Manzamines: Marine Bioactive Heterocycles
After the first discovery of manzamine A from a marine sponge by Sakai and colleagues in 1986, its derivatives have attracted much attention among chemists and biologists due to their structural complexity and diverse biological activities. So far, more t
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Manzamines: Marine Bioactive Heterocycles Ahmed H. H. El-Desoky and Sachiko Tsukamoto
Contents 1 Introduction 1.1 Discovery 1.2 Biological Activities 1.3 Biosynthesis 2 Recently Isolated Unique Manzamine Derivatives 2.1 Zamamidines A–D 2.2 Acanthomanzamines A–E 2.3 Kepulauamine A 2.4 Acantholactone and Acantholactam 2.5 Pre-neo-kauluamine 3 Recently Reported Biological Activities 3.1 Inhibition of the Proteasome 3.2 Anti-atherosclerotic Activity 4 Conclusions References
Abstract After the first discovery of manzamine A from a marine sponge by Sakai and colleagues in 1986, its derivatives have attracted much attention among chemists and biologists due to their structural complexity and diverse biological activities. So far, more than 100 manzamine-related alkaloids have been identified, most of which have a fused 6-, 6-, 5-, 8-, and 13-membered ring system connected to a β-carboline as shown in manzamine A. In addition, a variety of bioactivities including cytotoxic,
A. H. H. El-Desoky Pharmaceutical Industries Research Division, Pharmacognosy Department, National Research Centre, Giza, Egypt Graduate School of Pharmaceutical Sciences, Kumamoto University, Kumamoto, Japan e-mail: [email protected] S. Tsukamoto (*) Graduate School of Pharmaceutical Sciences, Kumamoto University, Kumamoto, Japan e-mail: [email protected]
A. H. H. El-Desoky and S. Tsukamoto
antimicrobial, antimalarial, anti-HIV, and insecticidal are reported. This review covers the recent reports of novel structures and biological activities of the manzamines. Keywords Anti-atherosclerosis · Anti-HIV · Antimalarial · Cytotoxicity · Manzamine · Marine sponge · Proteasome inhibitor
1 Introduction The manzamine family is a class of alkaloids isolated from marine sponges. More than 100 derivatives with novel structures and significant biological activities have been reported to date. This chapter focuses on recent reports of the manzamines.
1.1
Discovery
Manzamine A (1) (Fig. 1) was first isolated by Sakai et al. in 1986 from a marine sponge Haliclona sp. collected in Okinawa, Japan, as a cytotoxic compound against P388 mouse leukemia cells [1]. It is composed of a β-carboline conjugated with an aliphatic moiety with a high degree of complexity. The structure was unprecedently novel, with complicated fused and bridged 6-, 6-, 5-, 8-, and 13-membered rings. The absolute configuration was determined by X-ray analysis of its hydrochloride salt. Later on, manzamine derivatives were frequently isolated from marine sponges belonging to the genera Pellina [2], Xestospongia [3, 4], Haliclona [1, 4, 5], Pachypellina [6], Amphimedon [7–9], Petrosia [10], Cribochalina [10], and Acanthostrongylophora [11–14]. Fig. 1 Structure of manzamine A (1) N H
N H OH
N H
N
Manzamine A (1)
Manzamines: Marine Bioactive Heterocycles
1.2
Biological Activities
A variety of biological activities of manzamine A (1) and its related alkaloids have been reported. Cytotoxic activities were reported against mouse leukemia (P388) [1], human epidermoid carcinoma (K
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