However, the bioactivity study of benzyl benzoate and crotepoxide as the antibacterial activity were still limited. Therefore, the antibacterial activity of benzyl benzoate and crotepoxide against four pathogenic bacteria, i. The isolation steps were include the extraction by maceration with acetone, then the acetone extract was partitioned with n-hexane:methanol and ethyl acetate:water respectively. The isolation by liquid vacuum chromatography followed by column chromatography was obtained benzyl benzoate from the n-hexane fraction and crotepoxide from ethyl acetate fraction. The molecular structure of isolated compounds was identified based on NMR 1D and 2D spectroscopic data. The antibacterial activity assay of isolated compounds was carried out using the disc diffusion method.
|Published (Last):||8 August 2019|
|PDF File Size:||20.18 Mb|
|ePub File Size:||8.38 Mb|
|Price:||Free* [*Free Regsitration Required]|
Philip C. Veitch, Monique S. The cyclohexane diepoxide, crotepoxide 8 , was also obtained. Spectroscopic methods were used for structure determination. The methanol extract of the rhizomes of K. All rights reserved. Not surprisingly, studies on new compounds from K.
Some species also contain compounds of medicinal interest due to their antibacterial and antifungal activity Wilson et al.
Results and discussion as antioxidant or platelet activating properties Masuda et al. Kaempferia rotunda L. Although the essential oils of this species have been presence of several apolar components 1, 3—9 with similar described Sirat et al. These resembled the other aspects of its phytochemistry are less well studied. UV spectrum of senepoxide, a cyclohexene epoxide avail- It is, however, known to produce cyclohexane derivatives able as a standard in our natural product collection source: leaves of Friesodielsia obovata, Annonaceae.
Stevenson et al. Its 4 However, on CH2 The similarity between 1 ROE cor- 4 However, spectral features common to 1 and 3— indicated that these compounds were polyoxygenated 6 included resonances corresponding to a benzoyloxy- cyclohexane, rather than cyclohexene derivatives Tables methyl group and a benzoyl group.
A long-range correlation in the HMBC spectrum 4 Thus 3 was 4. An isomer, 4, for which the 2,6 Although, its H 1 4 OH 9 The similar multiplicities and coupling constants for the Fig. Constituents of Kaempferia rotunda rhizomes 1, 3—9 and related ring proton resonances of 3—6 noted in their 1H NMR spec- compounds.
Although relatively little has been published on the conformational analysis of cyclohexane in 2D NMR. The corresponding ring gesting that C-2 was the site of acetylation in these deriva- substituents are thus categorised as either quasi-axial or tives.
Zhou et al. Similarly, long-range correlations from a series of polyoxygenated cyclohexenes from Uvaria H-3 d 5. Thus 5 and 6 were determined similarly substituted to 3 3-benzoylbenzoyloxymethyl- to be 2-acetylbenzoylbenzoyloxymethyl-1,6-epoxy- 1,6-epoxycyclohexan-2,3,4,5-tetrol Fig.
For example, the 3JH-4,H-5 P. The 1H and 13C NMR spec- between the 1,6-epoxide group of 3 and the neighbouring tra of 7 further revealed resonances corresponding to a di- stereocentre at C-5 was established by analogy with data substituted double bond at d 5. In these Two sets of resonances rep- is encountered when an epoxide proton and a neighbouring resenting the methylene protons of benzoyloxymethyl ring proton are on the same face of the molecule i. These b,b , whereas when the protons are on opposite faces, the features provided useful starting points for the elucidation resulting coupling constant is less than 0.
The corresponding value for 3J2 0 ,3 0 of 5R,6R acetylbenzoyl benzoyloxymethyl-1,6-epoxy- 3. Although 3—6 have structural constraints of the bridged ring structure indi- not been reported previously, a related derivative, 2,3-dia- cated that with H-2 0 axial, H-3 0 must be equatorial.
Although corresponding 1H-1H coupling constants. The UV spectrum of this compound kmax and nm from the roots of Uvaria purpurea. This was also was similar to those of 1 and 3—6. Proposed mechanism of formation of 7 by Diels—Alder reaction. This type 8 are all constituents of Kaempferia rotunda, it is tempting of compound is commonly found in Populus and Salix to speculate that these compounds, and by implication, the Salicaceae , but does not appear to have been reported remaining polyoxygenated cyclohexane derivatives previously from the Zingiberaceae Hegnauer, ; Heg- described in this paper, have a common origin in nauer, The Diels- genated cyclohexane structurally related to 1, and previ- Alder adduct 7 was present in extracts of both fresh and ously reported to occur in K.
Further- also had antifeedant activity. These observations suggest that 7 results from enzyme-catalysed, rather than artefac- 3. Experimental section tual, processes. General experimental procedures SIMS contained resonances corresponding to an acylated sugar residue, two acetyl groups, an o-disubstituted phenyl NMR data were acquired on either Bruker Avance and a benzoyloxymethyl group.
Standard pulse 4 Duus et al. Chromatographic separation spectrum. Injection volumes were glucopyranoside, a new acylated derivative of salicin 10 ll and data analysis was performed using Xcalibur 1. Optical rotation measurements 2 Rhizomes of Kaempferia rotunda L. Rotundol 7 analysis of fresh plant material. A small amount of pure 6 5. Antifeedant activity is represented by positive for C21H21O8, The compounds were each tested at 3—4 con- 3. Jolad, S. Marco-Contelles, J.
Tam Bui and Alex cyclohexane epoxides: Sources, biological activities and synthesis. Antiox- London, for chiroptical data, and Mrs. Marianne Yule idant properties of gingerol related compounds from ginger. Biofactors for her help with the preliminary stages of the work. We 21, — Naik, J. This work was large cardamom Amomum subulatum Roxb. Flavour Frag. The re- — Pai, B. Occurrence of crotepoxide in Kaempferia rotunda L.
References Pancharoen, O. Cyclo- hexane diepoxides from Kaempferia rotunda. Phytochemistry 43, Atsumi, S. Iitaka, Y. Production isolation and structure Pino, J. Oil Res. Schulte, G. Antifungal activity of the essential oils of nine Zingiberaceae species. Studies on highly oxidized cyclohexanes. Constitution of a new key Pharm. Tetrahedron Lett. Boll, P. Behavioural and N. Neolignans, cyclohexanes and electrophysiological study of antifeedant mechanisms associated with alkaloids from Piper wightii.
Pays-Bas , 9— Chane-Ming, J. Chemical Sirat, H. Curcuma longa L. Carbohydrate structural hellitol. Sundaresan, S. Antimicrobial activity of Grossel, M. Alicyclic Chemistry. Oxford University Press, Curcuma zedoaria and Curcuma malabarica tubers. Ethnopharma- Oxford, pp. Hegnauer, R. Birkhauser Woerdenbag, H. Verlag, Basel. Composition of the essential oils of Kaempferia rotunda L.
Birkhauser Kaempferia angustifolia Roscoe rhizomes from Indonesia. Flavour Verlag, Basel.
Several species are cultivated in Coastal Southeast gardens for their attractive foliage and colorful flowers. They are commonly called peacock gingers. The correct identities of these plants can be confusing. Tim Chapman of Gingerwood Nursery has updated some of the names below. The cultivated plants, at least, are deciduous in winter.