Skip to main content
Erschienen in: Journal of Natural Medicines 2/2016

01.04.2016 | Note

Sulfotanone, a new alkyl sulfonic acid derivative from Streptomyces sp. IFM 11694 with TRAIL resistance-overcoming activity

verfasst von: Mohamed S. Abdelfattah, Naoki Ishikawa, Utpal K. Karmakar, Masami Ishibashi

Erschienen in: Journal of Natural Medicines | Ausgabe 2/2016

Einloggen, um Zugang zu erhalten

Abstract

One new alkyl sulfonic acid derivative, sulfotanone (1), and the known panosialin wA (2) were isolated from the methanolic extract of mycelium of Streptomyces sp. 11694. The structure of the new compound (1) was established by a combination of spectroscopic techniques, including HRESIMS, IR, 1D and 2D NMR measurements. Compound 1 (40 µM) in combination with TRAIL showed synergistic activity in sensitizing TRAIL-resistance in human gastric adenocarcinoma cell lines.
Anhänge
Nur mit Berechtigung zugänglich
Literatur
1.
Zurück zum Zitat Nam SJ, Kauffman CA, Jensen PR, Moore CE, Rheingold AL, Fenical W (2015) Actinobenzoquinoline and actinophenanthrolines A–C, unprecedented alkaloids from a marine actinobacterium. Org Lett 17:3240–3243CrossRefPubMed Nam SJ, Kauffman CA, Jensen PR, Moore CE, Rheingold AL, Fenical W (2015) Actinobenzoquinoline and actinophenanthrolines A–C, unprecedented alkaloids from a marine actinobacterium. Org Lett 17:3240–3243CrossRefPubMed
2.
Zurück zum Zitat Yang A, Si L, Shi Z, Tian L, Liu D, Zhou D, Proksch P, Lin W (2013) Nitrosporeusines A and B, unprecedented thioester-bearing alkaloids from the arctic Streptomyces nitrosporeus. Org Lett 15:5366–5369CrossRefPubMed Yang A, Si L, Shi Z, Tian L, Liu D, Zhou D, Proksch P, Lin W (2013) Nitrosporeusines A and B, unprecedented thioester-bearing alkaloids from the arctic Streptomyces nitrosporeus. Org Lett 15:5366–5369CrossRefPubMed
3.
Zurück zum Zitat Yang SX, Gao JM, Zhang AL, Laatsch H (2011) Sannastatin, a novel toxic macrolactam polyketide glycoside produced by actinomycete Streptomyces sannanensis. Bioorg Med Chem Lett 21:3905–3908CrossRefPubMed Yang SX, Gao JM, Zhang AL, Laatsch H (2011) Sannastatin, a novel toxic macrolactam polyketide glycoside produced by actinomycete Streptomyces sannanensis. Bioorg Med Chem Lett 21:3905–3908CrossRefPubMed
4.
Zurück zum Zitat Jin Y, Fotso S, Yongtang Z, Sevvana M, Laatsch H, Zhang W (2006) Halichondria sulfonic acid, a new HIV-1 inhibitory guanidino-sulfonic acid, and halistanol sulfate isolated from the marine sponge Halichondria rugosa Ridley & Dendy. Nat Prod Res 20:1129–1135CrossRefPubMed Jin Y, Fotso S, Yongtang Z, Sevvana M, Laatsch H, Zhang W (2006) Halichondria sulfonic acid, a new HIV-1 inhibitory guanidino-sulfonic acid, and halistanol sulfate isolated from the marine sponge Halichondria rugosa Ridley & Dendy. Nat Prod Res 20:1129–1135CrossRefPubMed
5.
Zurück zum Zitat Jacob C (2006) A scent of therapy: pharmacological implications of natural products containing redox-active sulfur atoms. Nat Prod Rep 23:851–863CrossRefPubMed Jacob C (2006) A scent of therapy: pharmacological implications of natural products containing redox-active sulfur atoms. Nat Prod Rep 23:851–863CrossRefPubMed
6.
Zurück zum Zitat Jimenez C (2001) Marine sulfur-containing natural products. Stud Nat Prod Chem 25:811–917 Jimenez C (2001) Marine sulfur-containing natural products. Stud Nat Prod Chem 25:811–917
7.
Zurück zum Zitat Son IH, Lee SI, Yang HD, Moon HI (2007) Bis(4-hydroxybenzyl)sulfide: a sulfur compound inhibitor of histone deacetylase isolated from root extract of Pleuropterus ciliinervis. Molecules 12:815–820CrossRefPubMed Son IH, Lee SI, Yang HD, Moon HI (2007) Bis(4-hydroxybenzyl)sulfide: a sulfur compound inhibitor of histone deacetylase isolated from root extract of Pleuropterus ciliinervis. Molecules 12:815–820CrossRefPubMed
8.
Zurück zum Zitat Song XQ, Zhang X, Han QJ, Li XB, Li G, Li RJ, Yang J, Jin-Chuan Z, Hong-Xiang L (2013) Xanthone derivatives from Aspergillus sydowii, an endophytic fungus from the liverwort Scapania ciliata S. Lac, and their immunosuppressive activities. Phytochem Lett 6:318–321CrossRef Song XQ, Zhang X, Han QJ, Li XB, Li G, Li RJ, Yang J, Jin-Chuan Z, Hong-Xiang L (2013) Xanthone derivatives from Aspergillus sydowii, an endophytic fungus from the liverwort Scapania ciliata S. Lac, and their immunosuppressive activities. Phytochem Lett 6:318–321CrossRef
9.
Zurück zum Zitat Haruki Y, Kazuro S, Qi X, Takayuki N, Maki S, Izumi O, Yoko T, Satoshi O (1995) New glycosidases inhibitors, panosialins D and wD produced by Streptomyces sp. OH-5186. J Antibiot 48:205–210CrossRef Haruki Y, Kazuro S, Qi X, Takayuki N, Maki S, Izumi O, Yoko T, Satoshi O (1995) New glycosidases inhibitors, panosialins D and wD produced by Streptomyces sp. OH-5186. J Antibiot 48:205–210CrossRef
10.
Zurück zum Zitat Kamiyama T, Umino T, Satoh T, Sawairi S, Shirane M, Onshima S, Yokos K (1995) Sulfobacins A and B, novel von Willebrand factor receptor antagonists I. Production, isolation, characterization and biological activities. J Antibiot 48:924–928CrossRefPubMed Kamiyama T, Umino T, Satoh T, Sawairi S, Shirane M, Onshima S, Yokos K (1995) Sulfobacins A and B, novel von Willebrand factor receptor antagonists I. Production, isolation, characterization and biological activities. J Antibiot 48:924–928CrossRefPubMed
11.
Zurück zum Zitat Abdelfattah MS, Toume K, Arai MA, Masu H, Ishibashi M (2012) Katorazone, a new yellow pigment with a 2-azaquinone-phenylhydrazone structure produced by Streptomyces sp. IFM 11299. Tetrahedron Lett 53:3346–3348CrossRef Abdelfattah MS, Toume K, Arai MA, Masu H, Ishibashi M (2012) Katorazone, a new yellow pigment with a 2-azaquinone-phenylhydrazone structure produced by Streptomyces sp. IFM 11299. Tetrahedron Lett 53:3346–3348CrossRef
12.
Zurück zum Zitat Abdelfattah MS, Toume K, Ishibashi M (2012) Yoropyrazone, a new naphthopyridazone alkaloid isolated from Streptomyces sp. IFM 11307 and evaluation of its TRAIL resistance-overcoming activity. J Antibiot 65:245–248CrossRefPubMed Abdelfattah MS, Toume K, Ishibashi M (2012) Yoropyrazone, a new naphthopyridazone alkaloid isolated from Streptomyces sp. IFM 11307 and evaluation of its TRAIL resistance-overcoming activity. J Antibiot 65:245–248CrossRefPubMed
13.
Zurück zum Zitat Abdelfattah MS, Toume K, Ishibashi M (2011) New pyranonaphthoquinones and a phenazine alkaloid isolated from Streptomyces sp. IFM 11307 with TRAIL resistance-overcoming activity. J Antibiot 64:729–734CrossRefPubMed Abdelfattah MS, Toume K, Ishibashi M (2011) New pyranonaphthoquinones and a phenazine alkaloid isolated from Streptomyces sp. IFM 11307 with TRAIL resistance-overcoming activity. J Antibiot 64:729–734CrossRefPubMed
14.
Zurück zum Zitat Abdelfattah MS, Toume K, Ishibashi M (2011) Isolation and structure elucidation of izuminosides A–C: a rare phenazine glycosides from Streptomyces sp. IFM 11260. J Antibiot 64:271–275CrossRefPubMed Abdelfattah MS, Toume K, Ishibashi M (2011) Isolation and structure elucidation of izuminosides A–C: a rare phenazine glycosides from Streptomyces sp. IFM 11260. J Antibiot 64:271–275CrossRefPubMed
15.
Zurück zum Zitat Abdelfattah MS, Toume K, Ishibashi M (2011) Izumiphenazine D, a new phenazoquinoline N-oxide from Streptomyces sp. IFM 11204. Chem Pharm Bull 59:508–510CrossRefPubMed Abdelfattah MS, Toume K, Ishibashi M (2011) Izumiphenazine D, a new phenazoquinoline N-oxide from Streptomyces sp. IFM 11204. Chem Pharm Bull 59:508–510CrossRefPubMed
16.
Zurück zum Zitat Abdelfattah MS, Toume K, Ishibashi M (2010) Izumiphenazines A–C: islation and structure elucidation of phenazine derivatives from Streptomyces sp. IFM 11204. J Nat Prod 73:1999–2002CrossRefPubMed Abdelfattah MS, Toume K, Ishibashi M (2010) Izumiphenazines A–C: islation and structure elucidation of phenazine derivatives from Streptomyces sp. IFM 11204. J Nat Prod 73:1999–2002CrossRefPubMed
17.
Zurück zum Zitat Ishibashi M, Ohtsuki T (2008) Studies on search for bioactive natural products targeting TRAIL signaling leading to tumor cell apoptosis. Med Res Rev 28:688–714CrossRefPubMed Ishibashi M, Ohtsuki T (2008) Studies on search for bioactive natural products targeting TRAIL signaling leading to tumor cell apoptosis. Med Res Rev 28:688–714CrossRefPubMed
18.
Zurück zum Zitat Minakawa T, Toume K, Arai MA, Koyano T, Kowithayakorn T, Ishibashi M (2013) Prenylflavonoids isolated from Artocarpus champeden with TRAIL-resistance overcoming activity. Phytochemistry 96:299–304CrossRefPubMed Minakawa T, Toume K, Arai MA, Koyano T, Kowithayakorn T, Ishibashi M (2013) Prenylflavonoids isolated from Artocarpus champeden with TRAIL-resistance overcoming activity. Phytochemistry 96:299–304CrossRefPubMed
19.
Zurück zum Zitat Karmakar UK, Ishikawa N, Toume K, Arai MA, Sadhu SK, Ahmed F, Ishibashi M (2015) Sesquiterpenes with TRAIL-resistance overcoming activity from Xanthium strumarium. Bioorg Med Chem 23:4746–4754CrossRefPubMed Karmakar UK, Ishikawa N, Toume K, Arai MA, Sadhu SK, Ahmed F, Ishibashi M (2015) Sesquiterpenes with TRAIL-resistance overcoming activity from Xanthium strumarium. Bioorg Med Chem 23:4746–4754CrossRefPubMed
20.
Zurück zum Zitat Yin HQ, Fu HW, Hua HM, Qi XL, Li W, Sha Y, Pei YH (2005) Two new sesquiterpene lactones with the sulfonic acid group from Saussurea lappa. Chem Pharm Bull 53:841–842CrossRefPubMed Yin HQ, Fu HW, Hua HM, Qi XL, Li W, Sha Y, Pei YH (2005) Two new sesquiterpene lactones with the sulfonic acid group from Saussurea lappa. Chem Pharm Bull 53:841–842CrossRefPubMed
21.
Zurück zum Zitat Ohtani I, Kusumi T, Kashman Y, Kakisawa H (1991) High-field FT NMR application of Mosher’s method; the absolute configurations of marine terpenoids. J Am Chem Soc 113:4092–4096CrossRef Ohtani I, Kusumi T, Kashman Y, Kakisawa H (1991) High-field FT NMR application of Mosher’s method; the absolute configurations of marine terpenoids. J Am Chem Soc 113:4092–4096CrossRef
22.
Zurück zum Zitat Loderer C, Ansorge-Schumacher MB (2015) Enzyme-catalysed regio- and enantioselective preparative scale synthesis of (S)-2-hydroxy alkanones. RSC Adv 5:38271–38276CrossRef Loderer C, Ansorge-Schumacher MB (2015) Enzyme-catalysed regio- and enantioselective preparative scale synthesis of (S)-2-hydroxy alkanones. RSC Adv 5:38271–38276CrossRef
23.
Zurück zum Zitat Lindhagen E, Nygren P, Larsson R (2008) The fluorometric microculture cytotoxicity assay. Nat Protoc 3:1364–1369CrossRefPubMed Lindhagen E, Nygren P, Larsson R (2008) The fluorometric microculture cytotoxicity assay. Nat Protoc 3:1364–1369CrossRefPubMed
24.
Zurück zum Zitat Horinaka M, Yoshida T, Shiraishi T, Nakata S, Wakada M, Nakanishi R, Nishino H, Matsui H, Sakai T (2005) Luteolin induces apoptosis via death receptor 5 upregulation in human malignant tumor cells. Oncogene 24:7180–7189CrossRefPubMed Horinaka M, Yoshida T, Shiraishi T, Nakata S, Wakada M, Nakanishi R, Nishino H, Matsui H, Sakai T (2005) Luteolin induces apoptosis via death receptor 5 upregulation in human malignant tumor cells. Oncogene 24:7180–7189CrossRefPubMed
25.
Zurück zum Zitat Hayakawa M, Nonomura H (1987) Humic acid-vitamin agar, a new medium for the selective isolation of soil actinomycetes. J Ferment Technol 65:501–509CrossRef Hayakawa M, Nonomura H (1987) Humic acid-vitamin agar, a new medium for the selective isolation of soil actinomycetes. J Ferment Technol 65:501–509CrossRef
Metadaten
Titel
Sulfotanone, a new alkyl sulfonic acid derivative from Streptomyces sp. IFM 11694 with TRAIL resistance-overcoming activity
verfasst von
Mohamed S. Abdelfattah
Naoki Ishikawa
Utpal K. Karmakar
Masami Ishibashi
Publikationsdatum
01.04.2016
Verlag
Springer Japan
Erschienen in
Journal of Natural Medicines / Ausgabe 2/2016
Print ISSN: 1340-3443
Elektronische ISSN: 1861-0293
DOI
https://doi.org/10.1007/s11418-015-0951-3

Weitere Artikel der Ausgabe 2/2016

Journal of Natural Medicines 2/2016 Zur Ausgabe