Scalarane-type Sesterterpenes from the Philippines Sponge Hyrtios sp.

doi:10.4217/OPR.2020.42.1.015

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2020 Vol.42, Issue 1 Preview Page Next Page

Article

Scalarane-type Sesterterpenes from the Philippines Sponge Hyrtios sp.: Jae-Hyeong Choi, Hyi-Seung Lee, and Wilfredo L. Campos

31 March 2020. pp. 15−20

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Abstract

The marine sponge Hyrtios sp. collected in the Philippines was extracted and partitioned. The resulting organic layer was purified by C₁₈ reversed-phase column chromatography and HPLC to achieve the separation of nine scalarane-type sesterterpenes, including one new compound with eight known scalarane analogs. The chemical structures of the isolated compounds 1−9 were elucidated by 1D and 2D NMR and MS data analysis. All nine compounds were evaluated for their antibacterial activities against three Gram-positive and three Gram-negative bacteria. The compound 3 exhibited potent antibacterial activities against Bacillus subtilis and Micrococcus luteus. The compounds 7 and 9 displayed considerable activities against Bacillus subtilis and the others had moderate results.

Keywords

marine sponge

scalarane

sesterterpene

Hyrtios sp.

antibacterial activities

References

Amina M, Al Musayeib NM (2018) Biological and medicinal importance of sponge. Ray S (ed) In: Biological resource of waters. IntechOpen, London, pp 201−230
Cimino G, De Napoli L, Fattorusso E (1978) 13C-NMR spectrum and absolute stereochemistry of furoscalarol. Tetrahedron Lett 19(23):2041−2044
Davis R, Capon R (1993) Two new scalarane sesterterpenes: Isoscalarafuran-A and-B, epimeric alcohols from a southern Australian Marine Sponge, Spongia hispida. Aust J Chem 46(8):1295−1299
De Rosa S, Puliti R, Crispino A, De Giulio A, Mattia C, Mazzarella L (1994) A new scalarane sesterterpenoid from the marine sponge Cacospongia mollior. J Nat Prod 57(2):256−262
Doi Y, Shigemori H, Ishibashi M, Mizobe F, Kawashima A, Nakaike S, Kobayashi J (1993) New sesterterpenes with nerve growth factor synthesis-stimulating activity from the Okinawan marine sponge Hyrtios sp. Chem Pharm Bull 41(12):2190−2191
Fattorusso E, Magno S, Santacroce C, Sica D (1972) Scalarin, a new pentacyclic C-25 terpenoid from the sponge Cacospongia scalaris. Tetrahedron 28(24):5993−5997
Fontana A, Cavaliere P, Ungur N, D'Souza L, Parameswaram P, Cimino G (1999) New scalaranes from the nudibranch Glossodoris atromarginata and its sponge prey. J Nat Prod 62(10):1367−1370
Fontana A, Mollo E, Ortea J, Gavagnin M, Cimino G (2000) Scalarane and homoscalarane compounds from the nudibranchs Glossodoris sedna and Glossodoris dalli: Chemical and biological properties. J Nat Prod 63(4):527−530
Gavagnin M, Mollo E, Docimo T, Guo Y-W, Cimino G (2004) Scalarane metabolites of the nudibranch Glossodoris rufomarginata and its dietary sponge from the South China Sea. J Nat Prod 67(12):2104−2107
Gonzalez MA (2010) Scalarane sesterterpenoids. Curr Bioact Compd 6(3):178−206
Iguchi K, Shimada Y, Yamada Y (1992) Hyrtiosal, a new sesterterpenoid with a novel carbon skeleton from the Okinawan marine sponge Hyrtios erectus. J Org Chem 57(2):522−524
Jaspars M, Jackson E, Lobkovsky E, Clardy J, Diaz MC, Crews P (1997) Using scalarane sesterterpenes to examine a sponge taxonomic anomaly. J Nat Prod 60(6):556−561
Kamel HN, Kim YB, Rimoldi JM, Fronczek FR, Ferreira D, Slattery M (2009) Scalarane sesterterpenoids: Semisynthesis and biological activity. J Nat Prod 72(8):1492−1496
Kashman Y, Rudi A (1997) The 13C-NMR spectrum and stereochemistry of heteronemin. Tetrahedron 33(22):2997−2998
Lee Y-J, Lee J-W, Lee D-G, Lee H-S, Kang J, Yun J (2014) Cytotoxic sesterterpenoids isolated from the marine sponge Scalarispongia sp. Int J Mol Sci 15(11):20045−20053
Liu Y, Wang L, Jung JH, Zhang S (2007) Sesterterpenoids. Nat Prod Rep 24(6):1401−1429
Miller JH, Singh AJ, Northcote PT (2010) Microtubulestabilizing drugs from marine sponges: Focus on peloruside A and zampanolide. Mar Drugs 8(4):1059−1079
Miyaoka H, Nishijima S, Mitome H, Yamada Y (2000) Three new scalarane sesterterpenoids from the Okinawan sponge Hyrtios erectus. J Nat Prod 63(10):1369−1372
Pettit GR, Cichacz ZA, Tan R, Herald DL, Melody N, Hoard MS, Doubek DL, Hooper JN (1998) Antineoplastic agents 385. The isolation and structure of a scalaranetype sesterterpene from the Indian Ocean Porifera Hyrtios erecta. Collec Czech Chem C 63(10):1671−1677
Pettit GR, Tan R, Melody N, Cichacz ZA, Herald DL, Hoard MS, Pettit RK, Chapuis J-C (1998) Antineoplastic agents 397: Isolation and structure of sesterstatins 4 and 5 from Hyrtios erecta (The Republic of Maldives). Bioorg Med Chem Lett 8(16):2093−2098
Roy MC, Tanaka J, De Voogd N, Higa T (2002) New scalarane class sesterterpenes from an Indonesian sponge, Phyllospongia sp. J Nat Prod 65(12):1838−1842
Ryu G, Matsunaga S, Fusetani N (1996) Three new cytotoxic sesterterpenes from the marine sponge Hyrtios cf. erectus. J Nat Prod 59(5):515−517
Song J, Jeong W, Wang N, Lee H-S, Sim CJ, Oh K-B, Shin J (2008) Scalarane sesterterpenes from the sponge Smenospongia sp. J Nat Prod 71(11):1866−1871
Ungur N, Kulciţki V (2004) Synthetic paths towards scalaranes: Assembling the scalaranic skeleton and further transformations. Phytochem Rev 3(3):401−415
Yu ZG, Bi KS, Guo YW (2005) Hyrtiosins A−E, five new scalarane sesterterpenes from the South China Sea sponge Hyrtios erecta. Helv Chim Acta 88(5):1004−1009

Information

Publisher :Korea Institute of Ocean Science and Technology
Publisher(Ko) :한국해양과학기술원
Journal Title :Ocean and Polar Research
Journal Title(Ko) :Ocean and Polar Research
Volume : 42
No :1
Pages :15−20
DOI :https://doi.org/10.4217/OPR.2020.42.1.015

[1] Amina M, Al Musayeib NM (2018) Biological and medicinal importance of sponge. Ray S (ed) In: Biological resource of waters. IntechOpen, London, pp 201−230

[2] Cimino G, De Napoli L, Fattorusso E (1978) 13C-NMR spectrum and absolute stereochemistry of furoscalarol. Tetrahedron Lett 19(23):2041−2044

[3] Davis R, Capon R (1993) Two new scalarane sesterterpenes: Isoscalarafuran-A and-B, epimeric alcohols from a southern Australian Marine Sponge, Spongia hispida. Aust J Chem 46(8):1295−1299

[4] De Rosa S, Puliti R, Crispino A, De Giulio A, Mattia C, Mazzarella L (1994) A new scalarane sesterterpenoid from the marine sponge Cacospongia mollior. J Nat Prod 57(2):256−262

[5] Doi Y, Shigemori H, Ishibashi M, Mizobe F, Kawashima A, Nakaike S, Kobayashi J (1993) New sesterterpenes with nerve growth factor synthesis-stimulating activity from the Okinawan marine sponge Hyrtios sp. Chem Pharm Bull 41(12):2190−2191

[6] Fattorusso E, Magno S, Santacroce C, Sica D (1972) Scalarin, a new pentacyclic C-25 terpenoid from the sponge Cacospongia scalaris. Tetrahedron 28(24):5993−5997

[7] Fontana A, Cavaliere P, Ungur N, D'Souza L, Parameswaram P, Cimino G (1999) New scalaranes from the nudibranch Glossodoris atromarginata and its sponge prey. J Nat Prod 62(10):1367−1370

[8] Fontana A, Mollo E, Ortea J, Gavagnin M, Cimino G (2000) Scalarane and homoscalarane compounds from the nudibranchs Glossodoris sedna and Glossodoris dalli: Chemical and biological properties. J Nat Prod 63(4):527−530

[9] Gavagnin M, Mollo E, Docimo T, Guo Y-W, Cimino G (2004) Scalarane metabolites of the nudibranch Glossodoris rufomarginata and its dietary sponge from the South China Sea. J Nat Prod 67(12):2104−2107

[10] Gonzalez MA (2010) Scalarane sesterterpenoids. Curr Bioact Compd 6(3):178−206

[11] Iguchi K, Shimada Y, Yamada Y (1992) Hyrtiosal, a new sesterterpenoid with a novel carbon skeleton from the Okinawan marine sponge Hyrtios erectus. J Org Chem 57(2):522−524

[12] Jaspars M, Jackson E, Lobkovsky E, Clardy J, Diaz MC, Crews P (1997) Using scalarane sesterterpenes to examine a sponge taxonomic anomaly. J Nat Prod 60(6):556−561

[13] Kamel HN, Kim YB, Rimoldi JM, Fronczek FR, Ferreira D, Slattery M (2009) Scalarane sesterterpenoids: Semisynthesis and biological activity. J Nat Prod 72(8):1492−1496

[14] Kashman Y, Rudi A (1997) The 13C-NMR spectrum and stereochemistry of heteronemin. Tetrahedron 33(22):2997−2998

[15] Lee Y-J, Lee J-W, Lee D-G, Lee H-S, Kang J, Yun J (2014) Cytotoxic sesterterpenoids isolated from the marine sponge Scalarispongia sp. Int J Mol Sci 15(11):20045−20053

[16] Liu Y, Wang L, Jung JH, Zhang S (2007) Sesterterpenoids. Nat Prod Rep 24(6):1401−1429

[17] Miller JH, Singh AJ, Northcote PT (2010) Microtubulestabilizing drugs from marine sponges: Focus on peloruside A and zampanolide. Mar Drugs 8(4):1059−1079

[18] Miyaoka H, Nishijima S, Mitome H, Yamada Y (2000) Three new scalarane sesterterpenoids from the Okinawan sponge Hyrtios erectus. J Nat Prod 63(10):1369−1372

[19] Pettit GR, Cichacz ZA, Tan R, Herald DL, Melody N, Hoard MS, Doubek DL, Hooper JN (1998) Antineoplastic agents 385. The isolation and structure of a scalaranetype sesterterpene from the Indian Ocean Porifera Hyrtios erecta. Collec Czech Chem C 63(10):1671−1677

[20] Pettit GR, Tan R, Melody N, Cichacz ZA, Herald DL, Hoard MS, Pettit RK, Chapuis J-C (1998) Antineoplastic agents 397: Isolation and structure of sesterstatins 4 and 5 from Hyrtios erecta (The Republic of Maldives). Bioorg Med Chem Lett 8(16):2093−2098

[21] Roy MC, Tanaka J, De Voogd N, Higa T (2002) New scalarane class sesterterpenes from an Indonesian sponge, Phyllospongia sp. J Nat Prod 65(12):1838−1842

[22] Ryu G, Matsunaga S, Fusetani N (1996) Three new cytotoxic sesterterpenes from the marine sponge Hyrtios cf. erectus. J Nat Prod 59(5):515−517

[23] Song J, Jeong W, Wang N, Lee H-S, Sim CJ, Oh K-B, Shin J (2008) Scalarane sesterterpenes from the sponge Smenospongia sp. J Nat Prod 71(11):1866−1871

[24] Ungur N, Kulciţki V (2004) Synthetic paths towards scalaranes: Assembling the scalaranic skeleton and further transformations. Phytochem Rev 3(3):401−415

[25] Yu ZG, Bi KS, Guo YW (2005) Hyrtiosins A−E, five new scalarane sesterterpenes from the South China Sea sponge Hyrtios erecta. Helv Chim Acta 88(5):1004−1009

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