{"id":58296,"date":"2024-06-25T11:02:23","date_gmt":"2024-06-25T11:02:23","guid":{"rendered":"https:\/\/biomedpharmajournal.org\/?p=58296"},"modified":"2024-07-03T17:23:13","modified_gmt":"2024-07-03T17:23:13","slug":"analysis-of-gc-ms-from-acetone-extract-of-canarium-odontophyllum-miq-stem-bark-dabai","status":"publish","type":"post","link":"https:\/\/biomedpharmajournal.org\/staging\/vol17no2\/analysis-of-gc-ms-from-acetone-extract-of-canarium-odontophyllum-miq-stem-bark-dabai\/","title":{"rendered":"Analysis of GC-MS from Acetone Extract of Canarium odontophyllum Miq Stem Bark (Dabai)"},"content":{"rendered":"\n

Introduction<\/strong><\/p>\n\n\n\n

The use of wild plants from nature\nfor medicinal purposes is a practice that has been practiced for centuries.\nThis practice is widely found among communities that practice traditional\nmedicine. This is because natural plants have rich sources of biologically\nactive compounds. 1<\/sup> Various natural products exhibit different\nbiological properties and have long been used as medicines with different\napplications. The use of natural products is not only used in traditional\nmedicine but the detailed research done on natural products allows them to be\nused in modern medicine. Various bioactive compounds from medicinal plants\nexhibit stimulating actions of pharmacological such as antifungal,\nantibacterial, anticancer, antiinflammatory and antioxidant properties. 2,3<\/sup>\nThe capability of these bioactive compounds needs to be analyzed first before\nbeing used in various diseases treatment. 2,4<\/sup> Crude plant extracts\nare often prepared from plant-based medicines consisting of a different\nphytochemicals complex mixture. 4<\/sup> These phytochemicals have a\ncomplex and unique structure, used in chronic and infectious diseases\ntreatment. 4,5<\/sup> A large group of bioactive secondary metabolites\nexist in many species of plant, but only a small part of them has been studied and\nmaintained as an important source of bioactive agents. In finding novel\ncompounds and quality control is very important to develop appropriate\nscreening methods. 6<\/sup> Various extractions and characterization from\nbioactive compounds of many medicinal plants have led to the delivery of specific\ndrugs with high profiles of activity. 7<\/sup><\/p>\n\n\n\n

Preliminary screening of medicinal\nplants through methods of chromatographic and spectrometric give general\ninformation about pharmacological and chemical activity\nand helps to choose biologically active plants. 8<\/sup> Within a\ndecade, there have been several dramatic advances in techniques of analytical\nincluding Ultraviolet-visible (UV) Spectroscopy, Thin Layer Chromatography\n(TLC), Gas Chromatography-Mass Spectrometry (GC-MS) and Nuclear Magnetic\nResonance Spectroscopy (NMR) which are the tools used for the process of\nisolation, identification and determination of the phytochemical structure of many\nbioactive therapeutic compounds found in medicinal plants. 9,10<\/sup> Best\ncombination of analytical techniques is gas chromatography-mass spectrometry\n(GC-MS) which is fast, sensitive and plays an important role in chemotaxonomic\nstudies and phytochemical analysis of medicinal plants containing biologically\nactive components. The GC-MS method can qualitatively and quantitatively\nidentify organic compounds in extracts. 11,12<\/sup><\/p>\n\n\n\n

The GC-MS method is used to\ndetermine and identify compounds found in plant samples including alcohols, long\nchain hydrocarbons, alkaloids, steroids, nitro compounds, amino acids, esters\nand organic acids. In addition, this GC-MS method only need a small volume of\nplant extracts. 11,13<\/sup> GC-MS was also performed for bioactive\ncompounds identified based on ions of MS fragment produced, retention time and\nthe percentage of bioactive compounds analyzed from the area of total peak.\nPhytochemicals were identified by comparing patterns of MS spectral with\nstandard mass spectra that available in the Mass Spectral Database of National\nInstitute of Standards and Technology (NIST). 12<\/sup> One of the most\naccurate methods for identifying many secondary metabolites found in plant\nextracts is GC-MS. 14<\/sup> Therefore, the technique of GC-MS was used in\nthis study, for the detection and identification of phytochemical compounds\nfound in the acetone extract of Canarium\nodontophyllum<\/em> stem bark (dabai).<\/p>\n\n\n\n

Canarium odontophyllum <\/em>is also known as ‘dabai’ and this\ndabai fruit is eaten by people in Sarawak. The fruit is a seasonal natural\nfruit that is less used because of its short lifespan. 15<\/sup> The fruit\nis purple in color and has one elongated seed (Figure\n1). 16<\/sup>\nThe fruit of C. odontophyllum <\/em>has\nphysical characteristics similar to olives and changes from light green to dark\npurple when ripe enough. This fruit is oval shaped with a mass of around 10.0g\n-18.0g, length 3.0cm – 4.0cm and diameter around 2.2cm – 3.0cm. The fruit of C. odontophyllum<\/em> has one seed located in\nthe middle with a hard and thick endocarp. The length of this fruit seed is\n3.5cm with a diameter of 1.6cm – 2.0cm while this seed is triangular in shape. 17<\/sup><\/p>\n\n\n\n

This C. odontophyllum<\/em> tree is moderately upright to approximately 40\u201350\nm (130\u2013160 ft) tall and has alternate, oval, spiral, pinnate leaves that are\nbetween 9.5 cm to 28 cm long and about 4 cm to 11 cm (Figure\n2). 18<\/sup>\nWhile the flowers of the C. odontophyllum<\/em>\nplant are whitish yellow (Figure 3). 19<\/sup> The stems and\nbranches of C. odontophyllum<\/em> plants\nare greenish gray, light brown or yellowish brown, usually scaly with many\nsmall lenticels and smooth. Furthermore, the outer bark of branches and trunks\nis thin, gray and usually soft in nature while the inner bark is reddish grey or\npinkish brown, smooth, laminated, layered, soft, moist with exudates, oily\nfluids, sticky, and strong produces an aromatic odor. 20-22<\/sup> The\nstems of C. odontophyllum<\/em> plants are\ncylindrical. 22<\/sup> Dabai\nhas wide potential to be marketed locally and exported internationally due to\nits high nutritional contents but still not yet exported internationally. Only\nfood-based products available and there is still no medicinal product developed\nfrom dabai.<\/p>\n\n\n\n\n\n
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Figure 1: Fruits and seed of C. odontophyllum<\/em><\/strong><\/p>\n

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Click here to view Figure<\/a><\/p>\n<\/td>\n<\/tr>\n<\/tbody>\n<\/table>\n\n\n\n
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Figure 2: The stem bark of C. odontophyllum <\/em>is greenish gray and scaly.18<\/sup><\/strong><\/p>\n

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Click here to view Figure<\/a><\/p>\n<\/td>\n<\/tr>\n<\/tbody>\n<\/table>\n\n\n\n
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Figure 3: Flowers and leaves of C. odontophyllum<\/em>.19<\/sup><\/strong><\/p>\n

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Click here to view Figure<\/a><\/p>\n<\/td>\n<\/tr>\n<\/tbody>\n<\/table>\n\n\n

Materials and Methods<\/strong><\/p>\n\n\n\n

Preparation of the Stem Bark Extract<\/strong><\/p>\n\n\n\n

First, dried the samples in an oven\nat 40\u00b0C until they reached a constant weight for several days. Then, grinding\nof the dried sample is done to get the sample in powder form. Powder of C. odontophyllum <\/em>stem bark was soaked in\nacetone solvent. The mixture was shaken using an electric shaker at room\ntemperature for 24 hours. Then, the solution was filtered using Whatman No. 1\nfilter paper to collect the obtained filtrate. The filtrate was mixed and\nconcentrated using a rotary evaporator under reduced pressure. The extract is\nfinally allowed to dry in fume hood to obtain crude acetone extract. 21<\/sup>\n100 mg of acetone extract was dissolved in 1 ml of absolute DMSO for the\npreparation of a stock solution with a concentration of 100 mg\/ml. Next, mixed\nthe stock solution using an autovortex and then centrifuged at 2500 rpm for 5\nminutes to ensure that all extracts were completely dissolved. The stock was\nfiltered using a 0.22 \u03bcm nitrocellulose filter membrane to ensure the extract\nwas free from contamination and stored in a refrigerator at -20\u02daC until use.<\/p>\n\n\n\n

GC\u2013MS Analysis<\/strong><\/p>\n\n\n\n

The active compounds in the acetone\nextract from stem bark of C.\nodontophyllum<\/em> were identified using the method of gas chromatography-mass\nspectrometry (GC-MS). Analysis of gas chromatography mass spectrometer (GC-MS)\nwas carried out using an Agilent 7890A gas chromatograph (GC) coupled directly\nto a mass spectrometer (MS) system equipped with a DB-5MS UI column (30.0 m x\n0.25 mm, film thickness 0.25 \u03bcm, 5% phenyl methylpolysiloxane) as well as\nconnected to an inert Agilent 5975C MSD with a three-axis detector and operated\nin a system of electron ionization with a 70 eV impact mode used. Helium gas is\nused at a constant flow rate of 1ml\/minute as a carrier gas. The powder form from\nacetone extract of C. odontophyllum<\/em>\nstem bark was diluted with a suitable solvent which is acetone and then the\nsolution was filtered. A particle-free dissolved acetone extract (1\u03bcl) was\ntaken using a syringe and injected into the injector in split mode with an\ninjector temperature of 250 C and an ion source temperature of 280 C. The\ntemperature oven was programmed with an increase of 10C\/ min from 40C\n(isothermal for 5 min), up to 300C\/min isothermal and held for 5 minutes. Mass\nspectra were taken at 70 eV, scan interval 0.5 s and fragments from 45 to\n450Da. The total time GC was run for 34 minutes. 13, 23<\/sup><\/p>\n\n\n\n

Identification of the Components <\/strong><\/p>\n\n\n\n

The percentage composition of the\ncrude extract components is demonstrated as a percentage by peak area. Raw GC\nchromatogram was shown all peaks using MSD Chemstation. Then, combined the\nresults in a single peak table. A library search was conducted for all peaks\nusing NIST\/EPA\/NIH (version 2.0) for the name, structure of the compounds and\nmolecular weight from the sample.<\/p>\n\n\n\n

Results and Discussion<\/strong><\/p>\n\n\n\n

Analysis of GC-MS was carried out on the acetone extract from C. odontophyllum<\/em> stem bark and a total of 24 phytoconstituents were detected. The chromatogram is displayed in Figure 4, while the constituent chemicals with molecular weight (MW), molecular formula, peak area (%) and retention time (RT) for each phytoconstituent are shown in Table 1. In Table 2 shown the phytoconstituent found in the extract and their activities. The highest peak area (%) for the acetone extract is alpha- amyrin (16.6644%) followed by beta- amyrin (4.6159%), beta sitosterol (3.3369%) and 9, 12-octadecadienoic acid (Z, Z)- (3.2045%). The lowest peak area (%) for the acetone extract is shown by bicyclo [3.1.0] hex-2-ene, 2-methyl-5-(1-methylethyl)- which is 0.0828%.<\/p>\n\n\n\n\n\n
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Figure 4: Chromatogram of acetone extract from stem bark of C. odontophyllum<\/em> by GC-MS<\/strong><\/p>\n

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Table 1: Phytoconstituents found in the acetone extract of C. odontophyllum<\/em> stem bark<\/strong><\/p>\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n
\n

No<\/strong><\/p>\n<\/td>\n

\n

RT (minute)<\/strong><\/p>\n<\/td>\n

\n

Name of compound<\/strong><\/p>\n<\/td>\n

\n

Molecular formula<\/strong><\/p>\n<\/td>\n

\n

Molecular weight (MW)<\/strong><\/p>\n<\/td>\n

\n

Peak area (%)<\/strong><\/p>\n<\/td>\n<\/tr>\n

\n

1<\/p>\n<\/td>\n

\n

7.7554<\/p>\n<\/td>\n

\n

Bicyclo [3.1.0] hex-2-ene, 2-methyl-5-(1-methylethyl)-<\/p>\n<\/td>\n

\n

C10<\/sub>H16<\/sub><\/p>\n<\/td>\n

\n

136.2340<\/p>\n<\/td>\n

\n

0.0828<\/p>\n<\/td>\n<\/tr>\n

\n

2<\/p>\n<\/td>\n

\n

8.8972<\/p>\n<\/td>\n

\n

Bicyclo [3.1.0] hexane, 4-methylene-1-(1-methylethyl)-<\/p>\n<\/td>\n

\n

C10<\/sub>H16<\/sub><\/p>\n<\/td>\n

\n

136.2340<\/p>\n<\/td>\n

\n

0.1020<\/p>\n<\/td>\n<\/tr>\n

\n

3<\/p>\n<\/td>\n

\n

15.2437<\/p>\n<\/td>\n

\n

Alpha Cubebene<\/p>\n<\/td>\n

\n

C15<\/sub>H24<\/sub><\/p>\n<\/td>\n

\n

204.3511<\/p>\n<\/td>\n

\n

0.1329<\/p>\n<\/td>\n<\/tr>\n

\n

4<\/p>\n<\/td>\n

\n

15.6538<\/p>\n<\/td>\n

\n

Copaene<\/p>\n<\/td>\n

\n

C15<\/sub>H24<\/sub><\/p>\n<\/td>\n

\n

204.3511<\/p>\n<\/td>\n

\n

0.0921<\/p>\n<\/td>\n<\/tr>\n

\n

5<\/p>\n<\/td>\n

\n

15.8178<\/p>\n<\/td>\n

\n

1H-Cyclopenta [1,3] cyclopropa [1,2] benzene,octahydro-7-methyl-3-methylene-4-(1-methylethyl)-,[3aS-(3a.alpha., 3b.beta., 4.beta., 7.alpha., 7aS*)]- (beta cubebene)<\/p>\n<\/td>\n

\n

C15<\/sub>H24<\/sub><\/p>\n<\/td>\n

\n

204.3511<\/p>\n<\/td>\n

\n

0.1775<\/p>\n<\/td>\n<\/tr>\n

\n

6<\/p>\n<\/td>\n

\n

17.3571<\/p>\n<\/td>\n

\n

Phenol, 2,4-bis(1,1-dimethylethyl)-<\/p>\n<\/td>\n

\n

C17<\/sub>H30<\/sub>OSi<\/p>\n<\/td>\n

\n

278.5050<\/p>\n<\/td>\n

\n

0.5372<\/p>\n<\/td>\n<\/tr>\n

\n

7<\/p>\n<\/td>\n

\n

18.2593<\/p>\n<\/td>\n

\n

(-)-Spathulenol<\/p>\n<\/td>\n

\n

C15<\/sub>H24<\/sub>O<\/p>\n<\/td>\n

\n

220.3505<\/p>\n<\/td>\n

\n

0.9400<\/p>\n<\/td>\n<\/tr>\n

\n

8<\/p>\n<\/td>\n

\n

18.3413<\/p>\n<\/td>\n

\n

9-Eicosene, (E)-<\/p>\n<\/td>\n

\n

C20<\/sub>H40<\/sub><\/p>\n<\/td>\n

\n

280.5316<\/p>\n<\/td>\n

\n

0.3050<\/p>\n<\/td>\n<\/tr>\n

\n

9<\/p>\n<\/td>\n

\n

18.4233<\/p>\n<\/td>\n

\n

Hexadecane<\/p>\n<\/td>\n

\n

C16<\/sub>H34<\/sub><\/p>\n<\/td>\n

\n

226.4412<\/p>\n<\/td>\n

\n

0.2202<\/p>\n<\/td>\n<\/tr>\n

\n

10<\/p>\n<\/td>\n

\n

20.5871<\/p>\n<\/td>\n

\n

5-Octadecene, (E)-<\/p>\n<\/td>\n

\n

C18<\/sub>H36<\/sub><\/p>\n<\/td>\n

\n

252.4784<\/p>\n<\/td>\n

\n

0.4770<\/p>\n<\/td>\n<\/tr>\n

\n

11<\/p>\n<\/td>\n

\n

20.7133<\/p>\n<\/td>\n

\n

Hexadecane,2,6,10,14-tetramethyl- (phytane)<\/p>\n<\/td>\n

\n

C20<\/sub>H42<\/sub><\/p>\n<\/td>\n

\n

282.5475<\/p>\n<\/td>\n

\n

0.9387<\/p>\n<\/td>\n<\/tr>\n

\n

12<\/p>\n<\/td>\n

\n

21.6912<\/p>\n<\/td>\n

\n

Nonadecane<\/p>\n<\/td>\n

\n

C19<\/sub>H40<\/sub><\/p>\n<\/td>\n

\n

268.5209<\/p>\n<\/td>\n

\n

0.3311<\/p>\n<\/td>\n<\/tr>\n

\n

13<\/p>\n<\/td>\n

\n

22.3535<\/p>\n<\/td>\n

\n

n-Hexadecanoic acid<\/p>\n<\/td>\n

\n

C16<\/sub>H32<\/sub>O2<\/sub><\/p>\n<\/td>\n

\n

256.4241<\/p>\n<\/td>\n

\n

2.4496<\/p>\n<\/td>\n<\/tr>\n

\n

14<\/p>\n<\/td>\n

\n

23.6279<\/p>\n<\/td>\n

\n

Heptacosane, 1-chloro-<\/p>\n<\/td>\n

\n

C27<\/sub>H55<\/sub>Cl<\/p>\n<\/td>\n

\n

415.179<\/p>\n<\/td>\n

\n

0.1509<\/p>\n<\/td>\n<\/tr>\n

\n

15<\/p>\n<\/td>\n

\n

24.0254<\/p>\n<\/td>\n

\n

9,12- Octadecadienoic acid (Z,Z)-<\/p>\n<\/td>\n

\n

C18<\/sub>H32<\/sub>O2<\/sub><\/p>\n<\/td>\n

\n

280.4455<\/p>\n<\/td>\n

\n

3.2045<\/p>\n<\/td>\n<\/tr>\n

\n

16<\/p>\n<\/td>\n

\n

24.1894<\/p>\n<\/td>\n

\n

9,12- Octadecadienoic acid, ethyl ester<\/p>\n<\/td>\n

\n

C20<\/sub>H36<\/sub>O2<\/sub><\/p>\n<\/td>\n

\n

308.4986<\/p>\n<\/td>\n

\n

0.5246<\/p>\n<\/td>\n<\/tr>\n

\n

17<\/p>\n<\/td>\n

\n

24.2462<\/p>\n<\/td>\n

\n

Octadecanoic acid<\/p>\n<\/td>\n

\n

C18<\/sub>H36<\/sub>O2<\/sub><\/p>\n<\/td>\n

\n

284.4772<\/p>\n<\/td>\n

\n

1.1298<\/p>\n<\/td>\n<\/tr>\n

\n

18<\/p>\n<\/td>\n

\n

24.4859<\/p>\n<\/td>\n

\n

10-Heneicosene (c,t)<\/p>\n<\/td>\n

\n

C21<\/sub>H42<\/sub><\/p>\n<\/td>\n

\n

294.5582<\/p>\n<\/td>\n

\n

0.5806<\/p>\n<\/td>\n<\/tr>\n

\n

19<\/p>\n<\/td>\n

\n

26.2018<\/p>\n<\/td>\n

\n

Heptafluorobutyric acid, hexadecyl ester<\/p>\n<\/td>\n

\n

C20<\/sub>H33<\/sub>F7<\/sub>O2<\/sub><\/p>\n<\/td>\n

\n

438.4636<\/p>\n<\/td>\n

\n

0.3939<\/p>\n<\/td>\n<\/tr>\n

\n

20<\/p>\n<\/td>\n

\n

26.6497<\/p>\n<\/td>\n

\n

Dehydroabietic acid<\/p>\n<\/td>\n

\n

C20<\/sub>H28<\/sub>O2<\/sub><\/p>\n<\/td>\n

\n

300.4351<\/p>\n<\/td>\n

\n

0.6012<\/p>\n<\/td>\n<\/tr>\n

\n

21<\/p>\n<\/td>\n

\n

26.9715<\/p>\n<\/td>\n

\n

Phenol, 2,4-bis(1-phenylethyl)-<\/p>\n<\/td>\n

\n

C22<\/sub>H22<\/sub>O<\/p>\n<\/td>\n

\n

302.4095<\/p>\n<\/td>\n

\n

0.7200<\/p>\n<\/td>\n<\/tr>\n

\n

22<\/p>\n<\/td>\n

\n

33.1350<\/p>\n<\/td>\n

\n

Beta Sitosterol<\/p>\n<\/td>\n

\n

C29<\/sub>H50<\/sub>O<\/p>\n<\/td>\n

\n

414.7067<\/p>\n<\/td>\n

\n

3.3369<\/p>\n<\/td>\n<\/tr>\n

\n

23<\/p>\n<\/td>\n

\n

33.5703<\/p>\n<\/td>\n

\n

Beta-Amyrin<\/p>\n<\/td>\n

\n

C30<\/sub>H50<\/sub>O<\/p>\n<\/td>\n

\n

426.7174<\/p>\n<\/td>\n

\n

4.6159<\/p>\n<\/td>\n<\/tr>\n

\n

24<\/p>\n<\/td>\n

\n

34.0876<\/p>\n<\/td>\n

\n

Alpha-Amyrin<\/p>\n<\/td>\n

\n

C30<\/sub>H50<\/sub>O<\/p>\n<\/td>\n

\n

426.7174<\/p>\n<\/td>\n

\n

16.6644<\/p>\n<\/td>\n<\/tr>\n<\/tbody>\n<\/table>\n

 <\/p>\n\n\n

Table 2: Phytoconstituents in the acetone extract of C. odontophyllum<\/em> stem barkand their activities.<\/strong><\/p>\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n
\n

No<\/strong><\/p>\n<\/td>\n

\n

Name of compound<\/strong><\/p>\n<\/td>\n

\n

Natural compound<\/strong><\/p>\n<\/td>\n

\n

Activity<\/strong><\/p>\n<\/td>\n<\/tr>\n

\n

1.<\/p>\n<\/td>\n

\n

Alpha cubebene<\/p>\n<\/td>\n

\n

Sesquiterpene<\/p>\n<\/td>\n

\n

Antioxidant,antiproliferative, antigenotoxic, antitumor. 24<\/sup><\/p>\n<\/td>\n<\/tr>\n

\n

2.<\/p>\n<\/td>\n

\n

Copaene<\/p>\n<\/td>\n

\n

Sesquiterpene<\/p>\n<\/td>\n

\n

Antipyretic, Antifungal, antioxidant properties, antigenotoxic and antioxidant against human lymphocytes. 24, 25<\/sup><\/p>\n<\/td>\n<\/tr>\n

\n

3.<\/p>\n<\/td>\n

\n

Spathulenol<\/p>\n<\/td>\n

\n

Sesquiterpene<\/p>\n<\/td>\n

\n

Anticholinesterase, antimycobacterial, antioxidant, antiproliferative, cytotoxicity. 26,27<\/sup><\/p>\n<\/td>\n<\/tr>\n

\n

4.<\/p>\n<\/td>\n

\n

Phenol,2,4-bis(1,1-dimethylethyl)-<\/p>\n<\/td>\n

\n

 Phenol<\/p>\n<\/td>\n

\n

Antioxidant, anti-inflammatory, Cytotoxicity, antibacterial, antifungal, antiviral, antimicrobial. 28<\/sup><\/p>\n<\/td>\n<\/tr>\n

\n

5.<\/p>\n<\/td>\n

\n

9-Eicosene, (E)-<\/p>\n<\/td>\n

\n

Alkene<\/p>\n<\/td>\n

\n

Antimicrobial, Cytotoxicity. 29<\/sup><\/p>\n<\/td>\n<\/tr>\n

\n

6.<\/p>\n<\/td>\n

\n

Bicyclo [3.1.0] hex-2-ene, 2-methyl-5-(1-methylethyl)- (alpha thujene)<\/p>\n<\/td>\n

\n

Monoterpene<\/p>\n<\/td>\n

\n

Antiproliferative, cytotoxic against cell line of breast cancer. 30<\/sup><\/p>\n<\/td>\n<\/tr>\n

\n

7.<\/p>\n<\/td>\n

\n

Bicyclo [3.1.0] hexane, 4-methylene-1-(1-methylethyl)- (sabinene)<\/p>\n<\/td>\n

\n

Monoterpene<\/p>\n<\/td>\n

\n

Antifungal, antiinflammatory, antioxidant, anticancer activity against colon cancer and melanoma cells, causing apoptosis in B16F10 melanoma cells. 31-33<\/sup><\/p>\n<\/td>\n<\/tr>\n

\n

8.<\/p>\n<\/td>\n

\n

Hexadecane<\/p>\n<\/td>\n

\n

Alkane<\/p>\n<\/td>\n

\n

Cytotoxicity, Antioxidant, Antimicrobial, Antidiabetic, Antiinflammatory. 34,35<\/sup><\/p>\n<\/td>\n<\/tr>\n

\n

9.<\/p>\n<\/td>\n

\n

Nonadecane<\/p>\n<\/td>\n

\n

Alkane<\/p>\n<\/td>\n

\n

AntiHIV, Antioxidant, Antibacterial, Antimicrobial, Cytotoxic effect. 36,37<\/sup><\/p>\n<\/td>\n<\/tr>\n

\n

10.<\/p>\n<\/td>\n

\n

n-Hexadecanoic acid<\/p>\n<\/td>\n

\n

Palmitic acid, Fatty acid<\/p>\n<\/td>\n

\n

Hypercholesterolemia, antioxidants,<\/p>\n

Antiandrogenic, Antibacterial, Antiinflammatory, anticancer effects. 38,39<\/sup><\/p>\n<\/td>\n<\/tr>\n

\n

11.<\/p>\n<\/td>\n

\n

Heptacosane, 1-chloro-<\/p>\n<\/td>\n

\n

Alkyl halide<\/p>\n<\/td>\n

\n

Antioxidant. 40<\/sup><\/p>\n<\/td>\n<\/tr>\n

\n

12.<\/p>\n<\/td>\n

\n

9,12-Octadecadienoic acid (Z,Z)-<\/p>\n

9,12-Octadecadienoic acid, ethyl ester<\/p>\n<\/td>\n

\n

Linoleic acid, ethyl ester<\/p>\n<\/td>\n

\n

Antioxidant, Antitumor, Antiinflammatory, hypocholesterolemic, antiandrogenic, antiarthritic, anticoronary, antihistamine, hepatoprotective. 41-43<\/sup><\/p>\n<\/td>\n<\/tr>\n

\n

13.<\/p>\n<\/td>\n

\n

Octadecanoic acid<\/p>\n<\/td>\n

\n

Stearic acid, Fatty acid<\/p>\n<\/td>\n

\n

Antifungal, Antitumor,<\/p>\n

Antibacterial, lowers LDL cholesterol, Anti-inflammatory,hypocholesterolemic, cancer prevention, hepatoprotective, antiviral, antioxidant. 29,44<\/sup><\/p>\n<\/td>\n<\/tr>\n

\n

14.<\/p>\n<\/td>\n

\n

Dehydroabietic acid<\/p>\n<\/td>\n

\n

Diterpenoid<\/p>\n<\/td>\n

\n

Act pharmacologically against aging, inflammation, bacterial infection, cancer and increased cell death in human epithelia and fibroblast cells. 45-47<\/sup><\/p>\n<\/td>\n<\/tr>\n

\n

15.<\/p>\n<\/td>\n

\n

Phenol,2,4-bis(1-phenylethyl)-<\/p>\n<\/td>\n

\n

Phenol<\/p>\n<\/td>\n

\n

Effects of apoptosis on human breast cancer cells. 48<\/sup><\/p>\n<\/td>\n<\/tr>\n

\n

16.<\/p>\n<\/td>\n

\n

Beta Sitosterol<\/p>\n

 <\/p>\n<\/td>\n

\n

Phytosterols<\/p>\n<\/td>\n

\n

Anti-diabetic, anti-inflammatory, anti-atherosclerotic, lipid-lowering and hepatoprotective, protection against oxidative damage, anti-tumor effect against lung, breast, prostate, kidney and colorectal cancer. 49-51<\/sup><\/p>\n<\/td>\n<\/tr>\n

\n

17.<\/p>\n<\/td>\n

\n

Beta-amyrin<\/p>\n<\/td>\n

\n

Triterpenoid<\/p>\n<\/td>\n

\n

Antitumor effect against Hep-G2 liver carcinoma cells, antiinflammatory, antifibrogenic antioxidant, antihyperglycemic, hypolipidemic effect, analgesic, antidepressant, gastroprotective, hepatoprotective, antipancreatic, cytotoxicity against several cancer cells such as promyelocytic leukemia HL-60, colon cancer HCT-8, glioblastoma SF-295, MDAMB-435 melanoma, colorectal and breast adenocarcinoma HCT 116, lung and liver carcinoma, pancreatic adenocarcinoma, kidney and prostate carcinoma. 52-57<\/sup><\/p>\n<\/td>\n<\/tr>\n

\n

18.<\/p>\n<\/td>\n

\n

Alpha-amyrin<\/p>\n<\/td>\n

\n

Triterpenoid<\/p>\n<\/td>\n

\n

Antiinflammatory, antioxidant, antihyperglycemic, hypolipidemic effect, analgesic, antidepressant, gastroprotective, hepatoprotective, antipancreatic, antileukemic agent, cytotoxicity against leukemic cells, cytotoxicity against several cancer cells such as promyelocytic leukemia HL-60, colon cancer HCT-8, glioblastoma SF-295, MDAMB-435 melanoma, HCT 116 colorectal and breast adenocarcinoma, lung and liver carcinoma, pancreatic adenocarcinoma, kidney and prostate carcinoma. 52,54,56,58<\/sup><\/p>\n<\/td>\n<\/tr>\n<\/tbody>\n<\/table>\n

 <\/p>\n\n\n

Different phytochemicals contain in\nplants, known as secondary metabolites. 59,60<\/sup> Phytochemicals are important\nin the industry of pharmaceutical for the preparation of therapeutic agents and\nthe new drugs development.61<\/sup> The new drugs development begins with\nthe identification of active principles from natural sources. New approach to\nfind therapeutically active compounds in various species of plants is by screening\nof plant extract. 38,62<\/sup> Phytochemicals such as saponins, alkaloids, flavonoids,\nterpenoids and tannins have some of biological properties including\nantiinflammatory, antioxidant, antiulcer, anticancer, and antidiarrhea\nactivity. 38<\/sup> Exposure through diet or drug administration to\nphytochemicals can stop or delay process of carcinogenic. Phytochemicals may\nplay an important role in decreasing the incidence of colon cancer. 63<\/sup>\nPolyphenols, such as phenolic acids, sesquiterpenoids and flavonoids are known\nfor their capability to induce apoptosis in colon cancer cells. 64,65<\/sup>\nThe results of phytochemical screening in previous studies shown that the\nphytochemicals found in acetone extract of C.\nodontophyllum<\/em> stem bark are flavonoids, saponins, tannins, phenolic\ncompounds and terpenoids may exhibit cytotoxicity and apoptosis effect against\nHCT 116 and function as anticancer agents. 21,66<\/sup> So, this study was\nconducted to identify which bioactive compound in this acetone extract may be\nresponsible for cytotoxicity and apoptosis effect against HCT 116.<\/p>\n\n\n\n

The highest peak area (%) for the\nacetone extract is alpha-amyrin followed by beta-amyrin. Alpha-amyrin and\nbeta-amyrin are triterpenoids which are active compounds that belong to the\nterpenoid group and have antimicrobial, antifungal and antiinflammatory effects.\n67<\/sup> Triterpenoids have also been reported to act as a potential\nsource of cytotoxicity in cancer cells. Calotroposide A isolated from the ethyl\nacetate extract of the roots of Calotropis\ngigantea<\/em> is a triterpenoid glycoside and reported can inhibit the growth of\nWiDr colon cancer cells. 68<\/sup> Triterpenoids are a vital group of\nterpenoids with bioactivity. 69<\/sup> Plant terpenoids have important\nfunctions in respiration, growth regulation and development, membrane fluidity\nand photosynthesis. 70<\/sup> Terpenoids are also found in Campsis grandiflora<\/em> leaves, cuticle wax\nof apple skin and Lantana camara L<\/em>. aerial\nparts. 71 <\/sup>In addition, terpenoids are also detected in Fusarium sp<\/em>. 72<\/sup>, Laurencia sp<\/em> (marine algae) 73<\/sup>\nand endophytic fungi Huperzia serrata<\/em>.\n74<\/sup> Terpenoid biosynthesis is important for agriculture, industry and\nliving organisms. Approximately 80,000 terpenoid compounds as secondary\nmetabolites have been found in nature and have performed various roles\n(functional and structural). 75<\/sup> Based\non this study, the main\nbioactive compound of this acetone extract which are alpha and beta-amyrin may\nbe responsible for the cytotoxicity and apoptotic effect against colorectal\ncancer cell, HCT 116 and capable\nof being developed as an anticancer agent.<\/p>\n\n\n\n

Conclusion<\/strong><\/p>\n\n\n\n

The present study of this analysis in acetone extract of C. odontophyllum <\/em>stem bark has suggested the presence of 24 of phytocompouds. Thus, this acetone extract was found to possess significant phytoconstituents and considered to have various medicinal properties. Alpha-amyrin and beta-amyrin are triterpenoid detected in acetone extract of  Canarium odontophyllum<\/em> stem bark that may contribute to the cytotoxicity and effect of apoptotic on HCT 116 cell. In conclusion, acetone extract of C. odontophyllum<\/em> stem bark capable of being developed as an anticancer agent against HCT 116 colorectal cancer cell. <\/p>\n\n\n\n

Acknowledgement<\/strong><\/p>\n\n\n\n

Instrument used in this study has been supported by Makmal Pencirian Struktur Molekul (MPSM), Centre for Research and Instrumentation Management (CRIM), Universiti Kebangsaan Malaysia (UKM).<\/p>\n\n\n\n

Conflict of Interest<\/strong><\/p>\n\n\n\n

No conflict of interest. <\/p>\n\n\n\n

Funding<\/strong> Sources<\/strong><\/p>\n\n\n\n

This project was funded by research code grant Research University Grant DIP-2018-034.<\/p>\n\n\n\n

Author Contributions<\/strong><\/p>\n\n\n\n

Assoc. Prof Dr\nDayang Fredalina Basri designed and lead the project. Siti Fairuz Ishak\nperformed the experiment and prepare the manuscript. Prof. Dr Fadilah Rajab\nsupervised the experiment.<\/p>\n\n\n\n

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