**2.7 Oxygenated hydrocarbon (fatty acids)**

Some of the compounds of fatty acid that has been found in the *C. inophyllum* leaves are tetradecanoic acid (myristic acid, C14H28O2), n-hexadecanoic acid (palmitic acid, C16H32O2), oleic acid (C18H34O2), and octadecanoic acid (stearic acid, C18H36O2) [49].

#### **2.8 Esters**

Some ester compounds that have been found in the *C. inophyllum* leaves are 1,2-benzenedicarboxylic acid (diisooctyl ester/phthalic acid, bis(6-methylheptyl) ester), 9,12-octadecenoic acid methyl ester, 16-octadecanoic acid methyl ester, heptadecanoic acid, and 16-methyl ester [49, 50].

### **2.9 Tannins**

In chemistry, there are two types of tannins, namely, (1) condensed tannins or flavolan and (2) hydrolyzed tannins.

## *2.9.1 Condensed tannins*

The condensed tannins are widespread in angiosperm plants, especially in woody plants. Another name of condensed tannins is proanthocyanidin because when they reacted with hot acid, some of the carbon-carbon connecting bond units disconnect and free monomer anthocyanidins. Most proanthocyanidin is procyanidin because when reacted with acids will produce cyanidin. Proanthocyanidin can be detected directly by dipping the plant tissue into 2 M HCl boil for half an hour that will produce a red color which can be extracted with amyl or butyl alcohol.

**35**

Calophyllum inophyllum*: Beneficial Phytochemicals, Their Uses, and Identification*

**No. Phytochemicals Chemical** 

3β, 23-Epoxy-friedelan-28-oic acid C30H48O3 [41] Friedelin C30H50O [4, 20, 28,

3-Oxofriedelin-28-oic acid [40, 41] Canophyllal C30H48O2 [20, 41] Canophyllol C30H50O2 [20, 41] Canophyllic acid (27-hydroxyacetate canophyllic acid) C30H50O3 [4, 20, 41] 3,4-Secofriedelane-3,28-dioic acid C30H50O4 [19] Inophynone C24H24O4 [20, 28] Isoinophynone C24H24O4 [20, 28] β-Amyrin C30H50O [20] Epifriedelanol C30H52O [41] 3-Oxo-27-hydroxyacetate friedelan-28-oic acid [19] Oleanolic acid C30H48O3 [41] Squalene C30H50 [50]

Cholesterol C27H46O [28] Campesterol C28H48O [20]

Biflavonoids C30H20O10 [49] Neoflavonoids C20H18O8 [49]

Amentoflavone C30H18O10 [20, 22, 40]

Inophyllum C C25H23O5 [12, 40, 42] Inophyllum E C25H22O5 [12, 40] Inophyllum B C25H24O5 [4, 42] Inophyllum P C25H24O5 [4, 42] Calophyllic acid C25H24O6 [4, 20, 40] Isocalophyllic acid C25H24O6 [20, 40] Inophyllum G-1 C25H24O5 [4, 42] Inophyllum G-2 C25H24O5 [4, 42] Calocoumarin-A [20] Calocoumarin-B [20] Calocoumarin-C [20] Apetalolide C26H24O5 [20] 4-Phenylcoumarins [20] Pyranocoumarins C20H18O4 [42]

Quercetin-3-O-α-L-rhamnoside (4H-1-benzopyran-4-one,2-

(3,4-dihydroxyphenyl)-3,5,7-trihydroxy)

**structure**

**References**

32, 41]

C15H10O7 [22, 49]

*DOI: http://dx.doi.org/10.5772/intechopen.86991*

1. Triterpenoids

2. Steroids

3. Flavonoids

4. Coumarins


Calophyllum inophyllum*: Beneficial Phytochemicals, Their Uses, and Identification DOI: http://dx.doi.org/10.5772/intechopen.86991*

*Phytochemicals in Human Health*

3-O-α-L-rhamnoside [8, 48].

C18H36O2) [49].

**2.8 Esters**

**Figure 8.**

*Molecular structure of flavone.*

**2.9 Tannins**

**2.7 Oxygenated hydrocarbon (fatty acids)**

heptadecanoic acid, and 16-methyl ester [49, 50].

flavolan and (2) hydrolyzed tannins.

*2.9.1 Condensed tannins*

Flavonoids have a variety of biological functions including pharmaceutical use and their function in plants. Examples of pigments in flowers, they provide color and attract insects for pollination. Flavonoids which are contained in the leaves have to prevent fungal infections and protect leaves from UV radiation [45]. In the aspect of pharmacology, flavonoids interact with cytochrome P450 and are used to treat heart disease. They are also known to have antioxidant activity and antifree radicals that are useful in anticancer and antiaging. Furthermore, they also have antileukemic activity, vitamin C, 5-lipoxygenase, cyclooxygenase inhibitors,

Several flavonoid compounds that have been isolated from the *C. inophyllum* leaves are bioflavonoids, neoflavonoid [48], amentoflavone [20, 40], and quercetin-

Some of the compounds of fatty acid that has been found in the *C. inophyllum* leaves are tetradecanoic acid (myristic acid, C14H28O2), n-hexadecanoic acid (palmitic acid, C16H32O2), oleic acid (C18H34O2), and octadecanoic acid (stearic acid,

Some ester compounds that have been found in the *C. inophyllum* leaves are 1,2-benzenedicarboxylic acid (diisooctyl ester/phthalic acid, bis(6-methylheptyl) ester), 9,12-octadecenoic acid methyl ester, 16-octadecanoic acid methyl ester,

In chemistry, there are two types of tannins, namely, (1) condensed tannins or

The condensed tannins are widespread in angiosperm plants, especially in woody plants. Another name of condensed tannins is proanthocyanidin because when they reacted with hot acid, some of the carbon-carbon connecting bond units disconnect and free monomer anthocyanidins. Most proanthocyanidin is procyanidin because when reacted with acids will produce cyanidin. Proanthocyanidin can be detected directly by dipping the plant tissue into 2 M HCl boil for half an hour that will produce a red color which can be extracted with amyl or butyl alcohol.

protein kinase C, tyrosine kinase, and genetic toxicity [27].

**34**


**37**

Calophyllum inophyllum*: Beneficial Phytochemicals, Their Uses, and Identification*

**No. Phytochemicals Chemical** 

a. (2S,3R)-2,3-Dihydro-5-hidroxy-2,3,8,8-tetramethyl-6-(1 phenylethenyl)-4H,8H-benzo [1,2-b:3,4-b'] dipyran-4-one

b. (2R,3R)-2,3-Dihydro-5-hidroxy-2,3,8,8-tetramethyl-6-(1 phenylethenyl)-4H,8H-benzo [1,2-b:3,4-b'] dipyran-4-one

Benzene (1-methyldodecyl) C19H32 [50]

12. Androstan-1α-ol-17-one,23 isopropylidenedioxy-4β-methyl- C23H36O4 [50] 13. Proanthocyanidin (condensed tannin) C31H28O12 [20, 49]

15. Asam inophylloidic C32H46O6 [12, 20] 16. Calaustralin C25H25O5 [12] 17. Shikimic acid C7H10O5 [40] 18. Brasiliensic acid C32H46O6 [12] 19. Adenanthin (7,8,12-tri-0-acetyl-3-desoxy-ingol3-one) C26H34O9 [51] 20. Carbazole C12H9N [51] 21. Diphenyl methane (1'-biphenyl, 2-methyl) C13H12 [51] 22. 2-Phenazinamine (1,1'-biphenyl, 4-azido) C12H9N3 [51]

**structure**

**References**

[14]

[14]

C16H17N [51]

When dry tissues are used, the result of tannins somewhat diminished because of

24. Phytol C20H40O [50, 51] 25 3,7,11,15-Tetramethyl-2-hexadecen-1-ol C20H40O [50] 26. Phenol (2,4-bis(1-phenylethyl)-phenol) C22H22O [50]

The hydrolyzed tannins are contained in dicotyledonous plants. They mainly consist of two classes; the simplest is galloylglucose. In this compound, glucose is surrounded by five or more galloyl ester groups. The second type is the core molecules of a compound gallic acid dimer, namely, hexahydroxidifenate acid that binds to glucose. Hydrolyzed tannins can be detected by determining the gallic acid

Some chemical compounds that have been found in the *C. inophyllum* leaves are azulene (C15H18), squalene (C30H50), 3-trifluoroacetyl pentadecane (pentadecyl trifluoroacetate), 1-monolinolein glycerol trimethylsilyl ether, cyclohexane, benzene, androstane [49], inophylloidic acid [12, 20, 52], shikimic acid [40], calaustralin, brasiliensic acid [12], adenanthin, carbazole, diphenyl methane, 2-phenazinamine, 5-aminomethyl-dibenzosuberane [50], phytol, phenol, and 3,7,11,15-tetramethyl-2-hexadecene-1-ol [49, 50]. The summary

the occurrence of sticking tannins in place within the cell.

23. 5-Aminomethyl-dibenzosuberane (2-naphtalenecarbonitrile,

of phytochemicals in *C. inophyllum* leaves is presented in **Table2**.

or ellagic acid in ether or ethyl acetate extracts.

*Phytochemicals contained in the C. inophyllum leaves.*

*2.9.2 Hydrolyzed tannins*

**Table 2.**

6-pentyl-)

**2.10 Other components**

*DOI: http://dx.doi.org/10.5772/intechopen.86991*

14. Benzodipyranone (chromone) derivatives:

11. Aromatic hydrocarbon:


Calophyllum inophyllum*: Beneficial Phytochemicals, Their Uses, and Identification DOI: http://dx.doi.org/10.5772/intechopen.86991*

#### **Table 2.**

*Phytochemicals in Human Health*

5. Xanthones

6. Oxygenated hydrocarbons (fatty acids)

7. Esters

ester)

10. Alicyclic compounds Cyclohexene,

9. Ethers

8. Alkenes (unsaturated compounds):

(trifluoroacetic, pentadecyl ester)

**No. Phytochemicals Chemical** 

Calophyllolides (calophyllolide 2a, 3a, 3b, 6) C26H24O5 [4, 12, 42]

Caloxanthone A C23H22O6 [4, 12] Caloxanthone B [4, 12] Caloxanthone C [4] Brasilixanthone-B C23H20O6 [20] Buchanaxanthone C14H10O5 [20] Inoxanthone C23H22O5 [12] Maclura xanthone C23H22O6 [12] Calophynic acid C35H44O6 [12] 3,4-Dihydroxyxanthone C13H8O4 [12, 19] Inophyxanthone A [21] Pancixanthone A C18H16O5 [21] Gerontoxanthone B C23H22O6 [21] Jacareubin (6-deoxyjacareubin) C18H14O6 [21, 22] Pyranojacaereubin C23H20O6 [21] 2-Hydroxyxanthone C13H8O3 [22] 4-Hydroxyxanthone C13H8O3 [22] 1,3,5-Trihidroxy-2-methoxyxanthone [22] Xanthone C13H8O2 [21]

Tetradecanoic acid (myristic acid) C14H28O2 [50] n-Hexadecanoic acid (palmitic acid) C16H32O2 [50] Oleic acid C18H34O2 [50] Octadecanoic acid (stearic acid) C18H36O2 [50]

Methyl linoleic (9,12-octadecanoic acid methyl ester) C19H34O2 [50, 51] Methyl oleate (16-octadecanoic acid methyl ester) C19H36O2 [51]

Azulene, 1,4-dimethyl-7-(1-methylethyl)- C15H18 [50]

1-Monolinoleoglycerol trimethylsilyl ether C27H54O4Si2 [50]

1,2-Benzenedicarboxylic acid (diisooctyl ester) (phthalic acid,

Methyl isostearate (heptadecanoic acid, 16-methyl, methyl

3-Trifluoroacetoxypentadecane (pentadecyl trifluoroacetate)

3-(1,5-dimethyl-4-hexenyl)-6-methylene-,[S-(R\*,S\*)]

bis(6-methylheptyl) ester) (diisooctyl phthalate)

**structure**

C24H38O4 [50]

C19H38O2 [51]

C17H31F3O2 [50]

C15H24 [50]

**References**

**36**

*Phytochemicals contained in the C. inophyllum leaves.*

When dry tissues are used, the result of tannins somewhat diminished because of the occurrence of sticking tannins in place within the cell.

#### *2.9.2 Hydrolyzed tannins*

The hydrolyzed tannins are contained in dicotyledonous plants. They mainly consist of two classes; the simplest is galloylglucose. In this compound, glucose is surrounded by five or more galloyl ester groups. The second type is the core molecules of a compound gallic acid dimer, namely, hexahydroxidifenate acid that binds to glucose. Hydrolyzed tannins can be detected by determining the gallic acid or ellagic acid in ether or ethyl acetate extracts.

#### **2.10 Other components**

Some chemical compounds that have been found in the *C. inophyllum* leaves are azulene (C15H18), squalene (C30H50), 3-trifluoroacetyl pentadecane (pentadecyl trifluoroacetate), 1-monolinolein glycerol trimethylsilyl ether, cyclohexane, benzene, androstane [49], inophylloidic acid [12, 20, 52], shikimic acid [40], calaustralin, brasiliensic acid [12], adenanthin, carbazole, diphenyl methane, 2-phenazinamine, 5-aminomethyl-dibenzosuberane [50], phytol, phenol, and 3,7,11,15-tetramethyl-2-hexadecene-1-ol [49, 50]. The summary of phytochemicals in *C. inophyllum* leaves is presented in **Table2**.
