Three new bisindole alkaloids of the hamacanthin class (1-3) and one new bisindole alkaloid of the topsentin class (6) were isolated along with known bisindole alkaloids (4, 5, 7-11) from the MeOH extract of a marine sponge Spongosorites sp. by bioactivity-guided fractionation. The planar structures were established on the basis of NMR, MS, and IR spectroscopic analyses. Configurations of compounds 1-4 were derived from 1H NMR data and optical rotation. Compounds 1, 4, 5, and 11 showed moderate to significant cytotoxicity against five human tumor cell lines, and compounds 1-5 showed weak antibacterial activity against clinically isolated methicillin-resistant strains.

Download full-text PDF

Source
http://dx.doi.org/10.1021/np049577aDOI Listing

Publication Analysis

Top Keywords

bisindole alkaloids
12
marine sponge
8
sponge spongosorites
8
cytotoxic bisindole
4
alkaloids marine
4
spongosorites three
4
three bisindole
4
alkaloids hamacanthin
4
hamacanthin class
4
class 1-3
4

Similar Publications

Glioma is recognized as one of the most lethal and aggressive brain tumors. Although the standard-of-care treatment for glioblastoma (GBM) involves maximal surgical resection and temozolomide (TMZ) chemotherapy, the discovery of novel anti-tumor agents from nature sources is an effective strategy for glioma treatment. In this study, we conducted a screening process to identify the bisindole alkaloid melodinine J (MDJ) from Melodinus tenuicaudatus.

View Article and Find Full Text PDF

Bisindole alkaloids constitute a significant class of natural compounds distinguished by their characteristic bisindole structure and renowned for their anticancer properties. Over the past six decades, researchers have isolated 425 microorganism-derived bisindole alkaloids (MDBAs). Among them, 187 MDBAs have demonstrated anticancer properties against various in vitro cancer cell lines, primarily by impeding the cell cycle, restraining cell proliferation, and inducing apoptosis and autophagy.

View Article and Find Full Text PDF

Cytotoxic monoterpenoid indole alkaloids from Tabernaemontana bovina.

Phytochemistry

February 2025

School of Pharmaceutical Sciences, College of Modern Biomedical Industry, Department of Zoology & Yunnan Key Laboratory of Pharmacology for Natural Products, Kunming Medical University, Kunming, 650500, People's Republic of China. Electronic address:

Chemical investigation of the native medicinal plant Tabernaemontana bovina led to the isolation of five previously unreported monoterpenoid indole alkaloids tabernovinaines A-E (1-5) together with twenty-seven known analogs (6-32), including a bisindole alkaloid 1 with the (E)-4-aminobut-3-en-2-one fragment, as well as a unique cage skeleton 2 containing 6/5/8/6/6 ring system. The chemical structures of these unreported compounds were elucidated using mass spectrometry, NMR spectroscopy, circular dichroism, density functional theory calculations, and derivatizations. The activity evaluation shows that the bisindole alkaloid 1 revealed a potential cytotoxic effect by inducing HepG2 cell apoptosis and damaging clonal sphere expansion.

View Article and Find Full Text PDF

Cathagines A-D, new bisindole alkaloids from Catharanthus roseus.

J Nat Med

November 2024

Faculty of Pharmaceutical Sciences, Hoshi University, Ebara 2-4-41 Shinagawa-ku, Tokyo, 142-8501, Japan.

Four new bisindole alkaloids, cathagines A (1)-D (4) consisting of an aspidosperma and the fused tetracyclic 3-spirooxindole derived from an iboga type skeleton were isolated from the whole plant of Catharanthus roseus. The structures including absolute stereochemistry were elucidated on the basis of 2D NMR data and CD spectra. Cathagine B (2) showed moderate anti-malarial activity against Plasmodium falciparum 3D7.

View Article and Find Full Text PDF

Synthesis, structural modification, and biological activity of a novel bisindole alkaloid iheyamine A.

Bioorg Chem

December 2024

Tianjin Key Laboratory of Structure and Performance for Functional Molecules, College of Chemistry, Tianjin Normal University, Tianjin 300387, China. Electronic address:

Diseases caused by plant viruses and pathogens pose a serious threat to crop yield and quality. Traditional pesticides have gradually developed drug resistance and brought certain environmental safety issues during long-term overuse. There is an urgent need to discover new candidate compounds to address these issues.

View Article and Find Full Text PDF

Want AI Summaries of new PubMed Abstracts delivered to your In-box?

Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!