Subscribe to RSS
DOI: 10.1055/s-2000-9901
Phytochemical Investigation of Aglaia andamanica
Publication History
Publication Date:
31 December 2000 (online)
Abstract
Four new compounds, the limonoid 24-epi-melianodiol (8), the tirucallane aglaiodiol (9), and the two cyclopentatetrahydrobenzopyran derivatives pyramidaglain A (11) and B (12) were isolated from the leaves of Aglaia andamanica Hiern (Meliaceae), together with the eleven known constituents β-sitosterol, β-sitosterol glucoside, cycloart-23E-ene-3β,25-diol (1), three flavonoids 5-hydroxy-3,4′,7-trimethoxyflavone (2), retusin (3) and pachypodol (4), the tirucallane 24-epi-piscidinol A (5), the lignan yangambin (6), the limonoid melianodiol (7), the bisamide pyramidatine (10) and the amino acid N-methyl-trans-4-hydroxy-L-proline (13). All structures were established by means of detailed spectroscopic analysis.
Key words
Aglaia andamanica - Meliaceae - 24-epi-melianodiol - aglaiodiol - pyramidaglain A - B
References
-
1 Pannell C M..
A Taxonomic Monograph of the Genus Aglaia Lour. (Meliaceae), . HMSO, London,; 1992 - 2 Brader G,, Vajrodaya S,, Greger H,, Bacher M,, Kalchhauser H,, Hofer O.. Bisamides, lignans, triterpenes, and insecticidal cyclopenta[b]benzofurans from Aglaia species. J. of Nat. Prod.. 1990;; 61 1482-90
- 3 Hayashi N,, Lee K-H,, Hall I H,, McPhail A T,, Huang H-C.. Structure and stereochemistry of (-)-odorinol, an antileukemic diamide from Aglaia odorata. . Phytochemistry. 1982;; 21 2371-3
- 4 Joshi M N,, Chowdhury B L,, Vishnoi S P,, Shoeb A,, Kapil R S.. Antiviral activity of (+)-odorinol. Planta Medica. 1987;; 53 245-55
- 5 Ishibashi F,, Satasook C,, Isman M B,, Towers G HN.. Insecticidal 1H-cyclopentatetrahydro[b]benzofurans from Aglaia odorata. . Phytochemistry. 1993;; 32 307-10
- 6 Mabberley D J,, Pannell C M,, Sing A M.. Flora Malesiana. ser. I. 1995;; 12 1-407
- 7 Jahodar L,, Grygarova V,, Budesinsky M.. Triterpenoids of Arctostaphylos uva-ursi roots. Pharmazie. 1988;; 83 442-3
- 8 Kojma H,, Sato N,, Hatano A,, Ogura H.. Sterol glucosides from Prunella vulgaris. . Phytochemistry. 1990;; 29 2351-5
- 9 Greca M della,, Fiorentino A,, Monaco P,, Previtera L.. Cycloartane triterpenes from Juncus effusus. . Phytochemistry. 1994;; 35 1017-22
- 10 Vidari G,, Finzi P V,, Bernardi M D.. Zingiberaceae flavonols and quinones in stems of Aframomum giganteum. . Phytochemistry. 1971;; 10 3335-9
- 11 Malan E,, Roux D G.. Flavonoids from Distemonanthus benthamianus Baillon. Methoxylated flavones and inter-relationships of benthamianin, a [2]benzopyrano[4,3-b][1]benzopyran. J. Chem. Soc., Perkin Trans. I. 1979;; 11 2696-703
- 12 Picker K,, Ritchie E,, Taylor W C.. Constituents of Eupomatia species III. New eupomatenoid lignans from the leaves and wood of Eupomatia laurina. . Aust. J. Chem.. 1973;; 26 1111-9
-
13 Agrawal P K..
Carbon-13 NMR of flavonoids, . Elsevier Science Publishing Com. Inc., New York,; 1989: 162-3 - 14 McChesney J D,, Dou J,, Sindelar R D,, Goins D K,, Walker L A,, Rogers R D.. Tirucallane-type triterpenoids: NMR and X-ray diffraction analyses of 24-epi-piscidinol A and piscidinol A. J. Chem. Crystallogr.. 1997;; 27 283-90
- 15 Anjaneyulu A SR,, Suryanarayana Murty V.. Chemical examination of heartwood of Guazuma tomentosa Kunth. Indian J. Chem. Sect. B. 1981;; 20,1 85-7
- 16 Marrien A,, Polonsky J.. The natural occurrence of melianodiol and its diacetate in Samadera madagascariensis (Simaroubaceae): Model experiment of melianodiol directed towards simarolide. J. Chem. Soc., Chem. Commun.. 1971;; 261-3
- 17 Saifah E,, Puripattanavong J,, Likhitwitayawuid K,, Cordell G A,, Chai H Y,, Pezzuto J M.. Bisamides from Aglaia species: Structure analysis and potential to reverse drug resistance with cultured cells. J. Nat. Prod.. 1993;; 56 473-7
- 18 Figliuolo R,, Naylor S,, Wang J,, Langenheim J H.. Unusual nonprotein imino acid and its relationship to phenolic and nitrogenous compounds in Copaifera. Phytochemistry. 1987;; 26 3255-9
- 19 Benosman A,, Richomme P,, Sevent T,, Perromat G,, Hadi A HA,, Bruneton J.. Tirucallane triterpenes from the stem bark of Aglaia leucophylla. . Phytochemistry. 1995;; 40 1485-7
- 20 Dumontet V,, Thoison O,, Omobuwajo O R,, Martin M-T,, Perromat G,, Chaironi A,, Riche C,, Pais M,, Sevenet T,, Hadi A HA.. New nitrogenous and aromatic derivatives from Aglaia argentea and A. forbesii. . Tetrahedron. 1996;; 52 6931-42
- 21 Bacher M,, Hofer O,, Brader G,, Vajrodaya S,, Greger H.. Thapsakins: possible biogenetic intermediates towards insecticidal cyclopenta[b]benzofurans from Aglaia edulis. . Phytochemistry. 1999;; 52 253-63
- 22 Malhotra B,, Onyilagha J C,, Bohm B A,, Towers G HN,, James D,, Harborne J B,, Fench C J.. Inhibition of tomato ringspot virus by flavonoids. Phytochemistry. 1996;; 43 1271-6
- 23 Funayama S,, Komiyama K,, Miyaichi Y,, Tomimori T,, Nozoe S.. Cytocidal and antimicrobial activity of flavonoids. Nat. Med.. 1995;; 49 322-8
- 24 Wu J,, Chun Y,, Ebizuka Y,, Sankawa U.. Biologically active constituents of Centipeda minima: Sesquiterpenes of potential anti-allergy activity. Chem. Pharm. Bull.. 1991;; 39 3272-5
- 25 Sciuto S,, Chillemi R,, Piattelli M,, Impellizzeri G.. The identification of 4-hydroxy-N-methylproline in the red alga Chondria coerulescenspectral information. Phytochemistry. 1983;; 22 2311-2
Dr. Professor A. W. Frahm
Department of Pharmaceutical Chemistry University of Freiburg
Hermann-Herder-Straße 9
79104 Freiburg
Germany
Email: awfrahm@ruf.uni-freiburg.de
Phone: +49-761-203-6351