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Author: Grafiati

Published: 6 September 2023

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1

Acquah, Kojo Sekyi, Denzil R. Beukes, Ronnett Seldon, Audrey Jordaan, Suthananda N. Sunassee, Digby F. Warner, and David W. Gammon. "Identification of Antimycobacterial Natural Products from a Library of Marine Invertebrate Extracts." Medicines 9, no. 2 (January 28, 2022): 9. http://dx.doi.org/10.3390/medicines9020009.

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Tuberculosis (TB) remains a public health crisis, requiring the urgent identification of new anti-mycobacterial drugs. We screened several organic and aqueous marine invertebrate extracts for their in vitro inhibitory activity against the causative organism, Mycobacterium tuberculosis. Here, we report the results obtained for 54 marine invertebrate extracts. The chemical components of two of the extracts were dereplicated, using 1H NMR and HR-LCMS with GNPS molecular networking, and these extracts were further subjected to an activity-guided isolation process to purify the bioactive components. Hyrtios reticulatus yielded heteronemin 1 and Jaspis splendens was found to produce the bengamide class of compounds, of which bengamides P 2 and Q 3 were isolated, while a new derivative, bengamide S 5, was putatively identified and its structure predicted, based on the similarity of its MS/MS fragmentation pattern to those of other bengamides. The isolated bioactive metabolites and semi-pure fractions exhibited M. tuberculosis growth inhibitory activity, in the range <0.24 to 62.50 µg/mL. This study establishes the bengamides as potent antitubercular compounds, with the first report of whole-cell antitubercular activity of bengamides P 2 and Q 3.

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2

Dao, Phi Thi. "SYNTHESIS OF N-ALKYL AMINO LACTAM DERIVATIVES." Vietnam Journal of Science and Technology 54, no. 2C (March 19, 2018): 291. http://dx.doi.org/10.15625/2525-2518/54/2c/11849.

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Bengamides are sponge-derived natural products of mixed biosynthesis (polyketides andamino acids), the first two members, isolated from Jaspidae sponges in coral surrounding Fijiislands, were reported in 1986. The main structural variation is located on the 3-aminocaprolactam moiety, and displays a wide range of biological activities, includingantitumor, antibiotic, and anthelmintic properties. These interesting biological activities havemade bengamides popular targets for synthesis and biological studies. There have been somereports on diverse modifications of the caprolactame unit, and indication that N-substitution oncaprolactam greatly influences the antitumor activity. In this paper, we reported the method forsynthesis of 6 amino lactams containing an additional N-alkyl group (4a-4c) and (8a-8c) forfurther synthesis of new bengamide analogues. Their structures were established by MS andNMR spectroscopies.

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3

García-Pinel, Beatriz, Cristina Porras-Alcalá, Laura Cabeza, Raul Ortiz, José Prados, Consolación Melguizo, Iván Cheng-Sánchez, Juan Manuel López-Romero, and Francisco Sarabia. "Bengamide Analogues Show A Potent Antitumor Activity against Colon Cancer Cells: A Preliminary Study." Marine Drugs 18, no. 5 (May 2, 2020): 240. http://dx.doi.org/10.3390/md18050240.

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The limited success and side effects of the current chemotherapeutic strategies against colorectal cancer (CRC), the third most common cancer worldwide, demand an assay with new drugs. The prominent antitumor activities displayed by the bengamides (Ben), a family of natural products isolated from marine sponges of the Jaspidae family, were explored and investigated as a new option to improve CRC treatment. To this end, two potent bengamide analogues, Ben I (5) and Ben V (10), were selected for this study, for which they were synthesized according to a new synthetic strategy recently developed in our laboratories. Their antitumor effects were analyzed in human and mouse colon cell lines, using cell cycle analysis and antiproliferative assays. In addition, the toxicity of the selected analogues was tested in human blood cells. These biological studies revealed that Ben I and V produced a significant decrease in CRC cell proliferation and induced a significant cell cycle alteration with a greater antiproliferative effect on tumor cell lines than normal cells. Interestingly, no toxicity effects were detected in blood cells for both compounds. All these biological results render the bengamide analogues Ben I and Ben V as promising antitumoral agents for the treatment of CRC.

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4

Chida, Noritaka, Takahiko Tobe, and Seiichiro Ogawa. "Total synthesis of bengamide E." Tetrahedron Letters 32, no. 8 (February 1991): 1063–66. http://dx.doi.org/10.1016/s0040-4039(00)74488-1.

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5

Liu, Wenming, Joanna M. Szewczyk, Liladhar Waykole, Oljan Repič, and Thomas J. Blacklock. "Total synthesis of bengamide E." Tetrahedron Letters 43, no. 8 (February 2002): 1373–75. http://dx.doi.org/10.1016/s0040-4039(02)00022-9.

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6

Kishimoto, Hisakazu, Hiroshi Ohrui, and Hiroshi Meguro. "An enantioselective synthesis of bengamide E." Journal of Organic Chemistry 57, no. 18 (August 1992): 5042–44. http://dx.doi.org/10.1021/jo00044a053.

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7

Liu, Qi Jun, Hong Li, Shao Peng Chen, and Guo Chun Zhou. "Synthesis of (3S,4R)-bengamide E." Chinese Chemical Letters 22, no. 5 (May 2011): 505–7. http://dx.doi.org/10.1016/j.cclet.2010.11.023.

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8

Metri, Prashant K., Raphael Schiess, and Kavirayani R. Prasad. "Enantiospecific Total Synthesis of (−)-Bengamide E." Chemistry - An Asian Journal 8, no. 2 (December 3, 2012): 488–93. http://dx.doi.org/10.1002/asia.201200999.

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9

Mukai, Chisato, Sameh M. Moharram, Osamu Kataoka, and Miyoji Hanaoka. "Highly stereocontrolled total synthesis of (+)-bengamide E." Journal of the Chemical Society, Perkin Transactions 1, no. 22 (1995): 2849. http://dx.doi.org/10.1039/p19950002849.

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10

Banwell, Martin G., and Kenneth J. McRae. "A Chemoenzymatic Total Synthesis ofent-Bengamide E." Journal of Organic Chemistry 66, no. 20 (October 2001): 6768–74. http://dx.doi.org/10.1021/jo0159486.

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11

Liu, Wenming, Joanna M. Szewczyk, Liladhar Waykole, Oljan Repic, and Thomas J. Blacklock. "ChemInform Abstract: Total Synthesis of Bengamide E." ChemInform 33, no. 23 (May 21, 2010): no. http://dx.doi.org/10.1002/chin.200223238.

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12

Phi, Thi Dao, Huong Doan Thi Mai, Van Hieu Tran, Bich Ngan Truong, Tuan Anh Tran, Van Loi Vu, Van Minh Chau, and Van Cuong Pham. "Design, synthesis and cytotoxicity of bengamide analogues and their epimers." MedChemComm 8, no. 2 (2017): 445–51. http://dx.doi.org/10.1039/c6md00587j.

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13

Chida, Noritaka, Takahiko Tobe, Shinsuke Okada, and Seiichiro Ogawa. "Total synthesis and absolute configuration of bengamide A." Journal of the Chemical Society, Chemical Communications, no. 15 (1992): 1064. http://dx.doi.org/10.1039/c39920001064.

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14

CHIDA, N., T. TOBE, and S. OGAWA. "ChemInform Abstract: Total Synthesis of Bengamide E (I)." ChemInform 22, no. 51 (August 22, 2010): no. http://dx.doi.org/10.1002/chin.199151282.

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15

Phi, Thi Dao, Huong Doan Thi Mai, Van Hieu Tran, Van Loi Vu, Bich Ngan Truong, Tuan Anh Tran, Van Minh Chau, and Van Cuong Pham. "Synthesis of bengamide E analogues and their cytotoxic activity." Tetrahedron Letters 58, no. 19 (May 2017): 1830–33. http://dx.doi.org/10.1016/j.tetlet.2017.03.077.

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16

Xu, David D., Liladhar Waykole, John V. Calienni, Lech Ciszewski, George T. Lee, Wenming Liu, Joanna Szewczyk, et al. "An Expedient Synthesis of LAF389, a Bengamide B Analogue." Organic Process Research & Development 7, no. 6 (November 2003): 856–65. http://dx.doi.org/10.1021/op0341162.

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17

MUKAI, C., S. M. MOHARRAM, O. KATAOKA, and M. HANAOKA. "ChemInform Abstract: Highly Stereocontrolled Total Synthesis of (+)-Bengamide E." ChemInform 27, no. 10 (August 12, 2010): no. http://dx.doi.org/10.1002/chin.199610321.

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18

KISHIMOTO, H., H. OHRUI, and H. MEGURO. "ChemInform Abstract: An Enantioselective Synthesis of Bengamide E (I)." ChemInform 24, no. 5 (August 21, 2010): no. http://dx.doi.org/10.1002/chin.199305296.

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19

Lu, Jing-Ping, Xiu-Hua Yuan, Hai Yuan, Wen-Long Wang, Baojie Wan, Scott G. Franzblau, and Qi-Zhuang Ye. "Inhibition of Mycobacterium tuberculosis Methionine Aminopeptidases by Bengamide Derivatives." ChemMedChem 6, no. 6 (April 4, 2011): 1041–48. http://dx.doi.org/10.1002/cmdc.201100003.

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20

Xu, Wei, Jing-Ping Lu, and Qi-Zhuang Ye. "Structural Analysis of Bengamide Derivatives as Inhibitors of Methionine Aminopeptidases." Journal of Medicinal Chemistry 55, no. 18 (September 14, 2012): 8021–27. http://dx.doi.org/10.1021/jm3008695.

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21

Banwell, Martin G., and Kenneth J. McRae. "ChemInform Abstract: A Chemoenzymatic Total Synthesis of ent-Bengamide E." ChemInform 33, no. 11 (May 22, 2010): no. http://dx.doi.org/10.1002/chin.200211187.

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22

Tai, Wan-Yi, Run-Tao Zhang, Yi-Ming Ma, Min Gu, Gang Liu, Jia Li, and Fa-Jun Nan. "Design, Synthesis, and Biological Evaluation of Ring-Opened Bengamide Analogues." ChemMedChem 6, no. 9 (June 15, 2011): 1555–58. http://dx.doi.org/10.1002/cmdc.201100164.

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23

Liu, Gang, Yi-Ming Ma, Wan-Yi Tai, Chuan-Ming Xie, Yu-Lin Li, Jia Li, and Fa-Jun Nan. "Design, Synthesis, and Biological Evaluation of Caprolactam-Modified Bengamide Analogues." ChemMedChem 3, no. 1 (January 11, 2008): 74–78. http://dx.doi.org/10.1002/cmdc.200700214.

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24

Sarabia, Francisco, Francisca Martín-Gálvez, Samy Chammaa, Laura Martín-Ortiz, and Antonio Sánchez-Ruiz. "Chiral Sulfur Ylides for the Synthesis of Bengamide E and Analogues." Journal of Organic Chemistry 75, no. 16 (August 20, 2010): 5526–32. http://dx.doi.org/10.1021/jo100696w.

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25

Zhang, Wenxuan, Qingzhao Liang, Hui Li, Xiangbao Meng, and Zhongjun Li. "Concise synthesis and antitumor activity of Bengamide E and its analogs." Tetrahedron 69, no. 2 (January 2013): 664–72. http://dx.doi.org/10.1016/j.tet.2012.11.004.

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26

Kinder,, Frederick R., Richard W. Versace, Kenneth W. Bair, John M. Bontempo, David Cesarz, Steven Chen, Phillip Crews, et al. "Synthesis and Antitumor Activity of Ester-Modified Analogues of Bengamide B." Journal of Medicinal Chemistry 44, no. 22 (October 2001): 3692–99. http://dx.doi.org/10.1021/jm010188c.

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27

Fernández, Rogelio, Michel Dherbomez, Yves Letourneux, Mohamed Nabil, Jean François Verbist, and Jean François Biard. "Antifungal Metabolites from the Marine SpongePachastrissasp.: New Bengamide and Bengazole Derivatives." Journal of Natural Products 62, no. 5 (May 1999): 678–80. http://dx.doi.org/10.1021/np980330l.

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28

Kong, Xue‐Qing, Bing‐Yan Wei, Chen‐Xi Yu, Xiang‐Na Guan, Wei‐Ping Ma, Gang Liu, Cai‐Guang Yang, and Fa‐Jun Nan. "Design, Synthesis and Biological Evaluation of Bengamide Analogues as ClpP Activators." Chinese Journal of Chemistry 38, no. 10 (July 2020): 1111–15. http://dx.doi.org/10.1002/cjoc.202000133.

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29

Lu, Jing-Ping, Xiu-Hua Yuan, and Qi-Zhuang Ye. "Structural analysis of inhibition of Mycobacterium tuberculosis methionine aminopeptidase by bengamide derivatives." European Journal of Medicinal Chemistry 47 (January 2012): 479–84. http://dx.doi.org/10.1016/j.ejmech.2011.11.017.

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30

Jamison, Matthew, Xiao Wang, Tina Cheng, and Tadeusz Molinski. "Synergistic Anti-Candida Activity of Bengazole A in the Presence of Bengamide A." Marine Drugs 17, no. 2 (February 7, 2019): 102. http://dx.doi.org/10.3390/md17020102.

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Bengazoles A–G from the marine sponge Jaspis sp. exhibit potent in vitro antifungal activity against Candida spp. and other pathogenic fungi. The mechanism of action (MOA) of bengazole A was explored in Candida albicans under both liquid culture and surface culture on Mueller-Hinton agar. Pronounced dose-dependent synergistic antifungal activity was observed with bengazole A in the presence of bengamide A, which is also a natural product from Jaspis sp. The MOA of bengazole A was further explored by monitoring the sterol composition of C. albicans in the presence of sub-lethal concentrations of bengazole A. The GCMS of solvent extracts prepared from liquid cultures of C. albicans in the presence of clotrimazole―a clinically approved azole antifungal drug that suppresses ergosterol biosynthesis by the inhibition of 14α-demethylase―showed reduced cellular ergosterol content and increased concentrations of lanosterol and 24-methylenedihydrolanosterol (a shunt metabolite of ergosterol biosynthesis). No change in relative sterol composition was observed when C. albicans was cultured with bengazole A. These results eliminate an azole-like MOA for the bengazoles, and suggest that another as-yet unidentified mechanism is operative.

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31

Kinder, Frederick R. "SYNTHETIC APPROACHES TOWARD THE BENGAMIDE FAMILY OF ANTITUMOR MARINE NATURAL PRODUCTS. A REVIEW." Organic Preparations and Procedures International 34, no. 6 (December 2002): 559–83. http://dx.doi.org/10.1080/00304940209355783.

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32

Kinder Jr., Frederick R., Richard W. Versace, and et al et al. "ChemInform Abstract: Synthesis and Antitumor Activity of Ester-Modified Analogues of Bengamide B." ChemInform 33, no. 9 (May 22, 2010): no. http://dx.doi.org/10.1002/chin.200209237.

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33

Dhimane, Hamid, and Safiul Alam. "A Concise Synthesis of Bengamide E and Analogues via E-Selective Cross-Metathesis Olefination." Synlett 2010, no. 19 (November 3, 2010): 2923–27. http://dx.doi.org/10.1055/s-0030-1259015.

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34

Chida, Noritaka, Takahiko Tobe, Katsuyuki Murai, Kaori Yamazaki, and Seiichiro Ogawa. "Stereoselective Conversion of L-Quebrachitol into a Novel Hydroxylated Caprolactam: Total Synthesis of Bengamide B." HETEROCYCLES 38, no. 11 (1994): 2383. http://dx.doi.org/10.3987/com-94-6869.

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35

Tietjen, Ian, David E. Williams, Silven Read, Xiaomei T. Kuang, Philip Mwimanzi, Emmanuelle Wilhelm, Tristan Markle, et al. "Inhibition of NF-κB-dependent HIV-1 replication by the marine natural product bengamide A." Antiviral Research 152 (April 2018): 94–103. http://dx.doi.org/10.1016/j.antiviral.2018.02.017.

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36

Mukai, Chisato, Osamu Kataoka, and Miyoji Hanaoka. "A cobalt-complexed propyanl in organic synthesis: A highly stereoselective total synthesis of bengamide E." Tetrahedron Letters 35, no. 37 (September 1994): 6899–902. http://dx.doi.org/10.1016/0040-4039(94)85036-4.

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37

Wenzel, Silke C., Holger Hoffmann, Jidong Zhang, Laurent Debussche, Sabine Haag-Richter, Michael Kurz, Frederico Nardi, et al. "Produktion mariner Naturstoffe aus der Klasse der Bengamide in Myxobakterien: Biosynthese und Struktur-Aktivitäts-Beziehungen." Angewandte Chemie 127, no. 51 (October 30, 2015): 15781–85. http://dx.doi.org/10.1002/ange.201508277.

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38

Hu, Xiaoyi, Yongjun Dang, Karen Tenney, Phillip Crews, Chiawei W. Tsai, Katherine M. Sixt, Philip A. Cole, and Jun O. Liu. "Regulation of c-Src Nonreceptor Tyrosine Kinase Activity by Bengamide A through Inhibition of Methionine Aminopeptidases." Chemistry & Biology 14, no. 7 (July 2007): 764–74. http://dx.doi.org/10.1016/j.chembiol.2007.05.010.

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39

Marshall, James A., and George P. Luke. "Stereoselective total synthesis of bengamide E from glyceraldehyde acetonide and a nonracemic .gamma.-alkoxy allylic stannane." Journal of Organic Chemistry 58, no. 23 (November 1993): 6229–34. http://dx.doi.org/10.1021/jo00075a017.

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40

Wenzel, Silke C., Holger Hoffmann, Jidong Zhang, Laurent Debussche, Sabine Haag-Richter, Michael Kurz, Frederico Nardi, et al. "Production of the Bengamide Class of Marine Natural Products in Myxobacteria: Biosynthesis and Structure-Activity Relationships." Angewandte Chemie International Edition 54, no. 51 (October 30, 2015): 15560–64. http://dx.doi.org/10.1002/anie.201508277.

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41

Martín-Gálvez, Francisca, Cristina García-Ruiz, Antonio Sánchez-Ruiz, Frederick A. Valeriote, and Francisco Sarabia. "An Array of Bengamide E Analogues Modified at the Terminal Olefinic Position: Synthesis and Antitumor Properties." ChemMedChem 8, no. 5 (March 19, 2013): 819–31. http://dx.doi.org/10.1002/cmdc.201300033.

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42

Sarabia, Francisco, and Antonio Sánchez-Ruiz. "Total Synthesis of Bengamide E and Analogues by Modification at C-2 and at Terminal Olefinic Positions." Journal of Organic Chemistry 70, no. 23 (November 2005): 9514–20. http://dx.doi.org/10.1021/jo0516032.

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43

MUKAI, C., O. KATAOKA, and M. HANAOKA. "ChemInform Abstract: A Cobalt-Complexed Propynal in Organic Synthesis: A Highly Stereoselective Total Synthesis of Bengamide E." ChemInform 26, no. 7 (August 18, 2010): no. http://dx.doi.org/10.1002/chin.199507220.

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44

CHIDA, N., T. TOBE, K. MURAI, K. YAMAZAKI, and S. OGAWA. "ChemInform Abstract: Stereoselective Conversion of L-Quebrachitol Into a Novel Hydroxylated Caprolactam: Total Synthesis of Bengamide B." ChemInform 26, no. 7 (August 18, 2010): no. http://dx.doi.org/10.1002/chin.199507256.

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45

Susilowati, Fitria, Respati Tri Swasono, Tatsufumi Okino, and Winarto Haryadi. "IN VITRO CYTOTOXIC ANTICANCER POTENTIAL OF BIOACTIVE FRACTION ISOLATED FROM INDONESIAN TIDAL SPONGE CALTHROPELLA SP." Asian Journal of Pharmaceutical and Clinical Research 12, no. 1 (January 7, 2019): 380. http://dx.doi.org/10.22159/ajpcr.2018.v12i1.23655.

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Objective: This study was taken to examine the cytotoxicity of the bioactive fraction isolated from marine sponge Calthropella sp. as a preliminary anticancer assay and identify its bioactive compounds.Methods: The cytotoxic activity was assessed by 3-(4,5-dimethylthiazol-2-y1)-2,5-diphenyltetrazolium bromide assay against three human cancer cell lines, namely human breast (MCF-7), human lung (H-460), and human liver (HepG-2). The bioactive compounds were identified using a high-resolution liquid chromatography–mass spectroscopy (LC–MS).Results: The active fraction 7 showed moderate to strong cytotoxic activity on all cell lines tested and promising a strong potent cytotoxicity against MCF-7 cell lines with IC50 value as low as 1.925 μg/mL comparable to control, cisplatin (IC50 0.977 μg/mL). In regard to the promising bioactive compounds, the high-resolution LC–MS predicted the existing of several known compounds such as bengamide Q, clavepictine A, 4’-N-methyl-5’- hydroxystaurosporine, carteriofenone A, and one strong possibility of a new compound.Conclusion: This study has revealed that the isolated bioactive fraction of Indonesian tidal sponge, Calthropella sp., possesses potential anticancer properties with a promising significant cytotoxicity on MCF-7 cell lines (IC50 1.925 μg/mL).

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46

Susilowati, Fitria, Respati Tri Swasono, Tatsufumi Okino, and Winarto Haryadi. "IN VITRO CYTOTOXIC ANTICANCER POTENTIAL OF BIOACTIVE FRACTION ISOLATED FROM INDONESIAN TIDAL SPONGE CALTHROPELLA SP." Asian Journal of Pharmaceutical and Clinical Research 12, no. 1 (January 7, 2019): 380. http://dx.doi.org/10.22159/ajpcr.2019.v12i1.23655.

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Objective: This study was taken to examine the cytotoxicity of the bioactive fraction isolated from marine sponge Calthropella sp. as a preliminary anticancer assay and identify its bioactive compounds.Methods: The cytotoxic activity was assessed by 3-(4,5-dimethylthiazol-2-y1)-2,5-diphenyltetrazolium bromide assay against three human cancer cell lines, namely human breast (MCF-7), human lung (H-460), and human liver (HepG-2). The bioactive compounds were identified using a high-resolution liquid chromatography–mass spectroscopy (LC–MS).Results: The active fraction 7 showed moderate to strong cytotoxic activity on all cell lines tested and promising a strong potent cytotoxicity against MCF-7 cell lines with IC50 value as low as 1.925 μg/mL comparable to control, cisplatin (IC50 0.977 μg/mL). In regard to the promising bioactive compounds, the high-resolution LC–MS predicted the existing of several known compounds such as bengamide Q, clavepictine A, 4’-N-methyl-5’- hydroxystaurosporine, carteriofenone A, and one strong possibility of a new compound.Conclusion: This study has revealed that the isolated bioactive fraction of Indonesian tidal sponge, Calthropella sp., possesses potential anticancer properties with a promising significant cytotoxicity on MCF-7 cell lines (IC50 1.925 μg/mL).

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47

MARSHALL, J. A., and G. P. LUKE. "ChemInform Abstract: Stereoselective Total Synthesis of Bengamide E from Glyceraldehyde Acetonide and a Nonracemic γ-Alkoxy Allylic Stannane." ChemInform 25, no. 10 (August 19, 2010): no. http://dx.doi.org/10.1002/chin.199410247.

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48

Johnson, Tyler A., Johann Sohn, Yvette M. Vaske, Kimberly N. White, Tanya L. Cohen, Helene C. Vervoort, Karen Tenney, Frederick A. Valeriote, Leonard F. Bjeldanes, and Phillip Crews. "Myxobacteria versus sponge-derived alkaloids: The bengamide family identified as potent immune modulating agents by scrutiny of LC–MS/ELSD libraries." Bioorganic & Medicinal Chemistry 20, no. 14 (July 2012): 4348–55. http://dx.doi.org/10.1016/j.bmc.2012.05.043.

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49

Mukai, Chisato, Osamu Kataoka, and Miyoji Hanaoka. "An efficient method for the optical resolution of 3-hydroxy-2-substituted-4-alkynoates: a highly stereoselective total synthesis of (+)-bengamide E1." Journal of Organic Chemistry 60, no. 18 (September 1995): 5910–18. http://dx.doi.org/10.1021/jo00123a030.

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50

Philip, Anijamol T., Eerlapally Raju, and Ramesh Ramapanicker. "Stereoselective Synthesis of Hydroxy Diamino Acid Derivatives and the Caprolactam Unit of Bengamide A through Organocatalytic α-Hydroxylation and Reductive Amination of Aldehydes." European Journal of Organic Chemistry 2016, no. 33 (October 20, 2016): 5502–10. http://dx.doi.org/10.1002/ejoc.201600842.

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