Chemical Constituents from Stem Bark and Roots of Clausena anisata

Abstract

Phytochemical investigations on the stem bark and roots of the tropical shrub Clausena anisata led to the isolation and characterization three carbazole alkaloids: girinimbine, murrayamine-A and ekeberginine; two peptide derivatives: aurantiamide acetate and N-benzoyl-l-phenylalaninyl-N-benzoyl-l-phenylalaninate; and a mixture of two phytosterols: sitosterol and stigmasterol. The structures of these compounds were established by nuclear magnetic resonance (1H-NMR, 13C-NMR, COSY, HSQC, HMQC, HMBC and NOESY) spectroscopy and electrospray ionization mass spectrometry (MS).

Total Synthesis of Carbazole Alkaloids – Ekeberginine, Harmandianamine A, and Furanoclausamine B

“…The reduction of 19 with diisobutylaluminium hydride (DIBAL‐H) followed by oxidation of the resulting mixture with MnO 2 furnished ekeberginine ( 20 )13 in 70 % yield. The spectroscopic data of the synthetic 20 are in good agreement with those of the natural product 7a. The first synthesis of 20 was recently reported by Knölker et al7b The present synthesis of 20 required five steps from commercially available 2‐acetoxy‐γ‐butyrolactone and aniline with an overall yield 31.5 %.…”

Carbazole Alkaloids from Stem Bark of Murraya koenigii (L.) Spreng

“…NMR) with previously reported literature values [9]. This compound was also earlier isolated from the same plant.…”

The use of Clausena anisata in insect pest control in Africa: A review

“…Furthermore, furanocoumarins can alter the detoxification capability of an organism, by reversibly or irreversibly inhibiting cytochrome P450 detoxification enzymes (Neal and Wu, 1994). A number of Mester et al, 1977Lakshmi et al, 1984Gebreyesus and Chapya, 1983Pitan et al, 2009 Mukandiwa et al, 201 Geranylcoumarin anisocoumarin A-J Stem bark Ngadjui et al, 1989a, b;Ngadjui et al, 1991 Furanocoumarin-lactone indicolactone anisolactone 2′,3′-epoxyanisolactone Okorie, 1975Chakraborty et al, 1995Ngadjui et al, 1989cSongue et al, 2012Ito et al,19982000;Tatsimo et al, 2015Ito et al, 2009 mukonidine clausine F Lactone carbazole alkaloids furanoclausamine A and B Stem Ito et al, 2009 Pyranocarbazole alkaloid mupamine Root bark Mester et al, 1977 Terpenes Ngassoum et al, 1999Gundidza et al, 1994Innocent and Hassanali, 2015Gundidza et al, 1994 germacrene-B (E)-β-ocimene terpinen-4-ol coumarin compounds have also been identified as the antifeedant actives in C. anisata which include imperatorin and xanthoxyletin (Gebreyesus and Chapya, 1983), osthol [2H-1-Benzopyran-2-one, 7-methoxy-8-(3-methyl-2-butenyl)] (Pitan et al, 2009) and seselin (2H,8H-Benzo[1,2-b:3,4-b']dipyran-2-one,8,8-dimethyl) (Mukandiwa et al, 2013).The exact mechanism of antifeedant action of coumarins is unknown.…”