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ORIGINAL ARTICLE
Year : 2010  |  Volume : 2  |  Issue : 2  |  Page : 69-71 Table of Contents     

Crystal and molecular structure of lancerodiol-p-hydroxybenzoate


1 Natural Products Chemistry Department, National Research Centre, Dokki, Giza, 12622, Egypt
2 Chemistry of Medicinal Plant Department, National Research Centre, Dokki, Giza, 12622, Egypt
3 Department of Chemistry, Aswan-Faculty of Science, South Valley University, Aswan, Egypt

Date of Submission11-Feb-2010
Date of Decision12-Feb-2010
Date of Web Publication03-May-2010

Correspondence Address:
Abou El-Hamd H Mohamed
Faculty of science, Aswan, Egypt Aswan
Egypt
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Source of Support: None, Conflict of Interest: None


DOI: 10.4103/0974-8490.62950

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   Abstract 

Lancerodiol-p-hydroxybenzoate was isolated from the leaves of Ferula sinaica L. (Apiaceae) as light needle crystals. This work reports for the first time the molecular structure and relative configuration of compound 1, established by X-ray analysis.

Keywords: Crystal structure, Ferula sinaica, lancerodiol, sesquiterpene


How to cite this article:
Abd El-Razek MH, Hegazy MEF, Mohamed AHH. Crystal and molecular structure of lancerodiol-p-hydroxybenzoate. Phcog Res 2010;2:69-71

How to cite this URL:
Abd El-Razek MH, Hegazy MEF, Mohamed AHH. Crystal and molecular structure of lancerodiol-p-hydroxybenzoate. Phcog Res [serial online] 2010 [cited 2020 Jan 28];2:69-71. Available from: http://www.phcogres.com/text.asp?2010/2/2/69/62950


   Introduction Top


The genus Ferula presents interesting phytochemical features. Ferula sinaica L. (Apiaceae) is widespread in Sinai peninsula, Egypt. The gum resins of the genus Ferula have been used in folklore medicine for treatment of various diseases. [1] Thus, Ferula communis L., its subspecies and varieties have been used as agents against hysteria and to treat dysentery, [2] Ferula jaeschkeana vatke has been applied to wounds and bruises, [3] and Ferula tingitana L. has proved to be a good source of ammoniac, an oleo-gum resin used in medicine. [4] The widespread sesquiterpene compounds in this genus are characteristic dauicanes, humulanes, himachalanes, germacranes, eudesmanes, and guainanes. [5] Chemically, the resin of the species is characterized by the presence of sesquiterpenes, [5],[6],[7],[8] sesquiterpene coumarines, [7],[8],[9] and monoterpenes. [9],[10],[11],[12] Investigation of the CH 2 Cl 2 :MeOH (1:1) extract of the leaves of F. sinaica led to the isolation of lancerodiol-p-hydroxybenzoate 1 . Herein, we describe the relative stereochemistry and the molecular structure of 1 by X-ray diffraction.


   Materials and Methods Top


General

Compound 1 [Figure 1], with a molecular formula C 22 H 28 O 5 , was isolated from CH 2 Cl 2 :MeOH (1:1) extract of the leaves of F. sinaica and was recrystallized from CDCl 3 . A colorless needle was mounted on glass fiber at room temperature. Preliminary examination and data collection were performed on Siemens P4 (oriented graphite monochromator; Mo-Kα radiation) at 293 K. Cell parameters were calculated from the least-squares fitting for 25 high angle reflections (2θ > 15). Omega scans for several intense reflections indicated acceptable crystal quality. Crystallographic data for the structural analysis [Figure 2] have been deposited with the Cambridge Crystallographic data center (CCDC) and allocated the deposition number CCDC 207262. These data can be obtained free of charge through the website www.ccdc. Cam.ac.uk/cants/retrieving html/or from the CCDC, 12 union Road, Cambridge CB2 1 EZ, UK; fax: +44-1223-336033; email: deposit@ccdc.cam.ac.uk.

Plant material

F. sinaica was collected in 2005 from El-Minia, Egypt. A voucher specimen of the collection was identified by Prof. Mohamed Jaber and was deposited at the Department of Botany, Aswan-Faculty of Science, Egypt.

Extraction and isolation

Air-dried and powdered leaves (200 g) of F. sinaica were extracted with CH 2 Cl 2 : MeOH (1:1) at room temperature for 24 h. The extract was concentrated in vacuo to give a residue (15 g) that was chromatographed by using flash column chromatography on a silica gel eluted with n-hexane-CH 2 Cl 2 step-gradient up to CH 2 Cl 2 and CH 2 Cl 2 -MeOH up to 15% MeOH (2 l each of the solvent mixture). The n-hexane-CH 2 Cl 2 fraction (1:3) was carefully chromatographed on a Sephadex LH-20 column eluted with n-hexane-CH 2 Cl 2 -MeOH (7:4:0.25) with increasing polarity to give compound 1 (21 mg).


   Results and Discussion Top


Colorless needle crystals suitable for X-ray diffraction were grown by slow evaporation of CDCl 3 solution. The crystal data [Table 1],[Table 2],[Table 3] for lancerodiol-p-hydroxybenzoate were as follows: orthorhombic, space group P2 1 2 1 2 1 with a = 8.179 (2) Ε, b = 14.165 (3) Ε, c = 17.408 (3) Ε, V = 2080.9 (8) Ε, Z = 4. The structure refined to R(F) = 0.0 725 [I > 2σ (I)] and wR(F2 ) = 0.1934 [I > 2σ(I)] for 2102 observed reflections with Mo-Kα radiation (λ = 0.71073 Ε). The scanning speed was varied according to the intensity, from a minimum of 1 to a maximum of 11/min.

 
   References Top

1.Boulus L. Medicinal Plants of North-Africa MI; Algonae: Michigan, USA; 1983  Back to cited text no. 1      
2.Miski MM, Mabry TJ. Daucane esters from Ferula communis subsp. communis. Phytochem 1985;24:1735-41.   Back to cited text no. 2      
3.Razdan TK, Qadri B, Qurishi MA, Khuroo MA, Kachroo PK. Sesquiterpene esters and sesquiterpene-coumarin ethers from Ferula jaeskeana. Phytochem 1989;28:3389-93.   Back to cited text no. 3      
4.French D. The Biology and Chemistry of the Umbelliferae Ed. Heywood VH, London: Academic Press; 1971. p. 385-412.  Back to cited text no. 4      
5.Gonzalez AG, Barrera JB. Progress in the chemistry of organic. Nat Prod 1995;64:1-92.  Back to cited text no. 5      
6.Appendino G, Jakupovic J, Alloati S, Ballero M. Daucane esters from Ferula arrigonii. Phytochem 1997;45:1639-43.  Back to cited text no. 6      
7.Su BN, Takaishi Y, Honda G, Itoh M, Takeda Y, Kodzhimatov OK, et al. Sesquiterpene coumarins and related derivatives from Ferula pallida. J Nat Prod 2000;63:436-40.  Back to cited text no. 7  [PUBMED]  [FULLTEXT]  
8.Su BN, Takaishi Y, Honda G, Itoh M, Takeda Y, Kodzhimatov OK, et al. Sesquiterpene phenylpropanoid and sesquiterpene chromone derivatives from Ferula pallida. J Nat Prod 2000;63:520-2.  Back to cited text no. 8  [PUBMED]  [FULLTEXT]  
9.Ahmed AA. Sesquiterpene coumarins and sesquiterpenes from Ferula sinaica. Phytochem 1999;50:109-12.  Back to cited text no. 9      
10.Ahmed AA. New sesquiterpenes from Ferula sinaica. J Nat Prod 1990;53:483-6.  Back to cited text no. 10  [PUBMED]    
11.Ahmed AA. Daucanes and other constituents from Ferula sinaica. Phytochem 1991;30:1207-10.  Back to cited text no. 11      
12.Al-Hazimi HM. Terpenoids and a coumarin from Ferula sinaica. Phytochem 1986;25:2417-9.  Back to cited text no. 12      


    Figures

  [Figure 1], [Figure 2]
 
 
    Tables

  [Table 1], [Table 2], [Table 3]



 

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