Malaysian Journal of Analytical Sciences Vol 22 No 3 (2018): 375 - 382

DOI: 10.17576/mjas-2018-2203-02

 

 

 

A-NOR STEROIDS FROM THE MARINE SPONGE, Clathria SPECIES

 

(Steroid A-nor daripada Span Laut, Spesies Clathria)

 

Idin Sahidin¹*, Carla Wulandari Sabandar¹, Wahyuni¹, Rini Hamsidi¹, Muhammad Hajrul Malaka¹, Baru Sadarun², La Ode Aslan²

 

¹Faculty of Pharmacy

²Faculty of Fisheries and Marine Science

Universitas Halu Oleo, Kendari 93232, Indonesia

 

*Corresponding author:  sahidin02@yahoo.com

 

 

Received: 22 August 2017; Accepted: 20 March 2018

 

 

Abstract

Chemical compounds classified as A-nor steroids (1–4) were isolated from a marine sponge of the Clathria sp., collected  from  Southeast  Sulawesi, Indonesia. Of these, one new compound, clathruhoate (1) was elucidated as 3β-(butyryloxymethyl)-A-nor-5α-cholestane. All compounds were obtained using silica gel chromatography techniques and their structures were determined based on 1D and 2D NMR spectroscopic measurements and comparison with values from literature. Meanwhile, all compounds were inactive for antimicrobial activity.

 

Keywords:  Clathria sp., marine sponge, A-nor steroid, 3β-(Butyryloxymethyl)-A-nor-5α-cholestane

 

Abstrak

Sebatian kimia diklasifikasikan sebagai steroid A-nor (1–4) telah diasingkan daripada span laut Clathria yang dikumpul  dari  Sulawesi  Tenggara,  Indonesia.  Satu  sebatian  baharu,  klathruhoat (1)  telah ditentukan sebagai 3β-(butiriloksimetil)-A-nor-5α-kolestan. Semua sebatian diperoleh dengan menggunakan teknik kromatografi gel silika dan struktur sebatian-sebatian ini telah ditentukan menggunakan spektroskopi 1D dan 2D NMR dan dengan perbandingan nilai dari kajian literatur. Sementara itu, semua sebatian didapati tidak aktif terhadap aktiviti antimikrob.

 

Kata kunci:  Clahtria sp., span laut, steroid A-nor, 3β-(Butiriloksimetil)-A-nor-5α-kolestan

 

References

1.       Spalding, M. D., Ravilious, C. and Green, E. P. (2001). World atlas of coral reefs. University of California Press, Berkeley, Los Angeles, CA: pp. 21 – 22.

2.       Mora, C., Chittaro, P. M., Sale, P. F., Kritzer, J.P. and Ludsin, S.A. (2003). Patterns and processes in reef fish diversity. Nature, 421: 933 – 936.

3.       van Soest, R. W. M. (1989). The Indonesia sponge fauna: a status report. Netherlands Journal of Sea Research, 23: 223 – 230.

4.       Soekarno, R. (1989). Comparative studies on the status of Indonesia coral reefs. Netherlands Journal of Sea Research, 23: 215 – 222.

5.       van Soest, R. (2017). Clathria Schmidt, 1982. In Wold Porifera Database. van Soest, R. W. M., Boury-Esnault, N., Hooper, J. N. A., Rützler, K., de Voogd, N. J., Alvarez de Glasby, B., Pisera, A. B., Manconi, R., Schoenberg, C., Klautau, M., Picton, B., Kelly, M., Vacelet, J., Dohrmann, M., Díaz, M. C., Cárdenas, P., Carballo, J. L. and Rios Lopez, P. (Eds). Accessed through: World Register of Marine Species (http://www.marinespecies.org/aphia.php?p=taxdetails&id=131868 on 2017-07-23).

6.       Sperry, S. and Crews, P. (1996). A novel alkaloid from the Indo-Pacific sponge Clathria basilana. Tetrahedron Letters, 37: 2389 – 2390.

7.       Capon, R. J., Miller, M. and Rooney, F. (2001). Mirabilin G: a new alkaloid from a southern Australian marine sponge, Clathria species. Journal of Natural Products, 64: 643 – 644.

8.       Zuleta, I. A., Vitelli, M. L., Baggio, R., Garland, M. T., Seldes, A. M. and Palermo, J. A. (2002). Novel pteridine alkaloids from the sponge Clathria sp. Tetrahedron, 58: 4481 – 4486.

9.       El-Naggar, M., Conte, M. and Capon, R. J. (2010). Mirabilins revisited: polyketide alkaloids from a southern Australian marine sponge, Clathria sp. Organic & Biomolecular Chemistry, 8: 407 – 412.

10.    Laville, R., Thomas, O. P., Berrué, F., Marquez, D., Vacelet, J. and Amade, P. (2009). Bioactive guanidine alkaloids from two Carribean marine sponges. Journal of Natural Products, 72: 1589 – 1594.

11.    Sun, X., Sun, S., Ference, C., Zhu, W., Zhou, N., Zhang, Y. and Zhou, K. (2015). A potent antimicrobial compound isolated from Clathria cervicornis. Bioorganic & Medicinal Chemistry Letters, 25: 67 – 69.

12.    Wei, X., Henriksen, N. M., Skalicky, J. J., Harper, M. K., Cheatham, T. E., III, Ireland, C. M. and Van Wagoner, R. M. (2011). Araiosamines A-D: tris-bromoindole cyclic guanidine alkaloids from the marine sponge Clathria (Thalysias) araiosa. The Journal of Organic Chemistry, 76: 5515 – 5523.

13.    Ohta, S., Okada, H., Kobayashi, H., Oclarit, J. M. and Ikegami, S. (1993). Clathrynamides A, B, and C: novel amides from a marine sponge Clathria sp. that inhibit cell division of fertilized starfish eggs. Tetrahedron Letters, 34: 5935 – 5938.

14.    Davis, R. A., Mangalindan, G. C., Bojo, Z. P., Antemano, R. R., Rodriguez, N. O., Concepcion, G. P., Samson, S. C., de Guzman, D., Cruz, L. J., Tasdemir, D., Harper, M. K., Feng, X., Carter, G. T. and Ireland, C. M. (2004). Microcionamides A and B, bioactive peptides from the Philippine sponge Clathria (Thalysias) abietina. The Journal of Organic Chemistry, 69: 4170 – 4176.

15.    Woo, J. –K., Jeon, J., Kim, C. –K., Sim, C. J., Oh, D. –C., Oh, K. –B. and Shin, J. (2013). Gombamide A, a cyclic thiopeptide from the sponge Clathria gombawuiensis. Journal of Natural Products, 76: 1380 – 1383.

16.    Khokhar, S., Pierens, G. K., Hooper, J. N. A., Ekins, M. G., Feng, Y. and Davis, R. A. (2016). Rhodocomatulin-type anthraquinones from the Australian marine invertebrates Clathria hirsuta and Comatula rotalaria. Journal of Natural Products, 79: 946 – 953.

17.    Capon, R. J., Miller, M. and Rooney, F. (2000). Clathrins A-C: metabolites from a southern Australian marine sponge, Clathria species. Journal of Natural Products, 63: 821 – 824.

18.    Rudi, A., Yosief, T., Loya, S., Hizi, A., Schleyer, M. and Kashman, Y. (2001). Clathsterol, a novel anti-HIV-1 RT sulfated sterol from the sponge Clathria species. Journal of Natural Products, 64: 1451 – 1453.

19.    Keyzers, R. A., Northcote, P. T. and Webb, V. (2002). Clathriol, a novel polyoxygenated 14β steroid isolated from the New Zealand marine sponge Clathria lissosclera. Journal of Natural Products, 65: 598 – 600.

20.    Santalova, E. A., Makarieva, T. N., Gorshkova, I. A., Dmitrenok, A. S., Krasokhin, V. B. and Stonik, V. A. (2004). Sterols from six marine sponges. Biochemical Systematics and Ecology, 32: 153 – 167.

21.    Gupta, P., Sharma, U., Schulz, T. C., McLean, A. B., Robins, A. J. and West, L. M. (2012). Bicyclic C21 terpenoids from the marine sponge Clathria compressa. Journal of Natural Products, 75: 1223 – 1227.

22.    Woo, J. –K., Kim, C. –K., Kim, S. –H., Kim, H., Oh, D. –C., Oh, K. –B. and Shin, J. (2014). Gombaspiroketals A-C, sesterterpenes from the sponge Clathria gombawuiensis. Organic Letters, 16: 2826 – 2829.

23.    Woo, J. –K., Kim, C. –K., Ahn, C. –H., Oh, D. –C., Oh, K. –B. and Shin, J. (2015). Additional sesterterpenes and a nortriterpene saponin from the sponge Clathria gombawuiensis. Journal of Natural Products, 78: 218 – 224.

24.    Inbaneson, S. J. and Ravikumar, S. (2012). In vitro antiplasmodial activity of Clathria vulpina sponge associated bacteria against Plasmodium falciparum. Asian Pacific Journal of Tropical Disease, 2012: 319 – 323.

25.    Eggersdorfer, M. L., Kokke, W. C. M. C., Crandell, C. W., Hochlowski, J. E. and Djerassi, C. (1982). Sterols in marine invertebrates. 32.¹ Isolation of 3β-(hydroxymethyl)-A-nor-5α-cholest-15-ene, the first naturally occurring sterol with a 15-16 double bond. The Journal of Organic Chemistry, 47: 5304 – 5309.

26.    Malik, S. and Djerassi, C. (1989). Minor and trace sterols in marine invertebrates. 61. Isolation and structure elucidation of new A-nor sterols from the marine sponge Phakellia aruensis. Steroids, 53: 271 – 284.

27.    Aknin, M., Gaydou, E. M., Boury-Esnault, N., Constantino, V., Fattorusso, E. and Mangoni, A. (1996). Nor-sterols in Axinella proliferans, sponge from the Indian Ocean. Comparative Biochemistry and Physiology, 113: 845 – 848.

28.    Minale, L. and Sodano, G. (1974). Marine sterols: unique 3β-hydroxymethyl-A-nor-5α-steranes from the sponge Axinella verrucosa. Journal of the Chemical Society, Perkin Transactions I: 2380 – 2384.

29.    Bibolini, L., Minale, L. and Sodano, G. (1978). Investigations on the ring contraction step in the biosynthesis of A-nor-stanols by the marine sponge Axinella verrucosa. Journal of the Chemical Society, Chemistry Communications: 524 – 525.

30.    Ngajow, M., Abidjulua, J. and Kamu, VS. (2013). Pengaruh antibakteri ekstrak kulit batang Matoa (Pometia pinnata) terhadap bakteri Staphylococcus aureus secara in vitro. Jurnal Mipa Unsrat Online, 2(2): 128 – 132.