Abstract
Three new polyacetylenic alcohols, siphonellanols A–C (1–3), together with two known polyacetylenic alcohols (4–5), were isolated from the CHCl3-soluble fraction of the methanolic extract of the marine sponge Siphonochalina siphonella, collected in Egypt. The structures of 1–3 were determined by spectroscopic analyses of their 1D-, 2D-NMR, and MS spectra and by comparisons with reported data. The cytotoxicity assay revealed that 1–3 exhibited moderate cytotoxic activities against a human cervical cancer cell line (HeLa), a human breast cancer cell line (MCF-7), and a human lung cancer cell line (A549) with IC50 values ranging from 25.9 to 69.2 μM.
Similar content being viewed by others
References
Youssef DT, Yoshida WY, Kelly M, Scheuer PJ (2000) Polyacetylenes from a Red Sea sponge Callyspongia species. J Nat Prod 63:1406–1410
Youssef DT, van Soest RW, Fusetani N (2003) Callyspongenols A-C, new cytotoxic C22-polyacetylenic alcohols from a Red Sea sponge, Callyspongia species. J Nat Prod 66:679–681
Mejia EJ, Magranet LB, De Voogd NJ, Tendyke K, Qiu D, Shen YY, Zhou Z, Crews P (2013) Structures and cytotoxic evaluation of new and known acyclic Ene-Ynes from an American Samoa Petrosia sp. Sponge. J Nat Prod 76:425–432
Lim YJ, Kim JS, Im KS, Jung JH, Lee CO, Hong J, Dk K (1999) New cytotoxic polyacetylenes from the marine sponge Petrosia. J Nat Prod 62:1215–1217
Ayyad SE, Angawy R, Alarif WM, Saqer EA, Badria FA (2014) Cytotoxic polyacetylenes from the Red Sea sponge Siphonochalina siphonella. Z Naturforsch 69c:117–123
Fusetani N, Shiragaki T, Matsunaga S, Hashimoto K (1987) Bioactive marine metabolites XX. Petrosynol and petrosynone, antimicrobial C30 polyacetylenes from the marine sponge Petrosia sp.: determination of the absolute configuration. Tetrahedron Lett 28:4313–4314
Tsukamoto S, Kato H, Hirota H, Fusetani N (1997) Seven new polyacetylene derivatives, showing both potent metamorphosis-inducing activity in Ascidian Larvae and antifouling activity against Barnacle Larvae, from the marine sponge Callyspongia truncate. J Nat Prod 60:126–130
Rotem M, Kashman Y (1979) New polyacetylenes from the sponge Siphonochalina sp. Tetrahedron Lett 34:3193–3196
Fusetani N, Sugano M, Matsunaga S, Hashimoto K (1987) H, K-ATPase inhibitors from the marine sponge Siphonochalina truncata: absolute configuration of siphonodiol and two related metabolites. Tetrahedron Lett 28:4311–4312
Patil AD, Kokke WC, Cochran S, Francis TA, Tomszek T, Westley JW (1992) Brominated polyacetylenic acids from the marine sponge Xestospongia muta: inhibitors of HIV protease. J Nat Prod 55:1170–1177
Dai J, Hallock YF, Cardellina JH II, Gray GN, Boyd MR (1996) Triangulynes A−H and triangulynic acid, new cytotoxic polyacetylenes from the marine sponge Pellina triangulata. J Nat Prod 59:860–865
Gunasekera SP, Faircloth GT (1990) New acetylenic alcohols from the sponge Cribrochalina vasculum. J Org Chem 55:6223–6225
Hallock YF, Cardellina JH, Balaschak MS, Alexander MR, Prather TR, Shoemaker RH, Boyd MR (1995) Antitumor activity and stereochemistry of acetylenic alcohols from the sponge Cribrochalina vasculum. J Nat Prod 58:1801–1807
Hooper JNA, van Soest RW (2002) Systema porifera: a guide to the classification of sponges. Springer, New York
El-Beih AA, El-Desoky AH, Al-Hammady MA, Elshamy AI, Hegazy MF, Kato H, Tsukamoto S (2018) New inhibitors of RANKL-induced osteoclastogenesis from the marine sponge Siphonochalina siphonella. Fitoterapia 128:43–49
Ali MS, Amina M, Al-Lohedan HA, Al Musayeib NM (2017) Elucidation of the interaction of human serum albumin with anti-cancer sipholane triterpenoid from the Red Sea sponge. Luminescence 32:223–230
Amina M, Ali MS, Al-Musayeib NM, Al-Lohedan HA (2016) Biophysical characterization of the interaction of bovine serum albumin with anticancer sipholane triterpenoid from the Red Sea sponge. J Mol Liq 220:931–938
El-Hawary SS, Sayed AM, Mohammed R, Hassan HM, Rateb ME, Amin E, Mohammed TA, El-Mesery M, Bin Muhsinah A, Alsayari A, Wajant H, Anany MA, Abdelmohsen UR (2019) Bioactive brominated oxindole alkaloids from the Red Sea sponge Callyspongia siphonella. Mar Drugs 17:465
Youssef DT, Ibrahim AK, Khalifa SI, Mesbah MK, Mayer AM, van Soest RW (2010) New anti-inflammatory sterols from the Red Sea sponges Scalarispongia aqabaensis and Callyspongia siphonella. Nat Prod Commun 5:27–31
Nguyen HM, Ito T, Win NN, Vo HQ, Nguyen HT, Morita H (2019) A new sterol from the Vietnamese marine sponge Xestospongia testudinaria and its biological activities. Nat Prod Res 33:1175–1181
Nguyen HM, Ito T, Kurimoto SI, Ogawa M, Win NN, Hung VQ, Nguyen HT, Kubota T, Kobayashi J, Morita H (2017) New merosesquiterpenes from a Vietnamese marine sponge of Spongia sp. and their biological activities. Bioorg Med Chem Lett 27:3043–3047
Ito T, Nguyen HM, Win NN, Vo HQ, Nguyen HT, Morita H (2018) Three new sesquiterpene aminoquinones from a Vietnamese Spongia sp. and their biological activities. J Nat Med 72:298–303
Mosmann T (1983) Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays. J Immunol Methods 65:55–63
Prema WCP, Nugroho AE, Awouafack MD, Win YY, Win NN, Ngwe H, Morita H, Morita H (2019) Two new quassinoids and other constituents from Picrasma javanica wood, and their biological activities. J Nat Med 73:589–596
Acknowledgements
This work was supported in part by Grants-in-Aid for Scientific Research from the Ministry of Education, Culture, Sports, Science and Technology, Japan (JSPS KAKENHI Grants JP17H05435 and 19H04649) and the TWAS-COMSTECH Research Grant Award_17-056 RG/PHA/AF/AC_C, TWAS/UNESCO, 2018.
Author information
Authors and Affiliations
Corresponding authors
Ethics declarations
Conflict of interest
The authors declare the following potential financial conflicts of interest.
Additional information
Publisher's Note
Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.
Electronic supplementary material
Below is the link to the electronic supplementary material.
Rights and permissions
About this article
Cite this article
Ki, DW., El-Desoky, A.H., Wong, C.P. et al. New cytotoxic polyacetylene alcohols from the Egyptian marine sponge Siphonochalina siphonella. J Nat Med 74, 409–414 (2020). https://doi.org/10.1007/s11418-019-01377-6
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11418-019-01377-6