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Table 1
Total identified 82.8 80.2 98.7 72.2 91.5 97.7

SHORT REPORT

Thearticlewaspublishedby Academy of Chemistry of Globe Publications

www.acgpubs.org/RNP © Published 06/01/2015 EISSN:1307-6167

Rec. Nat. Prod. 9:4 (2015) 592-596

Leaf Essential Oil Composition of Six Syzygium Species from the

Western Ghats, South India

Koranappallil B. Rameshkumar

1*

, Anu Aravind A. P.

1

and

Tharayil G. Vinodkumar

2

1

Phytochemistry and Phytopharmacology Division, Jawaharlal Nehru Tropical Botanic Garden and

Research Institute, Palode, Thiruvananthapuram, Kerala, India 695 562

2

Department of Botany, St. Thomas College, Ranni, Pathanamthitta, Kerala, India 689673

(Received December 28, 2012; Revised April 02, 2015, Accepted April 02, 2015)

Abstract: The Syzygium (Family: Myrtaceae) species are well known for their aromatic nature. Though 45

Syzygium species are reported from the Western Ghats region of India, the volatile oil chemistry of most of these

aromatic plants are uninvestigated. The present study reports the chemical constituents of the leaf essential oils

of 6 Syzygium species, S. arnottianum Walp., S. caryophyllatum (L.) Alston, S. hemisphericum (Wight) Alston,

S. laetum (Buch. Ham.) Gandhi, S. lanceolatum (Lam.) Wight & Arn. and S. zeylanicum (L.) DC. var.

zeylanicum, collected from the Western Ghats of Kerala. Sesquiterpenoids were the

all

Syzygium species studied

-caryophyllene and caryophyllene oxide were present in all the oils

except S. laetum. The open chain sesquiterpenoids (Z,E)-α-farnesene and (E)-nerolidol were characteristic of S.

laetum while phenyl propanoids were exclusively present in S. lanceolatum.

Keywords: Essential Oil; GC-MS; Syzygium arnottianum; Syzygium caryophyllatum; Syzygium hemisphericum;

1. Plant Source

Fresh leaves of the Syzygium species were collected from the forests of southern Western

Ghats, Kerala, India and voucher herbarium specimens (TBGT No.) of Syzygium arnottianum Walp.

(66407), Syzygium caryophyllatum (L.) Alston (50993), Syzygium hemisphericum (Wight) Alston

(50959), Syzygium laetum (Buch. Ham.) Gandhi (66409), Syzygium lanceolatum (Lam.) Wight &

Arn.(50992) and Syzygium zeylanicum (L.) DC. var. zeylanicum (50995) were deposited at the

JNTBGRI herbarium (TBGT). The plant materials were identified by Dr. T. G. Vinodkumar, St.

Thomas College, Ranni, Kerala.

2. Previous Studies

The genus Syzygium Gaertner (Family: Myrtaceae) is represented by nearly 1200 species in

the old world tropics and 45species are reported in the Western Ghats of India [1]. Literature searches

showed that there are no previous studies on the volatile constituents of the six Syzygium species

___________________________

* Corresponding author: E- Mail:

kbrtbgri@gmail.com

(K.B. Rameshkumar), Phone: +91-472-2869226

Fax: + 91-472-2869626.

reported here, while a few species such as S. aromaticum [2,3], S. cumini [4,5,6], S. guineense [7], S.

cordatum [8], S. gardneri [9] and S. semarangense [10] were investigated for their leaf volatile

Rameshkumar et.al., Rec. Nat. Prod. (2015) 9:4 592-596

593

chemical constituents. Though S. caryophyllatum (L.) Alston is different from S. aromaticum (L.)

Merr. & Perry (common clove tree), the chemistry of S. aromaticum has been reported under the title

of S. caryophyllatum (L.) Alston [3].

3. Present Study

Isolation of Essential Oil: The essential oils were isolated by hydrodistillation of the fresh

leaves (300g each) for 3 h. using a Clevenger type apparatus. The oils were dried over anhydrous

sodium sulphate and stored at 4

C until the analyses.

Analysis of Essential Oil: The GC-FID analysis was done on a Varian CP-3800 gas

chromatograph fitted with CP Sil 8CB fused silica capillary column (30 m, 0.32 mm i.d., film

thickness 0.25 µm) with FID detector using nitrogen as a carrier gas at flow rate of 1mL/ min. The

split ratio was 1:40, and 0.1μL oil sample (1:5 dilution in diethyl ether) was injected. Oven

temperature programme: injector temperature 220

C, oven temperature 50-230

C at 3

C/ min.,

detector temperature 250

C. Relative percentage of components was obtained from the peak area of

volatiles. The GC/MS analysis was done on a Hewlett Packard 6890 gas chromatograph fitted with a

cross-linked 5% PH ME siloxane HP-5 MS capillary column (30 m x 0.32 mm, film thickness 0.25

µm) coupled with a 5973 series mass selective detector under the following conditions with splitless

injection of 1.0 µL of essential oil (1:10 dilution in diethyl ether), helium as the carrier gas at 1.4 mL/

min constant flow mode. The temperature programme for the analysis of the oils were, injector

temperature 220

C, oven temperature 60

C to 246

C (3

C/min) and interface temperature 290

C. Mass

spectra: Electron Impact (EI

) mode, 70 eV and ion source temperature 250

C. The essential oil

components were identified based on by MS library search (Wiley 2.75), relative retention indices

calculated with respect to homologous of n-alkanes (C

-C

30

, Aldrich Chem. Co. Inc.) [11] and by

literature reference [12].

The leaf essential oil yield (%v/w) was higher for S. zeylanicum (0.33%), followed by S.

hemisphericum (0.17%), S. arnottianum (0.12%) and S. lanceolatum (0.10%), while the yield was

negligible for S. laetum (0.01%) and S. caryophyllatum (0.01%).The major volatile constituents

identified from the leaf essential oil of Syzygium species were caryophyllene oxide (15.4%) and selina-

11-en-4



-ol (13.0%) for S. arnottianum,



-caryophyllene (32.4%), 1-epi-cubenol (11.8%) and



cadinene (10.0%) for S. caryophyllatum,



-caryophyllene (40.5%) and



-humulene (39.7%) for S.

hemisphericum, (Z,E)-α-farnesene (21.5%), γ-amorphene (12.1%) and epi-α-cadinol (10.2%) for S.

laetum,



-humulene (23.1%),



-caryophyllene (16.1%) and phenyl propanal (13.5%)for S.

lanceolatum, and



-caryophyllene (11.1%), α-cadinol (12.2%), humulene epoxide II (17.6%)

caryophyllene oxide (18.9%) and



-humulene (24.0%) for S. zeylanicum.

Sesquiterpenoids were the predominant



compounds in all the



Syzygium species studied (Table

1). Among the sesquiterpenoids, caryophyllene or its derivatives were detected in all the Syzygium

species. In S. hemisphericum, 84.4% of the volatile constituents were caryophyllene analogues,

followed by S. zeylanicum (71.6%), S. lanceolatum (54.2%), S. caryophyllatum (44.3%), S.

arnottianum (20.2%) and S. laetum (2.8%).



-Caryophyllene and caryophyllene oxide were present in

all the oils except S. laetum.



-Humulene was a predominant constituents in all the oils except S.

arnottianum and S. laetum. Selinene and derivatives constituting 36.2% were predominant in S.

arnottianum while the open chain sesquiterpenoids (Z,E)-α-farnesene and (E)-nerolidol were

characteristic of S. laetum. Phenyl propanoids were exclusively present (14.4%) in S. lanceolatum and

phenyl propanal can be considered as the chemotaxonomic marker compound for S. lanceolatum.

Monoterpenoids were present in negligible amount only in S. hemisphericum(0.2%) and S. zeylanicum

(0.9%).

Leaf essential oil chemistry of Syzygium species

594

Table 1.Essential oil constituents of the leaves of Syzygium species.

Compound

RRI

S.arn

S.car

S.hem

S.lat

S.lan

S.zey

β-Pinene

969

-

-

0.2

-

(Z)



-Ocimene

1032

0.4

Linalool

1093

0.5

Phenyl ethyl alcohol

1100

0.9

Phenyl propanal

1156

-

-

13.5

δ-Elemene

1332

-

-

0.3



-Copaene

1368

5.8

1.3



-Bourbonene

1381

1.0



-Elemene

1383

3.0

5.6



-Gurjunene

1400

0.6



-Caryophyllene

1411

1.0

32.4

40.5

16.1

11.1

Aromadendrene

1431

-

-

1.2



-Humulene

1445

5.1

39.7

23.1

24.0

Alloaromadendrene

1451

-

-

0.5

γ-Muurolene

1472

-

-

1.8

-

(Z,E)-α-Farnesene

1475

-

-

21.5



-Selinene

1477

3.8

Selina-(4,11)-diene

1479

0.6



-Selinene

1481

8.8

0.4

2.9



-Selinene

1484

0.5

γ-Amorphene



1487

12.1



-Selinene

1490

3.9

0.6

3.1

α-Muurolene

1493

-

-

0.2



-Bisabolene

1497

0.7

δ-Amorphene

1504

-

-

7.2



-Cadinene

1506

1.3

4.2

0.1

-

trans-calamenene

1513

1.8



-Cadinene

1515

1.8

10.0

1.4

0.9

(E)-iso-γ-Bisabolene

1519

0.1

(Z)-Nerolidol

1523

2.5

(E)-Nerolidol

1553

6.9

Isocaryophyllene oxide

1555

1.0

Caryophyllenyl alcohol

1563

1.6

2.8

Spathulenol

1569

4.1

Caryophyllene oxide

1576

15.4

6.8

1.3

7.5

18.9

Globulol

1583

-

-

2.1

Viridiflorol

1585

4.2

0.7

0.8

Salvial-4(14)-en-1-one

1587

3.4

Widdrol

1589

1.3

Guaiol

1590

5.0

1,5,5,8-Tetramethyl, 3,7-

cycloundecadien-1-ol

1598

-

-

6.0

Humulene epoxide II

1600

-

-

1.3

7.1

17.6

1,10-Di-epi-cubenol

1611

1.5

0.9

3.0

1-Epi-cubenol

1619

11.8

Epi-α-cadinol

1628

-

-

10.2

Alloaromadendrene epoxide

1629

0.4

Caryophylla-4(12),8(13)-

dien-5-ol

1630

1.1

0.2

0.4

Epi-



-muuralol

1631

4.1

0.5

8.2

Selina,3,11-dien-6



-ol

1634

6.7

0.5

α-Muurolol

1635

0.2

Cubenol

1636

0.6



-Cadinol

1638

1.8

α-Cadinol

1643

-

-

1.0

4.6

12.2

Selina-11-en-4



-ol

1649

13.0

(Z)-14-Hydroxy

isocaryophyllene

1655

1.7

Eudesm-7(11)-en-4-ol

1689

0.8

Cyclocolorenone

1747

1.9

Total identified

82.8

80.2

98.7

72.2

91.5

97.7

Rameshkumar et.al., Rec. Nat. Prod. (2015) 9:4 592-596

595

Monoterpene hydrocarbons

0.2

0.4

Oxygenated monoterpenes

0.5

Total monoterpenes

-

0.2

0.9

Sesquiterpene hydrocarbons

24.6

57.5

84.2

42.6

55.8

37.3

Oxygenated sesquiterpenes

58.2

22.4

14.3

29.6

21.3

59.5

Total sesquiterpenes

82.8

80.2

98.5

72.2

77.1

96.8

Phenyl propanoids

-

-

14.4

RRI: Relative retention index calculated on HP-5 column, with respect to homologous of n-alkanes (C

-C

30

Aldrich Chem. Co. Inc.).

S.arn- Syzygium arnottianum, S.car- Syzygium caryophyllatum, S.hem- Syzygium

hemisphericum, S.lat- Syzygium laetum, S.lan- Syzygium lanceolatum, S.zey- Syzygium zeylanicum

4. Conclusion

Though the genus Syzygium includes important spice plants and medicinal plants like S.

aromaticum, S. cumini and S. jambos, most of the Western Ghats endemic Syzygium species are least

explored for their volatile constituents and bioactivities [13]. Essential oils are important as source of

valuable aroma chemicals, flavoring components and bioactive agents and the volatile chemical

profiles of Syzygium species revealed sesquiterpenoids, particularly caryophyllene isomers and

oxygenated derivatives of caryophyllene as the characteristic constituents. Caryophyllene and their

derivatives are known for their anti-inflammatory, analgesic, antipyretic, and platelet-inhibitory

actions, while its oxide has proven to be cytotoxic [14,15]. The present study is the first report of the

leaf volatile constituents of six Syzygium species, of which two are endemic to the Western Ghats of

south India.

References

[1]

S. M. Shareef, E. S. Santhosh Kumar and T. Shaju (2012). A new species of Syzygium (Myrtaceae) from

the southern Western Ghats of Kerala, India, Phytotaxa. 71, 10 16.

[2]

A. K. Srivastava, S. K. Srivastava and K. V. Syamsundar (2005). Bud and leaf essential oil composition

of Syzygium aromaticum from India and Madagascar, Flavour Fragr. J. 20, 51–53.

[3]

M. N. I. Bhuiyan, J. Begum, N. C. Nandi and F. Akter (2010). Constituents of the essential oil from leaves

and buds of clove (Syzigium caryophyllatum (L.) Alston), African J. Plant Sc. 4, 451-454.

[4]

H. O. Elansary, M. Z. M. Salem, N. A. Ashmawy and M. M. Yacout (2012). Chemical Composition,

Antibacterial and Antioxidant Activities of Leaves Essential Oils from Syzygium cumini L., Cupressus

sempervirens L. and Lantana camara L. from Egypt, J. Agri. Sc. 4, 144-152.

[5] A. A. Craveiro, C. H. S. Andrade, F. J. A. Matos, J. W. Alencer and M. I. L. Machado (1983). Essential

oil of Eugenia jambolana, J. Nat. Prod. 46, 591-592.

[6]

A. Kumar, A. A. Naqvi, A. P. Kahol and S. Tandon (2004). Composition of leaf oil of Syzygium cumini

L, from north India, Indian Perfum. 48, 439-441.

[7]

J. P. Noudogbessi, P. Yedomonhan, D. C. K. Sohounhloue, J. C. Chalchat and G. Figueredo (2008).

Chemical composition of essential oil of Syzygium guineense (Willd.) DC. var. guineense (Myrtaceae)

from Benin, Rec. Nat. Prod. 2, 33-38.

[8]

R. K. Chalannavar, H. Baijnath and B. Odhav (2011). Chemical constituents of the essential oil from

Syzygium cordatum (Myrtaceae), Afr. J. Biotechnol. 10, 2741-2745.

[9]

G. Raj, V. George, N. S. Pradeep and M. G. Sethuraman (2008) Chemical composition and antimicrobial

activity of the leaf oil of Syzygium gardneri Thw., J. Essent. Oil Res. 20, 72-74.

[10] L. J. Reddy and B. Jose (2011). Chemical composition and antibacterial activity of the volatile oil from

the leaf of Syzygium samarangense (Blume) Merr. & L.M. Perry, Asian J. Biochem. Pharmaceutical Res.

1, 263-269.

[11]

H. Van den Dool and P. D. Kratz (1963). A generalization of the retention index system including linear

temperature programmed gas Liquid partition chromatography, J. Chromatogr. 11, 463-471.

[12]

R. P. Adams (2007). Identification of essential oil components by gas chromatography/mass spectrometry,

Edition. Allured publishing Co. Carol Stream.

[13] D. Chattopadhyay, B. K. Sinha and L. K. Vaid (1998). Antibacterial activity of Syzygium species,

Fitoterapia 69, 356-367.

Leaf essential oil chemistry of Syzygium species

596

[14] R. R. P. Machado, D. F. Jardim, A. R. Souza, E. Scio, R. L. Fabri, A. G. Carpanez, R. M. Grazul, J. P. R.

F. de Mendonça, B. Lesche and F. M. Aarestrup (2013).The effect of essential oil of Syzygium cumini on

the development of granulomatous inflammation in mice, Rev. Bras. Farmacogn. 23, 488-496.

[15] J. J. Neung, M. Ashik, Y. M. Jeong, J. Ki-Chang, L. Dong-Sun, S. A. Kwang and K. C. Somi (2011).

Cytotoxic activity of β-caryophyllene oxide isolated from jeju guava (Psidium cattleianum Sabine) Leaf,

Rec. Nat. Prod. 5: 242-246.

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