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Journal articles on the topic 'Goniothalamin'

Author: Grafiati

Published: 4 June 2021

Last updated: 6 February 2022

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1

Goh, SH, GCL Ee, CH Chuah, and C. Wei. "Styrylpyrone Derivatives From Goniothalamus dolichocarpus." Australian Journal of Chemistry 48, no. 2 (1995): 199. http://dx.doi.org/10.1071/ch9950199.

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Styrylpyrone derivatives (+)-goniothalamin (1), (+)-goniothalamin epoxide (2) and (–)-iso-5-deoxygoniopypyrone (4b), and the acetogenin (+)-annonacin (7) were bioactive compounds isolated from the stem bark of Goniothalamus dolichocarpus. The stereochemical relationships for (+)-goniothalamin epoxide (2), (+)-isogoniothalamin epoxide (3) and (+)-goniodiol diacetate (6) were established by chemical transformations and single-crystal X-ray crystallography.

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2

Takemura, Tomoko, Tsunashi Kamo, Raihan Ismil, et al. "Plant Growth Inhibitor from the Malaysian Medicinal Plant Goniothalamus andersonii and Related Species." Natural Product Communications 7, no. 9 (2012): 1934578X1200700. http://dx.doi.org/10.1177/1934578x1200700924.

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A crude methanol extract of Goniothalamus andersonii J. Sinclair strongly inhibited elongation of lettuce ( Lactuca sativa L.) radicles. We conducted bioassay-guided purification of G. andersonii bark extract and obtained goniothalamin as the major bioactive compound. Its EC50 values against elongation of lettuce radicles and hypocotyls were 50 and 125 μmol L−1, respectively. Among the six species tested, timothy was the most sensitive to goniothalamin. Quantification of this compound in other Goniothalamus species suggested that the plant inhibitory activity of this genus is explainable by go

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3

Wasano, Naoya, Tomoko Takemura, Raihan Ismil, Baki Bakar, and Yoshiharu Fujii. "Transcriptomic Evaluation of Plant Growth Inhibitory Activity of Goniothalamin from the Malaysian Medicinal Plant Goniothalamus andersonii." Natural Product Communications 10, no. 5 (2015): 1934578X1501000. http://dx.doi.org/10.1177/1934578x1501000507.

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Goniothalamin produced by the Malaysian medicinal plant, Goniothalamus andersonii J. Sinclair, strongly inhibits plant growth. However, its mode of action has not been characterized at the gene expression level. We conducted DNA microarray assay to analyze the changes in early gene responses of Arabidopsis thaliana seedlings. After a 6-h exposure to goniothalamin, we observed an upregulation of genes highly associated with heat response, and 22 heat shock protein ( AtHSP) genes were upregulated more than 50 fold. Together with these genes, we observed upregulation of the genes related to oxida

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4

Ahmad, Fasihuddin Badruddin, Wan Ahmad Tukol, Siraj Omar, and Atan Mohd Sharif. "5-Acetyl goniothalamin, a styryl dihydropyrone from Goniothalamus uvaroides." Phytochemistry 30, no. 7 (1991): 2430–31. http://dx.doi.org/10.1016/0031-9422(91)83674-a.

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5

Sangrueng, Kallaya, Saksri Sanyacharernkul, Sirinapa Nantapap, Narong Nantasaen, and Wilart Pompimon. "Bioactive Goniothalamin from Goniothalamus tapis with Cytotoxic Potential." American Journal of Applied Sciences 12, no. 9 (2015): 650–53. http://dx.doi.org/10.3844/ajassp.2015.650.653.

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6

Semprebon, SC, Â. de Fátima, SR Lepri, D. Sartori, LR Ribeiro, and MS Mantovani. "(S)-Goniothalamin induces DNA damage, apoptosis, and decrease in BIRC5 messenger RNA levels in NCI-H460 cells." Human & Experimental Toxicology 33, no. 1 (2013): 3–13. http://dx.doi.org/10.1177/0960327113491506.

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(R)-Goniothalamin (R-GNT) is a secondary metabolite isolated from the plants of the genus Goniothalamus. This molecule has attracted the attention of researchers because of its selective cytotoxicity against tumor cells and its ability to induce apoptosis. (S)-Goniothalamin (S-GNT) is a synthetic enantiomer of R-GNT, and its mechanism of action is largely unknown. In this study, we investigated the activity of S-GNT in a human non-small cell lung cancer NCI-H460 cells. We observed that the cells exposed to this compound exhibited cytotoxicity in a concentration-dependent manner. Based on the d

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7

Harsh, Philip, and George A. O'Doherty. "De novo asymmetric syntheses of (+)-goniothalamin, (+)-goniothalamin oxide, and 7,8-bis-epi-goniothalamin using asymmetric allylations." Tetrahedron 65, no. 26 (2009): 5051–55. http://dx.doi.org/10.1016/j.tet.2009.03.097.

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8

Peng, Xiaoshui, Anpai Li, Hao Shen, Tongxing Wu, and Xinfu Pan. "Facile Enantioselective Synthesis of 6R-(+)-Goniothalamin and (6R, 7R, 8R)-(+)-Goniothalamin Oxide." Journal of Chemical Research 2002, no. 7 (2002): 330–32. http://dx.doi.org/10.3184/030823402103172176.

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Facile enantioselective total syntheses of 6R-(+)-goniothalamin 1 and (6R, 7R, 8R)-(+)-goniothalamin oxide 2 were achieved through the Sharpless kinetic resolution of racemic secondary 2- furylmethanol 3 in a short synthetic route.

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9

Rasol, Nurulfazlina Edayah, Fasihuddin Badruddin Ahmad, Chun-Wai Mai, et al. "Styryl Lactones from Roots and Barks Goniothalamus lanceolatus." Natural Product Communications 13, no. 12 (2018): 1934578X1801301. http://dx.doi.org/10.1177/1934578x1801301203.

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A new styryl lactone, 5 R,6 R-5-hydroxy-6-styryltetrahydropyrane-2-one 2 was isolated from the roots of an endemic Goniothalamus lanceolatus Miq. of Sarawak, Malaysia. Furthermore, seven previously undescribed diastereomers, 5 R,6 R-5-hydroxygoniothalamin 3, 5 R,6 R-5-acetylgoniothalamin 4, 6 S,7 S,8 S-goniodiol-7-monoacetate 5, 6 S,7 S,8 S-goniodiol-8-monoacetate 6, goniofupyrone B 7, deoxygoniopypyrone B 8 and 1 S,5 S,7 R,8 S,3- endo,7- endo-(+)-8- epi-9-deoxygoniopypyrone acetate 9, along with six known styryl lactones (1, 10–15) were also isolated and characterized. 6 S-goniothalamin 1 is

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10

Peng, Xiaoshui, Anpai Li, Hao Shen, Tongxing Wu, and Xinfu Pan. "Facile Enantioselective Synthesis of 6R-(+)-Goniothalamin and (6R,7R,8R)-(+)-Goniothalamin Oxide." ChemInform 34, no. 1 (2003): no. http://dx.doi.org/10.1002/chin.200301216.

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11

Fatima, Angelo, Cleide Viviane Martins, Maria de Resende, et al. "Antifungal Activity of Goniothalamin Enantiomers." Letters in Drug Design & Discovery 5, no. 1 (2008): 74–78. http://dx.doi.org/10.2174/157018008783406732.

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12

Pilli, Ronaldo Aloise, Ian de Toledo, Matheus Andrade Meirelles, and Thiago Augusto Grigolo. "Goniothalamin-Related Styryl Lactones: Isolation, Synthesis, Biological Activity and Mode of Action." Current Medicinal Chemistry 26, no. 41 (2020): 7372–451. http://dx.doi.org/10.2174/0929867325666181009161439.

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: This review covers the chemistry and biological aspects of goniothalamin-related styryl lactones isolated from natural sources. This family of secondary metabolites has been reported to display diverse uses in folk medicine, but only a limited number of these compounds have been throughly investigated regarding their biological profile. Herein, we cover the goniothalamin-related styryl lactones having a C6-C3-C4 framework which appeared in the literature for the first time in the period 2000-2017, and the reports on the synthesis, biological activity and mechanism of action which were publis

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13

Hosagoudar, V. B. "Black mildews on Goniothalamus species in Agasthyavanam National Park, Kerala, India." Journal of Applied and Natural Science 1, no. 1 (2009): 76–78. http://dx.doi.org/10.31018/jans.v1i1.42.

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The present study indicated that Goniothalamus rhynchantherus and G. wightii were infected by three black mildew fungi, namely, Amazonia goniothalami, Irenopsis goniothalami and Trichasterina goniothalami. These fungi have been described and illustrated in detail.

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14

Ramli, Rosdayati Alino, Wilford Lie, and Stephen G. Pyne. "Alkaloids from the Roots and Leaves of Stichoneuron halabalensis and their Acetylcholinesterase Inhibitory Activities." Natural Product Communications 8, no. 6 (2013): 1934578X1300800. http://dx.doi.org/10.1177/1934578x1300800603.

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A study of the hitherto unreported Stichoneuron halabalensis Inthachub led to the characterization of the known compounds (+)-α-tocopherol and ( R)-(+)-goniothalamin; four known Stemona alkaloids, bisdehydoxystemoninine A (1), stemoninine (2), sessilistemonamine C (3) and sessilistemonamine A (4); and three new alkaloids, stichoneurine C (5), D (6) and E (7). The structures of these compounds were determined on the basis of their spectroscopic data. Alkaloid 7 showed significant inhibitory activity against electric eel acetylcholinesterase (AChE) (IC50 5.90±0.084 μM), while goniothalamin and c

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15

Mosaddik, M. Ashik, M. Ekramul Haque, and M. Abdur Rashid. "Goniothalamin from Bryonopsis laciniosa Linn (Cucurbiataceae)." Biochemical Systematics and Ecology 28, no. 10 (2000): 1039–40. http://dx.doi.org/10.1016/s0305-1978(00)00017-x.

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16

Das, Biswanath, Siddavatam Nagendra, and Cheruku Ravindra Reddy. "Stereoselective total synthesis of (+)-cryptofolione and (+)-goniothalamin." Tetrahedron: Asymmetry 22, no. 11 (2011): 1249–54. http://dx.doi.org/10.1016/j.tetasy.2011.06.029.

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17

Gruttadauria, Michelangelo, Paolo Lo Meo, and Renato Noto. "Short and efficient chemoenzymatic synthesis of goniothalamin." Tetrahedron Letters 45, no. 1 (2004): 83–85. http://dx.doi.org/10.1016/j.tetlet.2003.10.115.

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18

O'Connor, Brian, and George Just. "Syntheses of argentilactone 11 and Goniothalamin 15." Tetrahedron Letters 27, no. 43 (1986): 5201–2. http://dx.doi.org/10.1016/s0040-4039(00)85168-0.

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19

Umar-Tsafe, Nasir, Mohamed Saifulaman Mohamed-Said, Rozita Rosli, Laily Bin Din, and Leslie C. Lai. "Genotoxicity of goniothalamin in CHO cell line." Mutation Research/Genetic Toxicology and Environmental Mutagenesis 562, no. 1-2 (2004): 91–102. http://dx.doi.org/10.1016/j.mrgentox.2004.05.011.

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20

Sam, T. W., Chew Sew-Yeu, Sabirin Matsjeh, E. K. Gan, Dzulkifli Razak, and Abdul L. Mohamed. "Goniothalamin oxide: An embryotoxic compound from (annonaceae)." Tetrahedron Letters 28, no. 22 (1987): 2541–44. http://dx.doi.org/10.1016/s0040-4039(00)95462-5.

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21

Raihan, I., R. Miyaura, B. B. Baki, and Y. Fujii. "Assessment of allelopathic potential of goniothalamin allelochemical from Malaysian plant Goniothalamus andersonii J. Sinclair by sandwich method." Allelopathy Journal 46, no. 1 (2019): 25–40. http://dx.doi.org/10.26651/allelo.j/2019-46-1-1196.

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22

Barcelos, Rosimeire Coura, Julio Cezar Pastre, Vanessa Caixeta, Débora Barbosa Vendramini-Costa, João Ernesto de Carvalho та Ronaldo Aloise Pilli. "Synthesis of methoxylated goniothalamin, aza-goniothalamin and γ-pyrones and their in vitro evaluation against human cancer cells". Bioorganic & Medicinal Chemistry 20, № 11 (2012): 3635–51. http://dx.doi.org/10.1016/j.bmc.2012.03.059.

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23

Al-Qubaisi, Mothanna, Rosli Rozita, Swee-Keong Yeap, Abdul-Rahman Omar, Abdul-Manaf Ali, and Noorjahan B. Alitheen. "Selective Cytotoxicity of Goniothalamin against Hepatoblastoma HepG2 Cells." Molecules 16, no. 4 (2011): 2944–59. http://dx.doi.org/10.3390/molecules16042944.

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24

Raitz, Ismael, Roberto Y. de Souza Filho, Lorena P. de Andrade, Jose R. Correa, Brenno A. D. Neto, and Ronaldo A. Pilli. "Preferential Mitochondrial Localization of a Goniothalamin Fluorescent Derivative." ACS Omega 2, no. 7 (2017): 3774–84. http://dx.doi.org/10.1021/acsomega.7b00416.

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25

Job, Andreas, Michael Wolberg, Michael Müller, and Dieter Enders. "Asymmetric Synthesis of S-(+)-Argentilactone and S-(-)-Goniothalamin." Synlett 2001, no. 11 (2001): 1796–98. http://dx.doi.org/10.1055/s-2001-18088.

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26

Chan, K. M., N. F. Rajab, M. H. A. Ishak, et al. "Goniothalamin induces apoptosis in vascular smooth muscle cells." Chemico-Biological Interactions 159, no. 2 (2006): 129–40. http://dx.doi.org/10.1016/j.cbi.2005.10.107.

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27

Pospíšil, Jiří, and István E. Markó. "Total synthesis of (R)-(+)-goniothalamin and (R)-(+)-goniothalamin oxide: first application of the sulfoxide-modified Julia olefination in total synthesis." Tetrahedron Letters 47, no. 33 (2006): 5933–37. http://dx.doi.org/10.1016/j.tetlet.2006.06.054.

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28

Kaid, Fahmi, A. M. Alabsi, Nashwan Alafifi, et al. "Histological, Biochemical, and Hematological Effects of Goniothalamin on Selective Internal Organs of Male Sprague-Dawley Rats." Journal of Toxicology 2019 (April 23, 2019): 1–13. http://dx.doi.org/10.1155/2019/6493286.

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Goniothalamin (GTN) is an isolated compound from several plants of the genus Goniothalamus, and its anticancer effect against several cancers was reported. However, there is no scientific data about effects of its higher doses on internal organs. Accordingly, this study aimed to evaluate the acute and subacute effects of higher doses of GTN on the hematology, biochemistry, and histology of selected internal organs of male Sprague-Dawley rats. In acute study, 35 rats were distributed in 5 groups (n=7) which were intraperitoneally (IP) injected with a single dose of either 100, 200, 300, 400, or

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29

Inayat-Hussain, S. H., L. T. Wong, K. M. Chan, et al. "RACK-1 overexpression protects against goniothalamin-induced cell death." Toxicology Letters 191, no. 2-3 (2009): 118–22. http://dx.doi.org/10.1016/j.toxlet.2009.08.012.

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30

Kabir, K. E., A. R. Khan, and M. A. Mosaddik. "Goniothalamin - a potent mosquito larvicide from Bryonopsis laciniosa L." Journal of Applied Entomology 127, no. 2 (2003): 112–15. http://dx.doi.org/10.1046/j.1439-0418.2003.00716.x.

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31

Mosaddik, M. Ashik, and M. Ekramul Haque. "Cytotoxicity and antimicrobial activity of goniothalamin isolated fromBryonopsis laciniosa." Phytotherapy Research 17, no. 10 (2003): 1155–57. http://dx.doi.org/10.1002/ptr.1303.

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32

Seyed, Mohamed Ali, Ibrahim Jantan, and Syed Nasir Abbas Bukhari. "Emerging Anticancer Potentials of Goniothalamin and Its Molecular Mechanisms." BioMed Research International 2014 (2014): 1–10. http://dx.doi.org/10.1155/2014/536508.

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The treatment of most cancers is still inadequate, despite tremendous steady progress in drug discovery and effective prevention. Nature is an attractive source of new therapeutics. Several medicinal plants and their biomarkers have been widely used for the treatment of cancer with less known scientific basis of their functioning. Although a wide array of plant derived active metabolites play a role in the prevention and treatment of cancer, more extensive scientific evaluation of their mechanisms is still required. Styryl-lactones are a group of secondary metabolites ubiquitous in the genusGo

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33

Martins, C. V. B., M. A. de Resende, D. L. da Silva, et al. "In vitro studies of anticandidal activity of goniothalamin enantiomers." Journal of Applied Microbiology 107, no. 4 (2009): 1279–86. http://dx.doi.org/10.1111/j.1365-2672.2009.04307.x.

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34

Kim, R. P. T., M. N. Khan, S. Y. Liew, and K. Awang. "Kinetic and Mechanistic Studies of Acidic Hydrolysis of Goniothalamin." Asian Journal of Chemistry 33, no. 5 (2021): 1176–82. http://dx.doi.org/10.14233/ajchem.2021.23158.

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The acidic hydrolysis of goniothalamin was studied on the spectrophotometric kinetic study at different concentration of hydrochloric acid and temperature to determine the stability of the compound. Stability tests were performed using UV-VIS detection. This is a two-step reaction that involves formation of intermediate product. Rate constant of reactant forming intermediate product obeyed pseudo-first-order kinetic, while the second step to form final product is independent on the concentration of HCl. The structure of final products was identified by NMR and MS. The acidic hydrolysis pathway

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35

Zohdi, Rozaini Mohd, Shahida Muhamad Mukhtar, Nur Vicky Bihud, et al. "In vivo Antiplasmodial and Toxicological Effects of Goniothalamus lanceolatus Crude Extracts." Natural Product Communications 12, no. 8 (2017): 1934578X1701200. http://dx.doi.org/10.1177/1934578x1701200826.

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This study is aimed at investigating the antiplasmodial activity and acute toxicity of the methanol (MeOH) extracts of the leaves and roots, and the dichloromethane (DCM) extracts of the stem bark, leaves, and roots of Goniothalamus lanceolatus. Phytochemical analysis was then carried out on the most active extract. In vivo antiplasmodial activity was assessed using the 4-day suppressive test against Plasmodium berghei ANKA (PbANKA) in mice. The plant extracts were administered intraperitoneally (i.p.) as a single dose (30 mg/kg) starting 4 h after infection. At a dose level of 30 mg/kg (i.p.)

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36

Bose, D., A. V. Reddy, and Bingi Srikanth. "A Concise Enantioselective Strategy to (+)-(R)-Goniothalamin and (+)-(R)-Goniothalamin Oxide by Employing Hydrolytic Kinetic Resolution and Ring-Closing Metathesis as Key Steps." Synthesis 2008, no. 15 (2008): 2323–26. http://dx.doi.org/10.1055/s-2008-1067175.

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37

Nahra, Fady, and Olivier Riant. "Recruiting the Students To Fight Cancer: Total Synthesis of Goniothalamin." Journal of Chemical Education 92, no. 1 (2014): 179–82. http://dx.doi.org/10.1021/ed500457d.

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38

Ali, A., M. McKeen, M. Hamid, et al. "Cytotoxicity and Electron Microscopy of Cell Death Induced by Goniothalamin." Planta Medica 63, no. 01 (1997): 81–83. http://dx.doi.org/10.1055/s-2006-957611.

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39

Honda, Toshio, Tetsuji Kametani, Kazuo Kanai, Yoko Tatsuzaki, and Masayoshi Tsubuki. "Enantioselective syntheses of (+)-acetylphomalactone and (6R)-(+)-goniothalamin from 2-furylmethanols." Journal of the Chemical Society, Perkin Transactions 1, no. 6 (1990): 1733. http://dx.doi.org/10.1039/p19900001733.

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40

Marquissolo, Cilene, Ângelo de Fátima, Luciana K. Kohn, Ana Lúcia T. G. Ruiz, João Ernesto de Carvalho, and Ronaldo A. Pilli. "Asymmetric total synthesis and antiproliferative activity of goniothalamin oxide isomers." Bioorganic Chemistry 37, no. 2 (2009): 52–56. http://dx.doi.org/10.1016/j.bioorg.2008.12.001.

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41

Orlikova, Barbora, Marc Schumacher, Tom Juncker та ін. "Styryl-lactone goniothalamin inhibits TNF-α-induced NF-κB activation". Food and Chemical Toxicology 59 (вересень 2013): 572–78. http://dx.doi.org/10.1016/j.fct.2013.06.051.

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42

Khaw-on, Patompong, Wilart Pompimon, and Ratana Banjerdpongchai. "Apoptosis Induction via ATM Phosphorylation, Cell Cycle Arrest, and ER Stress by Goniothalamin and Chemodrugs Combined Effects on Breast Cancer-Derived MDA-MB-231 Cells." BioMed Research International 2018 (November 26, 2018): 1–15. http://dx.doi.org/10.1155/2018/7049053.

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Goniothalamin (GTN), a styryl-lactone, exhibits inhibitory effects on many kinds of cancer cells in vitro. The objectives of this study were to investigate the anticancer activities of GTN and molecular signaling pathways associated with cell death in human breast cancer MDA-MB-231 cell line. GTN inhibited the growth of MDA-MB-231 cells. Apoptosis was confirmed by annexin V-FITC and PI staining, and apoptotic morphology was observed by microscopy. Reduction of mitochondrial transmembrane potential and enhanced caspases activities were found in GTN-treated MDA-MB-231 cells. GTN significantly al

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43

Alabsi, Aied Mohammed, Rola Ali, Abdul Manaf Ali, et al. "Induction of Caspase-9, Biochemical Assessment and Morphological Changes Caused by Apoptosis in Cancer Cells Treated with Goniothalamin Extracted from Goniothalamus macrophyllus." Asian Pacific Journal of Cancer Prevention 14, no. 11 (2013): 6273–80. http://dx.doi.org/10.7314/apjcp.2013.14.11.6273.

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44

Inayat-Hussain, S. H., R. Baker, D. Ross, L. B. Din, K. Yusoff, and A. M. Ali. "423 Characterization of goniothalamin induced apoptosis in HL-60 leukemia cells." Toxicology Letters 144 (September 2003): s114. http://dx.doi.org/10.1016/s0378-4274(03)90422-x.

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45

Vendramini-Costa, Débora Barbosa, Humberto Moreira Spindola, Glaucia Coelho de Mello, Edson Antunes, Ronaldo Aloise Pilli, and João Ernesto de Carvalho. "Anti-inflammatory and antinociceptive effects of racemic goniothalamin, a styryl lactone." Life Sciences 139 (October 2015): 83–90. http://dx.doi.org/10.1016/j.lfs.2015.08.010.

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46

Pastre, Julio C., Philip R. D. Murray, Duncan L. Browne, et al. "Integrated Batch and Continuous Flow Process for the Synthesis of Goniothalamin." ACS Omega 5, no. 29 (2020): 18472–83. http://dx.doi.org/10.1021/acsomega.0c02390.

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47

de Fátima, Ângelo, Luciana Konecny Kohn, Márcia Aparecida Antônio, João Ernesto de Carvalho, and Ronaldo Aloise Pilli. "(R)-Goniothalamin: total syntheses and cytotoxic activity against cancer cell lines." Bioorganic & Medicinal Chemistry 13, no. 8 (2005): 2927–33. http://dx.doi.org/10.1016/j.bmc.2005.02.007.

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48

de Fátima, Ângelo, Luciana K. Kohn, João Ernesto de Carvalho, and Ronaldo A. Pilli. "Cytotoxic activity of (S)-goniothalamin and analogues against human cancer cells." Bioorganic & Medicinal Chemistry 14, no. 3 (2006): 622–31. http://dx.doi.org/10.1016/j.bmc.2005.08.036.

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49

Wach, Jean-Yves, Stephan Güttinger, Ulrike Kutay, and Karl Gademann. "The cytotoxic styryl lactone goniothalamin is an inhibitor of nucleocytoplasmic transport." Bioorganic & Medicinal Chemistry Letters 20, no. 9 (2010): 2843–46. http://dx.doi.org/10.1016/j.bmcl.2010.03.049.

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50

Chen, Jun-Ling, Zheng-Wei You та Feng-Ling Qing. "Total synthesis of γ-trifluoromethylated analogs of goniothalamin and their derivatives". Journal of Fluorine Chemistry 155 (листопад 2013): 143–50. http://dx.doi.org/10.1016/j.jfluchem.2013.07.017.

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