Phragmalin Limonoids from Chukrasia tabularis var. velutina

Abstract

Two new C-15-acyl phragmalin limonoids, velutinalides A (2) and B (3), featuring a C-16/C-30 δ-lactone ring, and a new structurally related natural product, R310B8 (1), were isolated from the leaves of Chukrasia tabularis var. velutina. Their structures were elucidated on the basis of extensive spectroscopic data analyses and by comparison of their NMR data with those of related known compounds.

Key words

Maliaceae - Chukrasia tabularis var. velutina - C-15-acyl phragmalin limonoid - velutinalide

References

• 1 Nakatani M, Abdelgaleil S A M, Saad M M G, Huang R C, Doe M, Iwagawa T. Phragmalin limonoids from Chukrasia tabularis.  Phytochemistry. 2004;  65 2833-2841
• 2 Baxter R L, Dijksma F J J, Gould R O, Parsons S. β-dihydroentandrophragmin-ethyl acetate (1/0.355).  Acta Crystallogr Sect C Cryst Struct Commun. 1998;  54 1182
• 3 Wu J, Xiao Q, Huang J S, Xiao Z H, Qi S H, Li Q X, Zhang S. 8,9,30-phragmalin ortho esters from Xylocarpus granatum.  Org Lett. 2004;  6 1841-1844
• 4 Fan C Q, Wang X N, Yin S, Zhang C R, Wang F D, Yue J M. Tabularisins A–D, phragmalin ortho esters with new skeleton isolated from the seeds of Chukrasia tabularis.  Tetrahedron. 2007;  63 6741-6747
• 5 Saad M M G, Iwagawa T, Doe M, Nakatani M. Swietenialides, novel ring D opened phragmalin limonoid orthoesters from Swietenia mahogani JACQ.  Tetrahedron. 2003;  59 8027-8033
• 6 Chen Y Y, Wang X N, Fan C Q, Yin S, Yue J M. Swiemahogins A and B, two novel limoids from Swietenia mahogani.  Tetrahedron Lett. 2007;  48 7480-7484
• 7 Luo J, Wang J S, Huang X F, Luo J G, Kong L Y. Chukvelutilides A–F, phragmalin limonoids from the stem barks of Chukrasia tabularis var. velutina.  Tetrahedron. 2009;  65 3425-3431
• 8 Wu J, Xiao Q, Zhang S, Li X, Xiao Z H, Ding H X, Li Q X. Xyloccensins Q–V, six new 8,9,30-phragmalin ortho ester antifeedants from the Chinese mangrove Xylocarpus granatum.  Tetrahedron. 2005;  61 8382-8389
• 9 Abdelgaleil S A M, Doe M, Morimoto Y, Nakatani M. Rings B, D-seco limonoids from the leaves of Swietenia mahogany.  Phytochemistry. 2006;  67 452-458
• 10 Wikberg J E S, Rasoanaivo P, Benoit R, Razafimahefa A S. Novel compounds and pharmaceutical preparations from Neobeguea mahafalensis extracts and their use for treatment of sexual dysfunction. US Patent 145996A2 2008
• 11 Chen P Y. Meliaceae. In: Chen S K, editor Flora reipublicae popularis sinicae (Zhongguo Zhiwu Zhi). Volume 13 Beijing: Science Press; 1997: 47-48
• 12 Editorial Committee of the Administration Bureau of Traditional Chinese Medicine .Chinese materia medica (Zhonghua Bencao). Volume 5 Shanghai: Shanghai Science and Technology Press; 1999: 31-32
• 13 Luo J, Wang J S, Luo J G, Wang X B, Kong L Y. Chukvelutins A–C, 16-norphragmalin limonoids with unprecedented skeletons from Chukrasia tabularis var. velutina.  Org Lett. 2009;  11 2281-2284
• 14 Zhang C R, Yang S P, Zhu Q, Liao S G, Wu Y, Yue J M. Nortriterpenoids from Chukrasia tabularis var. velutina.  J Nat Prod. 2007;  70 1616-1619
• 15 Sun Y Q, Guo Y W. Gymonorrhizol, an unusual macrocyclic polydisulfide from the Chinese mangrove Bruguiera gymnorrhiza.  Tetrahedron Lett. 2004;  45 5533-5535
• 16 Wang J D, Guo Y W. Agallochaols A and B, two new diterpenes from the Chinese mangrove Excoecaria agallocha L.  Helv Chim Acta. 2004;  87 2829-2833
• 17 Wang J D, Zhang W, Li Z Y, Xiang W S, Guo Y W, Krohn K. Elucidation of excogallochaols A–D, four unusual diterpenoids from the Chinese mangrove Excoecaria agallocha.  Phytochemistry. 2007;  68 2426-2431
• 18 Liu H L, Huang X Y, Dong M L, Xin G R, Guo Y W. Piperidine alkaloids from Chinese mangrove Sonneratia hainanensis.  Planta Med. 2010;  76 920-922
• 19 Byon J C H, Kusari A B, Kuseti J. Protein-tyrosine phosphatase-1B acts as a negative regulator of insulin signal transduction.  Mol Cell Biochem. 1998;  182 101-108
• 20 Lammer C, Wagerer S, Saffrich R, Mertens D, Ansorge W, Hoffmann I. The cdc25B phorsphatase is essential for the G2/M phase transition in human cell.  J Cell Sci. 1998;  111 2445-2453
• 21 Wignot T M, Stewart R P, Schray K J, Das S, Sipos T. In vitro studies of the effects of HAART drugs and excipients on activity of digestive enzymes.  Pharm Res. 2004;  21 420-427