Isolation and Evaluation of Anti-Mycobacterial Activity of Alkaloid Compounds from Marine Invertebrate Sponge Haliclona sp.

http://www.doi.org/10.26538/tjnpr/v6i10.10

Authors

  • Wilmar Maarisit Department of Pharmacy, Indonesia Christian University, Tomohon North Sulawesi, 95362, Indonesia
  • Sonny D. Untu Department of Biology, Indonesia Christian University, Tomohon North Sulawesi, 95362, Indonesia
  • Yessie K. Lengkey Department of Biology, Indonesia Christian University, Tomohon North Sulawesi, 95362, Indonesia
  • Jeane Mongi Department of Pharmacy, Indonesia Christian University, Tomohon North Sulawesi, 95362, Indonesia
  • Jabes W. Kanter Department of Pharmacy, Indonesia Christian University, Tomohon North Sulawesi, 95362, Indonesia
  • Douglas N. Pareta Department of Pharmacy, Indonesia Christian University, Tomohon North Sulawesi, 95362, Indonesia
  • Chistel N. Sambou Department of Pharmacy, Indonesia Christian University, Tomohon North Sulawesi, 95362, Indonesia
  • Silvana L. Tumbel Department of Pharmacy, Indonesia Christian University, Tomohon North Sulawesi, 95362, Indonesia
  • Friska M. Montolalu Department of Pharmacy, Indonesia Christian University, Tomohon North Sulawesi, 95362, Indonesia
  • Sandra A. Korua Department of Agrotechnology, Indonesia Christian University, Tomohon North Sulawesi, 95362, Indonesia
  • Franky R. Tulungen Department of Agribusiness, Indonesia Christian University, Tomohon North Sulawesi, 95362, Indonesia

Keywords:

Antimycobacterial,, Structure elucidation,, Alkaloid,, Natural product,, Haliclona sp

Abstract

Marine invertebrate sponges are a rich source of new bioactive substances. The objective of this investigation was to isolate the anti-mycobacterium bioactive compounds from sponge Haliclona sp. A new alkaloid (1) was obtained through bioassay-guided purification together with eight previously known substances, including cyclostellettamines A (5), B (6), C (7), E (8), and F (9) and the haliclocyclamines A (2), B (3), and C. The structures of 1-9 were established applying spectroscopic analysis, including 1D NMR (1H and 13C-NMR), 2D NMR (HMQC, HMBC, 1H-1H COSY), mass spectroscopy, IR, and UV. Furthermore, the findings revealed that the compounds exhibited inhibitory activity against Mycobacterium smegmatis at 10 µg/disc.

References

World Health Organization (WHO). Global Tuberculosis Report. 2020.

World Health Organization (WHO). Global Tuberculosis Report. 2021.

Ryan NJ, and Han J. Delamanid : First Global Approval. Drugs. 2014; 74(9):1041–1045.

Xavier AS, and Lakshmanan M. Molecules of the Millennium Delamanid : A New Armor in Combating Drug - Resistant Tuberculosis. J. Pharmacol. Pharmacother. 2014; 5(3): 222– 225.

Carrol AR, Cop BR, Davis RA, Keyzers RA, Prinsep MR. Marine Natural Products. Nat. Prod. Rep. 2021; 38, 362-413

Carrol AR, Cop BR, Davis RA, Keyzers RA, Prinsep MR. Marine Natural Products. Nat. Prod. Rep. 2020; 37:175-223

Carrol AR, Cop BR, Davis RA, Keyzers RA, Prinsep MR. Marine Natural Products. Nat. Prod. Rep. 2019; 36:122-173

Maarisit W, Yamazaki H, Abdjul B, Takahashi O, Kirikoshi R, Namikoshi M. A New Pyranonaphtoquinone Derivative, 4- Oxo-Rhinacanthin A, from Roots of Indonesian Rhinacanthus nasutus. Chem. Pharm. Bull. 2017; 65(6):586–588.

Maarisit W, Abdjul DB, Yamazaki H, Kato H, Rotinsulu H, Wewengkang DS, Sumilat DA, Kapojos MM, Ukai K, Namikoshi M. Anti-Mycobacterial Alkaloids, Cyclic 3-Alkyl Pyridinium Dimers, from the Indonesian Marine Sponge Haliclona Sp. Bioorg. Med. Chem. Lett. 2017; 27(15):3503– 3506.

Yamazaki H, Nakayama W, Takahashi O, Kirikoshi R, Izumikawa Y, Sumilat DA, Mangindaan REP, Namikoshi M. Verruculides A and B, Two New Protein Tyrosine Phosphatase 1B Inhibitors from an Indonesian AscidianDerived Penicillium Verruculosum. Bioorg. Med. Chem. Lett. 2015; 25(16):3087–3090.

Yamazaki H, and Sumilat DA. A Polybromodiphenyl Ether from an Indonesian Marine Sponge Lamellodysidea Herbacea and Its Chemical Derivatives Inhibit Protein Tyrosine Phosphatase 1B, an Important Target for Diabetes Treatment. Nat. Med. 2012; 67(4):730–735.

Abdjul DB, Yaki A, Yamazaki H, Kirikoshi R, Takahashi O, Namikoshi M, Uchida R. Anti-mycobacterial haliclonadiamine alkaloids from the Okinawan marine sponge Haliclona sp. collected at Iriomote Island. Phytochem. Lett. 2018; 26:130–133

Bu YY, Yamazaki H, Ukai K, Namikoshi M. Anti- Mycobacterial Nucleosides Antibiotics from a Marine Derived Streptomyces sp. TPU 1236A. Mar. Drug. 2014; 12:6102- 6112.

Fusetan N, Asai N, and Matsunaga S. Cyclostellettamines A- F, Pyridine Alkaloids Which Inhibit Binding of Methyl Quinuclidinyl Benzilate (QNB) to Muscarinic Acetylcholine Receptors, from the Marine Sponge, Stefletta maxitnal. Tetrahedron Lett. 1994; 35(23):3967–3970.

Davies-coleman MT, Faulkner DJ, Dubowchik GM, Roth GP, Polson C, Fairchildt C. New EGF-Active Polymeric Pyridinium Alkaloid from the Sponge Callyspongia Fibrosa. J. Org. Chem. 1993; 58(22):5925–5930.

Wang GYS, Kuramoto M, Uemura D, Akihiro Y, Yamaguchi K, Yazawa K. Three Novel Anti-Microfouling Nitroalkyl Pyridine Alkaloids from the Okinawan Marine Sponge Callyspongia sp. Tetrahedron Lett. 1996; 37(11):1813–1816.

Zhang H, Loveridge ST, Tenney, K, and Crews, P. A new 3- alkylpyridine alkaloid from the marine sponge Haliclona sp. and its cytotoxic activity. Nat. Prod. Res. 2016; 30(11):1262- 1265.

Schmidt G, Timm C, Grube A, Volk CA, Ko c¨ k M. Viscosalines B1,2 and E1,2: challenging new 3-alkyl pyridinium alkaloids from the marine sponge Haliclona viscosa. Chem Eur J. 2012; 18:8180–8189.

Köck M, Muñoz J, Cychon C, Timm C, and Schmidt G. The Arctic sponge Haliclona viscosa as a source of a wide array of 3-alkyl pyridine alkaloids. Phytochem Rev. 2013; 12(3):391– 406.

Einarsdottir E, Magnusdottir M, Astarita G, Köck M, Ögmundsdottir H, Thorsteinsdottir M, Rap HT, Omarsdottir S, Paglia G. Metabolic Profiling as a Screening Tool for Cytotoxic Compounds: Identification of 3-Alkyl Pyridine Alkaloids from Sponges Collected at a Shallow Water Hydrothermal Vent Site North of Iceland. Mar.Drugs, 2017; 15(2):3-14.

Timm C, Mordhorst T, and Köck M. Synthesis of 3-alkyl pyridinium alkaloids from the Arctic sponge Haliclona viscosa. Mar.Drugs. 2010; 8:483–49

Kubota T, Kura K, Fromont J, and Kobayashi J. Pyrinodemins G–I, new bis-3-alkylpyridine alkaloids from a marine sponge Amphimedon sp. Tetrahedron. 2013; 69(1):96–100.

Xu NJ, Sun X, and Yan XJ. (2007). A new cyclostellettamine from sponge Amphimedon compressa. Chin. Chem. Lett. 2007; 18(8):947–950.

Hirano K, Kubota T, Tsuda M, Mikami Y, Kobayashi, J. Pyrinodemins B-D, Potent Cytotoxic Bis-Pyridine Alkaloids from Marine Sponge Amphimedon sp. Chem. Pharm. Bull. 2000; 48(7): 974–977.

Sun JZ, Jiang CS, Chen XQ, Chen KS, Zhen XC, van Soest RWM, and Guo YW. Topsendines A–F, new 3-alkylpyridine alkaloids from a Hainan sponge Topsentia sp. Tetrahedron. 2014; 70(19):3166–3171

.

Hitora, Y, Maeda R, Honda K, Sadahiro Y, Ise Y, Angkouw ED, Mangindaan REP, Tsukamoto S. Neopetrosidines A–D, pyridine alkaloids isolated from the marine sponge Neopetrosia chaliniformis and their cell cycle elongation activity. Bioorg. Med. Chem. 2021; 50:116461

Arai M, Kamiya K, Shin D, Matsumoto H, Hisa T, Setiawan A, Kotoku N, Kobayashi M. N-Methylniphatyne A, a New 3- Alkylpyridine Alkaloid as an Inhibitor of the Cancer Cells Adapted to Nutrient Starvation, from an Indonesian Marine Sponge of Xestospongia sp. Chem. Pharm. Bull. 2016; 64;766–771

Elissawy AM, Dehkordi ES, Mehdinezhad N, Ashour ML, and Pour PM. Cytotoxic Alkaloids Derived from Marine Sponges: A Comprehensive Review. Biomolecules. 2021, 11;258.

Damodaran V, Ryan JL, and Keyzers RA. Cyclic 3-alkyl pyridinium alkaloid monomers from a new Zealand Haliclona sp. Marine sponge. J. Nat. Prod.. 2013;76(10):1997–2001.

Andrade JT, Lima WG, Barbosa CS, Goncalves AMMN, Silva MKP, Morais FB, Palumbo JMC, Viana GHR, and Ferreira JMS. Antifungal Activity of a Novel 3-Alkylpyridine analog derived from Marine Sponge Alkaloid. An Acad Bras Cienc. 2021; 93(supll.4):e20200944.

Barbosa MCS, Barbosa CSB, Oliveira JT, Moreira NCS, Martins NRM, Gomes GKA, Caldeira CA, Costa MLA, Uimaraes DSL, Guimaraes L, Nascimento CS, Varotti FP, Viana GHR, Santos FV. Synthesis and evaluation of the mutagenicity of 3-alkylpyridine marine alkaloid analogues with anticancer potential. Mutat Res Toxicol Environ Mutagen. 2018; 825:31-39.

Kaplan AR, Schrank, CL, and Wuest WM. An Efficient Synthesis of 3-Alkylpyridine Alkaloids Enables Their Biological Evaluation. Chem. Med. Chem. 2021; 16(16):2487–2490.

Downloads

Published

2022-10-01

How to Cite

Maarisit, W., D. Untu, S., K. Lengkey, Y., Mongi, J., W. Kanter, J., N. Pareta, D., … R. Tulungen, F. (2022). Isolation and Evaluation of Anti-Mycobacterial Activity of Alkaloid Compounds from Marine Invertebrate Sponge Haliclona sp.: http://www.doi.org/10.26538/tjnpr/v6i10.10. Tropical Journal of Natural Product Research (TJNPR), 6(10), 1622–1625. Retrieved from https://tjnpr.org/index.php/home/article/view/1213

Most read articles by the same author(s)