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Journal articles on the topic 'Manzamine A'

Author: Grafiati

Published: 4 June 2021

Last updated: 1 February 2022

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1

Palem, Jayavardhana R., Mudit Mudit, Shao-chung V. Hsia, and Khalid A. El Sayed. "Discovery and preliminary structure-activity relationship of the marine natural product manzamines as herpes simplex virus type-1 inhibitors." Zeitschrift für Naturforschung C 72, no. 1-2 (2017): 49–54. http://dx.doi.org/10.1515/znc-2016-0080.

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Abstract Herpes simplex virus type-1 (HSV-1) is a member of alpha-herpesviridae family and is known to cause contagious human infections. The marine habitat is a rich source of structurally unique bioactive secondary metabolites. A small library of marine natural product classes 1–10 has been screened to discover a new hit entity active against HSV-1. Manzamine A showed potent activity against HSV-1 via targeting the viral gene ICP0. Manzamine A is a β-carboline alkaloid isolated from the Indo-Pacific sponge Acanthostrongylophora species. Currently, acyclovir is the drug of choice for HSV-1 in

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2

Ang, Kenny K. H., Michael J. Holmes, Tatsuo Higa, Mark T. Hamann, and Ursula A. K. Kara. "In Vivo Antimalarial Activity of the Beta-Carboline Alkaloid Manzamine A." Antimicrobial Agents and Chemotherapy 44, no. 6 (2000): 1645–49. http://dx.doi.org/10.1128/aac.44.6.1645-1649.2000.

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ABSTRACT Manzamine A, a β-carboline alkaloid present in several marine sponge species, inhibits the growth of the rodent malaria parasitePlasmodium berghei in vivo. More than 90% of the asexual erythrocytic stages of P. berghei were inhibited after a single intraperitoneal injection of manzamine A into infected mice. A remarkable aspect of manzamine A treatment is its ability to prolong the survival of highly parasitemic mice, with 40% recovery 60 days after a single injection. Oral administration of an oil suspension of manzamine A also produced significant reductions in parasitemia. The plas

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3

Lin, Li-Chun, Tzu-Ting Kuo, Hsin-Yi Chang, Wen-Shan Liu, Shih-Min Hsia, and Tsui-Chin Huang. "Manzamine A Exerts Anticancer Activity against Human Colorectal Cancer Cells." Marine Drugs 16, no. 8 (2018): 252. http://dx.doi.org/10.3390/md16080252.

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Marine sponges are known to produce numerous bioactive secondary metabolites as defense strategies to avoid predation. Manzamine A is a sponge-derived β-carboline-fused pentacyclic alkaloid with various bioactivities, including recently reported anticancer activity on pancreatic cancer. However, its cytotoxicity and mode of action against other tumors remain unclear. In this study, we exhibit that manzamine A reduced cell proliferation in several colorectal cancer (CRC) cell lines. To further investigate the manzamine A triggered molecular regulation, we analyzed the gene expression with micro

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4

Alam, Gemini, Puji Astuti, Subagus Wahyuono, Dinar Sari, and Mark T. Hamman. "STRUCTURE ELUCIDATION OF BIOACTIVE ALKALOID COMPOUNDS ISOLATED FROM SPONGE Petrosia sp COLLECTED FROM BUNAKEN BAY MENADO." Indonesian Journal of Chemistry 5, no. 2 (2010): 177–81. http://dx.doi.org/10.22146/ijc.21828.

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Two alkaloid compounds have been isolated from sponge Petrosia sp collected from Bunaken Bay Menado. These compounds have been found to inhibit several human cancer cell proliferation in vitro. Structure elucidation is needed to further characterize these bioactive compounds. The structure is determined by analyzing Ultra Violet (UV), Infra Red (IR), Mass Spectra (MS) and Nuclear Magnetic Resonance (NMR) spectra. Based on spectroscopic data, Thin Layer Chromatography (TLC) co-chromatograph with authentic samples and comparison with reported data the two compounds were identified as Manzamine A

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5

MaGee, David I., and Ellen J. Beck. "The use of the RambergBäcklund rearrangement for the formation of aza-macrocycles: a total synthesis of manzamine C." Canadian Journal of Chemistry 78, no. 8 (2000): 1060–66. http://dx.doi.org/10.1139/v00-103.

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A total synthesis of the marine alkaloid manzamine C has been accomplished. A Ramberg-Bäcklund reaction was used as a key step to construct the required azacycloundecene ring.Key words: alkaloid, macrocycle, RambergBäcklund, manzamine C.

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6

Mayer, Alejandro M. S., Mary L. Hall, Joseph Lach та ін. "RSK1 vs. RSK2 Inhibitory Activity of the Marine β-Carboline Alkaloid Manzamine A: A Biochemical, Cervical Cancer Protein Expression, and Computational Study". Marine Drugs 19, № 9 (2021): 506. http://dx.doi.org/10.3390/md19090506.

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Manzamines are complex polycyclic marine-derived β-carboline alkaloids with reported anticancer, immunostimulatory, anti-inflammatory, antibacterial, antiviral, antimalarial, neuritogenic, hyperlipidemia, and atherosclerosis suppression bioactivities, putatively associated with inhibition of glycogen synthase kinase-3, cyclin-dependent kinase 5, SIX1, and vacuolar ATPases. We hypothesized that additional, yet undiscovered molecular targets might be associated with Manzamine A’s (MZA) reported pharmacological properties. We report here, for the first time, that MZA selectively inhibited a 90 kD

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7

Nakagawa, Masako, Yasuhiro Torisawa, Toshihiro Hosaka, et al. "Dihydropyridinone approach to manzamines: An expedient construction of the tetracyclic core of manzamine A." Tetrahedron Letters 34, no. 28 (1993): 4543–46. http://dx.doi.org/10.1016/0040-4039(93)88081-s.

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8

Samoylenko, Volodymyr, Shabana I. Khan, Melissa R. Jacob, et al. "Bioactive (+)-Manzamine A and (+)-8-Hydroxymanzamine A Tertiary Bases and Salts from Acanthostrongylophora Ingens and Their Preparations." Natural Product Communications 4, no. 2 (2009): 1934578X0900400. http://dx.doi.org/10.1177/1934578x0900400204.

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The genus Acanthostrongylophora is famous for producing a wide array of manzamine alkaloids as natural hydrochloride salts. An examination of A. ingens has now yielded two tertiary bases, (+)-8-hydroxymanzamine A (1) and (+)-manzamine A (2), by chromatography over alumina using CHCl3-MeOH-NH3·H2O as solvent. In addition, (+)-8-hydroxymanzamine A hydrochloride (3) and (+)-manzamine A hydrochloride (4) were isolated under the same conditions from the same source by silica gel chromatography. The structures of 1-4 were determined from 1D- and 2D-NMR spectra and by circular dichroism experiments,

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9

Watanabe, Daisuke, Masashi Tsuda, and Jun'ichi Kobayashi. "Three New Manzamine Congeners fromAmphimedonSponge." Journal of Natural Products 61, no. 5 (1998): 689–92. http://dx.doi.org/10.1021/np970564p.

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10

BORMAN, STU. "First synthesis of manzamine A." Chemical & Engineering News 76, no. 25 (1998): 7. http://dx.doi.org/10.1021/cen-v076n025.p007.

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11

Toma, Tatsuya, Yoichi Kita, and Tohru Fukuyama. "Total Synthesis of (+)-Manzamine A." Journal of the American Chemical Society 132, no. 30 (2010): 10233–35. http://dx.doi.org/10.1021/ja103721s.

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12

Pandit, U. K., B. C. Borer, and H. Bieräugel. "Synthetic studies on manzamine A." Pure and Applied Chemistry 68, no. 3 (1996): 659–62. http://dx.doi.org/10.1351/pac199668030659.

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13

Pathak, Ravindra B., Benjamin C. Dobson, Nandita Ghosh, et al. "Synthesis of the tricyclic core of manzamine A." Organic & Biomolecular Chemistry 13, no. 11 (2015): 3331–40. http://dx.doi.org/10.1039/c4ob02582b.

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14

Torisawa, Yasuhiro, Akihiro Hashimoto, Masako Nakagawa, and Tohru Hino. "A total synthesis of manzamine c." Tetrahedron Letters 30, no. 47 (1989): 6549–50. http://dx.doi.org/10.1016/s0040-4039(01)89018-3.

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15

Sayed, Khalid A. El, Ashraf A. Khalil, Muhammad Yousaf, et al. "Semisynthetic Studies on the Manzamine Alkaloids#." Journal of Natural Products 71, no. 3 (2008): 300–308. http://dx.doi.org/10.1021/np0703702.

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16

Magnier, Emmanuel, and Yves Langlois. "Manzamine alkaloids, syntheses and synthetic approaches." Tetrahedron 54, no. 23 (1998): 6201—IN2. http://dx.doi.org/10.1016/s0040-4020(98)00357-3.

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17

Kim, Chang-Kwon, Riswanto Riswanto, Tae Hyung Won, et al. "Manzamine Alkaloids from an Acanthostrongylophora sp. Sponge." Journal of Natural Products 80, no. 5 (2017): 1575–83. http://dx.doi.org/10.1021/acs.jnatprod.7b00121.

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18

Baldwin, Jack E., Tim D. W. Claridge, Andrew J. Culshaw, Florian A. Heupel, Svatava Smrcková, and Roger C. Whitehead. "A biomimetic approach to the manzamine alkaloids." Tetrahedron Letters 37, no. 38 (1996): 6919–22. http://dx.doi.org/10.1016/0040-4039(96)01516-x.

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19

Winkler, Jeffrey D., Allyn T. Londregan, Justin R. Ragains, and Mark T. Hamann. "Synthesis and Biological Evaluation of Manzamine Analogues." Organic Letters 8, no. 15 (2006): 3407–9. http://dx.doi.org/10.1021/ol061320b.

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20

Baldwin, Jack E., Timothy D. W. Claridge, Andrew J. Culshaw, et al. "Investigations into the Manzamine Alkaloid Biosynthetic Hypothesis." Angewandte Chemie International Edition 37, no. 19 (1998): 2661–63. http://dx.doi.org/10.1002/(sici)1521-3773(19981016)37:19<2661::aid-anie2661>3.0.co;2-d.

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21

Duval, Romain, and Erwan Poupon. "ChemInform Abstract: Biomimetic Synthesis of Manzamine Alkaloids." ChemInform 42, no. 51 (2011): no. http://dx.doi.org/10.1002/chin.201151261.

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22

Ashok, Penta, Hiren Lathiya, and Sankaranarayanan Murugesan. "Manzamine alkaloids as antileishmanial agents: A review." European Journal of Medicinal Chemistry 97 (June 2015): 928–36. http://dx.doi.org/10.1016/j.ejmech.2014.07.006.

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23

Campbell, Jeffrey A., and David J. Hart. "Synthesis of a tetracyclic substructure of manzamine A." Tetrahedron Letters 33, no. 42 (1992): 6247–50. http://dx.doi.org/10.1016/s0040-4039(00)60944-9.

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24

Shilabin, Abbas Gholipour, Noer Kasanah, Babu L. Tekwani, and Mark T. Hamann. "Kinetic Studies and Bioactivity of Potential Manzamine Prodrugs." Journal of Natural Products 71, no. 7 (2008): 1218–21. http://dx.doi.org/10.1021/np800163u.

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25

Zhou, Bing-Nan, Carla Slebodnick, Randall K. Johnson, Michael R. Mattern, and David G. I. Kingston. "New Cytotoxic Manzamine Alkaloids from a Palaun Sponge." Tetrahedron 56, no. 32 (2000): 5781–84. http://dx.doi.org/10.1016/s0040-4020(00)00534-2.

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26

Lynch, V. M., Y. Liao, S. F. Martin, and B. E. Davis. "Structure of a tricyclic subunit of manzamine A." Acta Crystallographica Section C Crystal Structure Communications 48, no. 9 (1992): 1703–5. http://dx.doi.org/10.1107/s0108270192001045.

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27

MAGNIER, E., and Y. LANGLOIS. "ChemInform Abstract: Manzamine Alkaloids: Syntheses and Synthetic Approaches." ChemInform 29, no. 35 (2010): no. http://dx.doi.org/10.1002/chin.199835318.

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28

Fronczek, F. R., M. Donia, M. Reddy, K. V. Rao, J. Peng, and M. T. Hamann. "Hydrogen bonding and absolute configuration in manzamine alkaloids." Acta Crystallographica Section A Foundations of Crystallography 61, a1 (2005): c275. http://dx.doi.org/10.1107/s0108767305088276.

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29

Jakubec, Pavol, Alison Hawkins, Wolfgang Felzmann, and Darren J. Dixon. "Total Synthesis of Manzamine A and Related Alkaloids." Journal of the American Chemical Society 134, no. 42 (2012): 17482–85. http://dx.doi.org/10.1021/ja308826x.

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30

Pandit, U. K., B. C. Borer, H. Bieräugel, and Sirik Deerenberg. "Studies on the total synthesis of manzamine A." Pure and Applied Chemistry 66, no. 10-11 (1994): 2131–34. http://dx.doi.org/10.1351/pac199466102131.

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31

Coldham, Iain, Katherine M. Crapnell, Joan-Carles Fernàndez, et al. "A new stereoselective approach to the manzamine alkaloids." Chemical Communications, no. 17 (1999): 1757–58. http://dx.doi.org/10.1039/a904667d.

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32

AlTarabeen, Mousa, Georgios Daletos, Weaam Ebrahim, et al. "Ircinal E, a New Manzamine Derivative from the Indonesian Marine Sponge Acanthostrongylophora ingens." Natural Product Communications 10, no. 11 (2015): 1934578X1501001. http://dx.doi.org/10.1177/1934578x1501001136.

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Chemical investigation of the MeOH extract of the sponge Acanthostrongylophora ingens afforded the new manzamine derivative ircinal E (1), in addition to six known metabolites (2–7). The structure of the new compound was unequivocally elucidated using one- and two-dimensional NMR spectroscopy, as well as high-resolution mass spectrometry. Compounds 1–6 exhibited strong to moderate cytotoxicity against the murine lymphoma L5178Y cell line with IC50 values ranging from 2.8 to 21.7 μM.

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33

Kobayashi, Jun'ichi, Masashi Tsuda, and Daisuke Watanabe. "A New Manzamine Congener from Marine Sponge Amphimedon sp." HETEROCYCLES 50, no. 1 (1999): 485. http://dx.doi.org/10.3987/com-98-s(h)49.

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34

KOBAYASHI, Jun'ichi, and Masashi TSUDA. "Unique Ring Systems and Biogenetic Path of Manzamine Alkaloids." Journal of Synthetic Organic Chemistry, Japan 55, no. 12 (1997): 1114–23. http://dx.doi.org/10.5059/yukigoseikyokaishi.55.1114.

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35

Baldwin, J. "A biomimetic approach to the manzamine alkaloids; model studies." Tetrahedron Letters 35, no. 41 (1994): 7829–32. http://dx.doi.org/10.1016/s0040-4039(00)77383-7.

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36

Tsuda, Masashi, Daisuke Watanabe, and Jun'ichi Kobayashi. "Ma'eganedin A, a new manzamine alkaloid from Amphimedon sponge." Tetrahedron Letters 39, no. 10 (1998): 1207–10. http://dx.doi.org/10.1016/s0040-4039(97)10842-5.

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37

Brands, Karel M. J., Arthur A. P. Meekel, and Upendra K. Pandit. "Synthesis of the homochiral “tricyclic heart” of manzamine A." Tetrahedron 47, no. 10-11 (1991): 2005–26. http://dx.doi.org/10.1016/s0040-4020(01)96112-5.

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38

Sakai, Ryuichi, Tatsuo Higa, Charles W. Jefford, and Gerald Bernardinelli. "Manzamine A, a novel antitumor alkaloid from a sponge." Journal of the American Chemical Society 108, no. 20 (1986): 6404–5. http://dx.doi.org/10.1021/ja00280a055.

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39

Kamenecka, Theodore M., and Larry E. Overman. "An enantioselective approach to the synthesis of manzamine A." Tetrahedron Letters 35, no. 25 (1994): 4279–82. http://dx.doi.org/10.1016/s0040-4039(00)73333-8.

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40

El Sayed, K. A., M. Kelly, U. A. K. Kara, et al. "New Manzamine Alkaloids with Potent Activity against Infectious Diseases." Journal of the American Chemical Society 123, no. 9 (2001): 1804–8. http://dx.doi.org/10.1021/ja002073o.

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41

Kobayashi, Jun'ichi, Daisuke Watanabe, Naoko Kawasaki, and Masashi Tsuda. "Nakadomarin A, a Novel Hexacyclic Manzamine-Related Alkaloid fromAmphimedonSponge." Journal of Organic Chemistry 62, no. 26 (1997): 9236–39. http://dx.doi.org/10.1021/jo9715377.

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42

Baldwin, Jack E., Timothy D. W. Claridge, Andrew J. Culshaw, et al. "Studies on the Biomimetic Synthesis of the Manzamine Alkaloids." Chemistry - A European Journal 5, no. 11 (1999): 3154–61. http://dx.doi.org/10.1002/(sici)1521-3765(19991105)5:11<3154::aid-chem3154>3.0.co;2-7.

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43

BALDWIN, J. E., T. D. W. CLARIDGE, A. J. CULSHAW, F. A. HEUPEL, S. SMRCKOVA, and R. C. WHITEHEAD. "ChemInform Abstract: A Biomimetic Approach to the Manzamine Alkaloids." ChemInform 28, no. 4 (2010): no. http://dx.doi.org/10.1002/chin.199704219.

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44

Coldham, Iain, Katherine M. Crapnell, Joan-Carles Fernàndez, Jonathan D. Moseley, and Rémi Rabot. "Synthesis of the ABC Ring System of Manzamine A." Journal of Organic Chemistry 67, no. 17 (2002): 6181–87. http://dx.doi.org/10.1021/jo016376s.

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45

Humphrey, John M., Yusheng Liao, Amjad Ali, et al. "Enantioselective Total Syntheses of Manzamine A and Related Alkaloids." Journal of the American Chemical Society 124, no. 29 (2002): 8584–92. http://dx.doi.org/10.1021/ja0202964.

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46

Baldwin, Jack E., Tim D. W. Claridge, Florian A. Heupel, and Roger C. Whitehead. "A biomimetic approach to the manzamine alkaloids; model studies." Tetrahedron Letters 35, no. 42 (1994): 7829–32. http://dx.doi.org/10.1016/0040-4039(94)80129-0.

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47

Ashok, Penta, Swastika Ganguly, and Sankaranarayanan Murugesan. "Manzamine alkaloids: isolation, cytotoxicity, antimalarial activity and SAR studies." Drug Discovery Today 19, no. 11 (2014): 1781–91. http://dx.doi.org/10.1016/j.drudis.2014.06.010.

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48

Ashok, Penta, Hiren Lathiya, and Sankaranarayanan Murugesan. "ChemInform Abstract: Manzamine Alkaloids as Antileishmanial Agents: A Review." ChemInform 46, no. 32 (2015): no. http://dx.doi.org/10.1002/chin.201532307.

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49

Dewi, Ariyanti S., Tri A. Hadi, Nurrahmi D. Fajarningsih, Joanne T. Blanchfield, Paul V. Bernhardt, and Mary J. Garson. "Acanthocyclamine A From the Indonesian Marine Sponge Acanthostrongylophora ingens." Australian Journal of Chemistry 67, no. 9 (2014): 1205. http://dx.doi.org/10.1071/ch14107.

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A new 3-alkylpiperidine compound (–)-acanthocyclamine A (1) has been obtained from the methanolic extract of Acanthostrongylophora ingens (order Haplosclerida, family Petrosiidae) collected from Wakatobi Marine National Park in South East Sulawesi, Indonesia. The structure of 1 was investigated by extensive 1D- and 2D-NMR experiments. The absolute configuration of 1 was established by X-ray crystallography from anomalous dispersion effects using Cu radiation as C2 (R), C3 (R), C7 (R), and C9 (R). A plausible biosynthetic scheme leading to 1 is presented, and compared with the biosynthetic path

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50

Torisawa, Yasuhiro, Akihiro Hashimoto, Masako Nakagawa, Hiroko Seki, Ritsuko Hara, and Tohru Hino. "A total synthesis of manzamine C and its geometrical isomer." Tetrahedron 47, no. 38 (1991): 8067–78. http://dx.doi.org/10.1016/s0040-4020(01)91003-8.

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