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Y. A. T. Ngandjui et al.

forms a soluble ion pair with the alkaloids. The shifts obtained are particularly large for protons close to the protonated nitrogen, giving additional information on the structure and the stereochemistry of the alkaloid. Another way to obtain resolution of overlapping signals could be the application of the HOHAHA technique, which allows spectra to be obtained from separate spin systems, or the measurement of 2D J-resolved spectra.

The next step in the structure elucidation is the measurement of a 13C-NMR spectrum. Each carbon emits a signal at a shift characteristic of its molecular environment, e.g., aromatic, vinylic, with hetero-atomic substituents. Alkaloids groups have great variety of structure and also many characteristic peaks in 1H-NMR and 13C-NMR spectroscopic. The value of these peak depending of each alkaloids class. For this reason, we will choose and present the general characteristic peak of one class of alkaloids involved in the management of lifestyle diseases.

3.3.4 Characterization ofMonoterpene Indole

Alkaloids

Among alkaloids, monoterpene indole alkaloids were reported to exhibited good activity against lifestyle diseases [143, 144].

3.3.4.1 Qualitative Identication ofMonoterpene Indole Alkaloids

All alkaloids including monoterpene indole alkaloids react with reagents of Dragendorff, Mayer, and Wagner to give colored compounds.

3.3.4.2 Ultra Violet Spectral Properties

The UV spectrum of monoterpene indole alkaloids is carried out in MeOH and the characteristic absorption maxima are around 206–229nm, 276–299nm, 284–324nm, and 367– 392nm [144, 217, 218].

3.3.4.3 Infrared Spectral Properties

The characteristics IR absorptions bands are in the region of 1660–1645cm−1 for the six-member lactam ring, between 1597 and 1731cm−1 for the carbonyl function and at 3145 and 3433cm−1 for hydroxyl groups. In addition, absorptions bands at 3145–3364 cm−1 indicate the existence of N-H groups [144, 217, 219] (Table1).

3.4 Characterization Techniques

ofFlavonoids

In general, phenolic compounds were reported to exhibit good activities against lifestyle diseases. Among phenolic compounds, avonoids were the most reported to possess

such activities [220, 221]. Flavonoids can be identied through both qualitative analysis and spectroscopic methods.

3.4.1 Qualitative Methods

Most avonoids are positive to ferric chloride and Shinoda tests. They can also be positive to test of Molish if they possess sugar moiety in their structures [222].

3.4.2 Spectroscopic Methods

3.4.2.1 UV andIR Characteristic ofFlavonoids

The UV spectrum of avonoids is generally established in polar solvents such as MeOH or EtOH and two absorption maxima are observed, the range from 240 to 290nm (band II) due to ring A and the range from 300 to 400nm (band I) due to ring B, a cynnamoyle system. But these values highly depend on oxygenation pattern of a avonoid (the position and the number of hydroxyl groups) [223, 224] (Scheme 1 and Table2).

IR spectroscopy, compared to the above techniques shows little information, but important information on the elucidation of the structure of avonoids. In fact, most isoavones, hydroxylated avones, chalcones or dihydrochalcones show strong maximum absorption bands between 3200 and 3500 cm−1 due to hydroxyl groups [223]. In addition, an intense absorption band characteristic of the carbonyl group (C=O) of these compounds is observed around 1680cm−1 and is shifted to ca. 1620cm−1 when the C=O is chelated with a hydroxyl. In the IR spectrum of avonoids, an absorption band is also observed around 1600cm−1 due to aromatic double bonds [223, 225].

3.4.2.2 Electronic Impact Mass Spectrometry (EI-MS)

The mass spectrometry data are really necessary in avonoid structure elucidation. This technique is used for the determination of the molecular weight, for the establishment of the distribution of substituents between the A- and B-rings and also for the determination of the site of attachment and the nature of the sugar(s) in C-avonoid and O-glucosides of avonoids. The molecular weight of the basic avonoid nucleus is 222 a.m.u. for the avones, isoavones, and aurones; 224 a.m.u. for the avanones and chalcones; 238 a.m.u. for the avonols, and 240 a.m.u. for the dihydroavonols. From these basic molecular weights, the molecular weights of the elucidated compounds are deduced by adding the 16 mass units (a.m.u) for each -OH and 30 a.m.u. for each -OCH3.

The loss of some molecular ion fragments (M+) is very characteristic of avonoid mass spectra (Scheme 2). The signals displayed accurately indicate the molecular mass per unit

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C-NMR

Isodihydroaminocadambine [144]

H-NMR

C-NMR

64.6 3.09 44.9

22.3

2.68m

22.1 2.97m

27.5

2.45m

27.3 2.05m

120.9 5.33m 120.8

62.7

3.65 dd (12.1, 2.2)

62.4 3.86 dd (12.1, 5.7)

-methyl [143] Razyamide [143] Vincosamide-N-oxide [144]

H-NMR

– – – –

C-NMR

–

H-NMR

–

C-NMR

49.6

–

7.92s

–

3.61m

2.62m

50.3 3.67m

20.3 2.97m

2.65 brs

2.78 d (17.0)

52.7 3.17 dd (11.0, 4.5)

1.98m

33.6 2.45m

2.04 ddd (16.1, 10.3, 9.3)

32.1 2.64 brs

28.6 – 170.7 – 109.2 – 109.4

48.5 – 168.4 7.43s 149.2 7.31s 149.4

5.33 d (11.1)

59.0 5.38 d (1.9) 98.0 5.30 br d (9.5) 98.2

3.14 brs

116.8 1.79 brs 13.1 5.43 dd (10.2, 2.0)

63.9 3.91 d (13.6)

3.69 dd (12.1, 2.1)

C-NMR of some monoterpene indole alkaloids derivatives

6-nor-antirhine-N

H and

Table 1

H-NMR

3.29

1-CH31-NH

–

2 – 137.1 – 133.0 – 137.6 – 134.9

3 4.08 brs 55.6 4.45 d (7.6) 27.7 4.96m 73.9 4.56 brs 55.3

2.92 brs

4 – – – – – – – –

5 3.16 dd (9.0, 4.8)

6 – – 3.03m

7 – 107.5 – 107.8 – 110.2 – 110.4

8 – 128.3 – 126.3 128.6 – 128.8

9 7.38 d (7.8) 118.3 7.45 d (7.6) 118.1 7.38 d (7.6) 118.7 7.28m 118.8

10 6.96 ddd (7.8, 7.8, 1.2) 119.4 7.08 dd (7.6, 7.6) 119.5 7.03 ddd (8.1, 7.3, 1.1) 120.3 6.98t (7.3) 120.3

11 7.01 ddd (7.8, 7.8, 1.2) 121.4– 7.12 dd (7.6,7.6) 121.9 7.11 ddd (8.1, 7.3, 1.1) 122.5 7.07t (7.3) 122.7

12 7.30 d (7.8) 111.8 7.28 d (7.6) 111.1 7.30 d (8.4) 112.4 7.27m 112.5

13 – 137.3 – 136.6 – 134.7 – 137.9

2.10m

14 2.14m

1.55 dd (9.0, 4.2)

2.68m

15 1.66m 32.0 3.82 brs 53.7 2.80m 24.6 2.69m 25.1

16 1.70 ddd (16.8, 9.0, 4.2)

17 2.77m

18 5.05 d (1.8)

5.04 d (1.8)

19 5.69 ddd (18.6, 12.0, 9.6) 140.5 5.38 q (6.8) 121.9 5.63m 134.1 5.51 ddd (9.6, 7.7, 2.9) 134.5

20 2.28 brs 49.6 – 133.0 45.1 4.96 dd (9.5, 2.9) 44.9

3.62 dd (10.8, 6.0)

– – – – 4.62 d (7.8) 100.4 4.57 d (7.8) 100.62′– – – – 3.04t (8.9) 74.2 2.97 dd (13.1, 8.3) 74.43′– – – – 3.27m 77.8 3.33m 78.44′– – – – 3.23m 71.1 3.25m 71.55′– – – – 3.29m 77.9 3.24m 78.16′– – – – 3.89 dd (12.1, 5.4)

21 3.66 dd (10.8, 6.0)

22 – – – – – 169.0 3.31 brs 49.5

1′

– – 3.69s 51.2 – – – –

OCH

NH – – 7.92s – – – –

Band I(300-400)

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Benzoyl

Band II (245-295)

Scheme 1 Absorption bands of the benzoyl and cinnamoyl systems

Table 2 Ultraviolet-visible absorption ranges for avonoids [223]

Band II (nm) Band I (nm) Flavonoid type

230–270 340–390 Chalcones 230–270 380–430 Aurones 245–275 310–330

shoulder Ca. 320 peak Isoavones

250–280 310–350 Flavones 250–280 330–360 Flavonols (3-OH substituted)

250–280 350–385 Flavonols (3-OH free) 270–280 465–560 Anthocyanidins and anthocyanins 275–295 300–330

shoulder

Cinnamoyl

Isoavone

(5-deoxy-6,7-dioxygenated)

oxydation

Flavonones and dihydroavonols

Y. A. T. Ngandjui et al.

charge (m/z) of the fragments they represent. The exact molecular mass for each fragment can be measured to the nearest

0.0001 mass unit if the mass spectrometer is capable of producing a high-resolution mass spectrum. This information allows the precise molecular formula to be calculated from the peak of the molecular ion and the fragment ions [223].

The scheme below highlights the main mechanism of fragmentation [226].

3.4.2.3 1H and13C-NMR

The 1H-NMR spectrum appears important in some cases to distinguish the different subclasses of avonoids such as avanones, avones, and isoavones. From the following table some characteristic proton chemical shifts of avonoids are listed (Table3) [227, 228].

The 1H-NMR spectroscopy also has typical applications:

– In dening the oxygenation pattern of the three rings of

avonoid and in determining the position and number of

methyl groups;

– In distinguishing dihydroavonols, avonones, and

isoavones;

– In determining the number of sugars present and bound to

either α- or β- (by 1H-1H coupling constant);

– In detecting of hydrocarbon side chains such as C-linked

CH3 and C- or O-linked prenyl.

The 13C-NMR help to differentiate the ortho and meta dihydroxyl-substituted B-ring. In fact, when this ring carry

Scheme 2 Fragmentation pathways of avonoids

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Table 3 Approximate proton chemical shifts of avonoids [227]

Chemical shift (ppm) Proton type

ca. 1.7 Prenyl [-CH2-CH=C(CH3)2] methyl groups

(other protons: 3.5 and 5.2ppm) ca. 2.0 Acetate (-OCOCH 2–3 H-3 of avanones (two proton-multiplet)

4.2–6.0 H-2 dihydroavonols: 5.0ppm and H-2 of

avanones: 5–5.5ppm

6.0–8.0 A- and B-ring protons

7.5–8.0 H-2 of isoavones (singlet) 12–14 5-OH (usually observed when

solvent=DMSO-d6)

Table 4 13C-NMR chemical shift ranges of various avonoid carbon types [230]

Usual chemical shift range (ppm)

210–170 Carbonyl (4-keto, acyl)

Aromatic and olenic

150–130 (with ortho/para oxygenation) 165–155 (no ortho/para oxygenation)

125–90 (with ortho/para oxygenation) 135–125 (no ortho/para oxygenation)

Aliphatic

21 (CH2), 122 (CH), 131 (C), 18 (CH3)

55–63 (60–63 for O-disubstituted)

ca. 17–20 C-CH 80–40 (epicatechin C-4, 28ppm) Non oxygenyted (C-2, 3

ca. 100 Methylenedioxy 83–69 (C-1 of O-glycoside, ca.

100ppm)

) and aromatic C-CH

Carbon type

Oxygenated

Non-oxygenated

Isopropenyl [-CH2CH=C(CH3)2]

O-CH

, COCH

avanones)

Oxygenated (sugars)

only hydroxyl, signal is exhibited around 141–149ppm, and in the case of meta substitution, the signal is shifted to low eld around 151–159ppm [223, 229] (Table4).

The 13C-NMR of avonoids has also typical application in

the structure elucidation mainly in:

– Establishing the number of oxygenated carbons on the

avonoid nucleus, the total number of carbon atoms per

molecule and the number of carbons in the sugar moiety; – Identifying of C- and O-linked sugars and; – Determining inter-glycosidic linkage points, acyl substit-

uents, and the site of acylation.

The sugar carbon resonances in the 13C-NMR spectra of

some avonoid C- or O-glycosides are presented in the following table (Table5) [231].

Various avonoid aglycones have also characteristic signals in their 13C-NMR spectra and some of them are given in Table6.

3.5 Characterization Techniques

ofTerpenoids andSteroids

3.5.1 Mass Spectrometry

Several mass techniques can be used for the characterization of terpenoids including IE, FAB-MS, GC-MS, and HPLC-MS.For example, fast atom bombardment spectroscopy (FAB-MS) affords the exact molecular ion peak along with diagnostic fragmentation pattern of the terpenoid molecule. During the recent years, the structure determination of various terpenoids have been done using GC-MS, HPLC-MS spectrometry both coupled with computerized analysis and tandem MS spectral analysis and using FAB-MS in both positive and negative modes [232].

3.5.2 UV andIR Characteristics ofTerpenoids

Functional groups, as olenic bonds (double and triple bonds), carbonyl groups (aldehydes, ketones), carboxylic groups (carboxylic acid and its derivatives) present in terpenoids appear in the UV range between 200 and 350nm. In terpenoid structures, isolated double and triple bonds do not absorb at wavelengths above 200nm, while isolated ketones, aldehydes, carboxylic acids and their derivatives absorb at higher wavelengths with low intensities. Hence, both of the above-mentioned isolated chromophores are not of much value for the structure elucidation. However, UV data become valuable when the conjugated double bonds and α, β-unsaturated carbonyl group are present in the molecule [232].

The IR spectroscopy is commonly used for the identication and structural elucidation of new terpenoids. It gives information about functional groups [232].

3.5.3 Nuclear Magnetic Resonance

Spectroscopy (NMR)

The 1H-NMR and 13C-NMR spectroscopy are the most important tools required for the structure elucidation of terpenoids. The combination of 1D and 2D NMR techniques including COSY, TOCSY, ROESY, 2D-IN ADEQUATE, HMQC, HMBC, HETCOR, and selective INEPT are a great value for the structure elucidation of various terpenoids such as saponins and glycosides consisting of sugar moieties [232]. Terpenoids were greatly implicated in the management of lifestyle diseases. Among these terpenoids, pentacyclic triterpenoids is among the subclass of triterpene which exhibited good activity in the management of lifestyle diseases.

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Table 5 Sugar carbon resonances in the 13C-NMR spectra of some avonoid C- and O-glycosides [231]

Glycoside type C-1 C-2 C-3 C-4 C-5 C-6

O-glucoside (7-linked) 100.2 73.3 76.6 69.8 77.4 60.9 C-glucoside (8-linked) 73.9 71.4 78.8 70.8 81.4 61.5 O-galactoside (3-linked) 102.3 71.3 73.4 68.0 75.8 60.8 C-galactoside (8-linked) 73.9 68.5 75.4 69.1 80.5 61.3 O-α-rhamnoside (3-linked) C-α-rhamnoside (8-linked) O-xyloside (2″-O-linked) O-xyloside (6-linked) 74.6 70.3 78.5 70.0 70.0 – O-α-arabinoside (3-linked) O-α-arabinofuranoside (3-linked) C-α-arabinoside (8-linked) O-glucuronide(3-linked) 101.1 73.7 75.9 71.3 75.9 169.7 O-alloside (3-linked) 99.9 71.6 71.6 67.2 75.1 61.3 O-apioside (2″-O-linked)

101.9 70.4 70.6 71.5 70.1 17.3

77.3 75.0 75.5 72.2 72.2 18.1

102.4 73.7 75.9 69.4 65.5 –

101.8 71.7 70.8 65.9 64.1 –

108.1 82.1 77.2 86.2 61.0 –

74.4 68.2 74.5 68.9 71.0 –

109.0 76.5 79.1 74.0 64.4 –

Y. A. T. Ngandjui et al.

3.5.4 Characterization ofPentacyclic Triterpenoids

3.5.4.1 Qualitative Analysis

Most triterpenoids including pentacyclic triterpenoids respond positively to sulfuric vanillin and Liebermann– Burchard tests.

3.5.4.2 IR Spectroscopy

The Infrared spectrum makes it possible to identify the chemical functions present such as ketones, alcohol, carboxylic acid acetate groups, etc. which characterize most triterpenes [233].

The vibration of the hydroxyl group (OH) is observed between 3200 and 3300 cm−1; the carbonyl group (C=O) band is very intense around 1773 cm−1.The symmetrical deformation vibration of the ester methyl appears between 1370 and 1390 cm−1 and the vibration of the carboxylate group is located between 1100 and 1300cm−1 [234].

3.5.4.3 Mass Spectrometry

In mass spectroscopy, the fragments of the triterpenes are characteristics such as the peaks of fragmentation characteristic of the “Retro-Diels-Alder” mechanism by cleavage of the D/E and C/D cycles of the pentacyclic triterpenes [233]. Indeed, this method is advantageous in the elucidation of structures because it allows the identication of double bonds.

The retro Diels-Alder makes it possible to obtain, for pentacyclic triterpenes possessing a C-12 unsaturation such as urs-12-ene and olean-12-ene, a base peak at m/z=218. When substituents are observed on rings D and E, the value of the base peak may change. There will be a base peak at m/z=203 (218-Me) if there is loss of a methyl group during the elec-

tronic impact or values such as: m/z=248 (203+COOH), m/z=262 (203+COOMe), m/z=265 (203+COOH + OH) and m/z=276 (203+OAc) for substituents of the carboxyl, carbomethoxy, and hydroxyl type remaining on the ion of base peak. These data can, therefore, be used to predict the nature of substitutions on a skeleton [235].

Scheme 3 gives the different probable ions resulting from the Retro Diels-Alder type fragmentation of molecules of the urs-12-ene and olean-12-ene type [236].

Regarding pentacyclic triterpenoids of lupane and hopane types, there is be a base peak that will appear rather towards m/z=189 or m/z=191 when the substitution on the E ring is respectively isopropenyl or isopropyl [235].

3.5.4.4 1H and13C-NMR

The 1H-NMR spectrum of triterpenes is not very explicit. However, it exhibits a series of characteristic peaks in the range 0.5–2ppm, corresponding to the methyl groups. The prole (number, multiplicity, chemical shift) allows orientation regarding the type and series of the triterpene nucleus. The chemical shifts between 2 and 6ppm indicate the presence of functional groups like the hydroxyl, double bond, and carbonyl [233].

The 1H NMR is very characteristic and makes it possible to distinguish certain classes of pentacyclic triterpenes such as ursanes, oleananes, and lupanes. Indeed, the ursane and oleanene derivatives generally exhibit in the 1H-NMR spectrum a large triplet between 5.1 and 5.5ppm of coupling constant J = 3 Hz, characteristic of the vinyl proton H-12. Lup-20(29)-ene derivatives are generally characterized by the presence of two singlets of one proton each between 4.2 and 5.0ppm, characteristic of the 02 vinyl protons on carbon C-29 [237].

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C-1 C-2 C-3 C-4 C-5 C-6

C-NMR data of various avonoid aglycones [223]

Table 6

Flavonoid C-2 C-3 C-4 C-5 C-6 C-7 C-8 C-9 C-10 C-1′ C-2′ C-3′ C-4′ C-5′ C-6′ CH3Flavones

Apigenin 163.8 102.8 181.8 161.9 98.8 164.1 94.0 157.3 103.7 121.3 128.4 116.0 161.5 116.0 128.4

Luteolin 164.5 103.3 182.2 162.1 99.2 164.7 94.2 157.9 104.2 122.1 113.8 146.2 150.1 116.4 119.3

Tricetin 164.2 103.2 181.6 161.6 99.0 164.2 93.9 157.5 104.0 120.9 106.0 146.5 137.9 146.5 106.0

Flavonols

Kampferol 146.8 135.6 175.9 160.7 98.2 163.9 93.5 156.2 103.1 121.7 129.5 115.4 159.2 115.4 129.5

Quercetin 146.9 135.5 175.8 160.7 98.2 163.9 93.3 156.2 103.1 122.1 115.3 145.0 147.6 115.6 120.0

Patuletin 147.1 135.5 176.1 151.8 130.9 157.2 93.7 151.4 103.5 122.1 115.2 145.1 147.8 115.7 120.1 60.3

Isoavones

C-1′ C-2′ C-3′ C-4′ C-5′ C-6′

C=O

C-β C-α

Genistein 153.6 122.4 180.2 162.1 98.6 164.3 93.7 157.5 104.6 121.4 130.0 115.2 157.6 115.2 130.0

Chalcone

Isoliquiritigenin 143.8 117.8 191.4 113.2 164.6 102.6 165.4 107.9 132.3 125.8 130.6 115.8 159.9 115.8 130.6

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Scheme 3 RDA fragmentation of urs-12-ene and olean-12-ene derivatives

Y. A. T. Ngandjui et al.

For C-3 substituted hydroxylated triterpenes, the H-3 proton generally appears between 3.1 and 3.8 ppm while that of acetoxylated triterpenes resonate between 4.2 and

4.6ppm [238].

The methyl signals appearing between 0.5 and 2ppm make it possible to differentiate the types of pentacyclic triterpenes. For example, the unoxidized triterpenes of the olean-12-enes series have 08 singlet signals of 03 protons attributable to 08 angular methyls while those of the urs12- enes series possess 06 singlets of 03 protons and 02 doublets [239].

Regarding the 13C-NMR spectrum, it is more valuable in the structural determination of triterpene nuclei. It allows us to clearly demonstrate the 30 carbon atoms which constitute the backbone of triterpenes, and in particular the carbonyl, carboxylic acid, and alcohol groups, by their specic chemical shifts that is around 210ppm for a carbonyl (C=O), 170 ppm for a carboxylic acid (COOH) and 70ppm for an alcohol (OH) [233].The evolution of this elucidation technique has made it possible to distinguish between the derivatives of the urs-12-ene and olean-12-eneseries. This is made possible by the number of quaternary carbon atoms (which are 05in number for the urs-12-ene series and 06 for the olean-12-ene series) and the chemical shifts of the vinyl carbons C-12 and C-13 resonating respectively at 124.5 ppm (d) and 138 ppm (s) for urs-12-ene while for olean-12-ene the chemical shift of these carbons are at 122.5ppm (d) and

143.5ppm (s) [239].

3.5.5 Characterization Techniques ofSaponins

The structural determination of the aglycones is similar to those of simple terpenoids. However, the 1H-NMR spectrum in the pyridine solvent show the existence of anomeric proton between 4.3 and 6.9 ppm, as well as the

methyl doublets of deoxy-6-hexoses in the range of 1.4–

1.8 ppm. The high values of the coupling constants (J > 7.0 Hz) observed for the anomerous protons of D-glucose, D-galactose, and D-xylose is characteristic for the β-conguration while the small values (J=1–1.5Hz) observed for the L-rhamnose suggest α-conguration. 13CNMR spectrum analysis makes things even easier. The anomeric carbons resonate in a distinct region. This makes it possible to have an estimate of the amount of sugar present in the molecule. The conguration of the L-rhamnose anomere could also be conrmed from the chemical shifts of the C-3 and C-5 carbons. For β-L- rhamnopyranoside these carbons resonate at 75.4 and 73.5 ppm, while for α-L-rhamnopyranoside they are observed at 72.5 and

69.4ppm, respectively [240, 241].

4 Conclusion andOutlooks

Phenolic compounds, alkaloids, terpenoids, and steroids were frequently reported in the literature to exhibit promising activities against lifestyle diseases such as diabetes, cardiovascular diseases, cancers, and chronic respiratory diseases. In this chapter, the main characterization techniques such as infrared (IR), UV-visible, mass spectrometry, and nuclear magnetic resonance (NMR) spectroscopy of these classes of secondary metabolites were discussed. In order to optimize the identication and quantication of these classes of compounds in plants extracts as well as their subsequent isolation, standardized methods using more advanced techniques (metabolomics and molecular networking) needs to be established.

Acknowledgments The authors are grateful to the nancial support of the International Science Programme (ISP), the Natural Products

Chemical Characterization ofPhytoconstituents forLifestyle Diseases

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Research Network for Eastern and Central Africa (NAPRECA) and the University of South Africa (UNISA). The authors are also thankful to the Alexander von Humboldt Foundation (3.4-CMR-Hub) for the nancial support to the Centre of Competence for the Study of Antimicrobial Natural Products from Fungi (CECANAPROF).

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