Literature DB >> 34038132

Sinularamides A-G, Terpenoid-Derived Spermidine and Spermine Conjugates with Casitas B-Lineage Lymphoma Proto-Oncogene B (Cbl-b) Inhibitory Activities from a Sinularia sp. Soft Coral.

Wei Jiang1,2, Dongdong Wang2, Brice A P Wilson2, Donna Voeller3, Heidi R Bokesch2,4, Emily A Smith2,4, Stanley Lipkowitz3, Barry R O'Keefe2,5, Kirk R Gustafson2.   

Abstract

An extract of a Sinularia sp. soft coral showed inhibitory activity against the E3-ubiquitin ligase casitas B-lineage lymphoma proto-oncogene B (Cbl-b). Subsequent bioassay-guided separation of the extract provided a series of terpenoid-derived spermidine and spermine amides that were named sinularamides A-G (1-7). Compounds 1-7 represent new natural products; however, sinularamide A (1) was previously reported as a synthetic end product. The structures of sinularamides A-G (1-7) were elucidated by analysis of spectroscopic and spectrometric data from NMR, IR, and HRESIMS experiments and by comparison with literature data. All of the isolated compounds showed Cbl-b inhibitory activities with IC50 values that ranged from approximately 6.5 to 33 μM.

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Year:  2021        PMID: 34038132      PMCID: PMC9341130          DOI: 10.1021/acs.jnatprod.1c00367

Source DB:  PubMed          Journal:  J Nat Prod        ISSN: 0163-3864            Impact factor:   4.803


  17 in total

1.  RING fingers mediate ubiquitin-conjugating enzyme (E2)-dependent ubiquitination.

Authors:  K L Lorick; J P Jensen; S Fang; A M Ong; S Hatakeyama; A M Weissman
Journal:  Proc Natl Acad Sci U S A       Date:  1999-09-28       Impact factor: 11.205

Review 2.  Cbl and human myeloid neoplasms: the Cbl oncogene comes of age.

Authors:  Stephen C Kales; Philip E Ryan; Marion M Nau; Stanley Lipkowitz
Journal:  Cancer Res       Date:  2010-05-25       Impact factor: 12.701

3.  Cbl-b-dependent coordinated degradation of the epidermal growth factor receptor signaling complex.

Authors:  S A Ettenberg; A Magnifico; M Cuello; M M Nau; Y R Rubinstein; Y Yarden; A M Weissman; S Lipkowitz
Journal:  J Biol Chem       Date:  2001-05-24       Impact factor: 5.157

4.  Two stems with different characteristics and an internal loop in an RNA aptamer contribute to spermine-binding.

Authors:  Akihiro Oguro; Asumi Yanagida; Yuta Fujieda; Ryo Amano; Maina Otsu; Taiichi Sakamoto; Gota Kawai; Senya Matsufuji
Journal:  J Biochem       Date:  2017-02-01       Impact factor: 3.387

Review 5.  Molecular pathways: cbl proteins in tumorigenesis and antitumor immunity-opportunities for cancer treatment.

Authors:  Mariya S Liyasova; Ke Ma; Stanley Lipkowitz
Journal:  Clin Cancer Res       Date:  2014-12-04       Impact factor: 12.531

6.  Ablation of Cbl-b provides protection against transplanted and spontaneous tumors.

Authors:  Jeffrey Y Chiang; Ihn Kyung Jang; Richard Hodes; Hua Gu
Journal:  J Clin Invest       Date:  2007-03-15       Impact factor: 14.808

7.  Self antigens expressed by solid tumors Do not efficiently stimulate naive or activated T cells: implications for immunotherapy.

Authors:  D E Speiser; R Miranda; A Zakarian; M F Bachmann; K McKall-Faienza; B Odermatt; D Hanahan; R M Zinkernagel; P S Ohashi
Journal:  J Exp Med       Date:  1997-08-29       Impact factor: 14.307

8.  Spontaneous tumor rejection by cbl-b-deficient CD8+ T cells.

Authors:  Stefanie Loeser; Karin Loser; Martijn S Bijker; Manu Rangachari; Sjoerd H van der Burg; Teiji Wada; Stefan Beissert; Cornelis J M Melief; Josef M Penninger
Journal:  J Exp Med       Date:  2007-04-02       Impact factor: 14.307

9.  High throughput extraction of plant, marine and fungal specimens for preservation of biologically active molecules.

Authors:  Thomas G McCloud
Journal:  Molecules       Date:  2010-06-24       Impact factor: 4.411

10.  The E3 ligase Cbl-b and TAM receptors regulate cancer metastasis via natural killer cells.

Authors:  Magdalena Paolino; Axel Choidas; Stephanie Wallner; Blanka Pranjic; Iris Uribesalgo; Stefanie Loeser; Amanda M Jamieson; Wallace Y Langdon; Fumiyo Ikeda; Juan Pablo Fededa; Shane J Cronin; Roberto Nitsch; Carsten Schultz-Fademrecht; Jan Eickhoff; Sascha Menninger; Anke Unger; Robert Torka; Thomas Gruber; Reinhard Hinterleitner; Gottfried Baier; Dominik Wolf; Axel Ullrich; Bert M Klebl; Josef M Penninger
Journal:  Nature       Date:  2014-02-19       Impact factor: 49.962

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