Batzelline D and Isobatzelline E from the Indopacific Sponge Zyzzya fuliginosa

Abstract

Two new pyrroloquinoline alkaloids, isobatzelline E (1) and batzelline D (2), together with the known compounds batzelline C (3), isobatzelline C (4), and makaluvamine D (5), were isolated from an Indopacific collection of the marine sponge Zyzzya fuliginosa; the known compounds makaluvamines A (9), H (10), J (7), K (8), and P (6) were obtained from Z. fuliginosa collected in Papua New Guinea. The structures were elucidated by interpretation of 1D (1)H and (13)C NMR spectra and 2D HSQC and HSQC-LR spectra. Compounds 1-10 were isolated because the crude extracts of both Zyzzya species inhibited HIV-1 envelope-mediated cell fusion. However, the inhibition profile observed for the pure compounds 1-10 mirrors that reported for the inhibition of topoisomerase II by other pyrroloquinolines, leaving open the possibility that the activity results from interactions with DNA-modifying enzymes.

Structure elucidation of the new citharoxazole from the Mediterranean deep‐sea sponge Latrunculia (Biannulata) citharistae

“…[9] More recently, batzelline D and isobatzelline E have been identified from a Zyzzya sponge. [10] From a shallow water sponge, later identified as Zyzzya fuliginosa, Faulkner and coworkers isolated three closely related analogues damirone A, B and then C, which lack the chlorine atom at C-6 comparing with the batzellines. [11,12] Interesting cytotoxic activities are associated with some of these aromatic alkaloids.…”

Selective cytotoxic activity of the marine-derived batzelline compounds against pancreatic cancer cell lines

“…The isolation and chemical characterization of the batzellines used in this study were the subject of prior publications (4–6). They all share planar structures that contain a variant of a tricyclic pyrrolo[4,3,2-de]quinoline core ring structure (Figure 1).…”

“…The batzellines are pyrroloiminoquinones alkaloids obtained from the deep water Caribbean sponge Batzella sp (family Esperiopsidae, order Poecilosclerida) (4–6) that exhibit antifungal activity as well as cytotoxicity against murine leukemia cells (4). They are structurally related to other marine compounds such as the makaluvamines and the discorhabdins that exhibit strong cytotoxicity against many different cancer cell lines(7).…”

Total synthesis of zyzzyanones A–D

“…The main source of pyrrolo[4,3,2- de ]quinoline alkaloids are marine sponges of the genera Latrunculia , Batzella , Prianos and Zyzzya . 17,18 This series of alkaloids comprise of about 60 metabolites including makaluvamines, 19–24 discorhabdins, 25 batzellines, 26 epinardins, 27 isobatzellines, 26 veiutamine, 28 tsitsikammamines ( 2a,b ) 29,30 and wakayin ( 3 ). 31 Bioactivity of this class of alkaloids include topoisomerase I 19 and II 22 inhibition, antiproliferative activity against different cancer cell lines, 32,22 and antimicrobial activities.…”