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Wednesday, 14 September 2016
Fingerprint chemotaxonomic GC–TOFMS profile of wood and bark of mangrove tree Sonneratia caseolaris (L.) Engl.
Published Date
July 2011, Vol.15(3):229–237, doi:10.1016/j.jscs.2010.09.003
Open Access, Creative Commons license, Funding information
ORIGINAL ARTICLE
Title
Fingerprint chemotaxonomic GC–TOFMS profile of wood and bark of mangrove tree Sonneratia caseolaris (L.) Engl.
Author
Raza Murad Ghalib a,,
Rokiah Hashim a
Othman Sulaiman a
Mohd Fahmi B. Awalludin a
Sayed Hasan Mehdi a
Fumio Kawamura b
aSchool of Industrial Technology, USM, 11800 Pinang, Malaysia
bDepartment of Biomass Chemistry, Forestry and Forest Products, Research Institute, Tsukuba, Ibaraki 305-8687, Japan
Received 28 April 2010. Accepted 17 September 2010. Available online 23 September 2010.
Abstract
The bark and wood ofSonneratia caseolaris(L.) Engl. have been analyzed for chemical profile by GC–TOFMS. Overall thirty-two compounds from bark and twenty-eight compounds from wood have been detected. Sixteen constituents have been found to be common in both the extracts. GC–TOFMS chemical profile may be a significant finger print chemotaxonomic marker as an identity of this plant.
KEYWORDS
Sonneratia caseolaris (L.)
Berembang
Wood
Bark
Aromatic compounds
Alcohols
Phenols
Carboxylic acids
Amides
1 Introduction
Sonneratia caseolaris (L.) Engl. is commonly known as Berembang, pedada nasi, perangat, perepat merah or perepat laut, lamphu, am’-pie, lop ou, tapoo, tamoo or bogem (Mastaller, 1997). It grows wildly from Sri Lanka to Malay Peninsula and northern Australia. This species can also be found in Sumatra, Java, Borneo, Celebes, Philippines, Moluccas, Timor, New Guinea, Solomon Islands, and New Hebrides (Little, 1983). Berembang tree is a hard wood species (800 kg/m3). The sour taste of its young fruits can be used for vinegar, Oriental chutneys and curries. The ripe fruits are like cheese in taste and can be eaten raw or cooked. A clear jelly can be prepared from the pectinaceous fruits. Previously fatty acids, hydrocarbons, steroids, pectin, and sugars have been isolated from S. caseolaris (L.) Engl. (Hogg and Gillan, 1984, Xu et al., 1981 and Bandaranayake, 2002). Recently (−)-(R)-nyasol, (−)-(R)-4′-O-methylnyasol, 3,8-dihydroxy-6H-benzo[b,d]pyran-6-one, 3-hydroxy-6H-benzo[b,d]pyran-6-one, oleanolic acid, maslinic acid, Luteolin, luteolin 7-O-β-glucoside, and benzyl-O-β-glucopyranoside have been isolated from the dried and powdered fruits of S. caseolaris. All these isolated compounds were screened against a rat glioma C-6 cell line using the MTT assay method; only compounds (−)-(R)-nyasol, (−)-(R)-4′-O-methylnyasol and maslinic acid were found to show moderate cytotoxic activity (Wu et al., 2009). Sadhu et al. (2006) reported the isolation and identification of two flavonoids luteolin and luteolin 7-O-β-glucoside from the leaves of S. caseolaris and tested their antioxidant activity using 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging effect on a thin-layer chromatography. Both the compounds were found to possess antioxidant activity. Minqing et al. (2009) isolated twenty-four compounds including eight steroids, nine triterpenoids, three flavonoids and four benzenecarboxylic derivatives from stems and twigs of S. caseolaris. In the in vitro cytotoxic assay of these constituents against SMMC-7721 human hepatoma cells, compound 3′,4′,5,7-tetrahydroxyflavone exhibited significant activity with IC50 2.8 μg/mL, while oleanolic acid, 3,3′-di-O-methyl ether ellagic acid, and 3,3′,4-tri-O-methyl ether ellagic acid showed weak activity.
The fishermen use the pneumatophores of Berembang tree as corks or floats for fishing nets while the pulp of Berembang tree is suitable for Kraft paper production. The flowers of Berembang contain abundant honey (Backer and van Steenis, 1951). The Berembang tree is reported to be hemostat. The crabapple mangrove is a folk remedy for sprains, swellings, and worms (Duke and Wain, 1981). It is also used in poultices for cuts, bruises, sprains and swellings. The Malays use the old Berembang's fruit walls to expel intestinal parasites (Mastaller, 1997). The half-ripe fruits are good to cure coughs and the pounded leaves are good for hematuria and smallpox (Perry, 1980). In Eastern Africa the leaves are used as camel fodder (Field, 1995). Berembang is also used as firewood as it produces a lot of heat, ash and salts. The heavy timber is resistant to shipworm and pests; so it is used for building boats, piling and posts for bridges and houses. The wood of Berembang corrodes metal because of the timber's high mineral content (Mastaller, 1997). Berembang is among the mangroves to protect coastlines (Peter and Sivasothi, 1999). In this present study thirty-two compounds from bark and twenty-eight compounds from wood of S. caseolaris (L.) Engl. have been identified.
2 Experimental
2.1 General
The analyses and identification process of extractives were carried out by Mr. Noramin Mohd Noor, a Chemist Executive from Kedah BioResources Corporation Sdn. Bhd. Analytical results were generated with a LECO Pegasus time-of-flight mass spectrometer (TOFMS). The Pegasus GC–TOFMS instrument was equipped with an Agilent 6890 N gas chromatograph and an auto sampler. A HP-5, 30 m × 0.32 mm ID × 0.25 μm film thickness, capillary column was used for the chromatographic separation. The GC was operated with helium carrier gas at a corrected constant flow of 1.2 ml/min. The LECO ChromaTOF software was used for all acquisition control and data processing. The GC temperature program was set to an initial oven temperature of 80 °C for 5 min, followed by a temperature ramp of 5 °C/min, to a final temperature of 280 °C. The GC method injection port temperature was set at 250 °C and 1.0 μL of sample was injected in a splitless way. The MS transfer line temperature was set at 250 °C. The MS mass range was set at 39–550 amu with an acquisition rate of 15 spectra per second.
2.2 Plant material
The Bark and wood of S. caseolaris (L.) were collected from the Malay Peninsula and identified by Prof. Wazahat Hussain, Taxonomist, Department of Botany AMU Aligarh and Mrs. Siti Nurdijati Baharuddin, Taxonomist and lecturer, School of Biological sciences, USM, Malaysia. The sample voucher specimens of Bark and wood have been preserved in the School of Industrial Technology, Division Bioresources and Wood Technology, Laboratory No. 320, USM, Malaysia under voucher specimen numbers BSC/2012010, WSC/2112010.
2.3 Extraction and isolation
This paper also presents a comparative analysis of chemicals of bark (Fig. 1) and wood (Fig. 2) of S. caseolaris (L.) Engl.; air dried wood (30 g) and bark (30 g) of S. caseolaris (L.) Engl. were chipped into small pieces by using a chisel. Both the samples were milled using a grinder (Dietz-motoren GmbH & Co., KG) to make sawdust (to a size about 1–5 mm). Special care was taken during the grinding process to avoid over heating to the sample. The ground bark (5 g) and wood (5 g) of Berembang were separately extracted with hexane for three times successively for 1, 2 and 3 h. Both the hexane soluble parts of bark and wood were separately dried on the BÜCHI Rotavapor R-210 to give the solid mass of bark extract (23.0 mg) and wood extract (9.1 mg).
Figures 1 and 2. Bark sample , wood sample of Sonneratia caseolaris (L. Engl.).
3 Results and discussion
The comparative analysis of GC–TOFMS chromatograms of bark and wood of Berembang revealed some different peak patterns (Figure 3 and Figure 4). These results indicated the presence of some different chemical constituents in both bark and wood extracts. Both the extracts of Berembang tree show the presence of organic compounds, such as alkanes, alkenes, aromatic compounds, alcohols, phenols, carboxylic acids, amides and also amines (Tables 1 and 2). Overall 32 compounds from bark and 28 compounds from wood have been detected. Sixteen constituents have been found to be common in both the extracts which are (E)-2-octenal, nonanal, piperonal, 2-undecenal, 2,4-bis(1,1-dimethylethyl)-phenol, 1-hexadecene, hexadecanal, 1,2-benzenedicarboxylic acid bis(2-methylpropyl) ester, 7,9-di-tert-butyl-1-oxaspiro(4,5)deca-6,9-diene-2,8-dione, dodecanamide, 1-docosene, octacosane, ethaneperoxoic acid 1-cyano-1-[2-(2-phenyl-1,3-dioxolan-2-yl)ethyl]pentyl ester, pentadecane, (E,E)-2,4-decadienal, (Z)-2-decenal and hentriacontane. There are 16 different compounds in bark extract and 12 different compounds in wood extract. This is the first report of the presence of these components in the bark (Table 1) and wood (Table 1) of S. caseolaris L., respectively. The chemical profile of bark and wood extract identified by the GC–TOFMS analysis may be a finger print chemotaxonomic marker (Ge et al., 2008) for S. caseolaris (L.) Engl. Although more than 100 compounds could be detected in the analyzed extracts, only those with a similarity higher than 900 are presented in the chemical profile (Figure 5 and Figure 6).
Figure 3. Chromatograms of bark extract of Berembang.
Figure 4. Chromatograms of wood extract of Berembang.
In conclusion it may be said that a particular plant can be identified on the basis of its GC–TOFMS chemical profile of different extracts. The GC–TOFMS of a particular plant may be a significant fingerprint chemotaxonomic marker for the identity.
Acknowledgments
We would like to acknowledge Universiti Sains Malaysia (USM) for the University Grant 1001/PTEKIND/8140152.
Peter, K.L. Ng, Sivasothi, N., 1999. A Guide to the Mangroves of Singapore I: The Ecosystem and Plant Diversity. Singapore Science Centre, pp. 136–137.
, wood sample 
of Sonneratia caseolaris (L. Engl.).
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