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SHORT COMMUNICATION
Year : 2011  |  Volume : 3  |  Issue : 2  |  Page : 143-145  

Chemical constituents and biological studies of Origanum vulgare Linn.


CavinKare Research Centre, Ekkattuthangal, Chennai - 600 032, India

Date of Submission19-Oct-2010
Date of Decision08-Dec-2010
Date of Web Publication8-Jun-2011

Correspondence Address:
Gottumukkala Venkateswara Rao
CavinKare Research Centre, 12, Poonamalle Road, Ekkattuthangal, Chennai - 600 032
India
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Source of Support: None, Conflict of Interest: None


DOI: 10.4103/0974-8490.81964

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   Abstract 

Bioassay-guided isolation of methanolic extract of the leaves of Origanum vulgare Linn., yielded two protocatechuic acid ester derivatives, origanol A (1) and origanol B (2) along with ursolic acid (3), oleanolic acid (4), β-sitosterol (5), and triacontanol (6). Structures of the compound were established based on physical and spectral data (UV, IR, 1 H and 13 C NMR and mass). Origanol A (1) showed significant mushroom tyrosinase inhibition activity.

Keywords: Origanum vulgare Linn., origanol A and B, triterpene acids, tyrosinase inhibition, β-sitosterol


How to cite this article:
Rao GV, Mukhopadhyay T, Annamalai T, Radhakrishnan N, Sahoo M R. Chemical constituents and biological studies of Origanum vulgare Linn. Phcog Res 2011;3:143-5

How to cite this URL:
Rao GV, Mukhopadhyay T, Annamalai T, Radhakrishnan N, Sahoo M R. Chemical constituents and biological studies of Origanum vulgare Linn. Phcog Res [serial online] 2011 [cited 2018 Sep 23];3:143-5. Available from: http://www.phcogres.com/text.asp?2011/3/2/143/81964


   Plant Source Top


The genus Origanum (Labiatae) is very small, perennial herbs or shrubs distributed in the Mediterranean region and extra tropical Asia. Only one species, Origanum vulgare, occurs in India. The herb possesses an aromatic, thyme-like flavor. The leaves and tops before blooming have been used to flavor foods. This plant has been employed to flavor alcohol and beer. The Origanum oil possesses carminative, stomachic, diuretic, and emmenagogue properties; it is also applied in chronic rheumatism, tooth ache, and ear ache. The oil is also being used in veterinary liniments and also stimulates the growth of hair. In homoeopathy, it has been used for hysteric condition. It is also being used in healing lotions for wounds along with other herbs as an external application. [1],[2]


   Previous Study Top


Earlier various groups from different regions worked on this plant and reported variety of compounds, viz., phenolics, phenolic acids, esters and its glycosides, flavonoids, steroids, and some volatile compounds from different parts of the plant. Nineteen polar constituents were reported from the leaves of O. vulgare collected from Greece. These are apigenin, luteolin, chrysoeriol, diosmetin, quercetin, eriodictyol, cosmocide, vicenin-2, caffeic acid, rosmarinic acid, p-menth-3-ene-1,2-diol 1-O-β-glucopyranoside, thymoquinol 2-O-β-glucopyranoside, thymoquinol 5-O-β-glucopyranoside, thymoquinol 2,5-O-β-diglucopyranoside, 12-hydroxyjasmonic acid and its β-glucopyranoside, lithospermic acid B, epi-lithospermic acid B, and 10-epi-lithospermic acid. [3] Two anti-fungal active compounds, thymol and carvacrol, were reported from the oil. [4] Five antioxidant phenolic compounds, rosmarinic acid derivative, caffeic acid, protocatechuic acid, phenyl glucoside, and 2-caffeyloxy-3-[2-(4-hydroxybenzyl)-4, 5-dihydroxy]-phenyl propionic acid were reported from the same plant collected in Japan. [5] About 40 terpenoids were reported from the essential oil of O. vulgare collected from Germany. The major compounds are sabinene, 1,8-cineole, β-ocimene, β-caryophyllene, germacrene D, bicylcogermacrene, b-bisabolene, and spathulenol. [6] One new antioxidant, 4'-O-β-d-glucopyranosyl-4'-hydroxybenzyl protocatechuate, had been reported from the leaves of O. vulgare.[7],[8] Three DPPH radical scavengers - 4'-O-β-d-glucopyranosyl-3', 4'-dihydroxybenzyl protocatechuate, 4'-O-β-d-glucopyranosyl-3',4'-dihydroxybenzyl 4-O-methylprotocatechuate, 4'-O-β-d-glucopyranosyl-4' hydroxybenzyl protocatechuate - were reported from O. vulgare collected from Japan. [9]


   Present Study Top


General experimental procedure

Melting points reported are uncorrected. The 400 MHz NMR spectra were recorded on a Bruker AMX 400 in CD 3 OD with TMS an internal standard. The 13 C NMR spectra were recorded at 100 MHz in CD 3 OD. IR spectra were recorded on a Shimadzu IR prestige 21; UV spectra were recorded on Shimadzu UV spectrophotometer; mass spectra were on a Jeol SX 102/DA 6000 mass spectrometer. TLC was performed on pre-coated silica gel 60 F 254 plates (Merck) and the spots were visualized by exposure to iodine vapor or spraying with 5% sulfuric acid in methanol followed by heating the plate at 110°C for 5 min. Kojic acid was purchased from the M/s. Sigma-Aldrich, USA.

Plant material

The leaves of O. vulgare were collected in April, 2006, from Ooty, Tamilnadu, India, and was authenticated by Dr. P. Santhan, botanist, M/s. Durva Herbal Centre, Chennai. A voucher specimen (CK-15/06/OV) was deposited in M/s. CavinKare Research Centre, Chennai, India.

Extraction and isolation

The air-dried leaves of O. vulgare (700 g) were powdered coarsely, subjected to an extraction with methanol through soxhlet and the extract concentrated under reduced pressure to get crude methanol extract (92 g). Part of the extract (89.0 g) was subjected to vacuum liquid chromatography (VLC) on silica gel using hexane, hexane:ethyl acetate (98:2, 95:5), and methanol to get corresponding fractions 16.69 (Fr.1), 7.55 (Fr.2), 3.30 (Fr.3), and 39.65 g (Fr.4), respectively. The fraction 2 showed two spots on TLC, one major, and one minor compound along with some green color pigments. Fraction 2 was repeatedly purified over silica gel column, obtained compound (1, 240 mg) [9] and compound (2, 50 mg) [9] as amorphous powders [Figure 1]. The greenish residue (Fr.1) obtained from hexane was purified over silica gel column, followed by recrystallization to obtain four pure compounds - ursolic acid (3, 800 mg), [10] oleanolic acid (4, 20 mg), [11] b-sitosterol (5, 40 mg), [12],[13] and triacontanol (6, 120 mg). [12],[14] These structures were elucidated by physical and spectral data and by comparison with the previously published data
Figure 1: Chemical constituents of O. vulgare

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   Results Top


Compound 1: white powder; mp: 171-72 o C; IR:3392, 1718, 1606, 1033, and 759 cm -1 ; UV (nm): 222, 263, 295; 1 H NMR (CD 3OD): δ 3.30-3.52 (4H, m, H-2" to 5"), 3.71 (1H, m, H-6"), 3.88 (1H, d, J = 12.08 Hz, H-6"), 4.77 (1H, d, J = 7.2 Hz, H-1"), 5.17 (2H, s, H-7'), 6.79 (1H, d, J = 8.7 Hz, H-5), 6.83 (1H, dd, J = 8.7, 1.9 Hz, H-6'), 6.93 (1H, d, J = 1.7 Hz, H-2'), 7.18 (1H, d, J = 8.3 Hz, H-5'), 7.42 (1H, s, H-2), 7.44 (1H, m, H-6). 13 C NMR (CD 3 OD): d 122.5 (C-1), 117.3 (C-2), 146.2 (C-3), 151.6 (C-4), 115.7 (C-5), 123.5 (C-6), 167.6 (C-7), 133.2 (C-1'), 116.5 (C-2'), 148.1 (C-3'), 145.4 (C-4'), 118.5 (C-5'), 120.6 (C-6'), 67.0 (C-7'), 104.0 (C-1"), 78.3 (C-2"), 77.4 (C-3"), 74.7 (C-4"), 71.2 (C-5"), 62.3 (C-6"); ESIMS (rel.int.): m/z 438 (M + ).

Compound 2: white powder; mp: 150-55 o C; IR: 3373, 1701, 1602,1072, 765 cm -1 ; UV(nm): 222, 264, 295; 1 H NMR (CD 3OD): δ 3.28-3.43 (4H, m, H-2' to 5'), 3.61 (1H, br d, J =12.1 Hz, H-6"), 3.77 (1H, d, J =12.1 Hz, H-6"), 3.81 (3H, s), 4.69 (1H, d, J =7.3 Hz, H-1"), 5.09 (2H, s, H-7'), 6.79 (1H, dd, J = 8.5, 2.0 Hz, H-6'), 6.84 (1H, d, J = 2.0 Hz, H-2'), 6.88 (1H, d, J = 8.5 Hz, H-5), 7.09 (1H, d, J = 8.3 Hz, H-5'), 7.34 (1H, d, J = 2.0 Hz, H-2), 7.43 (1H, dd, J = 8.4, 2.0 Hz, H-6). ESIMS (rel.int.): m/z 452 (M + ).


   Biological Activity Studies Top


Tyrosinase inhibition activity was determined by dopachrome method using l-tyrosine as substrate. [15],[16] Fresh solutions of l-tyrosine (3 mM), buffer (pH 6.8, 50 mM), and a stock solution of 500 units/mL of mushroom tyrosinase were prepared. The reaction mixture constitutes 235 μL of l-tyrosine, 365 μL of buffer, 90 μL of enzyme, and 10 μL of inhibitor. The assay mixture was incubated at 37°C for 30 min. The dopachrome was measured spectrophoto­metrically at 475 and percentage of inhibition was calculated. It was found that the methanolic extract, fraction 2, and origanol A (1) showed significant tyrosinase inhibition activity whereas origanol B showed very weak activity. IC 50 value of origanol A (1) was found to be 2.47 mg/mL while the IC 50 value of the control (Kojic acid) was found to be 1.75 mg/mL [Table 1].
Table 1: Comparison of tyrosinase inhibition values

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   Conclusion Top


In conclusion, we have reported the isolation of six known compounds from this plant. The tyrosinase inhibition activity of crude extract, fractions, and two of isolated compounds were analyzed and one of the compound showed significant activity. Out of the six compounds mentioned in this paper, ursolic acid (3), oleanolic acid (4), b-sitosterol (5), and triacontanol (6) were isolated from the plant Origanum vulgare for the first time. The tyrosinase inhibition studies of the extract and the compound origanol A was reported for the first time. The present study of screening of bioactive secondary metabolites revealed O. vulgare as a source for the production of tyrosinase inhibitory compounds. These metabolites can be further exploited in cosmetic applications.


   Acknowledgement Top


We thank Mr. C. K. Ranganathan, CMD of CavinKare Pvt. Ltd., Chennai for providing the necessary facilities and constant encouragement. We also thank to Dr. P. Santhan for identification of the plant material and M/s. Suven Life Sciences, Hyderabad for providing the spectral data.

 
   References Top

1.Anonymous. The wealth of India. Vol 7. New Delhi: CSIR;2001. p. 105.  Back to cited text no. 1
    
2.Kirthikar KR, Basu BD. Indian medicinal plants. Vol 3. Allahabad: Bishan Singh Mahendra Pal Singh; 1994. p. 1986.  Back to cited text no. 2
    
3.Koukoulitsa C, Karioti A, Bergonzi C, Pescitelli G, Bari LD, Skaltsa H. Polar constituents from the aerial parts of Origanum vulgare L. ssp hirtum growing wild in Greece. J Agric Food Chem 2006;54:5388-92.  Back to cited text no. 3
    
4.Vijaya M, Cass I, Judy G, Talpur MA, Echard BW, Bagchi D, et al. Anti-fungal activities of Origanum oil against Candida albicans. Mol Cell Biochem 2001;228:111-7.  Back to cited text no. 4
    
5.Kikuzaki H, Nakatani N. Structure of a new antioxidative phenolic acid from oregano (Origanum vulgare L.). Agric Biol Chem 1989;53:519-24.  Back to cited text no. 5
    
6.Mockute D, Asa JJ, Bernotiene G. Volatile constituents of cultivated Origanum vulgare L., inflorescences and leaves. Chemija 2004;15:33-7.  Back to cited text no. 6
    
7.Nakatani N, Kikuzake H. A new antioxidative glucoside isolated from oregano (Origanum vulgare). Agric Biol Chem 1987;51:2727-32.  Back to cited text no. 7
    
8.Nakatani N, Kaneko K, Kojo K. 4-[3,4-(Dihydroxybenzoyloxy) methyl] phenyl-D-glucoside from oregano leaves as antioxidant. Jpn Kokai Tokkyo Koho 1987;6202-93.   Back to cited text no. 8
    
9.Matsura H, Chiji H, Asakawa C, Amano M, Yoshihara T, Mizutani J. DPPH radical scavengers from dried leaves of Oregano (Origanum vulgare). Biosci Biotech Biochem 2003;67:2311-6.  Back to cited text no. 9
    
10.Moghaddam FM, Farimani MM, Salahvarzi S, Amin G. Chemical constituents of dichloromethane extract of cultivated Satureja khuzistanica. Evid Based Complement Alternat Med 2007;4:95-8.  Back to cited text no. 10
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11.Gohari AR, Saeidnia S, Hadjiakhoondi A, Abdoullahi M, Nezafati M. Isolation and quantificative analysis of oleanolic acid from Satureja mutica Fisch. and C. A. Mey. J Med Plants 2009;8:65-9  Back to cited text no. 11
    
12.Maria YR, Angelina GM, Ma LV. Sterols, triterpenes and biflavonoids of V. jucundum and cytotoxicity activity of ursolic acid. Planta Med 2001;67:683-4.  Back to cited text no. 12
    
13.Boonyaratavej S, Petsom A. Chemical constituents of Bridelia tomentosa. J Sci Soc Thailand 1991;17:61-9.  Back to cited text no. 13
    
14.Chauhan JS, Sultan M, Srivastava K. Chemical constituents from Salmalia malbaricum. Can J Chem 1980;58:328-30.  Back to cited text no. 14
    
15.Lee KT, Kim BJ, Kim JH, Heo MY, Kim HP. Biological screening of 100 plant extracts for cosmetic use (I): Inhibitory activities of tyrosinase and DOPA auto-oxidation. Int J Cosmet Sci 1997;19:291-8.  Back to cited text no. 15
[PUBMED]    
16.Piao LZ, Park HR, Park YK, Lee SK, Park JH, Park MK. Mushroom tyrosinase inhibition activity of some chromones. Chem Pharm Bull (Tokyo) 2002;50:309-11.  Back to cited text no. 16
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