WLY. The analytes were eluted with a mobile phase of acetonitrile and 0.1% aqueous acetic acid. Mass detection was performed in both positive and negative ion mode. The MS/MS f

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5

Yang, Min, Xue Li, Lei Zhang, et al. "Ethnopharmacology, Phytochemistry, and Pharmacology of the Genus Glehnia: A Systematic Review." Evidence-Based Complementary and Alternative Medicine 2019 (December 14, 2019): 1–33. http://dx.doi.org/10.1155/2019/1253493.

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Glehnia littoralis Fr. Schmidt ex Miq, the sole species in the genus Glehnia (Apiaceae), has long been used in traditional Chinese medicine to treat fatigue, weakness, stomach-yin deficiency, lung heat, cough, dry throat, and thirst. Recently, G. littoralis has also been incorporated into a wide range of Chinese vegetarian cuisines. Based on the comprehensive information, advances in botany, known uses, phytochemistry, pharmacology, and toxicity of G. littoralis, we aim to highlight research gaps and challenges in studying G. littoralis as well as to explore its potential use in plant biotechn

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6

Kolomiets, Natalia Eduardovna, Roman Sergeevich Boev, Lyudmila Vladimirovna Zhalnina, et al. "CHEMICAL COMPOSITION AND BIOLOGICAL ACTIVITY OF METABOLITES OF SPECIES OF THE GENUS ARCTIUM L." chemistry of plant raw material, no. 2 (June 10, 2021): 29–57. http://dx.doi.org/10.14258/jcprm.2021028315.

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The review summarizes information from the literature on the distribution, study of the composition and biological activity of metabolites, total extracts of plants of the genus Arctium L. of the world flora. In Russia, the roots of three species are allowed to be harvested and used: A. lappa, A. tomentosum, A. minus. To date, the most studied composition of metabolites and pharmacological properties of great burdock. The chemical composition of A. atlanticum, A. debrayi, A. leiobardanum, A. neumani, A. platylepis, A. pseudarctium, A. sardaimionense, A. scanicum, A. nemorosum and A. palladini

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7

Christensen, Lars P., and Martin Jensen. "Biomass and content of ginsenosides and polyacetylenes in American ginseng roots can be increased without affecting the profile of bioactive compounds." Journal of Natural Medicines 63, no. 2 (2008): 159–68. http://dx.doi.org/10.1007/s11418-008-0307-3.

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8

Shiono, Yoshihito, Masatomo Haga, Hiromasa Koyama, Testuya Murayama, and Takuya Koseki. "Antifungal Activity of a Polyacetylene against the Fungal Pathogen of Japanese Oak from the Liquid Culture of the Edible Mushroom, Hypsizygus marmoreus." Zeitschrift für Naturforschung B 68, no. 3 (2013): 293–95. http://dx.doi.org/10.5560/znb.2013-2289.

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Three polyacetylene compounds, 1, 2 and 3, have been isolated from the organic extract of a liquid culture of Hypsizygus marmoreus (Peck.) Bigelow (Japanese name: Bunashimeji). The structures of 1, 2 and 3 were determined by using spectroscopic methods. Compound 3 is new, and was identified as 8(E)-decene-4,6-diyn-1,2,10-triol. Compound 1 exhibits antifungal activity against the pathogenic fungus Raffaelea quercivora responsible for Japanese oak wilt

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9

Li, Liang-Bo, Guang-Da Xiao, Wei Xiang, Xing Yang, Ke-Xin Cao, and Rong-Shao Huang. "Novel Substituted Thiophenes and Sulf-Polyacetylene Ester from Echinops ritro L." Molecules 24, no. 4 (2019): 805. http://dx.doi.org/10.3390/molecules24040805.

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Three new substituted bithiophenes (1–3), and one new sulf-polyacetylene ester, ritroyne A (16) were isolated from the whole plant of Echinops ritro together with twelve known substituted thiophenes. The structures were elucidated on the basis of extensive spectroscopic analysis including 1D and 2D NMR as well as MS. Furthermore, the absolute configuration of ritroyne A (16) was established by computational methods. In bioscreening experiments, four compounds (2, 4, 12, 14) showed similar antibacterial activity against Staphylococcus aureus ATCC 2592 with levofloxacin (8 µg/mL). Five compounds

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10

Chen, Wen-Hao, Xing-Ming Ma, Quan-Xiang Wu, and Yan-Ping Shi. "Chemical-constituent diversity of Tridax procumbens." Canadian Journal of Chemistry 86, no. 9 (2008): 892–98. http://dx.doi.org/10.1139/v08-097.

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Three new phytochemicals, a polyacetylene, 1,2-dihydrodendroarboreol B (1), an ionone derivative, (3S,5R,6S,7E)-3-tetradecanoate-5,6-epoxy-β-ionone (4), and a flavonol diglycoside, quercetagetin-3,6,4′-trimethoxy-7-O-neohesperidoside (38), along with 35 known compounds with diverse structures, were isolated from the EtOH extract of the aerial parts of Tridax procumbens. The structures of 1, 4, and 38 were determined on the basis of comprehensive methods including UV, IR, NMR, HR-ESI-MS, and CD, and by comparison of the spectroscopic data with those reported for structurally related compounds.

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11

Wang, Bang-Yan, Chen-Hao Zhu, Xue-Qiong Yang та ін. "Inducing Intermediates in Biotransformation of Natural Polyacetylene and A Novel Spiro-γ-Lactone from Red Ginseng by Solid Co-Culture of Two Gut Chaetomium globosum and The Potential Bioactivity Modification by Oxidative Metabolism". Molecules 25, № 5 (2020): 1216. http://dx.doi.org/10.3390/molecules25051216.

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The ω-hydroxyl-panaxytriol (1) and ω-hydroxyl-dihydropanaxytriol (2)—are rare examples of polyacetylene metabolism by microbial transformation, and these new metabolites (1, 2) from fermented red ginseng (FRG) by solid co-culture induction of two Chaetomium globosum should be the intermediates of biotransformation of panaxylactone (metabolite A). The metabolic pathway of panaxylactone was also exhibited. The ingredients of red ginseng (RG) also induced the production of rare 6/5/5 tricyclic ring spiro-γ-lactone skeleton (3). The ω-hydroxylation of new intermediates (1, 2) decreases cytotoxicit

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12

Kim, Bo-Ram, Sunil Paudel, Joo-Won Nam, Chang Jin, Ik-Soo Lee, and Ah-Reum Han. "Constituents of Coreopsis lanceolata Flower and Their Dipeptidyl Peptidase IV Inhibitory Effects." Molecules 25, no. 19 (2020): 4370. http://dx.doi.org/10.3390/molecules25194370.

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A new polyacetylene glycoside, (5R)-6E-tetradecene-8,10,12-triyne-1-ol-5-O-β-glucoside (1), was isolated from the flower of Coreopsis lanceolata (Compositae), together with two known compounds, bidenoside C (10) and (3S,4S)-5E-trideca-1,5-dien-7,9,11-triyne-3,4-diol-4-O-β-glucopyranoside (11), which were found in Coreopsis species for the first time. The other known compounds, lanceoletin (2), 3,2′-dihydroxy-4-3′-dimethoxychalcone-4′-glucoside (3), 4-methoxylanceoletin (4), lanceolin (5), leptosidin (6), (2R)-8-methoxybutin (7), luteolin (8) and quercetin (9), were isolated in this study and r

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13

Kim, Myeong, Ji Kim, Ahmed Syed, Young-Mi Kim, Kevin Choe, and Chul Kim. "Application of Centrifugal Partition Chromatography for Bioactivity-Guided Purification of Antioxidant-Response-Element-Inducing Constituents from Atractylodis Rhizoma Alba." Molecules 23, no. 9 (2018): 2274. http://dx.doi.org/10.3390/molecules23092274.

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Activity-guided separation of antioxidant response element (ARE)-inducing constituents from the rhizomes of Atractylodis Rhizoma Alba was performed by the combination of centrifugal partition chromatography (CPC) and an ARE luciferase reporter assay. From 3 g of the active n-hexane fraction, one polyacetylene, (6E,12E)-tetradeca-6,12-dien-8,10-diyne-1,3-diyl diacetate (47.3 mg), and two sesquiterpenes, atractylenolide I (40.9 mg), and selina-4(14),7(11)-dien-8-one (6.0 mg) were successfully isolated by CPC with n-hexane–ethyl acetate–methanol–water (8:2:8:2, v/v). The chemical structures of th

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14

Basnet, Buddha Bahadur, Baosong Chen, Yerlan Melsuly Suleimen, et al. "Cytotoxic Secondary Metabolites from the Endolichenic Fungus Hypoxylon fuscum." Planta Medica 85, no. 13 (2019): 1088–97. http://dx.doi.org/10.1055/a-0957-3567.

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AbstractAs part of our search for new cytotoxic and antimicrobial natural products from endolichenic fungi, 19 compounds including 1 new 10-member lactone (2), 1 new polyacetylene glycoside (3), 1 new brasilane-type sesquiterpenoid glycoside (4), and 2 isobenzofuran-1(3H)-one derivatives (5 and 6) were isolated from the solid culture of the endolichenic fungus Hypoxylon fuscum. Their structures were unambiguously elucidated by NMR spectroscopic data, MS, ECD (electronic circular dichroism) calculation, and chemical methods. The cytotoxic effects on K562, SW480, and HEPG2 cell lines and the ant

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15

Meng, He, Guo-Yu Li, Rong-Hua Dai, et al. "Two new polyacetylenic compounds fromAtractylodes chinensis(DC.) Koidz." Journal of Asian Natural Products Research 13, no. 4 (2011): 346–49. http://dx.doi.org/10.1080/10286020.2011.557662.

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16

Park, Hae Eun, Seok-Young Lee, Sun-Hee Hyun, Da Yeon Kim, Philip J. Marriott, and Hyung-Kyoon Choi. "Gas Chromatography/Mass Spectrometry-Based Metabolic Profiling and Differentiation of Ginseng Roots According to Cultivation Age Using Variable Selection." Journal of AOAC INTERNATIONAL 96, no. 6 (2013): 1266–72. http://dx.doi.org/10.5740/jaoacint.12-195.

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Abstract Ginseng roots are an important herbal resource worldwide, and the adulteration of ginseng with age is recognized as a serious problem. It is therefore crucial to develop objective criteria or standard protocols for differentiating ginseng root samples according to their cultivation age. The reported study used GC/MS combined with multivariate statistical analysis with variable selection to obtain metabolic profiling and an optimal partial least squares-discriminant analysis (PLS-DA) model for the differentiation of ginseng according to cultivation age. Relative levels of various metab

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17

Fiandanese, Vito, Daniela Bottalico, Giuseppe Marchese, and Angela Punzi. "Synthesis of polyacetylenic montiporic acids by means of organosilicon compounds." Journal of Organometallic Chemistry 690, no. 12 (2005): 3004–8. http://dx.doi.org/10.1016/j.jorganchem.2005.03.033.

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18

Wang, Haixing, Yuanyuan Li, Yeqing Huang, Chunyan Zhao, and Hon-Yeung Cheung. "Chemical Profiling of Lobelia chinensis with High-Performance Liquid Chromatography/Quadrupole Time-of-Flight Mass Spectrometry (HPLC/Q-TOF MS) Reveals Absence of Lobeline in the Herb." Molecules 23, no. 12 (2018): 3258. http://dx.doi.org/10.3390/molecules23123258.

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Lobelia chinensis is a kind of herbal medicine widely distributed and used in Asia. The chemical components of this herb, however, have not been well studied until now. Lobeline, as an essential and famous bioactive compound in Lobelia genus, has been assumed to be present in L. chinensis. In order to ascertain its presence and, more importantly, proper use of this herb, chemical profiling this herb with highly sensitive and high-resolution analytical mass spectrometry was applied. In this study, high-performance liquid chromatography coupled with quadrupole time-of-flight mass spectrometry (H

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19

Liang, Junya, Ci Song, and Jianping Deng. "Optically Active Microspheres Constructed by Helical Substituted Polyacetylene and Used for Adsorption of Organic Compounds in Aqueous Systems." ACS Applied Materials & Interfaces 6, no. 21 (2014): 19041–49. http://dx.doi.org/10.1021/am504943x.

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20

Ayer, William A., and Peter Craw. "Metabolites of the fairy ring fungus, Marasmiusoreades. Part 2. Norsesquiterpenes, further sesquiterpenes, and agrocybin." Canadian Journal of Chemistry 67, no. 9 (1989): 1371–80. http://dx.doi.org/10.1139/v89-210.

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The fungus Marasmiusoreades has previously been reported to produce the sesquiterpenes marasmone (1), anhydromarasmone (2), isomarasmone (3), and dihydromarasmone (4) when grown in liquid culture. We report herein several other sesquiterpene metabolites of the same skeleton but with differing oxidation patterns. The norsesquiterpenes O-formyloreadone (15a), 3α-hydroxyoreadone (15c), and dehydrooreadone (17b) are also reported. It is suggested that the formyl group in 15a is derived biogenetically from C-15 of a precursor sesquiterpene. Oxidation of 1α, 15-dihydroxymarasmene (13a), one of the n

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21

Pan, Weidong, Yongmin Zhang, Bixue Xu, Peixue Cao, and Guangyi Liang. "Two new naturally occurring optical polyacetylene compounds from Torricellia angulata var intermedia and the determination of their absolute configurations." Natural Product Research 20, no. 12 (2006): 1098–104. http://dx.doi.org/10.1080/14786410600743951.

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22

Chang, Shu-Lin, Cicero Lee-Tian Chang, Yi-Ming Chiang, et al. "Polyacetylenic Compounds and Butanol Fraction fromBidens pilosacan Modulate the Differentiation of Helper T Cells and Prevent Autoimmune Diabetes in Non-Obese Diabetic Mice." Planta Medica 70, no. 11 (2004): 1045–51. http://dx.doi.org/10.1055/s-2004-832645.

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23

Leonti, M., J. Gertsch, L. Casu, et al. "Bioactivity guided and random isolation of polyacetylenic compounds from Seseli praecox." Planta Medica 75, no. 09 (2009). http://dx.doi.org/10.1055/s-0029-1234333.

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