Lanostanes and friedolanostanes from the bark of Garcinia speciosa

• Published in: Phytochemistry (Oxford) Vol. 65; no. 4; pp. 393 - 398
• Main Authors: Vieira, Luis M.M., Kijjoa, Anake, Silva, Artur M.S., Mondranondra, Ing-On, Kengthong, Surapong, Gales, Luis, Damas, Ana Margarida, Herz, Werner
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 01.02.2004; Elsevier
• Subjects: 17,14-Friedolanostanes; Biochemistry & Molecular Biology; Biological and medical sciences; Chemical constitution; Fundamental and applied biological sciences. Psychology; Garcinia - chemistry; Garcinia speciosa; Guttiferae; Insecta; Invertebrates; Lanostanes; Life Sciences & Biomedicine; Molecular Conformation; Molecular Structure; Nuclear Magnetic Resonance, Biomolecular; Pathology; Plant Bark - chemistry; Plant Extracts - chemistry; Plant Extracts - isolation & purification; Plant physiology and development; Plant Sciences; Science & Technology; Stereoisomerism; Triterpenes - chemistry; Triterpenes - isolation & purification; X-Ray Diffraction; Garcinia speciosa; Lanostanes; 17,14-Friedolanostanes; Guttiferae; 17,14-friedolanostanes; ABIES-MARIESII; lanostanes; Ester; Molecular structure; Absolute configuration; Bark; Stereochemistry
• ISSN: 0031-9422; 1873-3700
• DOI: 10.1016/j.phytochem.2003.10.024

The CHCl 3 extract of the bark of Garcinia speciosa contained four 17,14-friedolanostanes and five lanostanes as well as friedelin and common plant constituents. The friedolanostanes were the previously known methyl ester of (24 E)-3α,23α-dihydroxy-17,14-friedolanostan-8,14,24-trien-26-oic acid and the methyl esters of three hitherto unknown acids, 3α-hydroxy-16α,23α-epoxy-17,14-friedolanostan-8,14,24-trien-26-oic acid, 3α,23α-dihydroxy-8α,9α-epoxy-17,14-friedolanostan-15-oxo-24-en-26-oic acid and 3α,23α-dihydroxy-17,14-friedolanostan-15-oxo-8(14),24-dien-26-oic acid. New lanostanes were 3β,9α-dihydroxylanost-24-en-26-al and the methyl ester of 3β-hydroxy-23-oxo-9,16-lanostadien-26-oic acid. Structures were established by analysis of spectroscopic data. In the case of the lanostanes the previously unassigned C-25 stereochemistry was shown to be 25 R by X-ray analysis of 3β-hydroxy-23-oxo-9,16-lanostadien-26-oic acid. In the case of the friedolanostanes the configuration at C-23 was established as 23 R, identical with the absolute configuration at C-23 of mariesiic acids A and B. Five 17,14-friedolanostanes and five lanostanes were isolated from the bark of Garcinia speciosa. Structures of new compounds were established by spectroscopic methods.