Geranins A and B, New Antiprotozoal A-Type Proanthocyanidins from Geranium niveum

• Published in: Journal of natural products (Washington, D.C.) Vol. 62; no. 5; pp. 705 - 709
• Main Authors: Calzada, Fernando, Cerda-García-Rojas, Carlos M, Meckes, Mariana, Cedillo-Rivera, Roberto, Bye, Robert, Mata, Rachel
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 01.05.1999; Amer Chemical Soc; American Society of Pharmacognosy
• Subjects: Animals; anthocyanidins; Anthocyanins - isolation & purification; Anthocyanins - pharmacology; antimicrobial properties; Antineoplastic Agents, Phytogenic - isolation & purification; Antineoplastic Agents, Phytogenic - pharmacology; Antiprotozoal Agents - isolation & purification; Antiprotozoal Agents - pharmacology; Biological and medical sciences; chemical constituents of plants; chemical structure; Chemistry, Medicinal; Drug Screening Assays, Antitumor; Entamoeba histolytica; Entamoeba histolytica - drug effects; epi-afzelechin-(4^b^18,2^b^1O^17)-afzelechin; epi-catechin-(4^b^18,2^b^1O^17)-afzelechin; General pharmacology; Geranium; Geranium niveum; Giardia lamblia; Giardia lamblia - drug effects; Humans; Life Sciences & Biomedicine; Magnetic Resonance Spectroscopy; Magnoliopsida - chemistry; Medical sciences; medicinal plants; Mexico; Models, Molecular; Molecular Conformation; nuclear magnetic resonance spectroscopy; Pharmacognosy. Homeopathy. Health food; Pharmacology & Pharmacy; Pharmacology. Drug treatments; Plant Roots - chemistry; Plant Sciences; Proanthocyanidins; Science & Technology; spectral analysis; Spectrometry, Mass, Fast Atom Bombardment; Tumor Cells, Cultured; Mexico; Central America; America; CONFIGURATIONS; SERIES; Antineoplastic agent; Pentacyclic compound; Lobosea; Cytotoxicity; Diplomonadida; Oxygen heterocycle; Flavonoid; Modeling; Medicinal plant; Acetal; Antiprotozoal agent; Polyphenol; Folk medicine; Dicotyledones; Angiospermae; Parasiticid; Molecular model; Aromatic compound; Geranium; Tumor cell; Human; Protozoa; Root; Pharmacognosy; Entamoeba histolytica; Geraniaceae; In vitro; Biological activity; Giardia lamblia; Cell line; Plant origin; Benzenic compound; Isolation; Spermatophyta; Structural analysis
• ISSN: 0163-3864; 1520-6025
• DOI: 10.1021/np980467b

Bioassay-guided fractionation of the antiprotozoal extract of Geranium niveum led to the isolation of two new A-type proanthocyanidins, epi-afzelechin-(4β→8,2β→O→7)-afzelechin (1) and epi-catechin-(4β→8,2β→O→7)-afzelechin (2). Compounds 1 and 2 were given the trivial names of geranins A and B, respectively. In addition, five known compounds, mahuannin B (3), reynoutrin (4), hyperin (5), methyl gallate (6), and 3-β-caffeoyl-12-oleanen-28-oic acid (7), were obtained. The structures of the new proanthocyanidins were elucidated by spectroscopic and chemical methods as well as CD measurements. Compounds 1, 2, and 4−7 were tested against axenically grown trophozoites of Giardia lamblia and Entamoeba histolytica.