A new monoglyceride, 1′,26′-bis-[(S)-2,3-dihydroxypropyl] hexacosanedioate (1a) and the new peltogynoid, entadanin (3), along with eight known compounds, were isolated from the stem bark of Entada abyssinica (Fabaceae). The structures of the new compounds were determined by detailed analyses of 1D and 2D NMR spectra, in combination with high-resolution mass spectrometry data, and by comparison with related data from the literature. The stereochemistry of 1a was derived by comparison of the optical rotation with reference data. Peltogynoids have been reported previously from other Fabaceae, however this is the first report of a peltogynoid from the genus Entada.
KatendeA.B. (1995) Useful trees and shrubs for Uganda. Identification, propagation and management for agricultural and pastoral communities. Regional Soil Conservation Unit (RSCU), Swedish International Development Authority (SIDA).
2.
LiangS., ChenH.S., WangH.P., JinL., QiaoL.M., LuJ. (2007) Study on chemical constituents of Tabernaemontana divaricata. Dier Junyi Daxue Xuebao, 28, 425–426.
3.
Bekele-TesemmaA., BirnieA., TengnasB. (1993) Useful trees and shrubs for Ethiopia. Regional Soil Conservation Unit (RSCU). Swedish International Development Authority (SIDA).
4.
HaileY., DelenasawY. (2007) Traditional medicinal plant knowledge and use by local healers in Sekoru District, Jimma Zone, Southwestern Ethiopia. Journal of Ethnobiology and Ethnomedicine, 3, 24–28.
5.
FreiburghausA.F., SteckH.P., BrunR. (1998) Bioassay-guided isolation of a diastereoisomer of kolavenol from Entada abyssinica active on Trypanosoma brucei rhodesiense. Journal of Ethnopharmacology, 61, 179–183.
6.
NyasseB., NgantchouI., TchanaE.M., SonkéB., DenierC., FontaineC. (2004) Inhibition of both Trypanosoma brucei blood stream form and related glycolytic enzymes by a new kolavic acid derivative isolated from Entada abyssinica. Pharmazie, 59, 873–875.
7.
TchindaT.A., FuendjiepV., MekonnenY., NgoM.B., DagneE. (2007) A bioactive diterpene from Entada abyssinica. Natural Product Communications, 2, 9–12.
8.
DebellaA., KunertO., SchmidM.G., MichlG., BucarF., AbebeD., HaslingerE. (2000) A diterpene, a flavonoid glycoside and a phytosterol from Entada abyssinica stem bark. Monatshefte für Chemie, 131, 401–408.
9.
YangN.Y., TaoW-W, DuanJ-A. (2009) Three new lipids from the seeds of Trogopterus xanthipes. Journal of Chemical Research, 423–426.
10.
NyonghaA.T., HussainH., DongoE., AhmedI., KrohnK. (2010) Hyloglyceride and hylodiglyceride: two new glyceride derivatives from Hylodendron gabunensis. Natural Product Communications, 5, 1939–1940.
11.
WuW-J, ChenH-J, WuY., LiuB. (2013) Synthesis and absolute configuration of hyloglyceride isolated from Hylodendron gabunensis. Tetrahedron, 70, 92–96.
12.
ZhaoQ.C., MansoorT.A., HongJ.K., LeeC.O., ImS.K., LeeD.S., JungJ.H. (2003) New lysophosphatidylcholines and monoglycerides from the marine sponge Stelletta sp. Journal of Natural Products, 66, 725–728.
13.
ShigaT., NabetaK., NakanoH., SuzukiT. (1987) Dicarboxylic acid esters as dermatological agents. U.S. patent 4661519 A.
14.
MabryT.J., MarkhamK.R., ThomasM.B. (1970) The systematic identification of flavonoids.Springer-Verlag, New York, p 41.
LinY-L, ShenC-C, HuangY-J, ChangY-Y. (2005) Homoflavonoids from Ophioglossum petiolatum. Journal of Natural Products, 68, 381–384.
17.
AhmaduA., AbdulkarimA., GrougnetR., MyrianthopoulosV., TillequinF., MagiatisP., SkaltsounisA-L. (2010) Two new peltogynoids from Acacia nilotica Delile with kinase inhibitory activity. Planta Medica, 76, 458–460; (b) Polasek J, Queiroz EF, Marcourt L, Meligova AK, Halabalaki M, Skaltsounis A-L, Alexis MN, Prajogo B, Wolfender J-L, Hostettmann K. (2013) Peltogynoids and 2-phenoxychromones from Peltophorum pterocarpum and evaluation of their estrogenic activity. Planta Medica, 79, 480–486.
18.
NairA.G.R., KrishnanS., RavikrishnaC., MadhusudananK.P. (1999) New and rare flavonol glycosides from leaves of Syzygium samarangense. Fitoterapia, 70, 148–151.
19.
GunstoneF.D., PollardM.R., ScrimgeourC.M., Vedanayagam. (1977) 13C nuclear magnetic resonance studies of olefinic fatty acids and esters. Chemistry and Physics of Lipids, 18, 115–129.
20.
HishamN.M.D., LipM.J., NohdM.J., NormahandA., NabilahN.F.M. (2011) Identification and isolation of methyl gallate as a polar chemical marker for Labisia pumila Benth. Journal of Tropical Agricultural and Food Science, 39, 279–284.
21.
LaatschH. (2013) AntiBase, a database for dereplication and structure determination of microbial natural products. Weinheim. Wiley VCH (http://wwwuser.gwdg.de/~hlaatsc/antibase.htm).
22.
AquinoR., CiavattaM.L., De TomasiN., Gacs-BaitzE. (1992) Tetranorditerpenoids from Detarium microcarpum. Phytochemistry, 31, 9–12.
23.
AvilaD., MedjinaJ.D. (1992) A new clerodane diterpenoid from Eperua leucanthan. Journal of Natural Products, 55, 845–850.
