Home | About PR | Editorial board | Search | Ahead of print | Current Issue | Archives | Instructions | Subscribe | Advertise | Contact us |   Login 
Pharmacognosy Magazine
Search Article 
  
Advanced search 
 


 
ORIGINAL ARTICLE
Year : 2010  |  Volume : 2  |  Issue : 2  |  Page : 72-75 Table of Contents     

Chemical constituents of Tephrosia purpurea


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

Date of Submission05-Feb-2010
Date of Decision08-Feb-2010
Date of Web Publication03-May-2010

Correspondence Address:
Abeer M Esmail
C/O. Prof. Abou El-Hamd H. Mohamed Chemistry Department, Aswan-Faculty of Science, South Valley University
Egypt
Login to access the Email id

Source of Support: None, Conflict of Interest: None


DOI: 10.4103/0974-8490.62951

Rights and Permissions
   Abstract 

In continuation of our chemical investigation on some medicinal plants of the genus Tephrosia, reinvestigation of the methylenechloride/methanol (1:1) extract of the aerial parts of Tephrosia purpurea yielded an aromatic ester 1, a sesquiterpene 2 and prenylated flavonoid 3. The structures of the compounds were established by comprehensive NMR studies, including DEPT, COSY, NOE, HMQC, HMBC, EIMS and CIMS.

Keywords: Aromatic ester, prenylated flavonoid, sesquiterpene, Tephrosia purpurea


How to cite this article:
Khalafalah AK, Yousef AH, Esmail AM, Abdelrazik MH, Hegazy ME, Mohamed AEH. Chemical constituents of Tephrosia purpurea. Phcog Res 2010;2:72-5

How to cite this URL:
Khalafalah AK, Yousef AH, Esmail AM, Abdelrazik MH, Hegazy ME, Mohamed AEH. Chemical constituents of Tephrosia purpurea. Phcog Res [serial online] 2010 [cited 2019 Oct 19];2:72-5. Available from: http://www.phcogres.com/text.asp?2010/2/2/72/62951


   Introduction Top


Tephrosia purpurea (Dil.) Pers, belongs to the family Fabaceae, subfamily Faboideae, tribe Millettieae, and it is a highly branched suberect herbaceous perennial, up to 60 m in height with spreading branches; the leaves are imparipinnate, with narrow, oblanceolate leaflets; the flowers are red or purple in extra-axillary racemes, the pods are slightly curved, 3-4.5 cm long, grey, smooth and containing 5-10 seeds per pod. [1],[2] The plant grows abundantly in the upper Gangetic plains, and western Himalayas. The herb is commonly grown as a green manure in paddy fields in India and in tobacco and rubber plantation in other countries. It grows ubiquitously in all soils, sandy, rocky and loamy. [3] In India and South Africa, it is used as a fodder before flowering, but in Australia it is reported to cause livestock poisoning. In northern India, dry plants are collected for fuel. All parts of the plant have tonic and laxative properties. The dried plant is deobstruent, diuretic and useful in treating bronchitis, bilious febrile attacks and obstructions of the liver, spleen and kidneys. It is also recommended as a blood purifier, in the treatment of boils and pimples and is considered a cordial treatment. In southern India, a decoction of the fruit is given for intestinal worms and a fruit extract is used to relieve bodily pains and inflammatory problems. The roots are bitter and the decoction is used as a nematicide for treatment against Toxocora canis larvae which cause a lung disease in Sri Lanka; it is also used for treating dyspepsia, colic, and chronic diarrhoea and as an antihelminthic. [3],[4],[5] Several reports of T. purpurea have demonstrated the presence of flavones, flavanones and prenylated flavonoids, [6],[7] chalcones, [7],[8],[9],[10],[11] and rotenoids. [9],[10] In continuation of our chemical investigation on some medicinal plants of the genus Tephrosia, [12],[13] reinvestigation of the methylenechloride extract of aerial parts of T. purpurea resulted in isolation and structural elucidation of three compounds: an aromatic ester 1, a sesquiterpene of the rare rotundane skeleton 2 and a prenylated flavonoid 3, isolated for the first time from this species.


   Materials and Methods Top


General

1 H-NMR (500 MHz, CDCl 3 ), 13 C-NMR (125 MHz, CDCl 3 ) and the 2D spectra were recorded on a JEOL 500 MHz, Lambda spectrometer, with TMS as an internal standard. EIMS was recorded on a JEOL SX102A mass spectrometer.

Plant material

The aerial parts of T. purpurea were collected in the spring of 2001 from Aswan Island, Aswan, South of Egypt. A voucher specimen has been deposited in the Herbarium of the Department of Botany, Faculty of Science, South Valley University, Aswan, Egypt.

Extraction and isolation

Air-dried aerial parts (500 g) were crushed and extracted with CH 2 Cl 2 -MeOH (1:1) at room temperature. After solvent removal, the residue (35 g) was subjected to CC on silica gel and eluted with n-hexane (2 l) followed by a gradient of n-hexane-CH 2 Cl 2 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 (9 mg) and compound 2 (8 mg). The CH 2 Cl 2 fraction (100%) was chromatographed on a Sephadex LH-20 column and eluted with n-hexane-CH 2 Cl 2 -MeOH (7:4:0.5), and it gave compound 3 (11mg).


   Results and Discussion Top


Compound 1 [Figure 1], showed ion peak [M+1] + at m/z 441 corresponding to the molecular formula C 24 H 24 O 8 in its CIMS. The low-resolution EIMS showed the molecular ion peak [M] + at m/z 440.147066 (calcd. 440.147118) that corresponds with the molecular formula C 24 H 24 O 8 . The structure of compound 1 was determined from careful investigation of the 1D and 2D NMR data. The 1 H-NMR spectrum [Table 1] showed a doublet at δ 7.06 (J = 8.5 Hz, H-2), which showed a correlation in 1 H- 1H COSY with a doublet of doublet at δ 7.12 (J = 8.5, 2 Hz, H-1); also, it showed a doublet of doublet at δ 6.44 (J = 15.8 Hz, H-8) and a doublet at δ 7.70 (J = 15.8 Hz, H-7). Four singlet signals appeared at δ 2.31, 2.32, 3.85, 3.86, respectively, for the two acetyl groups and the two methoxyl groups. Additionally, it revealed the presence of the other olifinic protons as a doublet of doublet of doublet at δ 6.30 for H-11 (J= 16, 13, 13 Hz). The methylene protons H-10 appeared as two broad doublets at δ 4.85 and 4.87 (J = 17.5 Hz). The 13 C-NMR data [Table 1] revealed the presence of 24 carbon signals that were resolved by DEPT experiments into 4 methyls, 10 methines, 1 methylene and 9 quaternary carbons. Moreover, all proton and carbon signals were established from the results of 1 H- 1 H COSY, HMBC. The HMBC showed important correlations namely, H-1 with C-5, C-3, C-2, C-1 and C-7 and H-14′ with C-18, C-16 and C-12. Also, the spectrum showed correlations of H-12 with C-10, C-14, C-18 and C-12; H-10 with C-15, C-11, C-12 and C-10; OMe with C-14, C-18 and C-17; H-15 with C-14, C-18, C-12 and C-17; H-5 with C-1, C-5, C-3 and C-7, H-2 with C-6, and C-4 and C-3. While comparing the spectral data of compound 1 with those of the compounds isolated before, [14] compound 1 was identified as 2-propenoic acid, 3-(4-(acetyloxy) -3-methoxypheny)-3(4-actyloxy)-3-methoxyphenyl)-2-propenyl ester.

Compound 2 [Figure 1], was assigned to be a sesquiterpene of the rare rotundane skeleton, 4-isopropyl-1,8-dimethyl-decahydro-azulene-5, 8, 9-triol. [15] Its EI mass spectrum showed the molecular ion peak at m/z = 256, corresponding to the molecular formula C 15 H 28 O 3 , some important fragments were observed at m/z 238, 220 and 195 due to the loss of water, isopropyl radical and another water molecule, respectively. The 1 H-NMR spectrum [Table 1] showed two doublet signals at δ 0.95 and 1.00 that revealed the presence of the isopropyl moiety. Additionally, the proton singlet at δ 1.24 was assigned for H-15 and that at δ 1.27 for H-14. A doublet at δ 4.12 suggested the presence of a carbon bearing oxygen. The 13 C-NMR spectrum [Table 1] revealed the presence of 15 nonequivalent carbon atoms, which resolved by DEPT experiments. It was determined that compound 2 possess four methyls, five methylenes and three methines. On the basis of these results, the structure of compound 2 was assigned to the sesquiterpene of rotundane skeleton 4-isopropyl-1,8-dimethyl-decahydro-azulene-5, 8, 9-triol, previously isolated from Ferula sinaica. [15]

Compound 3 [Figure 1], was established based on analysis of 1 H NMR, 13 C NMR, DEPT, 1 H- 1 H COSY, 1 H- 13 C COSY, HMBC and EIMS data. The EIMS spectrum showed a molecular ion peak [M] + at m/z 362 corresponding to the molecular formula C 22 H 18 O 5 . Examination of the 1 H-NMR spectroscopic data [Table 2] of compound 3 indicated the presence of a flavone structure. Two multiplets at δ 7.43 and 7.74 established the presence of B-ring flavone protons at H-2′, H-4′ and H-6′, as well as at H-3′ and H-5′. The signals at δ 1.65 (6H, s) and at δ 3.94 (3H, s), correspond to a gem-dimethyl group and a methoxy group, respectively. Also, it showed a singlet signal at δ 7.52 (1H, H-4″) and a doublet signal at δ 8.26 (1 H, d, J = 9 Hz, H-5), showed a correlation in 1 H- 1H COSY with a doublet signal at δ 7.08 (1H, d, J = 9 Hz, H-6). The 13 C-NMR and DEPT spectrum [Table 2] showed 22 carbon signals with two carbonyl carbon signals at δ 177.72 and 170.62: three methyls, nine methines and eight quaternary carbon atoms. HMBC analysis showed correlations between gem-dimethyl and C-5″ with H-4″, H-5 with C-4, C-7 and C-8a; H-6 with C-8 and C-4a; H-3 with C-2, C-4b and C4a; and OMe with C-7. Comparing the spectral data of compound 3 with those of the compounds isolated before, [16] identified compound 3 as apollinine.

 
   References Top

1.Warrier PK, Nambiar VPK, Ramankutty C, Vasudevan RN. Indian medicinal plants: a compendium of 500 species. Health and Fitness 1993;5:249.  Back to cited text no. 1      
2.Orwa C, Mutua A, Kindt R, Jamnadass R, Anthony S. a tree reference and selection guide. Agroforestree database; 2009.  Back to cited text no. 2      
3.Panda H. Medicinal plants cultivation and their uses. Health and Fitness; 2000:598.  Back to cited text no. 3      
4.Despande SS, Shah GB, Parmar NS. Antiulcer activity of Tephrosia purpurea in rats. Indian J Pharmacol 2003;35:168-72.  Back to cited text no. 4      
5.Lodhi S, Pawar RS, Jain AP, Singhai AK. Wound healing potential of Tephrosia purpurea (Linn.) Pers. in rats. J Ethnopharmacol 2006;108:204-10.  Back to cited text no. 5      
6.Gupta RK, Krishnamurti M, Parthasarathi J. Purpurin, a flavanone from Tephrosia purpurea seeds. Phytochemistry 1980;19:1264.  Back to cited text no. 6      
7.Pelter A, Ward RS, Rao EV, Ranga E, Raju N. Substituted flavonoids and 30-substituted 7-oxygenated chalcones from Tephrosia purpurea. J Chem Soc, Perkin Trans 1981;1:2491-8.   Back to cited text no. 7      
8.Sinha B, Natu AA, Nanavati DD. Prenylated flavonoids from Tephrosia purpurea seeds. Phytochemistry 1982;21:1468-70.  Back to cited text no. 8      
9.Ventakata R, Raju E, Ranga N. Two flavonoids from Tephrosia purpurea. Phytochemistry 1984;23:2339-42.   Back to cited text no. 9      
10.Chang LC, Chαvez D, Song LL, Farnsworth NR, Pezzuto JM, Kinghorn AD. Absolute configuration of novel bioactive flavonoids from Tephrosia purpurea. Org Lett 2000;2:515-8.   Back to cited text no. 10      
11.Saxena VK, Choubey A. A neoflavonoid glycoside from Tephrosia purpurea stem. Fitoterapia 1997;68:359-60.  Back to cited text no. 11      
12.Hegazy ME, Abd el-Razek MH, Nagashima F, Asakawa Y, Parι PW. Rare prenylated flavonoids from Tephrosia purpurea. Phytochemistry 2009;70:1474-7.  Back to cited text no. 12      
13.Khalafallah AK, Helaly SA, Yousef AH, El-Kanzi NAA, Mohamed A-EH. Prenylated Flavonoids from Tephrosia apollinea. Chin Che. Lett 2009;20:1465-8.  Back to cited text no. 13      
14.Metwally MA, Robert MK, Harold R. An acetylenic epoxide and a ferulate from Coreopsis Longula. Phytochemistry 1985;24:182-3.  Back to cited text no. 14      
15.Ahmed AA. New sesquiterpenes from Ferula sinaica. J Nat Prod 1990;53:483-6.  Back to cited text no. 15  [PUBMED]    
16.Ammar NM, Jarvis BB. Major flavonoids of Tephrosia nubica. J Nat Prod 1986;49:719.  Back to cited text no. 16      


    Figures

  [Figure 1]
 
 
    Tables

  [Table 1], [Table 2]


This article has been cited by
1 A kaempferol triglycoside from Tephrosia preussii Taub. (Fabaceae)
Yves Martial Mba Nguekeu,Maurice Ducret Awouafack,Pierre Tane,Marius Roch Nguedia Lando,Takeshi Kodama,Hiroyuki Morita
Natural Product Research. 2017; : 1
[Pubmed] | [DOI]
2 Natural Products from the Genus Tephrosia
Yinning Chen,Tao Yan,Chenghai Gao,Wenhao Cao,Riming Huang
Molecules. 2014; 19(2): 1432
[Pubmed] | [DOI]
3 Toxic and antifeedant activities of prenylated flavonoids isolated fromTephrosia apollineaL. against three major coleopteran pests of stored grains with reference to their structure–activity relationship
Gomah E. Nenaah
Natural Product Research. 2014; 28(24): 2245
[Pubmed] | [DOI]
4 Tephrosia purpurea: A Source of Larvicidal Compounds Against Aedes Aegypti
Angela M. C. Arriaga,Maria da Conceicao F. de Oliveira,Maria Gizele R. da Silva,Telma L. G. de Lemos,Francisca Renata L. da Silva,Leonardo C. Tavares,Ronaldo F. Nascimento,Grazielle T. Malcher,Gilvandete M. P. Santiago,Jackson N. Vasconcelos,Raimundo Braz-Filho
Chemistry of Natural Compounds. 2014; 50(6): 1125
[Pubmed] | [DOI]
5 Antifungal activity of prenylated flavonoids isolated from Tephrosia apollinea L. against four phytopathogenic fungi
Ammar, M.I. and Nenaah, G.E. and Mohamed, A.H.H.
Crop Protection. 2013; 49: 21-25
[Pubmed]
6 Antifungal activity of prenylated flavonoids isolated from Tephrosia apollinea L. against four phytopathogenic fungi
Mohamed I. Ammar,Gomah E. Nenaah,Abul Hamed H. Mohamed
Crop Protection. 2013; 49: 21
[Pubmed] | [DOI]
7 Assessment of in vitro Antacid Activity of Different Root Extracts of Tephrosia purpurea (L) Pers by Modified Artificial Stomach Model
S Sandhya,K Ramana Venkata,KR Vinod,Chaitanya Rsnakk
Asian Pacific Journal of Tropical Biomedicine. 2012; 2(3): S1487
[Pubmed] | [DOI]
8 Assessment of in vitro Antacid Activity of Different Root Extracts of Tephrosia purpurea (L) Pers by Modified Artificial Stomach Model
Sandhya, S. and Venkata, K.R. and Vinod, K.R. and Rsnakk, C.
Asian Pacific Journal of Tropical Biomedicine. 2012; 2(3 SUPPL.): S1487-S1492
[Pubmed]



 

Top
 
  Search
 
    Similar in PUBMED
   Search Pubmed for
   Search in Google Scholar for
 Related articles
    Access Statistics
    Email Alert *
    Add to My List *
* Registration required (free)  

 
  In this article
    Abstract
    Introduction
    Materials and Me...
    Results and Disc...
    References
    Article Figures
    Article Tables

 Article Access Statistics
    Viewed4045    
    Printed293    
    Emailed2    
    PDF Downloaded353    
    Comments [Add]    
    Cited by others 8    

Recommend this journal