Volatile Oil Composition of Morina longifolia Wall. ex. Dc. from Himalayan region of Uttarakhand

 

R. K. Joshi* and C. S. Mathela

1Department of Chemistry, Kumaun University, Nainital-263002, India

*Corresponding Author E-mail: raakeshjoshi@rediffmail.com

 

 

ABSTRACT

The chemical profile of the hydro distilled volatile oil obtained from the aerial parts of Morina longifolia Wall.ex.Dc. from Kumaun Himalaya was analyzed by capillary GC-FID and GC-MS. A total of 75 constituents identified the major constituents in leaf oil were germacrene D (10.75 %) α-pinene (4.84 %), bicyclogermacrene (4.26 %), α-cadinol (4.26 %), (E)-citronellyl tiglate (4.20 %) β-phellandrene (3.24 %).

 

KEYWORDS: Dipsaceae, volatile oil, germacrene D, GC-FID, GC-MS

 


INTRODUCTION:

Morina longifolia Wall. of family Dipsaceae is found at the height of 3000-3500 m. It has spiny margined leaves and long interrupted spike of flowers, but flowers white to rose pink and paired bracts subtending whorls with an enlarged ovate base and fused below. Flowers with long slender corolla tube to 2.5 cm, somewhat two lipped the lips to 6 mm, hairy. Leaves strap-shaped with shallow 3-spined lobes and long pointed spiny apex (Polunin and Stainton, 1984). It is commonly known as "Whorl flower". Its stem leaves and flowers are used in Tibetan medicine. They are said to have a sweet and astringent taste with a heating potency. They are digestive, emetic and stomachic and are used in the treatment of stomach disorders (Tsarong, 1994). The plant possesses strong aromatic properties, used as incense and in the preparation of dhup, agarbatties, etc (Chopra 1996). The root paste has been applied externally on wounds and the aroma of the flowers has been used for unconsciousness in Indian traditional medicine (Gaur, 1999).The plant used in treatment of maggot wounds (Handoo, 2006).

 

Previous reports on Morina species showed that five new phenylpropanol derivatives, called morinins, as well as two known compounds as 3, 4-dimethoxycinnamylalcohol methyl ether, and p-methoxycinnamaldehyde, reported from the methanol extracts of the roots of the medicinal Chinese plant, M. chinensis.( Bao-Ning SU et al., 1999)

 

A novel acylated flavonol glycoside, quercetin 3-O-[2' "-O-(E)-caffeoyl]-alpha-L-arabinopyranosyl-(1-6)-beta-D-galactopyranoside was isolated from whole plant of Morina nepalensis var. alba (Tang et al., 2002). Seven new phenylpropanol derivatives, named morinins A-G (1-7), along with five known compounds, 4-O-methylcinnamyl alcohol, 4-O-methylcinnamyl methyl ether, 4-O-methylcinnamyl acetate, p-methoxybenzaldehyde, and 4-O-methyl-(E)-coniferyl alcohol, have been isolated from the roots of the medicinal Chinese plant, Morina chinensis (Yoshihisa Takaishi et al., 1999). Two novel tetrahydropyran sesquineolignans with a new carbon skeleton, named morinols A-B and other ten novel neolignans, named morinols C-L along with two known lignans, pinoresinol and lariciresinol, have been isolated from the roots of Chinese medicinal herb, Morina chinensis (Bao-Ning Su et al., 1999). In general, wild plants have been regarded as a natural reservoir of novel and more exotic fragrances however even after the assessment of Morina longifolia properties and its use in traditional medicine; the attention has been limited because of the lack of information about its chemical composition (S.K. Bhattacharjee, 2000)

 

Volatile oils are generally complex mixtures of different compounds like sesquiterpenes. Potential synergistic as well as antagonistic effects should be taken into account during evaluation of their biological activities. Essential oils can be antimicrobial, cytotoxic or antiseptic. The essential oils can be used as an alternative to antibiotics due to numerous side effects of existing antibiotic drugs (http://www.therapeuticoils.com).

In the present investigation an attempt was made to carry out the study of composition of volatile oils of Morina longifolia collected from Western Himayan region of Uttrakhand.

 

MATERIALS AND METHODS:

Plant Material:

The fresh aerial parts of M. longifolia were collected from Milam glacier of Kumaun Himalaya at the altitude of 3600m. Plant herbaria were identified in Botanical Survey of India and Forest Research Institute, Dehradun. The voucher specimen (No.CHEM/DST/06/03) has been deposited in the Phytochemistry Research Laboratory, Kumaun University, Nainital.

 

Oil Isolation:

The fresh plant materials (1.5 kg each) were subjected to steam distillation using a copper electric still, fitted with spiral glass condensers the yields 0.32%. The distillates were saturated with NaCl and extracted with n-hexane and dichloromethane. The organic phase was dried over anhydrous Na2SO4 and the solvent was distilled off in a rotary vacuum evaporator at 30o C.

 

GC and GC-MS analysis:

The GC analysis was run on Nucon 5765 gas chromatograph (Rtx-5 column, 30 m 0.32 mm i.d., FID), split ratio 1: 48, N2 flow of 4 kg/cm2 and on Thermo Quest Trace GC 2000 interfaced with Finnigan MAT PolarisQ ion trap mass spectrometer fitted with a Rtx-5 (Restek Corp.) fused silica capillary column (30 mm 25 mm; 0.25 μm film coating). The column temperature was programmed from 60oC-210o at 3oC /min. using He as carrier gas at 1.0 mL/min. The injector temperature was 210oC, injection size 0.1μL prepared in n-hexane, split ratio 1:40. MS were taken at 70 eV with mass scan range of m/z 40-450 amu.

 

 

 

Table 1 Volatile oil composition of the aerial parts of Morina longifolia

S. No

Compounds

RI

%Compo-sition (FID)

Mode of Identifica-tion

1.

n-heptanal

899

2.36

a, b

2.

tricyclene

926

4.34

a, b

3.

α-thujene

931

t

a, b

4.

α-pinene

939

4.84

a, b

5.

camphene

953

0.13

a, b

6.

benzaldehyde

961

t

a, b

7.

sabinene

976

0.11

a, b

8.

β-pinene

980

0.55

a, b

9.

6-methyl-5-hepten-2-one

985

0.24

a, b

10.

2-octanone

988

0.16

a, b

11.

myrcene

991

2.96

a, b

12.

2-octanol

997

0.10

a, b

13.

α-phellandrene

1005

0.67

a, b

14.

α-terpinene

1018

t

a, b

15.

p-cymene

1026

0.34

a, b

16.

β-phellandrene

1031

3.24

a, b

17.

1,8-cineole

1033

0.26

a, b

18.

(Z)-β-ocimene

1040

0.15

a, b

19.

(E)-β-ocimene

1050

0.22

a, b

20.

cis-sabinene hydrate

1068

0.11

a, b

21.

terpinolene

1088

1.01

a, b

22.

trans-sabinene hydrate

1068

0.54

a, b

23.

linalool

1098

1.27

a, b

24.

trans-thujone

1114

0.55

a, b

25.

cis-p-menth-2-en-1-ol

1121

0.21

a, b

26.

chrysanthenone

1123

0.12

a, b

27.

trans-p-menth-2-en-1-ol

1140

t

a, b

28.

borneol

1165

t

a, b

29.

terpinen-4-ol

1177

t

a, b

30.

α-terpineol

1189

0.67

a, b

31.

hexyl butyrate

1191

1.27

a, b

32.

verbenone

1204

0.73

a, b

33.

citronellol

1228

0.89

a, b

34.

bornyl acetate

1285

0.99

a, b

35.

trans-sabinyl acetate

1290

0.13

a, b

36.

(E)-methyl cinnamate

1301

0.77

a, b

37.

δ-elemene

1339

t

a, b

38.

α-cubebene

1351

0.58

a, b

39.

citronellyl acetate

1354

2.73

a, b

40.

β-bourbonene

1384

0.49

a, b

41.

β-cubebene

1390

t

a, b

42.

α-gurjunene

1409

0.12

a, b

43.

β-caryophyllene

1418

1.42

a, b

44.

β-gurjunene

1432

0.16

a, b

45.

α-humulene

1454

0.67

a, b

46.

γ-gurjunene

1473

0.17

a, b

47.

γ-muurolene

1477

t

a, b

48.

germacrene D

1480

10.75

a, b,c

49.

cis-β-guaine

1490

t

a, b

50.

bicyclogermacrene

1495

4.26

a, b

51.

α-muurolene

1499

1.65

a, b

52.

germacrene A

1503

1.93

a, b

53.

cubebol

1514

t

a, b

54.

δ-cadinene

1524

1.23

a, b

55.

germacrene B

1556

0.85

a, b

56.

germacren D-4-ol

1574

1.29

a, b

57.

spathulenol

1576

1.14

a, b

58.

caryophyllene oxide

1581

3.30

a, b

59.

(E)-2-hexenyl benzoate

1583

2.08

a, b

60.

humulene epoxide-II

1606

t

a, b

61.

10-epi-γ-eudesmol

1619

0.95

a, b

62.

γ-eudesmol

1630

0.32

a, b

63.

epi-α-cadinol

1640

1.90

a, b

64.

β-eudesmol

1649

t

a, b

65.

α-cadinol

1653

4.26

a, b

66.

bulnesol

1666

0.85

a, b

67.

(E)-citronellyl tiglate

1667

4.20

a, b

68.

β-bisabolol

1671

1.70

a, b

69.

α-bisabolol

1683

3.02

a, b

70.

(Z,E)-farnesol

1697

0.29

a, b

71.

(E,E)-farnesol

1722

1.57

a, b

72.

curcumenol

1726

0.50

a, b

73.

oplopanone

1733

1.11

a, b

74.

pimaradiene

1941

3.90

a, b

75.

sandaracopimara-8 (14),15-diene

1960

1.07

a, b

Aliphatic compunds

5.97

 

Monoterpene hydrocarbons

18.56

 

Oxygenate monoterpenes

14.41

 

Sesquiterpene hydrocarbon

24.28

 

Oxygenated sesquiterpenes

22.20

 

Diterpenoids

4.97

 

Total identified

90.39

 

a=Retention Index (RI) on Rtx-5 capillary column, b=MS (GC-MS), c= 1H NMR 13C NMR data,

Compounds >3.0% represented in bold face, t= trace (<0.1%)

 

The identification was done on the basis of Linear Retention Index (LRI, determined with reference to homologous series of n-alkanes (C9-C24 Polyscience Corp., Niles IL) under identical experimental conditions, co-injection with standards (Sigma), MS Library search (NIST and WILEY), by comparing with the MS literature data(Adams, 1995).

 

RESULTS AND DISCUSSION:

The GC and GC-MS analysis of leaf oil of Morina longifolia, identified constituents of the oil are listed in Table 1 in order of their elution in Rtx-5column. The major constituents in leaf oil were germacrene D (10.75 %) α-pinene (4.84 %), bicyclogermacrene (4.26 %), α-cadinol (4.26 %), (E)-citronellyl tiglate (4.20 %) β-phellandrene (3.24 %). Morina species showed that, a new aromatic glycoside characterized as 2,6-dihydroxy-5-methoxy-(3-C-glucopyranosyl) benzoic acid was isolated along with four known compounds from the aerial parts of Morina longifolia (Bodakhe et al., 2010). Previous study of essential oil of M. longifolia showed as a totally different composition as β-myrcene as major constituents has been reported from different regions (R.S. Chauhan et al., 2012; D. K. Semwal et al., 2010). We can see that the results of our work is totally different with previous one, this also showed that the oil composition vary with different regions.

 

ACKNOWLEDGMENT:

The authors are grateful to the Department of Science and Technology (DST) New Delhi for GC-MS grant. We are also thankful to BSI, Dehradun for the identification of the plant.

 

REFERENCES:

1.        Adams, R.P, 1995.Identification of Essential Oil Components by Gas Chromatography/ Mass Spectroscopy. Allured Publishing Corporation. Carol Stream, IL., USA.

2.        Bodakhe SH, Ram A, Pandey DP. A new aromatic glycoside from Morina longifolia Wall. Asian Journal of Chemistry. 2010; 22: 2789-93.

3.        Chopra, R.N., Nayer, S.L.,Chopra, I.C., 1956. Glossary of Indian Medicinal Plants, pp.105, Council of

4.        Industrial and Scientific Research, New Delhi.

5.        Gaur, R.D., 1999. Flora of District Garhwal North West Himalaya (With ethno botanical notes). 1st ed. Srinagar Garhwal, India, Trans Media, pp.550.

6.        Handoo S. 2006 A surveys of plants used for wound healing in animals, Veterin J 1:2.

7.        Polunin, O., Stainton, A., 1984. Flowers of the Himalaya,Oxford University Press, New Delhi.

8.        Tsarong, T. J., Tibetian., 1994. Medicinal Plants, pp.94, Tibetian Medical Publications, New Delhi.

9.        Tang, R., Xie, H., Liu, X., Wang, D. and Yang, C., A novel acylated flavonol glycoside from Morina nepalensis var. alba. Fitoterapia, 2002, 73, 1.

10.     Su, Bao-Ning., Takaishi, Yoshihisa 1999 Morinins LP, Five New Phenylpropanol Derivatives from Morina chinensis Chem. Pharm. Bull. 47(11) 15691572) 1569

11.                 Su Bao-Ning, Takaishi Yoshihisa, Duan Hong-Quan, Chen Bei, Phenylpropanol Derivatives from Morina chinensis J. Nat. Prod. 1999, 62, 1363-1366

12.     Su Bao-Ning, Takaishi Yoshihisa Kusumi Takenori, 1999 Twelve Novel Sesquineolignans and Neolignans Morinols A-L, With a New Carbon Skeleton isolated from Marina chinensis Tetrahedron 55 (1999) 14571-14586

13.     S.K. Bhattacharjee, Handbook of Aromatic Plants. Pointer Publisher, Jaipur (2000).

14.     www.therapeuticoils.com

 

 

 

Received on 26.12.2012 Accepted on 02.02.2013

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