LIST OF SENIOR PROJECTS

1978

1

The Food-dye Extraction from Lae
Abstract -
1979

2

Chemical Constituents of Flowers of Delonix regia
 
Abstract
Crude ethanolic extract from flowers of Delonix regia was used for phytochemical screening test. It was shown that there were no cardiac glycoside, saponin or coumarin. However, there were leucoanthocyanin (flavonoid pigment) and alkaloid (quarternary alkaloid and/or amine oxide base). 205 gm of crude ethanolic extract (32.3%) was treated with ether, then the ether extract was washed with acid and then with alkalis. Only 0.51% by weight of the crude extract of the acid-dissolved and alkali-dissolved substances were obtained. Ether was completely evaporated from the neutral fraction, the residue of 2.2% by weight of the crude extract then analysed by column chromatography using alumina as packing material. 0.16 gm of pure crystal (0.08% by weight of the crude extract) with m.p. 138-138.5?C was obtained from the petroleum ether-chloroform fraction (3:1). The results of chemical, physical investigation and IR spectrum of the crystal indicated that it was b -sitosterol. The other fractions from the column chromatography were oily and the colors varied from light yellow to yellowish-red. Thin layer chromatography showed a mixture of substances present. Some fractions contained nitrogenous compound.

3

The Determination of the Chemical Compositions of Leaves and Stems of Coccinia indica
 
Abstract
Coccinia indica is a vegetable which has been found in many countries in Asia and Africa, and also in Thailand. Leaves of Coccinia indica are part normally eaten. Chemical compositions of the vegetable has been investicated (1)-(8). The stems and leaves of Coccinia indica growing in Thailand, are reported medicinally in lowering sugar in the blood, however there are no details on chemical compositions.
The study was done by extracting fresh leaves with 80% ethanol and the ethanolic extract was reextracted with petroleum ether and chloroform respectively. Chemical tests showed that flavonoid, steroid were present in petroleum ether extract; flavonoid, steroid, organic compounds with mild reducing property were present in chloroform extract; reducing sugar and amino acids were present in aqueous ethanolic extract. White needle crystal with m.p. 76.5-78.5?C was isolated from the petroleum ether extract by alumina column chromatography. The other white needle crystal with m.p. 69.5-71.0?C was isolated from the chloroform extract by silica gel column chromatography. The evidence by paper chromatography using n-butanol : ethanol : H2O (2 : 2 : 1 by volume) as solvent indicated that there were six free amino acids; Aspartic acid, g -Aminobutyric acid, Alanine, Methionine, Threonine, and Valine containing in the aqueous ethanolic part.

4

Screening Tests for Saponins and Coumarins in Thai Medicinal Plants
 
Abstract
Four hundred and twenty four samples of Thai medicinal plants were tested for saponins and coumarins. The test for saponins were conducted on aqueous extracts from dried ground plants by Froth Test and the additional test on 80% ethanol extracts was performed by Liebermann-Burchard Test. For the coumarin tests the moist ground plants were used and tested by ultraviolet light.
The result showed that sixty six samples of the plants gave positive test for saponin; twenty two samples were steroidal sapogenin; twenty-four samples were triterpenoidal sapogenin; twenty samples were unidentified. Three samples gave positive test for coumarins.
1980

5

Phytochemical Screening Test for Cardiac Glycosides in Thai Medicinal Plants
 
Abstract
Cardiac glycoside is a group of organic compounds, usually of plant origin and comprising of a sugar-portion linked to a non-sugar moiety in a particular manner. Cardiac glycosides are used therapeutically to strengthen a weekened heart and thus allow it to function more efficiently. The therapeutic efficiency depends both on the structure of the genin and the type and manner of sugar units to which it is attached. In a phytochemical screening program for cardiac glycosides, initial extraction on plant materials using 80% ethanol should be treated with lead (II) acetate to precipitate tannin and then extracted with chloroform. Chemical tests applied to the detection of cardiac glycosides are carried out by applying three reagents to the extract to detect the steroid nucleus, the unsaturated lactone ring at C17, and the deoxy sugar at C3. These reagents are Liebermann-Burchard, Kedde, and Keller-Kiliani reagents respectively. The result of the investigation of cardiac glycoside from 414 samples of thai medicinal plants, cardiac glycoside was definitely present in 17 samples of plants, in the other 9 samples the test indicated the possibility of the cardiac glycoside presence. Most of the plants (about 300 samples) gave positive test for steroid nucleus which may exist freely of as a glycoside. Steroid nucleus, unsaturated lactones and deoxy sugars were not present in 22 samples.

6

The Screening Test of Flavonoid Compounds in Thai Medicinal Plants
 
Abstract -

7

Phytochemical Screening Test for Alkaloids in Thai Medicinal Plants
 
Abstract
Four hundred and forty samples of Thai medicinal plants were tested for alkaloids. The study was done by extracting ground dried plant with 80% ethanol and crude ethanolic extract was treated with 2 M. HCl. The acid dissolved solution was preliminary tested for alkaloid and quaternary amine and or amine oxide base by precipitating with alkaloid reagents. And 231 samples were found to contain alkaloids.
1981

8

The Determination of the Chemical Composition of Leaves of Streblus asper Lour.
 
Abstract
Dry leaves of Streblus asper Lour. were extracted with hexane and ethanol respectively. The results from preliminary tests of the crude hexane extract indicated the presence of steroids, triterpenoids and mild reducing organic compounds while the ethanolic extract contained alkaloids, free deoxy sugars and reducing sugars. The crude hexane extract was separated by column chromatography using silica gel as an absorbent. The following were obtained, namely, myricyl acetate (m.p. 70-71?C), a triterpenoid (m.p. 213-215?C) and 4 unidentified compounds (m.p. 94-95?C, 86-87?C, 67-67.5?C and 56-58?C respectively).
The crude ethanolic extract was further extracted in successive order by hexane, chloroform, ethyl acetate, ethanol and water. Preliminary tests of each extracted portion indicated that three steroids were present in the hexane portion, whereas free deoxy sugars were found in both hexane and chloroform portions. Furthermore, positive test for alkaloids from the crude ethanolic extract was performed and yielded some free alkaloids with high polarity.

9

Chemical Constituents of Streblus asper Lour. (Wood)
 
Abstract
Two crystalline compounds, m.p. 136-137?C and 217-220?C, were isolated from the crude hexane extract of the ground dried wood of Streblus asper Lour. Their physical properties, chemical reactions and spectral data confirmed the compound having m.p. 136-137?C to be b -sitosterol (C29H50O). The other compound, m.p. 217-222?C, was found to be a triterpenoid, probably the a -amyrin acetate. The phytochemical screening of the crude ethanolic extract gave the positive test for alkaloids and cardiac glycosides.

10

Chemical Constituents From Petroleum Ether Extraction of Lagerstromia Flosresginae, Retz Leaves
 
Abstract
Three different types of compounds, m.p. 55-57?C, m.p. 74-75?C and m.p. 83-84?C, were isolated from crude petroleum ether extracts of ground dried Lagerstromia Floresginae, Retz leaves and the structure of them were investigated.
From spectroscopic data and chemical properties; the solid m.p. 55-57?C, was found to be a mixture of long chain hydrocarbons, hentriacontane (C31H64) and tritriacontane (C33H68). The analysis of compound, m.p. 74-75?C, fitted best the melecular formular C50H100O2, which was found to be a long chain ester, dotriacontanyl n-octadecanoate; and the compound, m.p. 83-84?C, was concluded to be a long chain alcohol, 1-hentriacontanol (C31H64O).

11

Chemical Constituents in the Root of Streblus asper Lour.
 
Abstract
The root of dried Streblus asper Lour. was ground and extracted with hexane. The crude extract was very difficult to separate and purify. Column chromatography was performed twice together with one short column chromatography and one preparative thick-layer chromatography; the white solid, m.p. 179-183?C was finally separated.
The dried ground root then was extracted with 95% ethanol. The presence of glucose was identified by the technique of paper chromatography. Considerable amount of KCl was found and identified by ordinary chemical method and atomic absorption spectroscopy. The remaining was a solid with buff color which was very hygroscopic.
1982

12

Chemical Constituents of Leaves of Streblus asper Lour.
 
Abstract
Four crystalline compounds, m.p. 65-66?C, 70-71?C, 80-84?C and 136-137?C, were isolated from the crude hexane extract of the ground dried leaves of Streblus asper Lour. Their physical properties, chemical reactions and spectral data confirmed the compound having m.p. 136-137?C to be the b -sitosterol, m.p. 70-71?C and 65-66?C seem to be the myricyl acetate and octacosyl acetate, compound m.p. 80-84?C requires further purification. Four crystalline compounds, m.p. 43-45?C, 47-48?C, 52-53?C and 65-67?C were isolated from the crude chloroform extract require further purificaton.

13

Sorbitol from Cassava Starch
 
Abstract
This project had hydrolyzed cassava starch to reducing sugar by termamyl enzyme and amyloglucosidase enzyme, and studied the proper condition of hydrolysis by vary pH and time. The most proper condition was using termamyl enzyme at pH 7.0-8.0, temperature 90-95?C and amyloglucosidase at pH 4.0-5.0, temperature 60?C which got reducing sugar 96%. And reducing sugar was reduced to sorbitol by hydrogenateion with raney mickel as catalyst. High percentage yield of sorbitol was got by hydrogenation at high temperature and high pressure. Besides, this project studied the proper method to the determination of reducing sugar in 3 method, volumetric titration, gravimetric method and spectrophotometric method.
1983

14

Chemical Constituents from the Bark of Amoora gigantea Picrre ex Laness
 
Abstract -

15

The Chemical Composition of Stems of Zizyphus attopoensis Pierre
 
Abstract
Dry stems of Zizyphus attopoensis Pierre were extracted with hexane. The crude hexane extract was separated by column chromatography using alumina as an adsorbent. Four compounds were obtained (m.p. 136-137?C, 154-155?C, 147-148.5?C and 151-153?C respectively). Preliminary tests of these four compounds indicated that they are steroids.

16

Chemistry and Utilization of Pluchia indica and Wedelia urticacfolia
 
Abstract
Pluchia indica leaves and Wedelia urticacfolia leaves underwent hydrostem distillation, Pluchia indica leaves yielded 0.017% of oil while 0.014% of oil was obtained from Wedelia urticacfolia leaves. The analysis of Pluchia indica leaves oil by gas chromatography-mass spectrometer (GC-MS) indicated the presence of 7 compounds, including 2 monoterpene alcohols, 1 sesquiterpene hydrocarbon and 4 sesquiterpene alcohols. These compounds accounted for 81.82% of the oil. By comparison with standard mass spectrum indicated that sesquiterpene hydrocarbon is b -caryophyllene which accounts for 7.89% of the oil and one of sesquiterpene alcohol is b -santalol which accounts for 10.69% of the oil. The analysis of Wedelia urticacfolia leaves oil by the same method indicated the presence of 5 compounds, including 1 sesquiterpene hydrocarbon, 2 sesquiterpene alcohols and 2 other compounds. These compounds accounted for 33.44% of the oil. The crude dichloromethane extraction of dry stem of Pluchia indica was separated by column chromatography using silica gel as an adsorbent. Two solid compounds were obtained. One which has melting point 167-168?C is stigmasterol. The amount of another solid obtained was too small to be identified.

17

Chemical Constituents of Crataeva nurvala Ham. (Stem-bark)
 
Abstract
Five crystalline compounds, m.p. 66-7?C, 86?C, 212-3.5?C, 137-8.5?C and 232-5.5?C, were isolated from the crude hexane extract of the ground and dried stem-bark of Crataeva nurvala Ham. Their physical properties, chemical reactions and spectral data indicated that the first compound was a long chain hydrocarbon, possibly hentriacontane (C31H64) with traces of tritriacontane (C33H68). The second compound was thought to be a long chain alcohol which could be myricyl alcohol (C30H62O). The third and the fourth compounds were confirmed to be lupeol (C30H50O) and b -sitosterol (C29H50O) respectively. The last compound was a steroid, the quantity of which was not sufficient to elucidate.
1984

18

Chemical Constituents from the Flower of Tridax Procumbens Linn.
 
Abstract   in Thai

19

The Determination of Some Chemical Constituents in the Stems of Zizyphus attopoesis Pierre.
 
Abstract
Three compounds were isolated from the crude chloroform extract of the dried stems of Zizyphus attopoensis Pierre. They were purified and characterized as stigmasterol (m.p. 155-157?C), a glycoside (m.p. 285-287?C) which was hydrolysed to produce glucose and a steroid, and possibly a g -lactone (m.p. 284-286?C). The structural elucidation of these compounds was carried out by means of spectroscopic and chromatographic techniques as well as comparisons with its authentic sample such as stigmasterol.

20

Chemistry and Utilization of Rhizophora apiculata
 
Abstract
The extraction of leaves, wood, branches, barks and roots of Rhizophora apiculata with dichloromethane and 95% ethanol yielded the crude dichloromethan extract 4.60%, 0.22%, 1.25%, 0.75% and 0.70% (w/w), the crude ethanolic extact 10.28%, 24.60%, 10.99%, 16.80% and 5.78% (w/w), and the inorganic salts which were mainly chloride salts of sodium, potassium and magnesium 0.78%, 0.02%, 1.17%, 0.22% and 0.08% (w/w) respectively. The crude ethanolic extract showed extremely antifungal activity against Helminthosporium teres. The crude ethanolic extract of leaves was then equilibrated between chloroform and water (1:1) by liquid-liquid extractor. The separation of crude chloroform extract by aluminium oxide column chromatography yielded 2 pure compounds. One, m.p. 80-83?C was obtained in small amount which was indufficient for structural identification and the other one which was decomposed at 280-283?C. Its physical properties, chemical reactions and spectral data confirmed that the latter compound was b -sitosteryl-3-O-b -D-glucopyranoside.

21

Chemical Constituents of Crataeve nurvala Ham (Leaf)
 
Abstract
Systematic extraction of the leaves of Crataeva nurvala led to the isolation of the unidentified hydrocarbon and ester from the hexane extract, tetratriacontanol (C34H69OH) and b -sitostryl-b -D-glucopyranoside from the ethanolic extract.

22

Chemistry and Utilization of Suaeda maritima
 
Abstract
The extraction of leaves, stems and roots of Suaeda maritima with dichloromathane and ethanol yielded the crude dichloromethane extract 1.28%, 0.84% and 0.47%, the crude ethanol extract 1.27%, 0.21% and 0.05% and the inorganic salts which were mainly sodium chloride 0.45%, 0.75% and 0.37% respectively. The crude dichloromethane extract showed boll weevil antifeedant activity (% T/C = 11) and both crude dichloromethane and ethanol extract showed moderated antifugal activity against Helminthosporium teres. The separation of the crude dichloromethane extract of leaves by silica gel column chromatography yielded 3 crystalline compounds, m.p. 84-85?C, 135-137?C and 62-64?C.
Their physical properties, chemical reactions and spectral data confirmed that the first two compounds were the mixture of saturated long chain alcohol (C28H58O, C30H62O and C32H66O) and b -sitosterol. The amount of the last compound was too small to be identified.

23

Chemical Constituents of Lagerstroemia Floresginae, Retz. Stem I
 
Abstract
Nine different compounds were isolated from the crude hexane extract of ground dried Lagerstroemia Florezginae, Retz stems by mean of column chromatography. The structures of five compound were investigated by their physical properties, spectroscopic data and chemical analyses. They were found to be hentriacontane (C31H64), tritriacontane (C33H68), dotriacontyl eicosanoate (C52H104O2), 1-dotriacontanol (C32H66O) and b -sitosterol. Besides these known compounds, unidentified steroidal ester, hydroxy ketone, triterpenoid and glycoside were also obtained.

24

Chemical Constituents of Lagerstroemia Floresginae, Retz. Leaves II
  
Abstract
Besides the four different compounds; hentriacontane (C31H64), tritriacontane (C33H68), dotriacontyl eicosanoate (C52H104O2) and 1-dotriacontanol (C32H66O), b -sitosterol (C29H50O) was also isolated from the crude hexane extract of Lagerstroemia Floresginae, Retz leaves. The yellow solid obtained from the crude ethanolic extract was found to be ellagic acid. Metal ions in the aqueous extract, such as K, Na, Ca, Zn, Fe, Cu and Al, were determined by Atomic Absorption Spectrophotometer.
1985

25

Chemical Constituents in Ethanolic Extract of Lagerstroemia flos-reginae, Retz. Leaves and Stems
 
Abstract
Dotriacontyl eicosanoate (C54H104O2) and 1-dotriacontanol (C32H66O) were isolated from the crude dichloromethane extract of dried Lagerstroemia flos-reginae, Retz. leaves by mean of column chromatography. Besides these known compounds, unidentified steroids, triterpenoids and esters were also obtained from dried stems. Ellagic acid and reducing sugars were found in the crude ethanolic extract which formerly extracted by dichloromethane of both leaves and stems while amino acids were found only in leaves. Metal ions, such as K, Na, Mg, Ca, Al, Fe, Zn and Cu wree determined by Atomic Absorption Spectrophotometer.

26

Chemical Constituents from Stems of Acalypha siamensis Oliv. ex Gage
 
Abstract
From the stems of Acalypha siamensis oliv. ex gage; four crystalline compounds, m.p. 68-69?C, 82-83?C, 76.5-78?C and 143-146?C, were isolated from the crude hexane extract (0.28% w/w), their physical properties, chemical properties and spectral data confirmed that the first compound was a crystalline mixture of long chain hydrocarbons (heptacosane, octacosane, nonacosane, triacontane, hentriacontane, dotriacontane, tritriacontane, tetratriacontane and pentatriacontane). The second compound was tridecanyltetraconsanate (C37H74O2, I), the third was tetratriacontanoic acid (C34H68O2, II) and the fourth was the mixture of stigmasterol (C29H48O, III) and b -sitosterol (C29H50O, IV).
The crude water extract (0.80% w/w) gave galactose and glucose, together with amino acid proline, tyrosine, aspartic, valine, alanine, serine, threonine, phenylalanine and arginine.
From the crude chloroform extract (0.40% w/w), a white solid m.p. 71-73?C was obtained. The IR spectrum showed the presence of carboxylic group and further characterization is in progress.

                

                (I)                                     (II)

                               (III)                                          (IV)

27

Chemical Constituents from the Flowers of Tridax procumbens Linn.
 
Abstract
The crude methanol extract after hexane extraction was extracted by chloroform and 1-butanol respectively. The two compounds isolated were identified by means of infrared spectrum, nuclear magnetic resonance spectrum and mass spectrum. One substance, white needle, was the mixture of stigmasterol and b -sitosterol, m.p. 146-149?C. Another substance, white powder, was the mixture of stigmastrylglucoside and b -sitosterylglucoside decomposition point 226-228?C.

28

Chemical Constituents of Streblus asper Lour.
 
Abstract
Five crystalline compounds, m.p. 77-8?C, 222-3?C, 210-3?C, 136-7?C and 75-6?C, were isolated from the crude hexane extract of the ground and dried wood of Sterblus asper Lour. Their physical properties, chemical reactions and spectral data indicated that the first compound was an ester of b -sitosterol and long chain carboxylic acid. The others were confirmed to be a -amyrin acetate (C32H52O2), lupeol acetate (C32H52O2), b -sitosterol (C29H50O) and hexacosanoic acid (C26H52O2), respectively. The extraction of the methanolic fraction between dichloromethane and water led to K+, Mg2+,PO43-, SO42-, Cl-, salts of low molecular weight amines, glucose and fructose in aqueous layer and unpurified lactones in dichloromethane layer.
1986

29

Chemical Constituents of Suaeda maritima <L.> Dum.
 
Abstract
The extraction of the over ground (leaves, branches and stems) of Suaeda maritima with dichloromethane and ethanol yielded the crude dichloromethane extract 4.27% and the crude ethanol extract 11.10%. The crude dichloromethane extract showed the boll weevil antifeedant activity (% T/C = 11) and both crude dichloromethane and ethanol extract showed moderate antifungal activity against Helminthosporiumteres. The separation of the crude dichloromethane extract by silica gel column chromatography yielded 2 compounds, m.p. 74-76?C and m.p. 84-85?C. Their physical properties, chemical reactions and spectral data indicated that the first compound was wax (C30-C32) of long chain fatty acid and long chain alcohol and the second compound was the mixture of saturated long chain alcohol (C28H58O, C30H62O and C32H66O). The equilibration of the ethanol crude extract with CHCl3:H2O (1:1) yielded the chloroform soluble part and water soluble part 1.62% and 3.98% respectively. The separation of the chloroform crude extract by aluminium oxide column chromatography yielded 2 compounds, one was b -sitosterol and the other, m.p. 143-145?C, was too small to be identified. The quanlitative analysis of the water soluble part found rhamnose, 14 amino acids and chloride salts of sodium, potassium and magnesium.

30

Chemical Constituents of the Leaves Bridelaia tamantosa Blume.
 
Abstract  -

31

Chemical Constituents from the Fruits of Piper ribesoides Wall.
 
Abstract  -
1987

32

Chemical Constituents from the Fruits of Piper ribesoider Wall.
 
Abstract
The fruits of Piper ribesoides Wall. were extracted by hexane and ethanol consecutively. The ethanol extract was further tritulated with chloroform-water. The novel ester isolated from the crude chloroform extract was identified as 2-isobornyl-(4-hydroxy)cinnamate melting point 164-165?C and molecular formular C19H24O3. Its structure was elucidaton on the basis of physical properties, chemical properties, spectral data and x-ray crystallography.
However, the crude chloroform extract still composed of at least 5 compounds in essential oil, but have to be further studied their structure.

33

Chemistry and Comparison of Constituents in the Parts of Acanthus ilicifolius Linn. & Acanthus ebracteatus Vahl.
 
Abstract
This study and comparison of constituents of Acanthus ilicifolius (Linn.) and Acanthus ebrateatus (Vahl.) used the method that homogenized each fresh parts; leaves, stems, flowers, fruits and roots of 2 species with chloroform-methanol-water. This method is suitable for the extraction of lipid compounds from fresh parts and it consume less time and solvent. Crude extracts were separated into two fractions; the chloroform fraction and the methanol-water fraction. The followings were found in the CHCl3 fractions of 2 species; steroid compounds in all parts especially in leaves and fruits of A. ilicifolius, Benzoxazoline-2-one in stems, fruits and roots of A. ilicifolius and roots of A. ebrateatus, stigmasteryl-b -D-glucopyranoside in fruits and roots of A. ilicifolius and fruits of A. ebrateatus, b - and a -amyrin in leaves of A. ebrateatus. Those lipids which were mentioned above showed only very small amount all TLC of the methanol-water crude extracts but the detection under ultraviolet light indicated that further investigation should have done. The preparative TLC of the methanol-water extracts of the fruits of A. ilicifolius yielded 3 pure compounds, compound A m.p. 217-218?C, compound B m.p. 224-226?C and compound C which decomposes at 243-246?C. The IR spectra indicated that they were glycosides. The proton NMR and Mass spectra of the first two compounds suggested that the aglycones of both compounds were flavonoids. The amount of those 3 isolated compounds is not enough to identifed the structure.

34

Chemical Constituents of the Wood of Bridelia tomentosa Blume.
 
Abstract
The dried woods of Bridelia tomentosa Bl. were extracted by methanol, the crude methanolic extract then was extracted by hexane and chloroform. The crude hexane and chloroform extracts were separated by means of column chromatography using silica gel as an adsorbent. Hexane, chloroform and methanol were used as eluents consecutively. After many purifications using the technique of preparative thin-layer chromatography, recolumn chromatography and recrystallization, the mixture of two solids were obtained. From physical properties, chemical analyses and spectroscopic data, the mixture was found to be steroids, m.p. 135-141?C. One of the two compounds is stigmaterol, C29H48O and the other one is b -stigmasterol, C29H50O3.
The tests for flavonoids, coumarins, alkaloids, saponins, cardiac glycosides and tannins were also reported.

35

Chemical Constituents of the Barks of Bridelia tomentosa Blume.
 
Abstract
The dried ground barks of Bridelia tomentasa Bl. were extracted by methanol. The crude methanolic extract then was extracted by hexane and chloroform. The hexane and chloroform extracts were column chromatographed using silica gel as an adsorbent. Three solids were separated. From physical properties, chemical analyses, and spectroscopic data, the first substance, white needles with m.p. 147-152?C is the mixture of stigmasterol and b -stigmaterol C29H48O and C29H50O respectively. The second substance, white amorphous solids with m.p. 84-85?C is expected to be the mixture of long chain carboxylic acids, dotriacontanoic acid (C32H64O2) and tetratriacontanoic acid (C34H68O2). The third substance, C32H52O3, white needles with m.p. 151-153?C is expected to be a triterpenoid may be either 24,24-dimethyllanosta-7(8), 25-diene-3-one or 24,24-dimethyllanosta-9(11), 25-diene-3-one. The structure is still being investigated.

36

Chemical Constituents of the Root of Derris trifoliata Lour.
 
Abstract
Five compounds, m.p. 79-80?C, 167-168.5?C, 212-214?C, 222?C (dec.) and 75-76?C, were isolated from the chloroform soluble fraction of the crude ethanolic etract of the ground and dried root of Derris trifoliata Lour. Their physical properties, chemical reactions and spectral data indicated that the first three compounds were hexacosanol (C26H54O), stigmasterol (C29H48O) and lupeol (C30H50O). The fourth compound, decomposed at 222?C, was expected to be the methyl and methoxy substituted flavonoid with molecular weight 406. The compound was a mixture of this compound is being investigated. The fifth compound was a mixture of long chain fatty acids of molecular formula C26H52O2, C28H56O2 and C30H60O2. In addition, K+, Na+, Mg2+,Zn2+, Fe2+, Cl-, amino acids, glucose, fructose and sucrose could be detected in the water soluble fraction.
1988

37

Sorbitol Synthesis
 
Abstract
The most proper method for analysis the mixture solution of sorbitol and glucose was the titration of glucoss by Fehling’s solution. On the variation of reaction conditions for catalytic reduction of glucose to sorbitol, the optimum condition of the experiment was 60% concentration of glucose solution, at pH 8.5, 25 grams of Raney Nickel, temperature 120-130?C, pressure 200 pounds/quare inch, reaction time 3 hours. The reaction of the optimum reaction yielded sorbitol 97%.

38

Chemical Substances from Baliospermum axillare Blume. (Stem)
 
Abstract
Systematic extraction of the ground and dried stem of Baliospermum axillare Bl. led to the isolation of five compound, mp. 138-143?C, 292-293?C, 196-199?C, 91-93?C and 255?C (dec.). The first four compounds were isolated from the hexane extract and the fifth from the dichloromethane extract. Their physical properties, chemical reactions and spectral data indicated that the first one was a mixture of b -sitosterol and stigmasterol. The others were 3a -acetoxytaraxer-14-en-28b -oic acid, 5a -stigmastane-3,6-dione, stigmast-4-en-3-one, a mixture of b -sitosterryl-b -D-glucopyranoside and stigmasteryl-b -D-glucopyranoside respectively.
1990

39

Chemical Constituents of the Root of Suregada multiflorum <A. Juss> Baill.
 
Abstract
The ground rhizomes of Zingiber rubens Roxb. were processed by steam distillation. Both dried and fresh rhizomes gave the same bluish-green essential oil (0.40% of dried rhizomes and 0.28% of fresh rhizomes). Analyses of essential oil by gas chromatograph-mass spectrometer (GC-MS) showed that twelve compounds were the main components of the oil (84.05%). Four of these compounds were identified by computer as a -pinene, conphene, b -pinene and compaene.
The residue from steam distillation was extracted with acetone by maceration. Then the acetone extract was separated by means of quick column chromatography using siliga gel as an adsorbent. Five substances were obtained. From physical properties, chemical analyses, and spectroscopic data, one of these substances, apparently a mixture of crystals between white shining plates and white needles with m.p. 134-139?C was found to be the mixture of stigmasterol (C29H48O) and b -sitosterol (C29H50O). The other four substances are still being investigated. However, three of them, yellow substances with m.p. 174-176?C, 172-173?C and 213-215?C are expected to be phenolic compounds. The fifth substance, white solid with m.p. 121-124?C is expected to be aliphatic alcohol.
The tests for metals and non-metals, amino acids and sugars were also reported.

40

Chemical Constituents of Zingiber rubens Roxb.
 
Abstract
The ground dried roots of Suregada multiflorum (A.Juss.) Baill. were extracted with hexane, chloroform and methanol respectively. The hexane, chloroform and methanol extracts were separated by quick column chromatography using silica gel as an adsorbent. Three solid substances were obtained. From physical properties, chemical analysis and spectroscopic data, the first substance, whited amorphous solid with m.p. 77-80?C, was believed to be the mixture of five compounds containing long chain aliphatic esters and long chain aliphatic hydrocarbons. The second substance small white needles with m.p. 205-206.5?C was the mixture of three triterpenoids with molecular formular C30H50O. Two triterpenoids searched by computer were believed to be a -amyrin and bauerenol (D:C-Friedours-7-en-3-ol(3.beta)). The third substance, small white cubes with m.p. 171-176?C was believed to be sucrose.

41

Chemical Constituents of Root Breynia glauca Craib.
 
Abstract
The biological and chemical constituent study of leaves of Hyptis sauveolens Poit. showed that the 95% ethanol extracts (2.39% w/w) were known to have antifungal and rice growth inhibitor activity. Silica gel quick column chromatography of the crude ethanol extracts were separated to 5 fractions. The fractions number 2 and 3 were shown high rice growth inhibitor effect both to rice leaf and root length at dose 0.1 gram. The 8 combined fractions of the result of re-column chromatography of the fraction number 2 were subjected to the rice growth inhibitor bioassay and the combined fraction number 5 were shown to inhibit, 3.38% of root length and 24.92% of the leaf length at dose 0.01 gram. The fraction number 5 were separated by HPLC into 8 fractions. All fraction show high inhibition of rice root especially the fraction number 1-3 were shown 100% inhibitor of the root length at dose 0.0005 gram. While every fractions were not shown higher inhibitor of the leaf length than the substance isolation before the HPLC separation. Separation and purification yield 4 compounds. The first substance, white amorphus solid, with m.p. 52-54?C is expected to be the long chain hydrocarbon. The second substance, white needles, with m.p. 135-137?C is b -sitosterol. The third and the fourth substances, white amorphous solids, with m.p. 175-177?C and 250-253?C repectively which has not been known yet.

42

Chemical Constituents of Hyptis suaveolens Poit. <Leaves>
 
Abstract  -
1991

43

Chemical Constituents from Leaves of Derris trifoliata Lour.
 
Abstract
Three compounds, m.p. 214-215?C, 129-130?C and 93-95?C were isolated from the chloroform soluble fraction of the crude ethanolic extract of the ground and dried leaves of Derris trifoliata Lour. Their physical properties, chemical reactions and spectral data indicated that the first substance was the mixture of b -amyrin (C30H50O) and lupeol (C30H50O), the second was the mixture of b -sitosterol (C29H50O), stigmasterol (C29H48O) and campesterol (C28H48O) and the third compond, m.p. 93-95?C, was expected to be flavanone of the molecular formula C25H28O5. The complete structure of the third compound is being investigated.
1992

44

Chemical Constituents of the Leaves of Breynia glauca Craib
 
Abstract
The ground dried leaves of Breynia glauca Craib were extracted with hexane, dichloromethane and methanol respectively. The hexane and dichloromethane extracts were separated by quick column chromatography using silica gel as an adsorbent. The substances separated by quick column chromatography were purified by means of recrystallization, recolumn chromatography and preparative high performance liquid chromatography (preparative HPLC). Three solid substances were obtained. From physical properties and spectroscopic data, the first substance, lustrous white plate C30H62O, mp. 83.0-83.5?C was believed to be a saturated long chain alcohol, 1-triacontanol. The second substance, white plate, mp. 61.0-62.0?C was believed to be a mixture of saturated long chain hydrocarbons. The third substance, white amorphous solid, mp. 76.0?C was believed to be a mixture of long chain esters.

45

Chemical Substances from the flowers of Lilium primulinum, Bak. var. burmanicum (Stearn)
 
Abstract
Systematic extraction of the ground and dried flowers of Lilium primulinum, Bak. var. burmanicum Stearm. Led to the isolation of 8 compounds, m.p. 58.0, 79.0-80.0, 81.0, 107.0-108.0, 74.0-75.0, 129.0-130.0, 281.0-282.0 (dec.) and 275.0-276.0?C. The first four compounds were isolated from the hexane extract, the fifth and sixth compounds were found in both hexane and methanolic extract and the last two compounds were isolated from the methanolic extract. Their physical properties, chemical reactions and spectral data indicated that the first one was a mixture of saturated long chain hydrocarbons (C25 – C31), the second was a mixture of aliphatic esters of saturated long chain carboxylic acids (C15, C16 , C21, C22, C24 , C26, C28, C29, C32, C34) and saturated long chain alcohols (C26 – C31). The third was a mixture of saturated long chain alcohols (C27, C29 – C31). The fourth was cycloartenone or 9,19-cyclolanost-24-en-3-one (C30H48O). The fifth was a mixture of saturated long chain carboxylic acids (C16, C18, C21, C22, C23 , C25, C26, C28, C30, and C33). The sixth was a mixture of cholesterol (C27H45O), campesterol (C28H48O), stigmasterol (C29H48O) and b -sitosterol (C29H50O). The investigation of the last two compounds is in progress.
1993

46

Chemical Substances from the leaves of Baliospermum axillare Blume.
 
Abstract
Systematic extraction of dried leaves of Baliospermum axillare Bl. Led to the isolation of eleven substances. Three of them are solid which melt at 71.0-72.0, 135.0-137.0 and 88.0-89.0?C and eight substances are oil. The first two solid substances and all of the eight oils were isolated from the hexane extract, the third solid was found in both hexane and dichloromethane extract. Their physical properties, chemical reactions and spectral data indicated that the first one was a mixture of saturated long chain hydrocarbons (C29 - C34), the second was a mixture of b -sitosterol (C29H50O) and stigmasterol (C29H48O). The third substance was a mixture of saturated long chain alcohols. The hexane extract consists of C30, C32, C34 and C35. The dichlorometane extract consists of C30, C32, C34 and C36. The fourth substance which is oil was expected to be triglycerides of 12-methyltridecanoic acid and 14-methylpentadecanoic acid with some other components. The other only substances were not investigated.
1995

47

Chemical Substances from the Nuts of Calophyllum inophyllum Linn.
 
Abstract
Systematic extraction of the dried and ground nuts of Xalophyllum inophyllum led to the isolation of six substances. Four of them can be identified according to their physical properties, chemical reactions and spectral data. Calophyllolide was found in both the hexane and dichloromethane ectracts. Inophyllolide (cis and trans) was found in the hexane extract. Stigmasterol and a mixture of stigmasteryl-3-O-b -D-glucopyranoside, b - stigmasteryl-3-O-b -D-glucopyranoside and campesteryl-3-O-b -D-glucopyranoside were found in the dichloromethane extract. Investigation of two unknown compounds, one from the dichloromethane extract and one from hexane, is in progress. In addition, the saponifiable matter of the crude hexane exact was methylated. The GC-MS of the methyl ester showsfour fatty acids : Palmitic acid, stearic acid, oleic acid and linoleic acid.
 

48

Structure and Galleria mellonella's Antifeedant Activity Relationship Studies of Eugenol and Related Compounds
 
Abstract
Twenty-one compounds stemmed from eugenol, its derivatives and related compounds were synthesizied. Those compounds shared some common features:

Where: R1: -CH2CH=CH2 or –CHO or –COOH or –CH2OH or –CH=CHCOOH or CH-CH-COOCH3
R2: -CH2Ph or -CH3 or –H

R3: -H or –CH3 or –CH2CH3 or –CH2Ph or –C(O)CH3 or CH2COOH or –C(O)Ph

The eugenol and the synthesized compounds were subsequently evaluated for the antifeedant activity against Galleria mellanella. It was found that there was a relationship between the structures and antifeedant activity. When R1 and R3 were small and less polar substituents and R2 was a large group, the tendency of antifeedant was high. Moreover, it was observed that a liquid sample revealed a better activity than that of a solid sample.

49

Agrochemical substances from Root of Cogongrass (Imprtata cylindrica)
 
Abstract  -

50

Chemical Constituents of the Flowers of Sonneratia caseolaris Engl.
 
Abstract
Dried flowers of Sonneratia caseolaris Engl. Were extracted with hexane, dichlorometane, ethyl acetate and methanol. Fractionation of crude extracts by column chromatography led to the isolation of ten substances. Eight substances were characterized by mean of physical properties, TLC with authentic samples, chemical reactions and spectral data. Eight substanes were a mixture of straight long chain hydrocarbons (C23-C33), a mixture of straight long chain esters, a mixture of straight long chain alcohols (C26, C30, C33), a mixture of steroids (b -sitosterol and stigmasterol), kaempferol, qrercetin, gallic acid and b -sitosterol -3-O-b -D-glucopyranoside. The investigation of the other two compounds is in progress.
1996

51

A Search for Bioactive Compounds from Phyllanthus niruri Linn.
 
Abstract
From preliminary bioassay results indicated that the chloroform and ethylacetate crude extracts of the whole plant of Phyllanthus niruri Linn. were slightly high toxicity to brine shrimp. Fractionation of crude extracts by chromatography techniques led to the isolation of 4 substances. All isolated substances were characterized by mean of physical properties, TLC with authentic samples, chemical reaction and spectroscopic evidences. Three substances found in chloroform crude extract ere a mixture of lomg chain alcohols, a mixture of long chain carboxylic acid and a mixture of steroides (major component: cholesterol). One compound found in ethyacetate crude extract was gallic acid. This compound exhibited LC50 5.3655 m g/ml in the brine shrimp lethality assay and inhibited rice growth (1.5 g/cellulose 1.5 g), 87.32 % inhibition for root and 100 % for shoot.

52

Chemical Constituents and Biological Activity of Boesenbergia pandurata
 
Abstract -

53

Chemical Constituents and Biological Activity of Rhinacanthus nasutus Kurz.
 
Abstract  -
1997

54

Structure and Mimosa pigra Linn. Antigrowth Activity Relationship Studies of Cinnamic Acid and Derivatives and Dicoumarol Compounds
 
Abstract
Eleven cinnamic acid derivatives deived from Knoevenagel condensation between malonic acid and interested aromatic aldehydes and fifteen dicoumarols attained from nucleophilic substitution reaction between 4-hydroxycoumarin and interested aromatic aldehydes were synthesized. All synthesized compounds were subsequently evaluates for the antigrowth activity of Mimosa pigra Linn. It was found that both groups of compounds revealed promising activity. The representatives that showed higher activity were composed of halogen, methoxy and hydroxy substituents. Several synthesized compounds were found to be comparable to availably commercial herbicides and showed promising tendency to develops to be new agrochemicals.

55

Chemical Constituents and Biological Activity of the Flowers of Calophyllum inophyllum Linn.
 
Abstract
Dried flowers of Calophyllum inophyllum Linn. Were extracted with hexane, dichloromethane and methanol, respectively. The crude hexane and methanolic extracts showed antibacterial activity against Staphylococcus aureus, Salmonella derby and Bacillus cereus. Fractionation of these two crude extracts by column chromatography led to the isolation of seven substances. Five substances were characterized by mean of physical properties, TLC with authentis samples and spectral data. Five substances were a mixture of long chain esters and a mixture of long chain alcohols (C28,C30,C33) which found in the hexane extract and a mixture of steroids (stigmasterol, b -sitosterol ), quercetin and myricetin were found in methanolic extract. The investigation of the other two substances is in progress.
The bioassay results indicated that myricetin and aromatic compound (T7) showed antibacterial activity against Bacillus cereus and Staphylococcus aureus at dose level 300 microgram/disc. Besides, myricetin also showed activity against Escherichia coli.

56

Comparative Chemical Constituents of Young and Mature Betel Nuts (Areca catechu Linn.)
 
Abstract
This study focused on the comparison of chemical constituents between young and mature betal nuts. The peal of fresh young betal nuts and peal of dried mature betal nuts were extracted tannin with acetone, water, ether, ethyl acetate and butanol, respectively. For tannin extract from peal of young betal nuts and peal of mature betal nuts yielded 13.71 % and 34.98% by weight, respectively. The peal and kernal of young betal nuts and mature betal nuts were extracted alkaloids with ether, methanol and ethyl acetate, respectively. For alkaloids extract from peal of young betal nuts, peal of mature betal nuts, kernal of young betal nuts and kernal of mature betal nuts yielded 17.56%, 16.97% , 19.12% and 34.79% by weight, respectively.
Each crude extract was fractionated by open column chromatography and then analyzed the isolated substances with HPLC by compares with standards arecaidine and Arecoline. The qualitative and quantitative analysis results indicated that arecaidine and arecoline contained in kernal of young betal nuts 0.1929% and 0.2805% by weight of fresh young betal nuts, respectively. For the mature betal nuts contained arecaidine and arecoline 0.4087% and 0.313% by weight of fresh mature betal nuts, respectively.

57

Structure and Bioactivity Relationship Studies of Flavonoids and Related Compounds
 
Abstract
Twenty-one compounds in the class of flavanones, flavones, chalcones and related compounds were synthesized. These compounds were subsequently evaluated for the antibacterial activity, the activity of root and shoot of giant mimosa and the brine shrimp toxicity test. It was found that flavanone bearing chlorosubstituent at C-4 possessed mire antibacterial activity than that at C-2 and chalcone with methoxy substituent at C-4 revealed more antigrowth activity on the shoot of giant mimosa. Furthermore, chalcone with bromo substituent at C-3 provided the best brine shrimp toxicity activity among the synthesized compounds.
1998

58

Chemical Constituents and Biological Activity of the Flowers of Mammea siamensis
 
Abstract
Dry flowers of Mammea siamensis Kosterm. Were extracted with hixane, dichloromethane, ethyl acetate and methanol respectively. The crude hixane extract showed antibacterial activity against bacillus cereus, Staphylococcus aureus, Listeria monocytogenes, and flat sour spoilage bacteria. Fractionation of this crude extract by column chromatography lec to the isolation of five substances. Four substance were characterized by mean of physical properties, GC, TLC with authentic samples and spectral data. Four substances were a mixture of steroids (stigmasterol, b -sitosterol(T1), 6-butyryl-5-hydroxy-4-phenylseselin(T2), 5-hydroxy-6-(2-methylpentyryl)-7,8-(2-a -hydroxyidopropyl-2,3-dihydrofuranyl)-4-phenylcoumarin(T4u), 5-hydroxy-6-pentyryl-7,8-(2-a -hydroxyisopropyl-2,3-dihydrofuranyl)-4-phenylcoumarin(T4l). The investigation of the other one (T3) is in progress.
The bioassay result indicated that T3 showed antibacterial activity against Listeria monocytogenes, Bacillus cereus and flat sour spoilage bacteria at dose level 300 microgram/disc.

59

Searching for Chemicals Possessing Mimisa pigra Linn. Antigrowth Activity
 
Abstract
Two approaches were carried out in order to search for chemicals that possess the antigrowth activity against Mimosa pigra Linn., i.e., extraction bioactive compounds from weeds and structure activity relationship study of synthesized compounds and biological activity.
In the case of extraction bioactive compounds from weeds, three weeds were selected. They are Cyperus rotundus Linn., Fimbristylis littoralis Gandich and Leptochloa chinensis (L.) Nees. from the bioassay results. It is clearly indicted that the dichloromethane crude extract from Cyperus rotundus Linn. At dose level 10,000 ppm reealed the modt antigrowth activity. In the view of synthesis of herbicides, two classes of compounds were prepared. They are 3 compounds in cinnamic acid with one heteroatom class and 20 compounds from phenoxyacetic acids and related compounds class. The bioassay results of testing these synthesized compounds on antigrowth activity of Mimosa pigra Linn. Showed that pyridine-2,6-dicarboxylic acid revealed interseting results. In addition, in phenoxyacetic acid class, most compounds that showed activity are those contained chloro as substituents. From this study, it showed that some synthesized compounds displayed good activity equal to or better than commercial available herbicides. These compounds exhibited good tendency for further development as herbicides in the future.
1999

60

Methodology for the Synthesis of Acid Chloride and Its Applications
 
Abstract    -

61

A Search for Bioactive Compounds towards Pomacea canaliculata Lamarck
(Golden Apple Snail) from Datura metel Linn.
 
Abstract
Acidic extraction of the crude ethanolic extract from the leaves of Datura metel Limm. Led to the isolation of two fractions, alkaloid and non-alkaloid. Both fractions were bioassayed for lethality test against Pomacea canaliculata Lamarck. The alkaloid fraction exhibited strong activity was further investigated and fractionated by quick column chromatography. After purification, it gave two alkaloids. Based on physical properties, chemical reactions, spectroscopic data and comparison with the authentic samples on TLC plate, the two compounds were found to be atropine and scopolamine.

62

Searching for Agrochemicals from Some Thai Plants
 
Abstract
The fruits of Ardisia colorata Roxb., the leaves and the twigs of Mulberry alba Linn., theleaves of Piper sarmentosum Roxb. And the flowers of Eugenia caryophyllus (Spreng.) Bullock & S.G.Harrison were extracted with dichloromethane and methamol. All extracts were bioassayed for lethality test against brine shrimp, Arthemia salina Linn. The crude extracts of the flowers of Eugenia were found to be promising. Therefore, the latter was extracted with hexane, dichloromethane, ethyl acetate and methanol, respectively. The separation of dichloromethane and ethyl acetate crude extracts by quick column chromatography and the purification of crude hexane via the extraction and distillation yielded 4 substances. Based on physical properties, chemical reaction and spectroscopic data, the principle substance of hexane and dichloromethane was fully characterized as eugenol which displayed high toxicity against brine shrimp. Two substances were found to be steroid and triterpenoid. The other was observed to possess very high activity; however it was not a single component.

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