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Identification of chemical compounds present in different fractions of Annona reticulata L. leaf by using GC–MS a

Soumya P. Rout & Durga M. Kar

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Department of Pharmacology, School of Pharmaceutical Sciences, Siksha ‘O’ Anusandhan University, Kalinga Nagar, Ghatikia, Bhubaneswar 751003, OdishaIndia Published online: 22 Jul 2014.

To cite this article: Soumya P. Rout & Durga M. Kar (2014): Identification of chemical compounds present in different fractions of Annona reticulata L. leaf by using GC–MS, Natural Product Research: Formerly Natural Product Letters, DOI: 10.1080/14786419.2014.939084 To link to this article: http://dx.doi.org/10.1080/14786419.2014.939084

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Natural Product Research, 2014 http://dx.doi.org/10.1080/14786419.2014.939084

SHORT COMMUNICATION Identification of chemical compounds present in different fractions of Annona reticulata L. leaf by using GC –MS Soumya P. Rout* and Durga M. Kar Department of Pharmacology, School of Pharmaceutical Sciences, Siksha ‘O’ Anusandhan University, Kalinga Nagar, Ghatikia, Bhubaneswar 751003, Odisha, India


(Received 13 May 2014; final version received 24 June 2014) GC –MS analysis of fractions prepared from hydro-alcoholic extract of Annona reticulata Linn (Family Annonaceae) leaf revealed the presence of 9,10dimethyltricyclo[4.2.1.1(2,5)]decane-9,10-diol; 4-(1,5-dihydroxy-2,6,6-trimethylcyclohex-2-enyl)but-3-en-2-one; 3,7-dimethyl-6-nonen-1-ol acetate; 9-octadecenamide, (Z)-; glycerine; D -glucose,6-O-a-D -galactopyranosyl-; desulphosinigrin and a-methylD -mannopyranoside as few of the major compounds in different fractions. The presence of these compounds in the plant has been identified for the first time. Keywords: Annona reticulata; GC– MS technique; anti-hyperglycaemic

1. Introduction Annona reticulata Linn (Family Annonaceae), commonly called as bullock’s heart or raamphal plant, is widely distributed all over India and are tall, with many branches, bearing nutritious fruits. The leaves are used as insecticides, anthelmintic and styptic, and are also used externally as suppurant (Suresh et al. 2011). Ethanolic extracts of leaves had been reported to possess anticancer activity and aqueous leaf extract to ameliorate hyperthyroidism (Zaman & Pathak 2013). The plant is reported to contain acetogenins, terpenes, kaurenoic acid, b-sitosterol, 16ahydro-19-al-ent-kauran-17-oic acid, 6b-hydroxystigmast-4-en-3-one, 7-acetoxy-16b-entkauran-19-oic acid, 16a-hydro-ent-kauran-17,19-dioic acid,(2S)-di-O-methylquiritigenin, triterpenoids (Thang et al. 2013), pentadecanoic acid, methyl ester (CAS), RS-3-methyl-4(2-oxo-2phenyl ethyl)cyclopent-2-en-1-one, 1-hydroxyoctan-4-one, diallyl 2-diazosuccinatea, 5-ethylpyrogallol (Rajini & Jothi Nisha 2013), R-pinene, a-pinene, myrcene, limonene, terpinen-4-ol, germacrene D (Pino et al. 2003), etc. Leaf is known to contain anonaine, roemerine, norcorydiene, corydine, norisocorydine, dienone isocorydine, norlaureline, glaucine hyperoside, rutin and quercetin, n-hexacosanol, n-octacosanol, n-triacontanol, 16-hentriacontanone, campsterol, stigmasterol and b-sitosterol, essential oils, carvone, linalool, (þ )O-methyl armepavine and flavonoids (Zaman & Pathak 2013). Our previous study has revealed that the hydro-alcoholic extract of the leaf possesses antihyperglycaemic potential (Rout et al. 2013). Since there is no relevant report on the constituents of A. reticulata leaf responsible for anti-hyperglycaemic activity, this study was initiated to identify the compounds present in the leaves of A. reticulata, which may reveal an insight for its anti-hyperglycaemic property.

*Corresponding author. Email: [email protected] q 2014 Taylor & Francis

9,10-Dimethyltricyclo[4.2.1.1(2,5)]decane-9,10-diol 4-(1,5-Dihydroxy-2,6,6-trimethylcyclohex-2- enyl)but-3-en-2-one n-Hexadecanoic acid Phytol 3,7-Dimethyl-6-nonen-1-ol acetate 9-Octadecenamide, (Z)9,10-Secocholesta-5,7,10(19)-triene-3,24,25-triol,(3 a,5Z,7E)Ethyl iso-allocholate Glycerine D -Glucose, 6-O-a-D -galactopyranosyla-D -Glucopyranoside, O-a-D -glucopyranosyl-(1.fwdarw.3)-a-D -fructofuranosyl Desulphosinigrin Glycerine a-D -Glucopyranose,4-O-a-D -galactopyranosyla-Methyl-D -mannopyranoside Desulphosinigrin

Chloroform fraction

Hydro-alcoholic fraction

Methanol fraction

Ethylacetate fraction

Compound #

Fraction #

Table 1. Major compounds identified from different fractions of A. reticulata L. leaf.


10.52 10.75 12.46 13.98 8.86 23.12 29.17 30.15 2.98 9.05 9.94 10.70 2.70 7.40 9.99 10.50

Retention time #

MW # 196 224 256 296 212 281 416 436 92 342 504 279 92 342 194 279

Molecular formula # C12H20O2 C13H20O3 C16H32O2 C20H40O C13H24O2 C18H35NO C27H44O3 C26H44O5 C3H8O3 C12H22O11 C18H32O16 C10H17NO6S C3H8O3 C12H22O11 C7H14O6 C10H17NO6S

11.42 10.88 8.18 9.74 33.58 20.45 4.74 10.27 53.38 26.27 3.41 10.26 18.90 16.15 19.36 24.47

Peak area % #

2 S.P. Rout and D.M. Kar


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2. Results and discussion The mass spectra of the compounds found in different fractions prepared from hydro-alcoholic extract of A. reticulata leaf were matched with the National Institute of Standards and Technology (NIST) library and the major compounds have been listed in Table 1. The major components of chloroform fractions are 9,10-dimethyltricyclo[4.2.1.1(2, 5)]decane-9,10-diol (11.42%), 4-(1,5-dihydroxy-2,6,6-trimethylcyclohex-2-enyl)but-3-en-2-one (10.88%), phytol (9.74%) and n-hexadecanoic acid (8.18%). The major compounds of ethylacetate fraction are 3,7-dimethyl-6-nonen-1-ol acetate (33.58%), 9-octadecenamide,(Z)- (20.45%), ethyl isoallocholate (10.27%) and 9,10-secocholesta-5,7,10(19)-triene-3,24,25-triol,(3a,5Z,7E)(4.74%). The major compounds in the methanol fraction are glycerine (53.38%), D -glucose, 6-O-a-D -galactopyranosyl- (26.27%), desulphosinigrin (10.26%) and a-D -glucopyranoside, O-a-D -glucopyranosyl-(1.fwdarw.3)-a-D -fructofuranosyl (3.41%). Similarly, the major compounds identified in the hydro-alcoholic fraction are desulphosinigrin (24.47%), a-methyl-D -mannopyranoside (19.36%), glycerine (18.90%) and a-D -glucopyranose, 4-O-aD -galactopyranosyl- (16.15%). The major compounds have been searched in Dr Duke’s Phytochemical and Ethnobotanical Database for any reported anti-hyperglycaemic property and had been found that none of the compounds have been reported earlier. 3. Conclusion Any one or more compounds present in the plant may be responsible for the anti-hyperglycaemic effect observed earlier; therefore, additional studies are required to be conducted to identify the compound(s) responsible for anti-hyperglycaemic property of the hydro-alcoholic extract. Supplementary material Experimental details relating to this article are available online. Acknowledgements We would like to thank Mr S. Kumaravel, Quality Manager, Indian Institute of Crop Processing Technology, Thanjavur, India and Director, Indian Institute of Crop Processing Technology, Thanjavur, India for their support in carrying out the GC – MS analysis.

References Pino JA, Marbot R, Fuentes V. 2003. Characterization of volatiles in bullock’s heart (Annona reticulata L.) fruit cultivars from Cuba. J Agric Food Chem. 51:3836–3839. Rajini R, Jothi Nisha MR. 2013. Potential bioactivity of Annona reticulata l. leaf extract and its compound identification by GCMS. Int J Sci Innovations Discov. 3:202–211. Rout SP, Kar DM, Mohapatra SB, Swain SP. 2013. Anti-hyperglycemic effect Annona reticulata l. Leaves on experimental diabetic rat model. Asian J Pharm Clin Res. 6:56–60. Suresh HM, Shivakumar B, Hemalatha K, Heroor SS, Hugar DS, Sambasiva Rao KRS. 2011. In vitro antiproliferative activity of Annona reticulata roots on human cancer cell lines. Pharmacogn Res. 3:9–12. Thang TD, Kuo P-C, Huang G-J, Hung NH, Huang B-S, Yang M-L, Luong NX, Wu T-S. 2013. Chemical constituents from the leaves of Annona reticulata and their inhibitory effects on NO production. Molecules. 18:4477– 4486. Zaman K, Pathak K. 2013. Pharmacognostical and phytochemical studies on the leaf and stem bark of Annona reticulata Linn. J Pharmacogn Phytochem. 1:1–7.