Petersaponins III and IV, Triterpenoid Saponins from Petersianthus macrocarpus

• Published in: Journal of natural products (Washington, D.C.) Vol. 63; no. 5; pp. 716 - 719
• Main Authors: Olugbade, Tiwalade A, Ogundaini, Abiodun, Birlirakis, Nicolas, Païs, Mary, Martin, Marie-Thérèse
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 01.05.2000; Amer Chemical Soc
• Subjects: Chemistry, Medicinal; Chromatography, High Pressure Liquid; Hydrolysis; Life Sciences & Biomedicine; Magnetic Resonance Spectroscopy; Mass Spectrometry; Optical Rotation; Pharmacology & Pharmacy; Plant Epidermis - chemistry; Plant Extracts - chemistry; Plant Sciences; Plants, Medicinal - chemistry; Saponins - chemistry; Saponins - isolation & purification; Science & Technology; Triterpenes - chemistry; Triterpenes - isolation & purification
• ISSN: 0163-3864; 1520-6025
• DOI: 10.1021/np990638s

Two new triterpenoid saponins, petersaponins III and IV (1 and 2), were isolated from an n-butanol extract of the bark of Petersianthus macrocarpus. They possess 21-O-benzoyl-22-O-acetylbarringtogenol C and 21-O-2-furoxyl-22-O-tigloylbarringtogenol C as the aglycon, respectively. For both 1 and 2, the trisaccharide moiety linked to C-3 of the aglycon consists of d-glucuronic acid, d-xylose, and d-galactose, while a l-rhamnose unit is linked to C-28. The structures of 1 and 2 were elucidated by extensive NMR experiments including 1H−H (COSY, HOHAHA, NOESY) and 1H−13C (HMQC and HMBC) spectroscopy and by chemical evidence.