Three new cyclic peroxides from the marine sponge Plakortis aff simplex
- PMID: 12762807
- DOI: 10.1021/np020589a
Three new cyclic peroxides from the marine sponge Plakortis aff simplex
Abstract
In our continuing program to identify bioactive compounds from marine invertebrates, the MeOH-EtOAc (1:1) extract of the sponge Plakortis aff simplex, collected in Madagascar, was found to be cytotoxic to a series of human tumor cells. From this sponge, three new compounds and one known one, two new 1,2-dioxane peroxylactones named plakortolides H (1) and I (2), and one new 1,2-dioxolane, designated andavadoic acid (3), have been isolated and their structures elucidated. In addition, the known N(3)-methyladenine (4) was isolated, to the best of our knowledge, for the first time from a marine source. Andavadoic acid (3) showed significant activity against 13 tumor cells with GI(50) values in the submicromolar range.
Similar articles
-
Cyclic peroxides derived from the marine sponge Plakortis simplex.J Nat Prod. 2005 May;68(5):759-61. doi: 10.1021/np049665v. J Nat Prod. 2005. PMID: 15921424
-
Antineoplastic agents. 535. Isolation and structure of plakorstatins 1 and 2 from the Indo-Pacific sponge Plakortis nigra.J Nat Prod. 2004 Sep;67(9):1611-3. doi: 10.1021/np040043j. J Nat Prod. 2004. PMID: 15387674
-
Mycaperoxide H, a new cytotoxic norsesterterpene peroxide from a Thai marine sponge Mycale sp.J Nat Prod. 2003 Feb;66(2):289-91. doi: 10.1021/np020417d. J Nat Prod. 2003. PMID: 12608869
-
Marine spongean cytotoxins.J Nat Toxins. 1999 Jun;8(2):249-58. J Nat Toxins. 1999. PMID: 10410335 Review.
-
[Advance in studies on mechanism of active anti-tumor compounds from sponge].Zhongguo Zhong Yao Za Zhi. 2012 Oct;37(19):2842-5. Zhongguo Zhong Yao Za Zhi. 2012. PMID: 23270219 Review. Chinese.
Cited by
-
Aplysinopsin-type and Bromotyrosine-derived Alkaloids from the South China Sea Sponge Fascaplysinopsis reticulata.Sci Rep. 2019 Feb 19;9(1):2248. doi: 10.1038/s41598-019-38696-3. Sci Rep. 2019. PMID: 30783134 Free PMC article.
-
Aromatic cyclic peroxides and related keto-compounds from the Plakortis sp. component of a sponge consortium.J Nat Prod. 2009 Aug;72(8):1547-51. doi: 10.1021/np900310j. J Nat Prod. 2009. PMID: 19618913 Free PMC article.
-
Bioactive Cycloperoxides Isolated from the Puerto Rican Sponge Plakortis halichondrioides.J Nat Prod. 2010 Oct 22;73(10):1694-700. doi: 10.1021/np100461t. Epub 2010 Oct 5. J Nat Prod. 2010. PMID: 20923180 Free PMC article.
-
Recent trends in the structural revision of natural products.Nat Prod Rep. 2018 Jun 20;35(6):514-531. doi: 10.1039/c8np00011e. Nat Prod Rep. 2018. PMID: 29623331 Free PMC article. Review.
-
Synthesis of five- and six-membered cyclic organic peroxides: Key transformations into peroxide ring-retaining products.Beilstein J Org Chem. 2014 Jan 8;10:34-114. doi: 10.3762/bjoc.10.6. eCollection 2014 Jan 8. Beilstein J Org Chem. 2014. PMID: 24454562 Free PMC article. Review.
Publication types
MeSH terms
Substances
LinkOut - more resources
Full Text Sources