Three New Tricyclic Guanidine Alkaloids from the Sponge Batzella sp

• Published in: Journal of natural products (Washington, D.C.) Vol. 60; no. 7; pp. 704 - 707
• Main Authors: Patil, Ashok D, Freyer, Alan J, Offen, Priscilla, Bean, Mark F, Johnson, Randall K
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 01.07.1997; Amer Chemical Soc; American Society of Pharmacognosy
• Subjects: ALCALOIDE; ALCALOIDES; ALKALOIDS; ANTIVIRAL; ANTIVIRAL AGENTS; BAHAMAS; Batzella; batzelladines; BINDING SITES; Biological and medical sciences; CHEMICAL COMPOSITION; CHEMICAL STRUCTURE; CHEMISTRY; Chemistry, Medicinal; CHIMIE; COMPOSICION QUIMICA; COMPOSITION CHIMIQUE; EPONGE; ESPECTROMETRIA; ESPONJAS; ESTRUCTURA QUIMICA; General pharmacology; GENERO HUMANO; GENRE HUMAIN; GUANIDINA; GUANIDINE; GUANIDINES; HERPETOVIRIDAE; HUMAN IMMUNODEFICIENCY VIRUS; INHIBICION; INHIBITION; Life Sciences & Biomedicine; MANKIND; Marine; Medical sciences; mirabilin b; Pharmacognosy. Homeopathy. Health food; Pharmacology & Pharmacy; Pharmacology. Drug treatments; Plant Sciences; Porifera; ptilocaulins; QUIMICA; Science & Technology; SPECTRAL ANALYSIS; SPECTROMETRIE; SPECTROMETRY; SPONGES; STEREOCHEMISTRY; STRUCTURE CHIMIQUE; VIRICIDAS; Central America; America; West Indies; Bahamas; PTILOCAULIN; CRAMBE-CRAMBE; PTILOMYCALIN-A; CRAMBESCIDINS; Marine environment; Alkaloid; Porifera; Nitrogen heterocycle; Tertiary alcohol; Animal origin; Isolation; Guanidines; Invertebrata; Tricyclic compound; Structural analysis
• ISSN: 0163-3864; 1520-6025
• DOI: 10.1021/np970014r

During the large-scale isolation of the batzelladines A and B, which are inhibitors of gp120-CD4 binding, we isolated 19 minor guanidine alkaloids. Three new tricyclic guanidine alkaloids isolated from this group were named 8a,8b-dehydroptilocaulin (2), 8a,8b-dehydro-8-hydroxyptilocaulin (3), and 1,8a;8b,3a-didehydro-8-hydroxyptilocaulin (5). The recently described mirabilin B (4) was also isolated. The structures and relative stereochemistry of these compounds were determined by spectral analysis and by comparison with spectral data of ptilocaulin (1).