23

2

2.1 (Coconut) Cocos nucifera Linn.

(Taxonomic classification)

Class : Angiospermae Subclass : Monocotyledoneae

Order : Palmales Family : Palmae

Subfamily : Cocoideae Tribe : Cocoideae

Genus : Cocos Species : Nucifera

2.1.1 (, 2541)

( 12-14 12-14 ) 200-250 6 6 6 (Fibrous drupe) (Nut) 3 (Exocarp) (Mesocarp) 4-8 (Endocarp)

24

(Husk or shell) (Endosperm) Seed coat Seed coat 1-2

2.1.2

(, 2547) 3 2

(60-80 ) 8-10

3-4 9-10 30-40 Coco Nino

25

3 (1) 1 (Sawi hybrid No.1) (MYD x WAT) 5 ( 1) (2) 60 (Chumphon hybrid No.60) (WAT x THT) 5 1 (3) 2 (MYD x THT) 3 2 ( 1) 1

(/)

(/)

(%w/w) 1 2,300 572 68 60 2,204 628 64-67 2 1,800 500 66 1,084 374 59-60 : (2552)

2.1.3

26

2552 1.49 1.38 ( 2) 2 2543-2552

(1,000 )

(1,000 )

(1,000 )

()

(/)

()

2543 2,049 1,970 1,795 911 2,008 3,605 2544 1,956 1,897 1,935 1,020 1,984 3,838 2545 1,887 1,833 2,037 1,111 2,608 5,313 2546 1,792 1,740 2,117 1,217 2,688 5,691 2547 1,724 1,690 2,126 1,258 3,456 7,347 2548 1,687 1,659 1,940 1,170 3,488 6,768 2549 1,632 1,614 1,815 1,125 4,640 8,423 2550 1,611 1,598 1,722 1,077 3,312 5,702 2551 1,543 1,538 1,484 966 4,792 7,111 2552 1,493 1,487 1,381 929 4,624 6,386 : (2552) 73% 27% .. 2530 85% 12 10

27

1 19.5 2 15.3 10.9 6 1.5 ( 3) 3 10

2549-2551 (1,000 ) (1,000 ) ()

2549 2550 2551 2549 2550 2551 2549 2550 2551 67,789 69,619 69,988 57,535 60,618 60,857 849 871 870 16,563 18,125 18,438 17,125 19,625 19,500 1,034 1,083 1,058 20,859 20,999 21,123 14,958 14,853 15,320 717 707 725 12,168 12,125 12,125 10,190 10,894 10,894 837 898 898 1,811 1,770 1,672 2,978 2,831 2,759 1,644 1,599 1,651 2,468 2,468 2,468 2,116 2,181 2,200 858 884 892 1,614 1,598 1,536 1,815 1,722 1,484 1,125 1,077 966 1,026 1,069 1,116 1,132 1,167 1,246 1,104 1,092 1,117 837 846 864 1,001 1,035 1,086 1,196 1,224 1,256 1,238 1,269 1,269 660 677 677 533 534 534 1,081 1,075 1,088 513 530 555 474 493 510 8,127 8,277 8,291 5,046 5,103 5,136 621 617 619 : (2552)

(FAO) 2553 62.45 33.07% 6 1.3 2.08% (FAO, 2012)

28

1 2553 : FAO (2012)

2.2 (Saturated fat)

(Unsaturated fat)

2.2.1 2

(, (FAO), 2548)

2.2.1.1. (Hot pressed)

(Copra)

29

2

. (Screw press) 5-10% (Crude coconut oil)

. RBD (Refining) (Bleaching) (Deodorization) () (Free fatty acid) 0.1%

2.2.1.2. (Cold pressed)

(Virgin coconut oil, VCO) 2 (Dry process) (Wet process) (, 2548)

. 60 12%

30

. 1:1 (Boiling) (Distillation) (Centrifugation method) (Fermentation method) 24 24-26 35-40

31

2.2.2 2.2.2.1 90%

8-12 (, 2553) (Capric acid, C10) (Lauric acid, C12) (Myristic acid, C14) 4-8, 43-53 16-21% (Asian and Pacific Coconut Community, 2003) (Unsaturated fatty acid) 9% (Oleic acid, C18:1) (Linoleic acid, C18:2)

4 Vegetable oils

Fatty acid (%w/w)

C8:0 C10:0 C12:0 C14:0 C16:0 C18:0 C18:1 C18:2 C18:3 Others Coconut oil 7.0 5.4 48.9 20.2 8.4 2.5 6.2 1.4 - - Palm kernel - 1.2 51.6 22.9 12.2 1.3 10.8 - - - Sunflower - - - - 6.3 3.0 43.7 47.0 - - Rice bran - - - 0.4 22.9 1.8 42.5 30.5 1.4 0.5 Safflower - - - 0.3 11.9 2.3 29.2 55.9 0.4 - Groundnut - - - - 14.0 3.8 41.9 34.7 1.0 4.6 Palm - - 0.2 1.1 42.6 3.8 41.9 10.4 - - Olive - - - - 12.0 3.5 75.7 7.9 0.5 1.4 Soy been - - - - 11.6 4.0 18.8 56.1 8.5 1.0 Linseed - - - - 7.1 2.0 19.9 17.3 53.7 0.4

: Krishna et al. (2010)

32

2.2.2.2 (Fatty acid) (Saturated fatty acid)

12 (C12:0) C12 H24 O2 (Medium chain fatty acid, MCFA) (Coconut oil) (Palm kernel oil) 50% 6.2, 3.1 2.9%

2 : (2556)

(Antimicrobial) Enig (1999) (Monoglyceride) (Monolaurin) (Colostrum) 6 (Enig, 1996) (Enig, 1999) Young et al. (2009) 3 Propionibacterium acnes 0-50 g/mL 80 g/mL Skrivanova et al. (2005) Bergsson et al. (2001) (Gram-positive bacteria)

http://www.foodnetworksolution.com/vocab/wordcap/fatty%20acidhttp://www.foodnetworksolution.com/vocab/wordcap/saturated%20fatty%20acidhttp://www.foodnetworksolution.com/vocab/wordcap/medium%20chain%20fatty%20acidhttp://www.foodnetworksolution.com/vocab/wordcap/coconut%20oilhttp://www.foodnetworksolution.com/vocab/wordcap/palm%20kernel%20oilhttp://www.foodnetworksolution.com/vocab/wordcap/%E0%B8%99%E0%B8%A1http://www.foodnetworksolution.com/vocab/wordcap/%E0%B8%88%E0%B8%B8%E0%B8%A5%E0%B8%B4%E0%B8%99%E0%B8%97%E0%B8%A3%E0%B8%B5%E0%B8%A2%E0%B9%8C

33

Laureles et al. (2002) 17 9 5 3 47.3-50.6% Tagunan green dwarf (TACD) PCA 15-8 (TACD x Bago-Oshiro Tall) 50.50 50.45% Roger (2010) (PB121+, 49.49% ) (Malayan yellow dwarf, 49.49% )

Kumar (2011) 100 60 14 34 (Klapawangi tall, KWGT) (52.2% ) Assa et al. (2010) 4 1 (West african tall, WAT) 2 (Malayan yellow dwarf Equatorial guinea green dwarf) 1 (PB121+)

3 (1) Acetyl-CoA carboxylase

(2) Phosphatidic acid phosphatase (3) Acyl-ACP-thioesterase

ACP

Thioesterase

Acetyl coenzyme A (Acetyl CoA)

Acetyl CoA

2

16

4 (1) (Condensation)

34

Acetyl-CoA Malonyl-CoA Acetyl-ACP

Malonyl-ACP

Acetyl-ACP ( 2

) Acetyl group ( 2 ) AcetylACP

Malonyl-ACP Malonyl-ACP 3 2

Acetyl-ACP (2) (Reduction) 1

-Ketoacyl-ACP reductase (Keto group)

NADPH D-3-Hydroxyacyl-ACP (3)

(Dehydration) D-3-Hydroxyacyl-ACP

3-Hydroxyacyl-ACP dehydrase trans-2-

Enoyl-ACP (4) (Reduction) 2

Enoyl-ACP reductase NADPH

Fatty acyl-ACP

2 Malonyl-ACP 3

2 1 CO2 (Rawsthorne, 2002)

( 6 ) ( 8 12 ) ( 14 ) Thioesterase Laurate-CoA-preferring lysophosphatitic acid acyltransferase (LPAAT) 12 (Knutzon et al., 1995)

2.2.2.3

(Halliwell et al., 1995) (Scavenge) (Chelate) Superoxide

35

dismutase (SOD), Catalase (CAT), Glutathione peeroxidase (GPX), Glutathione reductase (GR), Glutathione S-transferase (GST) Glutathione, Lipoic acid, Ceruloplasmin, Albumin, Transferrin Tocopherol, Carotenoids, Ascorbic acid Polyphenols (Sies, 1993)

. 2-methylchromanol

2 (Tocopherol) (Tocotrienol) 4 (-), (-), (-) (-)

-Tocopherol/ Tocotrienol R1=R2=CH3 -Tocopherol/ Tocotrienol R1=CH3 R2=H -Tocopherol/ Tocotrienol R1=R2H -Tocopherol/ Tocotrienol R1=H R2=CH3

3 : Theriault et al. (1999)

(Lipid autoxidation) (Combs, 1992) (Electron-acceptor antioxidants) Peroxyl (Burton and Traber, 1990)

-tocopherol + LOO -tocopherol + LOOH

36

-tocopherol Peroxyl (LOO--tocopherol)

-tocopherol + LOO LOO--tocopherol

1.1 3.1 100 40-60 (Santos et al., 2005)

.

(-OH-group) (Phenol) 1 1 (Glycosides) (Cell vacuole) 4 (Flavonoid compounds) (Phenolic acid) (Hydroxycinnamic acids derivatives) (Lignans) B-ring Hydroxylation (Williamson et al., 2000)

37

4 : Balasundram et al. (2006)

Peroxyl (Packer et al., 1999) 2 Lipoxygenase (Cofactor) (Rice-Evans et al., 1996)

Marina et al. (2008) 25 100 13 100 (Seneviratne et al., 2008) Dia et al. (2005)

38

7 (Phytosterols) 400-1,200 Campesterol, Stigmasterol, -Sitosterol -5-Avenasterol (Wang et al., 2002)

2.2.3 (Medium chain fatty acid,

MCFAs) 8-12 70% (Long chain fatty acid, LCFAs) (High density lipoprotein, HDL) HDL

2.2.3.1.

(Low density lipoprotein, LDL) LDL

39

MCFAs HDL (Kaunitz and Dayrit, 1992) 14 (18 ) (28 ) (50 ) (3,150 ) (3,500 ) Hostmark et al. (1980) 10% (w/w) 10% (w/w) LDL HDL 6 Kinosian et al. (1994) (Total cholesterol) HDL LDL 200 (Cholesterol ratio) HDL HDL 5.0 5.0 5.0 Mendis et al. (1989) HDL LDL LDL HDL 179.6 146.0 LDL 131.6 100.3 HDL

40

HDL 43.4 25.4 4.14 5.75 ( 5.0 ) () 5 5 (mg/dL) Total Cholesterol LDL HDL Total Cholesterol : HDL 179.6 131.6 43.4 4.14 146.0 100.3 25.4 5.75 : Mendis et al. (1989) LDL (Low density lipoprotein) HDL (High density lipoprotein)

Prior et al. (1981) Polynesians 2 Pukapukans Tokelauans 50 ( ) LDL HDL Halden and Lieb (1961) Hypercholesterolemics 170-370 170-270 (5% w/w) (5% w/w) 140-240 Hasim et al. (1959) Hypercholesterolemics 29% ( 6) Ahrens et al. (1957)

41

Hypercholesterolemics 450 367

6

Serum cholesterol (mg/dl) % Change Before adding fat After adding coconut oil

364 214 -41.2 358 272 -24.0 353 281 -20.4 336 240 -28.6 315 198 -37.1 416 274 -34.1 348 245 -29.6 331 265 -19.9 489 361 -26.2 310 289 -6.8

Mean 362 256 -29.3 : Hashim et al. (1959)

LDL HDL LDL 5

42

5 LDL : Theriault et al. (1999)

LDL (Very low density lipoprotein, VLDL) VLDL LDL LDL (LDL receptor) VLDL LDL LDL (LDL VLDL ) LDL Theriault et al. (1999) VLDL LDL LDL LDL LDL LDL LDL

43

2.2.3.2. Reddy and Maeura (1984)

Azoxymethane Adenocarcinomas 10 (32%) (3%) Adenocarcinomas 3% 7%

2.2.3.3. Ortiz-Caro et al. (1986)

(Hypothyroid)

6

44

6 : Dayrit (2003)

(Triglyceride, TG) (Phospholipids, PL) Dayrit et al. (2003) (Long chain triglycerides, LCTs) (Pancreatic lipase enzyme) TG (Cholesterol ester, CE) (Hydrolyze) TG TG CE (Systemic circulation) VLDL TG CE VLDL TG (Intermediate density lipoprotein, IDL) IDL LDL (Peripheral tissue) LDL TG CE LDL CE CE LDL

45

CE CE HDL (Medium chain triglycerides, MCTs) LCTs MCTs MCTs (Cholesterol cycle) ( 7)

7 : Enig (1999)

(Thermogenesis)

(Dayrit, 2003) Enig (1999)

46

( 1 )

2.2.3.4. Enig (1998)

Helicobacter pyroli (H. pylori) Candida albicans HIV Projan et al. (1994) MCTs 4 (Isaacs and Thormar, 1991; Isaacs et al., 1990)

2.3

( 8) Non-ionic surfactant Kabara (1977)

8 : Ettinger (2013)

47

2.3.1

(Shibasaki, 1982) (Projan et al., 1994) 7 7 Lipid-coated Bacteria Lipid-coated Viruses Listeria monocyatogenes Human Immunodeficiency Virus (HIV) Helicobacter pylori (gram-negative) Measles virus Hemophilus influenza (gram-negative) Herpes simplex virus-1 Staphylococcus aureus Herpes simplex virus-2 Streptococcus agalactiae Hepatitis C virus Groups A, B, F & G streptococci Herpes viridae (all) Gram-positive organisms Sarcoma virus Gram-negative organisms Syncytial virus Human lymphotropic viruses (Type I) Vesicular stomatitis virus Visna virus Cytomegalovirus Epstein-Barr virus Influenza virus Pneumonovirus Sarcoma virus Syncytial virus Rubeola virus

: Enig (1998, 1999) Dayrit (2000) HIV HIV

15 HIV 6

48

HIV 7 15 3 8 6 HIV Cytomegalovirus (CMV) (Macallan et al., 1993) H. pylori (Petschow et al., 1996) Bergsson et al. (2002) 6 6 H. pylori H. pylori 37 10 H. pylori 0.15 mM H. pylori 5.97 log10 CFU H. pylori 6 log 10 CFU 0.63 mM H. pylori 1.25 mM H. pylori 1 H. pylori H. pylori 0.63 mM 2.50 mM 5.00 mM H. pylori

2.3.2

(Kabara et al., 1972) Uncoating

49

(Kabara, 1993) (Galbraith and Miller, 1973)

2.3.2.1.

Peptidoglycan ( Glycopeptides Mucopeptide Murein) Lipopolysaccharide Peptidoglycan Polysaccharide N-Acetylglucosamine (GlcNAC) N-acetylmuramate (MurNAC) side chain (Preston et al., 1996) Peptidoglycan

2.3.2.2. Osmotic

barrier - Proton motive force K+

2.3.2.3. 2 Deoxyribonucleic acid (DNA) Ribonucleic acid (RNA)

2.3.2.4. mRNA

Translation Ribosome Ribosome 70s ( 2 30s 50s)

50

mRNA

2.3.3 2

(220-250 0C) (Yield) By-product (Berger et al., 1992) (Mild reaction condition)

2.3.3.1.

35-60% 35-50% 1-20% 1-10% Nakamura et al. (2008) 4 ZrOCl2.8H2O, AlCl3.6H2O, Fe2(SO4)3.nH2O Zr(SO4)2.4H2O ZrOCl2.8H2O AlCl3.6H2O 74% 76% Fe2(SO4)3.nH2O Zr(SO4)2.4H2O ZrOCl2.8H2O AlCl3.6H2O 9

9 : Nakamura et al. (2008)

Glycerol

51

2.3.3.2.

1,3-spesific lipase 2,3-spesific lipase 10

10 : Fureby et al. (1997)

. (EC.3.1.1.3)

(Rathi et al., 2001; Jaeger and Reetz, 1998) ( ) (Stehr et al., 2003; Steiner and Williams, 2002; Pandey et al., 1999) Jaeger and Reet (1998)

52

(Cofactors) (Enantioselectivity)

. 20

(Modification) - (Flavors) Pabai et al. (1995) (Inter-esterification) Senanayaka and Shaida (2000) PS-30 Pseudomonas sp. (Acidolysis) (Borage oil) (Evening primrose, EPO) (Eicosapentaenoic acid, EPA)

Weber et al. (2001) Candida rugosa

.

3 (Stereochemical specificity)

53

transesterification

- 3

1 3 (1,3 Sn specificity) 1 3 (Primary alcohol) (Diol) Pseudomonas sp., Bacillus themoleovorans ID-1, Bacillus sterothemophilus L1 Bacillus thermocatenulatus (Sugihara et al., 1994; Rua et al., 1997; Schmidt-Dannert et al.,1994; Gao et al., 2000) 2 (2 Sn specificity) Rhizopus niveus (Bornscheuer et al., 1999) (Okumura et al., 1979) 3 ( 11) (Okumura et al., 1979) Geotrichum candidum Pseudomonas cyclipium (Rua et al., 1997; Gao et al., 2000)

11 () 1 3 1 3 (), 3 (), 1 () : Ghazali et al. (1995)

54

-

Penicillium camembertii (Macrae, 1983) Jacobsen and Poulsen (1995) 2 A B Geotrichum candida A B Rathi et al. (2001) Pseudomonas sp. (Linseed oil) Litthauer et al. (2002) Psudomonas luteola (Monoester) Candida deformans Turner et al. (2003) Pseudomonas roquefertii (Tririsinolein) 1,2(2,3)- (Dirisinolein) (Diisopropyl ether) (Water activity, aw) 0.11 0.53 aw 0.11 0.53 93 88% 1,2(2,3)- 71 88% aw 0.11 0.53 Yamaguchi et al. (1991) Pseudomonas camembertii 90% 76% Pseudomonas camembertii 1(2)- 1,2(2,3)-

55

.

(Robert, 1997) Oil-water interface (Fogarty, 1983; Macre, 1983) (Active site) (Polypeptides) (Hydrophobic amino acid) (-Helix lid) (Serine) 2 (Histidine) (Aspartic acid) (Balcao et al., 1996) (Serine hydroxyl) (Electric charges shifts) (Carboxylic acid) Acyl enzyme Proteic network Acyl enzyme

(Mild reaction condition) (Yield)

. Panicillium camembertii

(Lipase G)

56

(Acyl donor) (Conversion) 90% 70% (Yamaguchi et al., 1991) Freitas et al. (2010) Lipase G 6 93% (60% ) 50% 46% Lipase G (60% ) Rhizomucor miehei (Lypozyme) (Rodriques and Lafuente, 2010) 1 3 (1,3 Sn specificity) (Ferreira-Dias et al., 2001) Langone et al. (1999) Lypozyme 1% 26 56% 34% Lipozyme

.

Langone and SentAnna. (1999) 1 9% 60 26

57

(R) = 1.0 9% 65% Pereira et al. (2004) 55 Lypozyme 0.2-5.8% (R) = 1.0 6 Lipozyme 3.0-5.8% (42-45% ) Lipozyme 3.0%

.

Nandi et al. (2004) Candida rugosa (C. rugosa) Amano 30 lipase Amano 30 lipase C. rugosa lipase Amano 30 lipase C. rugosa lipase 50.3% 100 (Fraction I) 5% 46.2 23.0% (Medium chain fatty acid, MCFAs) Fraction I MCFAs 140 (Fraction II) 63.0% 68.4% Fraction II Fraction I Fraction II Rhizomucor miehei (Lypozyme) 8 6.5% 8

58

Fraction I 18.9% 62.4% 12.2% Fraction II 55.3% (36.9% ) 4.2 3.6%

.

(Malcata et al., 1990) Pereira et al. (2004) (48-62 ) 55 6 45.5, 26.8, 3.1 24.6% Langone et al. (1999) (60 90 ) 30%