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Chemical composition and biological properties of plant

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Chemical composition and biological properties of plant Powered By Docstoc
					                        รองศาสตราจารย ดร อรพน เกดชชน
                   รองศาสตราจารย ดร ณฎฐา เลาหกลจตต
           School of Bioresources and Technology
King Mongkut’s University of Technology Thonburi ,
                                           Bangkok
Aromatic and medicinal plants
are important for
pharmaceutical, food and
fragrance industries although
they contain a small fraction of
volatile oil.
 Essential oils are interested in aromatherapy
 for healing, cleansing, preservative, and
 mood-elevating attributes.
Essential oils refer to the subtle,
aromatic and volatile liquids extracted
from the flowers, seeds, leaves,
stems, bark and roots of herbs,
bushes, shrubs and trees .

Chemically, in the essential oils that
can derived to primarily composed of
mono- and sesquiterpenes and
aromatic etc.
Essential oils found in 108 families and > 2000 species.


Gramineae    Labiatae   Lauraceae   Myrtaceae           Oleaceae




 Pinaceae   Rosaceae    Rutaceae    Santalaceae      Umbelliferae


                                          http://www.nazflora.org/Dicots.htm
             Umbelliferae
           Umbelliferae

Eryngium foetidum                    Centella asiatica
     (ผกชฝรง)                                (บวบก)


Angelica acutiloba                      Carum carvi
      (ตงกย)                               (หอมปอม)


Apium graveolen                    Cuminum cyminum
     (คนชาย)                                 (ยหรา)


Foeniculum vulgare                Coriandrum sativum
    (ผกชลอม )                                 (ผกช)

                            http://en.wikipedia.org/wiki/Umbelliferae
                                              Coriander
                                Kingdom:       Plantae
                                Family:        Umbelliferae
                                Genus:          Coriandrum
                                Species:        C. sativum
                                Binomial name: Coriandrum sativum
Ø All parts of the plant are edible used in cooking.


Øseeds are used a carminative and a digestive aid the relief of
  anxiety and insomnia in Iran



ØIt helps to detoxify the body and to stimulate the spleen.
Coriander oil has a sweet, spicy, warm smell, is nearly
colorless to pale yellow and has a watery viscosity.

The therapeutic properties of coriander oil are analgesic,
aphrodisiac, antispasmodic, carminative, depurative,
deodorant, digestive, carminative, fungicidal, lipolytic,
stimulant and stomachic.
Commercial Used




                  Herrero et al., 2010
Chemical composition of essential oil from Coriander .

                    53 compounds are detected

  Essential oils   Composition                          Composition
   Compound           (%)        Essential oils compound
                                                            (%)
γ-Terpinene           14,42      Eugenol                    0.9
γ-Terpinene
β-Pinene
                    (14.42%)
                       1,82      Undecanal                 0.58
β-Myrcene             0.55       Myrtenyl acetate          0.43
m-Cymene              1.27       Citronellyl acetate        1,36
                                 Geranyl acetate (17.57%)
                                 Geranyl acetate           17,57
Limonene               .0.4
Linalool
Linalool           (37.65%)
                      37,65      Caryophyllene             0.33
Citronellal           1.96       Curcumene                 0.98
Borneol               0.32
                                 α-Cedrene
                                 α-Cedrene            (3.87%)
                                                            3,87
                                 α-Farnesene               1.22
Terpinyl acetate      0.31
                                 β-Bisabolene               0.8
Citronellol           1.31       β-Sesquiphellandrene      1.56
Citral                1.36       Others                    7.16
Geraniol              1.87
                                                           Bhuiyan, et.al., 2009
The complicated volatile compounds in essential oil could be
divided into 4 groups:

                      Aliphatic compound

                      Benzene derivatives


                      Terpene derivatives


                       Others compound


                                                      http://www.wikipedia.org/
In aliphatic compounds, carbon atoms can be joined together
in straight chains, branched chains, or non-aromatic rings

  • Aliphatic Alcohol



    cis-3-hexen-1-ol        cis-2-hexen-1-ol                   1-octen-3-ol


  • Aliphatic aldehydes


              n-octanal                             trans-2-hexanal

                       http://isostar.ccdc.cam.ac.uk/html/classes/Ligand_Acyclic_links_O_C_H_only.html
• Aliphatic ketones
3-hydroxy-2-butanone (acetoin)


diacetyl (2,3-butanedione)



• Aliphatic esters
C6 alcohol-acetate : fruity notes
C8-12 acetate : blossom fragrance
C12 : conifer notes
acetate-ester : fatty-soapy odour




      Ethyl acetate             Benzyl acetate             Linalyl acetate
                      http://isostar.ccdc.cam.ac.uk/html/classes/Ligand_Acyclic_links_O_C_H_only.html
Benzene is an organic chemical compound with the
molecular formula (C6H6 ) n
Benzene is an aromatic hydrocarbon, a cyclic
hydrocarbon with a continuous pi bond
• Hydrocarbon

2. Benzenoid alcohol




  Cinnamic-alcohol   Cinnamaldehyde   Phenylacetaldehyde
                                      http://en.wikipedia.org/wiki/Benzene
3. Benzenoid ketone

4. Ester of aromatic alcohols and aliphatic
acids



   Benzylacetate              Benzyl benzoate




              Phenylethyl acetate



                                    http://en.wikipedia.org/wiki/Benzene
Terpenes are derived biosynthetically from units of isoprene,
which has the molecular formula (C5H8 ) n. That may be
classified by the number of terpene units in the molecule.




                                            http://en.wikipedia.org/wiki/Terpene
the molecular formula C10H16. Monoterpenes may be
linear (acyclic) or contain rings.


Acyclic               Mycrene


Monocyclic            Menthol


Bicyclic              Camphor


                                    http://en.wikipedia.org/wiki/Terpene
The molecular formula C15H24. Like monoterpenes, sesquiterpenes
may be acyclic or contain rings, including many unique
combinations.

  Acyclic
                            Farnesene
  Monocyclic
                            Humulene
  Bicyclic
                            Vetivazulene
  Tricyclic
                            Longifolene
                                               http://en.wikipedia.org/wiki/Terpene
  Diterpenes are composed for four isoprene
  units and have the molecular formula C20H32

      Retinol :




Triterpenes consist of six isoprene units and have
the molecular formula C30H48

     Lanosterol :

                                     http://en.wikipedia.org/wiki/Terpene
http://www.wikipedia.org/
The volatile oil composition may change from the
natural odor depending on the extraction
method (Anitescu et al, 1997).
    Compositions         Hydrodistillation   Ethanol   supercritical carbon dioxide
       Linalool                 ü              ü                    ü
      Terpinene                 ü              ü
      Camphor                   ü                                   ü
      Limonene                  ü                                   ü
      α-pinene                  ü                                   ü
     γ-terpinene                ü                                   ü                 The volatile oil
     C-terpinene                                                    ü                  composition
      Coumarins                                                     ü                  may change
       Geraniol                 ü                                   ü
                                                                                         from the
   Geranyl acetate              ü                                   ü
  Phenylpropanoids              ü
                                                                                       natural odor
      P-cymene                  ü                                   ü                 depending on
      Myrcene                   ü                                   ü                 the extraction
     Terpenolene                ü                                   ü                     method
      Camphene                  ü                                   ü
     Terpinolene                ü                                   ü
     α- terpineol               ü                                   ü
Trans-sabinene hydrate                                              ü
      Citronello                                                    ü
     n - Octanol                                                    ü
                                                                                           Anitescu et al, 1997
Plant extracts Production
     Methods                       Final products                              notes
                                                                        Suitable for extracts
    Enfleurage                  Enfleurage absolutes
                                                                          flavor of flowers
                                                                        Need a high energy,
    Expression                       Essential oils                     suitable for extracts
                                                                        citrus peel, low yield
                             Concrete (crude extracts)
                      a waxy, semisolid, dark-colored material free
 Solvent extraction             from the original solvent             Easy, simple, low energy
                                      Absolutes
                              Free from wax and resinoids

                                     Essential oils
   Steam/hydro         concentrate hydrophobic liquid containing      High yield compared with
                         volatile aroma compounds and rich of
    distillation                  bioactive compounds
                                                                              expression
                          (aliphatic, terpene, benzene, others)
Extraction

Flavor + fragrance ทสกดจากพช เรยก “pomades, concretes, 
absolutes, resinoids or tincture

1.  Pomades ประกอบดวยไขมนทมสารใหกลนหอมอย เตรยมโดยวธ 
hot or cold    
     enfleurage จากดอกไม
-   Hot enfleurage วธเกาแกในการเกบรกษากลนหอม 
โดยนำดอกไมหรอสวนตางๆ ของพช จมใน wax เหลว + รอน
-   Cold enfleurage ใชไขมนเปนตว adsorp volatile component 
ทปลอยจากดอกไม โดยเอาดอกไมสดใสไวในชนไขมน 
ซงไขมนประกอบดวย lard + beef tallow ซง spread 
บนกระจกแกวในภาชนะปด เปนวธใชแทนการสกดดวย solvent
2. Concretes สกดสวนตางๆของพชดวย solvent ชนด non polar solvent (toluene,
hexane, petroleum ether) เมอระเหยสวนทเหลอจะมvolatile fragrance + non volatile
รวมทง wax cpds.
        Concrete มลกษณะเหมอน pomades ไมละลายใน alc ...
มขอจำกดในการนำมาใช   perfume แตใชใหกลนสบ
     Concrete สกดมาจากดอกไม(กหลาบมะล เปนตน) สวนตางๆ ของพช
(lavender, violet leaf เปนตน)
 3. Absolutes เตรยมจาก concrete ละลายใน ethanol ตกตะกอนท temp ตำ à
กรอง à ระเหย EtOH ออก è wax – free เรยก absolute ... ละลายไดในEtOH ใช
perfume ingredients
 4. Resinoids เตรยมจากยางไม(plant exudates) สกดดวย solvent เชน methanol,
EtOH, Toluene à yield 50 – 95% product เหนยว ทำเจอจางเตมphthalates หรอ
benzyl benzoate เพอปรบปรงคณสมบตการไหล         และการนำไปใช
       resinoid ประกอบดวย nonvolatile + resinoid cpds. ตางจากoleoresin ซงไดจาก
pepper, ginger, vanilla oleoresins ใช solvent สกดจาก spices solvent ทใชขนกบชนด
spices หรอ supercritical CO2 เปนตวสกด pepper + ginger oleoresins ม volatile aroma +
pungency
 5. Tinctures เปนสารทละลายในalc. เตรยมโดย Treat natural raw material ดวย
         Extraction methods
Ø Expression
Ø Distillation
      -Hydrodistillation
      -Steam distillation
      - Simultaneous distillation extraction
      - Vacuum distillation
Ø Solvent extraction
      - Enflurage
      - Liquid-liquid extraction
      - Soild-liquid extraction
      - Supercritical fluid extraction

                               http://en.wikipedia.org/wiki/Essential_oil#Production
                                       Advantage
                                       - Low cost
                                       - simple

                                       Disadvantage
                                       - High energy
                                       - Long time




http://www.weloveshopping.com/template/e1/showproduct.php?shopid=221389&productid=CHH8
Distillation is a method of separating mixtures based
 on differences in their volatilities in a boiling liquid
mixture. Distillation is a unit operation, or a physical
  separation process, and not a chemical reaction.




                                        http://en.wikipedia.org/wiki/Distillation
Hydrodistillation
                    • Traditional method of extraction 

                      Advantage
                      -Easy separation

                      Disadvantage
                      - Combustion of the
                        sample
                      - Degradation of
                        volatile compound



                        http://en.wikipedia.org/wiki/Distillation#Hydrodistillation
ØSteam distillation


                               •  distilling compounds  
                                   which are heat-sensitive




            Advantage          Disadvantage
   - Easy separation    - Degradation of some
   - Easy operation       analytes
                        - Sample impurities
                        -Expensive equipment


                        http://en.wikipedia.org/wiki/Distillation#Steam_distillation
ØSimultaneous distillation extraction (SDE)

                       Advantage
                       - Semi-volatile and heat-
                         stable component
                       - High recovery
                       - rapid

                       Disadvantage
                        - concrete
                       - Degradation of volatile
                         compound
                       - Thermal degradation

                                   http://en.wikipedia.org/wiki/Distillation
Vacuum distillation

                          •low temperature distillation

                          •Principle: pressure above  
                            mixture is reduced to less 
                            than its vapor pressure 




         Advantage                Disadvantage
  - Prevention degradation - Use strong instrument
                           - Expensive
                           - Weak volatiles
                                 http://en.wikipedia.org/wiki/Vacuum_distillation
3. Solvent extraction
 ØEnfleurage



                          •  Enfleurage  uses  odorless
                              fats that are solid at room  
                              temperature


          Advantage             Disadvantage
  • simple               * long time of extraction
  •Suitable for flower   * Not use a wide range of
  extraction             material
                                   http://en.wikipedia.org/wiki/Enfleurage
ØLiquid-liquid extraction (LLE)

  v Partition

  v Extraction of a substance with 
       different densities

            Advantage               Disadvantage
   - Easy to separate         - Large volumes of
   - Extractions normally       organic solvents
     performed at room
     temperature

                                http://en.wikipedia.org/wiki/Liquid-liquid_extraction
Ø Soild-liquid extraction
  •Base on like dissolve like 
  •Use solvent to separate  desired 
    compound    from  solid sample

              Advantage
  - Analyze in one extraction step

             Disadvantage
  - Loss of certain compounds
  - The time for an average            Soxhlet extractor 
    Soxhlet extraction ranges
    from 1 to 72 h.
                                         http://en.wikipedia.org/wiki/Liquid
ØSupercritical fluid extraction (SFE)


 Supercritical fluids provide a
 higher solubility of the
 components of the volatile
 oil, as well as improved mass-
 transfer rates. Moreover, the
 manipulation of parameters
 as temperature and pressure
 leads to the extraction of
 different components.


                                        Reverchon and De Marco, 2006
ØSupercritical fluid extraction (SFE)
Supercritical fluid extraction (SFE)

                        - Dense gases 


                        - Critical temperature 
                        & pressure


                        - Resemble both 
                        liquids & gases
Critical properties of various solvents




                                          Reid et al., 1987
    Super Critical CO2 Extraction
DISADVANTAGE
Boiling point, Artifact formation partial loss of
extracted volatiles
ADVANTAGES
Easy to remove, Not harmful, odorless, 
tasteless, non flammable, Inexpensive in high 
purity, moderate condition = 310C  74 bar , no 
degradation ---->labile flavor compounds 
selectivity, aroma & flavor-->resemblance  to 
original material
     SOLUBILITY UNDER LIQUID CO2
1. MW < 500 daltons
2.Low - medium MW of halocarbon, aldehyde, keton,
   ester, alcohol, ether
2.Low MW , non polar, aliphatic hydrocarbons -- 20
carbons
4. Polar organic -- low solubility
5. Polar groups -- OH, COOH, N decrease solubility
•Chorophyll, carotenoids, amino acid, fruit acid
  --->insoluble
2.Alkaloids, phenols, aniline compounds
    ----> poor solubility
      The application of liquid CO2
  HOP, 
  OLEORESIN,           FLAVOR, FRAGRANCE, AND COLORANTS
  Basils, VANILLA, 
  ONION  OIL, 
  CITRUS  OIL, 
  APPLE JUICE, 
                               CONCERN HEALTH
  PEAR, COFFEE,                     AND
  ORANGE, 
  Coliander                      ENVIRONMENT

Consumer demand, new, improved, natural, high quality
                    SUPERCRITICAL REGION                      SUPERCRITICAL REGION


                                                                        TOTAL EXTRACTION
 Pressure (bar)




                                                        FRACTIONATION
                  SOLID

                                  LIQUID

                          TRIPLE POINT CRITICAL POINT
                                                                        DEODERIZATION

Pc = 73.8 bar                                      Tc = 31.1 ˚c
                                       GAS


                               Temperature (˚c)
                                                                                Laohakunjit .,2010
Factor affecting on quality of extract by SFE

     Ø Temperature

             Ø Pressure


                   ØParticle size


                                ØTime



                             Pourmortazavi et al., 2007 and Bensebia et al., 2009
          2. Continuous Solvent Extraction




                                   Condenser




                                  Beverage sample

Solvent (Ether)                  Holes at the bottom
 Water Bath                      of the tube
                                                                 Persicaria odorata
                                         v   Common name               : Vietnamese coriander
                                         v   Thai name                 : Pak-Paeow
                                         v   Family                    : Polygonaceae
                                         v   Usually use for culinary herbs

                            Method of                Type of
     Author                                                                           Result
                            extraction               extracts
                     extracted with 15 mL of                       has a total phenolic compounds and
Zheng, and Wang      phosphate buffer (75 mM,    Crude extract     antioxidant activity of 3.09± 0.12 and
(2001)               pH 7.0)                                       22.30±0.68 respectively
                                                                   The Persicaria odorata
Starkenmann, et al   Hydrodistillation           Essential oil     has a strong coriander leaf odor due to it’s
(2006)                                                             high content aliphatic aldehydes.

                                                                   Polygonum odoratum or Persicaria odorata
                                                                   has an antimicrobial activity against Bacillus
                                                                   cereus, Escherichia coli, Listeria
                                                                   monocytogenes, Pseudomonas fluorescens,
Nanasombat                                                         Staphylococcus aureus, Yersinia
 And Teckchuen       Methanol extract            Crude extract
(2009)                                                             enterocolitica
                                                                    And also has an antioxidant activity, and
                                                                   Total phenolics compounds of 315.4 ± 18.8
                                                                   and 52.0 ± 0.0 (µg Gallic Acid Equivalents
                                                                   (GAE)/mg dry extract)
                                                                     Suaeda maritima
                                              v Common name                : Annual sea blite
                                              v Thai name                  : Cha-kram
                                              v Family                     : Amaranthaceae
                                              v Include in halophyte plant group
                                              v Salt content in the tissues is very high -> can act as
                                              antimicrobial agent
                              Method of
      Author                                          Type of extracts                    Result
                              extraction
                                                                          Total phenolic of 23.5 ± 4.2 µg/mL
Agoramoorthy, et       Whole Dry plant               Whole dry plant
al.(2008)                                                                 Radical scavenging activity >250
                                                                          (3343.0 ± 902.8) µg/mL
                                                                          Show inhibition activity against Bacillus
Kumar, et al. (2009)   Methanol extract              Crude extract        cereus, Bacillus megaterium and
                                                                          Streptococcus lactis
                       Solvent (methanol)
Bobbarala, et al.                                                         Show an antifungal activity and MIC
                       extraction with soxhlet       Crude extract
(2009)                                                                    value of 10-20 and ± 80 µmg/ml
                       apparatus

                                                                          Could inhibit the growth of bacterial
                       Solvent extraction                                 strains; B. cereus, L. mesenteroid, L.
Wannu, et al.          (petroleum ether and          Crude extract        plantarum and S. aureus which their
(2010).                ethanol)                                           inhibition zone were 13.25, 16.00, 19.55
                                                                          and 15.65 mm, respectively.
                                                                       Piper sarmentosum
                                                v   Common name             : Wild betel
                                                v   Thai name               : Cha-plu
                                                v   Family                  : Piperaceae
                                                v   Culinary and medicine herbs
                           Method of                  Type of
      Author                                                                       Result
                           extraction                 extracts
                                                                    The highest antioxidant activity was detected in G.
Chanwitheesuk, et al. Methanol extraction       Crude extract       inodorum, followed by P. sarmentosum and M.
(2005)                                                              arvensis, respectively.

                        Methanol extrcation                         Piper sarmentosum showed anti bacterial activity
Zaidan, et al (2005)    in sohxlet apparatus    Crude extract       against S.aureus

                                                                    The study demonstrated the efficacy of Piper
Vagashiya, et al.       Methanol extract, for Crude extract         sarmentosum, P. argyrophillum, P. longum, P. betle
(2007)                  24 h                                        as a antiinflammatory agents
                                                                    Essential oil has an antitermite activity against
Chieng, et al. (2008)   Hydrodistillation       Essential oil       larvae of Artemia salina
                                                                    Piper sarmentosum ethanol extract has only
                                                                    antifungal activity for C.albicans
Taweechaisupapong,      Hydrodistillation and   Essential oil and   MBC of Piper sarmentosum against A.
et al. (2010).          ethanol extract         concretes           actinomycetemcomitans and C.albicans are 2.5 and
                                                                    1.25 mg/ml respectively.
                                                                    Piper sarmentosum ethanol extract has
                        Ethanol and water                           antibacterial activity against Vibrios and Shigella
Kondo, et al. (2010).   extraction              Crude extraction    with the MIC value 0.625->5 and >5 mg/ml
                        (maseration)                                respectively.
Application of essential oil in chicken meat
   Several type of plant has been use for preservatives in chicken meat
       Research                       Type of plant extract                           Purpose of use

                                                                        Antibacterial agents in raw chicken meat
Lemay, et al (2002)        Mustard oil                                  against Eschericia coli, Brochothrix
                                                                        thermosphacta, Lactobacillus alimentarius

                                                                        Antibacterial agents against Psychrotrops
                           Oregano essential oil
Oral, et al (2009)                                                      bacteria, Lactic Acid Bacteria, Yeast,
                                                                        Pseudomonas enterobactericeae
                           bay leaf (Laurus mobilis L.) essential oil
                           (0.5% v/w) with modified atmosphere          To control Listeria monocytogenes and
Irkin and Esme (2009)
                           (MAP) (20%CO2/80%N2) and vacuum              Eschericia coli ground chicken breast meat
                           packaging stored at 4°C
                                                                        Preservatives on ready to cook chicken
Giatrakou, et al (2010)    Chitosan and Thyme oil
                                                                        product
Fratianni, et al. (2010)   Thyme and Balm oil                           Preservatives on chicken breast meat
Rattanachaikunsopon
                           Coriandrum sativum oil in various            To controlling Campylobacter jejuni in raw
and Phumkhachorn
                           concentrations (0.1, 0.25, and 0.5%)         meat in various storage temperatures
(2010)

      No report about the application of essential oil or plant extract
       from Vietnamese coriander, annual sea blite and wild betel
Extraction process
                           Sample preparation                   Dry sample : 20 gr
                                                            Composition : (1:2 w/v ratios)


   Hydrodistillation                             Solvent Extraction

 Dry sample       : 500 gr                                           Petroleum
                                       Ethanol        Acetone
 Fresh sample     : 1000 gr                                            ether
 Time             : 24 h.
                                      24 hour extraction
                                                                   1st extracts
                                        (1st extraction)

        Essential oil                      Residue
  (dry and fresh sample)
                                      72 hour extraction
                                                                  2nd extracts
                                       (2nd extraction)

                                           Residue
                                                                  Wax washing
  Physical, chemical, and                                           process

 biological activity analysis
                                        absolutes
Physical, chemical, and biological
activity analysis
                   Analysis
Physical properties :
- Percent of yield extraction
- Optical rotation                                      The best plant
- Color                                                    extracts
- Refractive index.
Chemical properties :
- Volatile compounds analysis
- Total phenolics compounds                      Application into the raw chicken
Biological activities :
                                                               meat
- Antibacterial activity
- Minimum Inhibitor Concentration (MIC) values
- Antioxidant activity (DPPH and ABTS methods)
Volatile compound analysis
 Analyzed using GC-MS system, equipped with :
 •30 m x 0.25 mm i.d. x 0.25 µm film thickness,
 •DB-5ms capillary column.
 •The carrier gas was helium at flow rate 0.56682 ml/min, and 1 µml of sample (100 ppm
 concentration) was injected directly
 •The injector and detector temperatures were 230oC and 250oC respectively.
 •The running methods were splitless mode, pressure: 3 psi, oven temperature: 70 oC
 then 10oC/min. to 140oC, and then 5oC/min. to 240oC

                         • Sample concentration : 100 ppm
                            • Volume injection : 1 µL




      § Compared with WILEY257 and NIST library use a % quality
                         match greater than 85%
         § RI calculation based on n-alkane standard (C10-C20)
Volatile compound analysis
       Essential oil
                                        % of Composition                                                                  % of
                                    a                                                                           a
 No.       Volatile compound   RI                          No.             Volatile compound               RI        Composition
                                        Fresh     Dry                                                               Fresh Dry
  1.   eucalyptol              1051
                                         0.31       -      14.       alpha,-curcumene                     1490
                                                                                                                     3.16 4.49
  2.   undecane                1108
                                           -      0.14     15.       eremophillene                        1508
                                                                                                                     6.89 4.20
  3.   1-nonanol               1174
                                           -      0.09     16.       7-epi-alpha-selinene                 1537
                                                                                                                       -      2.59
  4.   decanal                 1212
                                         7.32     4.47     17.       ledol                                1550
                                                                                                                     5.99       -
  5.   decanol                 1274
                                           -      3.34     18.       nerolidol                            1564
                                                                                                                       -      3.67
  6.   undecanal               1311
                                         0.58     0.57     19.       globulol                             1587
                                                                                                                     0.95       -
  7.   n-decanoic acid         1358
                                         0.21       -      20.       caryophyllene oxide                  1601
                                                                                                                     2.04 5.64
  8    1-Nonene                1374
                                           -      2.02     21.       cubenol                              1640
                                                                                                                     0.08       -
  9.   beta-elemene            1401
                                         0.64       -      22.       eupatoriochromene                    1664
                                                                                                                    21.71 20.94
 10.   dodecanal               1417
                                        19.96    18.72     23.       drimenol                             1790
                                                                                                                     4.74 4.34
 11.   beta-caryophyllene               11.07    11.40     24.       Hexahydro farnesyl                                -      0.60
                               1441                                  acetone                              1842
 12.   allo-aromadendren       1456
                                         0.49       -      25.       isophytol                            1945
                                                                                                                     0.39 0.17
 13.   alpha.-caryophyllene    1476
                                        12.57    11.62     26.       n-hexadecanoic acid                   1959
                                                                                                                     0.91 0.99
                                                                 a
                                                                     Retention indices calculated based on n-alkane standard (C10-C20)

   Starkenmann et al, (2008) mentioned the major compounds of this plant are
                          decanal and caryophyllene.
Volatile compound analysis                                                         Plant extract
                                                                 % of Composition
No.          Volatile compound          RIa
                                               Petroleum ether          Acetone                 Ethanol
                                                1st       2nd     1st             2nd     1st             2nd
 1.    beta-pinene                      981      -         -     8.06         16.55      13.10              -
 2.    beta-cis-ocimene                 1025     -         -       -               -     1.61               -
 3.    3-carene                         1037     -         -       -          2.08         -                -
 4.    ocimene                          1050     -         -     17.90        36.46      26.44              -
 5.    decanal                          1208   18.43     12.09   7.73         4.64       4.42               -
 6.    methyl hydrocinnamate            1278     -         -       -               -     2.57               -
 7.    ethyl dihydrocinnamate           1351     -         -     1.77         4.24       2.71               -
 8     copaene                          1388     -         -       -          8.52       6.00               -
 9.    dodecanal                        1409   53.12     38.36   27.14        8.06       7.21         11.35
 10.   caryophyllene                    1435   5.42       8.07   6.26         6.49       7.07             11.01
 11.   cyclododecane                    1471   6.13       6.47     -               -       -                -
 12.   1,1-diethoxydecane               1472     -         -     8.10              -       -          19.03
 13.   germacrene d.                    1495     -         -     2.40         3.06         -                -
 14.   3,5-di-tert-butylphenol          1505     -         -     5.78             4.81   9.16         10.70
 15.   dehydro-cyclolongifolene oxide   1657   8.21      16.48     -               -       -                -
 16.   eupatoriochromene                1657     -         -     5.52              -     8.00         19.49
 17.   neophytadiene                    1834   2.88       5.30   4.71         5.09       6.08               -
 18.   ethyl hexadecanoate              1989   5.80      13.24   4.62              -     5.61         28.43
Physical properties                                                Annual sea blite

        Extraction methods   Refractive index   Optical rotation       Color appearance
   Ethanol 1st                    1.363             -21.10 o       Clear dark green and yellow

   Ethanol 2nd                    1.363             -22.85 o       Clear dark green and yellow

   Petroleum ether 1st            1.364             -19.80 o            Clear light yellow

   Petroleum ether 2nd            1.363             -15.95 o            Clear light yellow

   Acetone 1st                    1.363             -21.50 o            Clear light green

   Acetone 2nd                    1.363             -20.05 o            Clear light green

   Hydrodistillation-Dry            -                  -                        -

   Hydrodistillation-Fresh          -                  -                        -


 The physical properties in refractive index, optical rotation, color appearance were not
                      different with vietnamese coriander results.
Volatile compound analysis
 Analyzed using GC-MS system, equipped with :
 •30 m x 0.25 mm i.d. x 0.25 µm film thickness,
 •DB-5ms capillary column.
 •The carrier gas was helium at flow rate 0.56682 ml/min, and 1 µml of sample (100 ppm
 concentration) was injected directly.
 •The injector and detector temperatures were 230oC and 250oC respectively.
 •The running methods were splitless mode, pressure: 3 psi, oven temperature: 40 oC
 then rate 8oC/min. to 100oC, then rate 15oC/min. to 180oC, and the last rate 12oC/min.
 to 280oC
                         • Sample concentration : 1000 ppm
                            • Volume injection : 0.5 µL




      § Compared with WILEY257 and NIST library use a % quality
                         match greater than 85%
         § RI calculation based on n-alkane standard (C10-C20)
  The
  End
     Assoc. Prof.Dr. Natta Laohakunjit
Assoc. Prof. Dr. Orapin Kerdchoechuen

				
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