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RESEARCH ARTICLE
Year : 2009  |  Volume : 1  |  Issue : 4  |  Page : 162-165 Table of Contents     

Damarane Triterpene from Cleome arabica


1 Department of Chemistry, Aswan-Faculty of Science, South Valley University, Aswan, Egypt
2 Department of Pharmaceutical Chemistry and Pharmacognosy, Faculty of Pharmacy, Applied Sciences University, Amman 11931, Jordan
3 Chemistry of Medicinal Plant Department, National Research Centre, Dokki, Giza, 12622, Egypt
4 Nagahama Institute of Bio-Science and Technology, Nagahama, Shiga 526-0829, Japan

Date of Submission20-Apr-2009
Date of Decision02-Jun-2009
Date of Acceptance02-Jun-2009
Date of Web Publication2-Jan-2010

Correspondence Address:
Abou-El-Hamd H Mohamed
Department of Chemistry, Aswan-Faculty of Science, South Valley University, Aswan
Egypt
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Source of Support: None, Conflict of Interest: None


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   Abstract 

A damarane triterpene was isolated from the aerial parts of Cleome arabica L. (Capparaceae). The structure of the compound was elucidated by extensive spectroscopic methods including 1 D- [ 1 H and 13 C] and 2D- NMR experiments [COSY, HMQC, HMBC] as well as HRMALDITOFMS analysis.

Keywords: Cleome arabica, Damarane triterpene


How to cite this article:
Khalafallah AK, Mohamed AEH, Yousof AH, Hussien TA, Mohamed-Elamir F H, Shinji O. Damarane Triterpene from Cleome arabica. Phcog Res 2009;1:162-5

How to cite this URL:
Khalafallah AK, Mohamed AEH, Yousof AH, Hussien TA, Mohamed-Elamir F H, Shinji O. Damarane Triterpene from Cleome arabica. Phcog Res [serial online] 2009 [cited 2019 Aug 24];1:162-5. Available from: http://www.phcogres.com/text.asp?2009/1/4/162/58082


   Introduction Top


In Egyptian flora, about ten species of the genus Cleome (Capparaceae) have been recorded. Some of them showed medical values as an anthelmintic and a counterirritant in chronic painful joints and folk remedy for infantile convulsions [1],[2],[3] . Chemical investigations of some Cleome species led to isolation and identification of triterpenoids, nor triterpenoids and furanolignans [4],[5],[6],[7] . The aerial parts of four Cleome species were investigated for their surface flavonoids, affording ten methylated flavonoids as 5, 7, 4′-trihydroxy-3-methoxyflavone (isokaempferide), 5, 7 ,4′-trihydroxy-3,3′-dimethyoxyflavone, 5, 7, 4′-trihydroxy-6,3′-dimethoxyflavone (jaceosidin), 5,4′-dihydroxy-3, 6, 7-trimethoxy-flavone (penduletin), 5, 7, 3′,4′-tetrahydroxy-3,6-dimethoxyflavone (axillarin), 5, 7, 4′-trihydroxy-6, 3′,5′-trimethoxyflavone, 5,4′-dihydroxy-3, 6, 7,3′-tetramethoxyflavone (chrysosplenetin), 5,3′-dihydroxy-3, 6, 7,4′,5′-pentamethoxyflavone, 5,4′-dihydroxy-3, 6, 7, 8,3′-pentamethoxyflavone and 5-hydroxy-3, 6, 7,3′,4′,5′-hexamethoxyflavone [8] . Here we wish to report the isolation and elucidation of a damarane type triterpene (1) from Cleome arabica L.


   Materials and Methods Top


General

NMR spectra were measured with a Bruker AMX-400 spectrometer, with TMS as an internal standard. CC: Silica gel (Merck, 60-120 mesh) and Sephadex LH-20 (Pharmacia). TLC and Preparative TLC: Silica gel 60 GF 254 (Merck). The compound was visualized either by spraying with vanillin reagent or under UV lamp.

Plant material

Cleome arabica was collected in 2003 from El-Minia, Egypt. A voucher specimen of the collection was identified by Prof. Mohamed Jaber and was deposited in the Department of Botany, Aswan Faculty of Science, Egypt.

Extraction and isolation

Air dried and powdered aerial parts (300 g) of Cleome arabica were extracted with CH2Cl2 at room temperature for 24 h. The extract was concentrated in vacuo to give a residue (25 g), which was chromatographed by using flash column chromatography on a silica gel with n-hexane-CH2Cl2 step-gradient. The CH2Cl2 fraction (100 %) was carefully chromatographed on a Sephadex LH-20 column eluted with n-hexane-CH2Cl2 -MeOH (7: 4: 0.5) with increasing the polarity to give a damarane triterpeneoid, compound 1 (20 mg).


   Results and Discussion Top


The methylene chloride extract of the air-dried aerial parts of C. arabica was chromatographed on silica gel and Sephadex LH-20 columns to give a triterpenoid type damarane (1). The low resolution mass spectrum showed the molecular ion peak [M] + at m/z = 474. The HRMALDITOFMS exhibited the molecular ion peak [M+ Na] + at m/z = 497.3607 (calcd. 497.3608), in accord with the molecular formula of C30H52O5 . The structure of compound 1 was determined from careful investigation of 1D and 2D NMR measurements. The 1 H NMR spectrum of compound 1 revealed the presence of seven tertiary methyl singlets at δ 0.84, 1.13, 1.20, 1.12, 0.98, 1.02 and 0.88, each integrating for 3H. Additionally, it showed the oxygenated methylene protons as a pair doublet of doublets at δ 3.73 (J = 8.8, 2.2 Hz) and 4.24 (J = 8.8, 2.2 Hz), correlated in 1 H- 13 C COSY with one carbon signal at δ 68.0, C-19. Also, it showed the oxygenated methine proton as a triplet signal at δ 3.73 (J = 7.5) correlated in 1 H- 13 C COSY with a carbon signal at δ 83.2, C-24. The latter proton showed correlation in 1 H- 1 H COSY with multiplet signals at δ 1.75 and 1.90, H-23. Moreover the 1 H-NMR revealed the presence of several multiple signals for most protons. The 13 CNMR data [Table 1] revealed the presence of thirty carbon atoms and their multiplicities (by DEPT analysis) confirmed the number of hydrogen atoms of the formula given above. The carbon atoms were assigned as seven methyl carbons at δ = 16.1, 23.4, 27.4, 24.3, 18.6, 26.9, 15.3 (C-18, C-21, C-26, C-27, C-28, C-29, C-30), ten methylene carbons at δ = 35.6, 29.6, 22.7, 31.4, 27.5, 25.6, 33.4, 19.9, 68.0, 26.3 (C-1, C-2, C-6, C-7, C-11, C-12, C-15, C-16, C-19, C-23), five methine carbons at δ 50.0, 43.2, 45.4, 49.4, 83.2 (C-5, C-9, C-13, C-17, C-24) and seven quaternary carbons at δ = 98.5, 40.5, 49.6, 35.5, 39.3, 86.2, 71.5 (C-3, C-4, C-8, C-10, C-14, C-20, C-25). Furthermore, all proton and carbon signals were determined by 1 H- 1 H COSY, HMQC and HMBC [Table 1]. Confirmation the structure of compound 1 was given by the results of the 2D hetero nuclear multiple bond correlation [HMBC] analysis [Table 1], [Figure 1]. The most important correlations were observed between H-1 (δH 2.17 m) with C-2 (δC 29.6), C-5 (δC 50.0), C-10 (δC 35.5); H-15 (δH 1.30 m) with C-13 (δC 45.4), C-14 (δC 39.3), C-16 (δC 19.9), C-17 (δC 49.4), C-30 (δC 15.3), H-18 (δH 0.84 s) with C-7 (δC 31.4), C-8 (δC 49.6), C-9 (δC 43.2), C-14 (δC 39.3); H-19 (δH 4.24 dd) with C-1 (δC 35.6), C-5 (δC 50.0), C-10 (δC 35.5); H-21 (δH 1.13 s) with C-17 (δ,sub>C 49.4), C-20 (δC 86.2), C-22 (δC 36.0); H-23 (δH 1.90 m) with C-22 (δC 36.0); ); H-24 (δH 3.73 dd) with C-26 (δC 27.4), C-27 (δC 24.3); H-26 (δH 1.20 s) with C-24 (δC 83.2), C-25 (δC 71.5), C-27 (δC 24.3) and H-28 (δH 0.98 s) with C-3 (δC 98.5), C-4 (δC 40.5), C-5 (δC 50.0), C-29 (δC 26.9). The stereochemistry of 1 was deduced from the chemical shifts and the values of coupling constants and confirmed by the NOESY spectrum with inspection of Drieding models. The NOESY spectrum indicated clear effects between H-30α (δH 0.88, s) and H-17 (δH 1.80, m), between H-18β (δH 0.88, s) and H-17 (δH 1.80, m), between H-18β (δH 0.84, s) and H-19 (δH 4.24, dd) as well as between H-29α (δH 1.02, s) and H-1 (δH 2.17, m), H-2 (δH 2.13, m). All previous data proved that compound 1 was a rare damarane triterpene, isolated for the first time from Cleome arabica [11] .


   Acknowledgement Top


The author thanks the late Prof. Ahmed A. Ahmed for his help and assistance. God bless him.

 
   References Top

1.El-Hadidi and Fayed M., a. Taekholma, (1994/1995), 15.  Back to cited text no. 1      
2.Boulos L. Medicinal plants of North Africa, (1983), 52.  Back to cited text no. 2      
3.Ray A. B., Chattopadhyay S.K., Konno C. and Hikino H. Structure of cleomiscosin A, a coumarino-lignoid of Cleome viscosa seeds. Tetrahydron lett., 21: 4477 (1980).  Back to cited text no. 3      
4.El-Askany and Hesham I. 15α-Acetoxy deomblynal A from Cleome amblyo­carpa. Molecules, 10: 971-977 (2005).  Back to cited text no. 4      
5.Ahmed A. A., Kattab A. M., Botige S. G., MaO Y. Q., Minter D. E., Rein­ecke M. G., Watson W. H. and Mabry T. J. 15α-Acetoxy deomblynal A from Cleome amblyocarpa. J. Nat. Prod., 64: 106-107 (2001)  Back to cited text no. 5      
6.Qin Guo-wei, Hamed A. I., El-Emry N. A., Chen Ye-Gao, Wang Li-Quan, Cheung K. K., Cheng Kin-Fai. New trinortriterpenoid from Cleome chrysan­tha Planta Med., 66: 191-193 (2000).  Back to cited text no. 6      
7.Nagaya H., Itokawa S. and Takeya K. Antitumer dammarane triterpenoid steroids and their manufacture from Cleame africana. Jpnkokai Tokkyo Koho, pp. 13 (1997).  Back to cited text no. 7      
8.Sharaf M., Mansour R. M. A. and Saleh N. A. M. Exudate flavonoids from aerial parts of four Cleome species. Bio chemical systematics and Ecology, 20: 443-448 (1992).  Back to cited text no. 8      
9.Alyousuf M. H., Bashir A. K., Crabb T. A. and Blunden G. Shiromool 1,10-epoxides from Teucrium stocksianum. Biochemical Systematics and Ecology, 27: 107-109 (1999).  Back to cited text no. 9      
10.Apperidino G., Jakupovic J., Jakupavic S. Sesquiterpenoids from Pallenis pinosa Phytochem., 46: 1039-1043 (1997).  Back to cited text no. 10      
11.Tsichritzis F., abdel-Mogib M. and Jakupovic J. Dammarane triterpenes from Cleome africana. Phytochem., 33: 423-425 (1993)  Back to cited text no. 11      


    Figures

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    Tables

  [Table 1]



 

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