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Natural products isolated from Casimiroa

  • Khun Nay Win Tun , Nanik Siti Aminah EMAIL logo , Alfinda Novi Kristanti , Hnin Thanda Aung and Yoshiaki Takaya
Published/Copyright: July 2, 2020
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Open Chemistry
From the journal Open Chemistry Volume 18 Issue 1

Abstract

About 140 genera and more than 1,600 species belong to the Rutaceae family. They grow in temperate and tropical zones on both hemispheres, as trees, shrubs, and herbs. Casimiroa is one of the genera constituting 13 species, most of which are found in tropical and subtropical regions. Many chemical constituents have been derived from this genus, including quinoline alkaloids, flavonoids, coumarins, and N-benzoyltyramide derivatives. This article reviews different studies carried out on aromatic compounds of genus Casimiroa; their biological activities; the different skeletons of coumarins, alkaloids, flavonoids, and others; and their characteristic NMR spectral data.

Keywords: aromatic compounds; Casimiroa; NMR spectral data; Rutaceae

1 Introduction

Natural products, including plants, animals, microorganisms, and marine organisms, have been used by humans as medicines to prevent and treat diseases since ancient times. According to historical records, the use of plants as medicines is an traditional practice and started with human interaction with the environment [1,2,3,4,5]. Both in the developing and developed countries, people rely on herbal medicine because of fewer side effects [6,7]. There are many plants used in folk medicine. Many plant-based bioactive substances have been isolated, characterized, and used in pure form or as suitable derivatives for the therapeutic purpose [8,9]. The World Health Organization estimates that 80% of the world’s population rely on traditional medicines for their primary health care needs [10]. The therapeutic potential of plants lies in chemical substances that produce a definite physiological action on man and animals. The key bioactive compounds in plants are produced as secondary metabolites [11,12].

Plants of Casimiroa belong to the Rutaceae family, which grows as tree in the tropical and subtropical areas of Central America and Mexico, the Caribbean, the Mediterranean region, India, Southeast Asia, South Africa, Australia, and New Zealand. This genus constitutes 13 species, and most of them, both wild and cultivated, are found in Mexico. The best-known species is Casimiroa edulis La Llave, also called “sapote blanco,” “Mexican apple,” “white sapote,” “Casimiroa,” and “sapote blance” by native people. Its fruit are edible [13,14]. Traditionally, the fruit and leaves of Casimiroa species are used to treat anxiety, as sedatives, and to treat dermatological conditions [15]. The pharmacological studies of an aqueous extract and alcohol extracts of the seeds and leaves of C. edulis exhibited the cardiovascular, anticonvulsant, sedative activities, anti-inflammatory, antimutagenic, diuretic activities, hypnotic, antihypertension, diuretic, anti-inflammatory muscle relaxant, and contractile properties. The pharmacological activities of the bioactive compounds from Casimiroa were also reported. Several species of this genus have been reported to possess interesting secondary metabolites. Among the major constituents of Casimiroa species are alkaloids, flavonoids, coumarins, limonoids, and N-benzoyltyramide derivatives [16,17,18,19,20,21,22,23,24,25,26,27,28,29,30,31,32,33,34,35,36,37,38]. The structures of the isolated compounds were elucidated based on the spectroscopic data, including NMR spectroscopy. This article also includes a review of characteristic NMR data of various classes of compounds from this genus.

2 Plant description

Plant descriptions of the best known species from Casimiroa are presented as follows:

Kingdom

Plantae

Order

Sapindales

Family

Rutaceae

Genus

Casimiroa

Species

C. edulis

Botanical name

Casimiroa edulis La Llave

English name

White sapote

Myanmar name

Tha-kyar-tee

C. edulis is 4.6–18.3 m high. Flowers are small, odorless, and pale green to cream color with five sepals, petals, and stamens. Fruits are round, ovary, or ovoid and golden-yellow when ripe. The leaflets are ovate and 4.5–12 cm long and 1–5 cm wide, with cuneate base, subserrate margins, bright green, glabrous or with scattered pubescence on the veins, pinnate vennation, and anastomising at the margins. The apex is acuminate.

2.1 Casimiroa tetrameria

C. tetrameria is about 50 ft height with dense, white, furry underside leaves. The small flowers grow in big groups and blossom many times a year, with fruit ripening after 6–8 months. This plant is originally from Southern Mexico, and it is not grown commercially.

2.2 Casimiroa pringlei

C. pringlei is a small tree found in central Mexico, which is about 4 m tall. There were no other literature references found. There were no reports about plant descriptions for other species.

3 Chemical constituents

Recently, many chemical constituents have been derived from Casimiroa. These compounds can be classified into four groups: coumarins, alkaloids, flavonoids, and four N-benzoyltyramide derivatives. Name of the compounds and the corresponding plant sources are presented in Tables 1, 3, 6, 7, 11, 14, and 18.

Table 1

Pharmacological properties of compounds obtained from Casimiroa species

Compound (Cp)Biological activitiesPlantPart usedRef.
Umbelliferone (1)Anticoagulant C. edulisLeaves[25]
Esculetin (2)Anticoagulant C. edulisLeaves[25]
Herniarin (3) Vasodilation and radical scavenging C. edulis and C. pubescensSeeds[31]
3-(1′,1′-Dimethyl-allyl)-herniarine (4)—C. pubescensRoots[36]
Auraptene (5)—C. pubescensRoots[36]
Table 3

Pharmacological properties of compounds isolated from various Casimiroa species

Compound (Cp)Biological activitiesPlantPart usedRef.
Xanthotoxol (6)AnticoagulantC. edulisLeaves[25]
Bergapten (7)Antidiabetic C. edulisStem bark[38]
5-Methoxy-8-hydroxypsoralen (8)—C. edulisSeeds[66]
Isopimpinellin (9)Antidiabetic and Antimutagenic C. edulis and C. pubescensSeeds[24,33,38]
Imperatorin (10)Anticoagulant, vasodilation, and radical scavengingC. edulis and C. pubescensSeeds[25,31]
(R,S)-8-[(6,7-Dihydroxy-3,7-dimethyl-2-octenyl)oxy]psoralen (11)AntimutagenicC.edulisSeeds[24]
8-Geranyloxypsoralen (12)Vasodilation and radical scavenging C. edulis and C. pubescensSeeds & leaves[31]
8-(3′-Hydroxymethyl-but-2-enyloxy)-psoralen acetate (13)Adipogenesis C. edulis & C. pringleiLeaves[29]
Phellopterin (14)Antimutagenic C. edulisSeeds[24]
(R,S)-5-Methoxy-8-[(6,7-dihydroxy-3,7-dimethyl-2-octenyl)oxy]psoralen (15)Antimutagenic C. edulisSeeds[24]
5-Methoxy-8-geranyloxypsoralen (16)—C. edulisSeeds[66]
8-(3′-Hydroxymethyl-but-2-enyloxy)-5-methoxypsoralen acetate (17)Adipogenesis C. edulisLeaves[29]
5-Methoxy-8-(3″-hydroxymethyl-but-2″-enyloxy)-psoralen (18)—C. tetrameriaLeaves[30]
5-Methoxy-8-(4′-acetoxy-3′-methyl-but-2-enyloxy) psoralen (19)Solid tumor selective cytotoxicityC. tetrameriaSeeds & leaves[33]
Table 6

Pharmacological properties of compounds isolated from Casimiroa species

Compound (Cp)Biological activitiesPlantPart usedRef.
Proline (20)CardiovascularC. edulisSeeds[35]
N-Methylproline (21)CardiovascularC. edulisSeeds[35]
N-Monomethylhistamine (22)CardiovascularC. edulisSeeds[35]
N,N-Dimethylhistamine (23)CardiovascularC. edulisSeeds[35]
Synephrine acetonide (24)CardiovascularC. edulisSeeds[35]
γ-Amino-butyric acid (25)CardiovascularC. edulisSeeds[35]
Casimiroedine (26)CardiovascularC. edulisSeeds[35]
Table 7

Pharmacological properties of compounds obtained from Casimiroa species

Compound (Cp)Biological activitiesPlantPart usedRef.
4-Methoxy-1-methyl-2(1H)-quinolinone (27)Antimutagenic C. edulisSeeds[24]
Edulitine (28)—C. edulisTrunk & root bark[23]
Casimiroin (29)Antimutagenic C. edulisSeeds[24]
Dictamnine (30)—C. edulisBark[23]
γ-Fagarine (31)Antimutagenic C. edulisSeeds & bark[23,24]
Skirnmianine (32)—C. edulisBark[23]
Table 11

Pharmacological properties of quinolinone alkaloids obtained from Casimiroa species

Compound (Cp)Biological activitiesPlantPart usedRef.
1-Methyl-2-phenyl-4-quinolone (33)Solid tumor selective cytotoxicityC. tetrameriaSeeds[33]
Edulein (34)—C. edulisTrunk & root bark[23]
5-Hydroxy-1-methyl-2-phenyl-4-quinolone (35)Antimutagenic C. edulisSeeds[24]
5,6-Dimethoxy-2-(3′-methoxyphenyl)-1H-quinolin-4-one (36)—C. edulisLeaves[28]
5,6-Dimethoxy-2-(3′,4′-dimethoxyphenyl)-1H-quinolin-4-one (37)—C. edulisLeaves[28]
5,6-Dimethoxy-2-(2′,5′,6′-tri-methoxyphenyl)-1H-quinolin-4-one (38)Antihypertensive C.edulisLeaves & Fruits[27,28]
5,8-Dimethoxy-2-(3′-methoxy-phenyl)-3-propyl-1H-quinolin-4-one (39)Antihypertensive C. edulisFruits[27]
5,8-Dimethoxy-2-(3′,4′-di-methoxyphenyl)-3-propyl-1H-quinolin-4-one (40)Antihypertensive C. edulisFruits[27]
2-(2′-Hydroxy-4′-methoxy-phenyl)-5,8-dimethoxy-3-propyl-1H-quinolin-4-one (41)Antihypertensive C. edulisFruits[27]
Table 14

Pharmacological properties of flavonoids obtained from Casimiroa species

Compound (Cp)Biological activitiesPlantPart usedRef.
6,7-Dimethoxyflavone (42)Antioxidant & antidiabetic C. edulisStem bark[37]
6-Hydroxy-5-methoxyflavone (43)AntioxidantC. edulisSeeds[26]
Zapotinin (44)—C. edulisSeeds[66,96]
5,6,2′-Trimethoxyflavone (45)Antimutagenic & solid tumor selective cytotoxicityC. edulis & C. tetrameriaSeeds[24,29,37]
5,6,3′-Trimethoxyflavone (46)—C. sapotaLeaves[97]
5,6,2′,3′-Trimethoxyflavone (47)—C. sapotaLeaves[97]
5,7,3’,5’-Tetramethoxy-flavone (48)Solid tumor selective cytotoxicityC. edulis & C. tetrameriaSeeds[33]
5,6,3′,5′-Tetramethoxy-flavone (49)—C. tetrameriaSeeds[98]
Zapotin (50)Antimutagenic & solid tumor selective cytotoxicityC. edulis & C. pubescensSeeds[24,33]
Zapotinin acetate (51)—C. edulisSeeds[66,96]
5,6,2′,3′,4′-Pentamethoxyflavone (52)Vasodilation & radical scavenging C. pubescens, C. edulis & C. sapotaSeeds[32]
5,6,2′,3′,6′-Pentamethoxy-flavone (53)—C. tetrameriaLeaves[30]
5,6,2′,3′,4′,6′-Hexamethoxy-flavone (54)—C. tetrameriaLeaves[98]
5,6,2′,3′,5′,6′-Hexamethoxy-flavone (55)—C. tetrameria & C. edulisLeaves[29,30]
5-Methoxyflavone 6-O-β-d-glucoside (56)Antioxidant C. edulisLeaves[26]
Quercetin (57)Antioxidant C. edulisLeaves[26]
Quercetin 3-O-rutinoside (58)AntioxidantC. edulisLeaves[26]
Kaempferol 3-O-rutinoside (59)—C. tetrameriaLeaves[98]
Quercetin 3-O-glucoside (60)—C. tetrameriaLeaves[98]
Kaempferol 3-O-glucoside (61)—C. tetrameriaLeaves[98]

4 Coumarins

Coumarin, being one of the members of the benzopyrone family, comprises a large group of compounds. More than 1,300 naturally occurring coumarins have been isolated from plants, bacteria, and fungi. It was first isolated from tonka bean and is reported in about 150 different species, distributed over nearly 30 different families, of which a few important ones are Rutaceae, Umbelliferae, Orchidaceae, Leguminosae, Labiatae, Clusiaceae, Guttiferae, Caprifoliaceae, Oleaceae, Nyctaginaceae, and Apiaceae. Coumarin is also found in fruits, green tea, and other foods such as chicory. Natural coumarins are mainly classified into six types based on their chemical structures. They are simple coumarins, furano coumarins, dihydrofurano coumarins, pyrano coumarins (linear and angular types), phenyl coumarins, and bicoumarins [39,40,41]. Coumarin is a plant-derived natural product known for its pharmacological properties such as anti-inflammatory [42,43], antibacterial [42], anticoagulant [44], antifungal [45,46], antiviral [47,48], anticancer [49,50,51], antidiabetic [52,53], antihypertensive [54], anticonvulsant [55], antioxidant [56,57,58,59], antimicrobial [60], and neuroprotective properties [61]. Casimiroa is the abundant source of coumarins. Simple coumarins, umbelliferone (1), esculetin (2), herniarin (3), 3-(1′,1′-dimethyl-allyl)-herniarine (4), and auraptene (5) were isolated from various parts (leaves, seeds, and roots) of C. edulis and Casimiroa pubescens [25,31,36]. Fourteen furocoumarins, xanthotoxol (6), bergapten (7), 5-methoxy-8-hydroxypsoralen (8), isopimpinellin (9), imperatorin (10), (R,S)-8-[(6,7-dihydroxy-3,7-dimethyl-2-octenyl)oxy]psoralen (11), 8-geranyloxypsoralen (12), 8-(3′-hydroxymethyl-but-2-enyloxy)-psoralen acetate (13), phellopterin (14), (R,S)-5-methoxy-8-[(6,7-dihydroxy-3,7-dimethyl-2-octenyl)oxy]psoralen (15), 5-methoxy-8-geranyloxypsoralen (16), 8-(3′-hydroxymethyl-but-2-enyloxy)-5-methoxypsoralen acetate (17), 5-methoxy-8-(3″-hydroxymethyl-but-2″′-enyloxy)-psoralen (18), and 5-methoxy-8-(4′-acetoxy-3′-methyl-but-2-enyloxy) psoralen (19) were also identified from various parts (leaves, stem bark, and seeds) of C. edulis, C. pubescens, and C. tetrameria [24,25,29,30,31,33,38,66]. The structures of various coumarin compounds are shown in Figure 1 and 2, and their NMR (1H NMR and 13C NMR) data are listed in Tables 2, 4, and 5.

Figure 1 Structures of simple coumarins of Casimiroa.
Figure 1

Structures of simple coumarins of Casimiroa.

Figure 2 Structures of furanocoumarins from Casimiroa.
Figure 2

Structures of furanocoumarins from Casimiroa.

Table 2

13C and 1H NMR (δ, ppm) chemical shift data of simple coumarins isolated from genus Casimiroa

Carbon no.Cp 1 [62]Cp 2 [64]Cp 3 [63]Cp 4 [36]Cp 5 [65]
δCδHδCδHδCδHδC (prediected)δHδCδH
2162.9—162.9—161.1—159.7—161.4—
3113.76.16111.06.16112.56.25131.1—113.06.23
4145.07.77144.77.77143.37.62138.07.54143.67.61
4a112.2—111.3—112.5—112.5—112.5—
5129.67.39111.56.74128.77.37129.87.36128.87.34
6113.76.77143.2—113.06.85111.06.83113.36.83
7162.0—150.8—162.8—160.2—162.2—
8102.86.71102.26.93100.86.82100.66.83101.76.80
8a156.2—149.1—155.8—156.9—155.9—
7 O-Me————55.73.8655.83.88——
1′——————40.3—65.64.58
2′——————145.66.19118.55.45
3′——————112.65.09, 5.13142.5—
4′————————39.62.10
5′————————26.32.12
6′————————123.75.06
7′————————132.1—
8′————————25.81.65
9′————————17.81.59
10′————————16.91.75
1′-Me-a——————26.21.50——
1′-Me-b——————26.21.50——
Table 4

13C and 1H NMR chemical shift data (δ, ppm) of furanocoumarins isolated from genus Casimiroa

Carbon no.Cp 6 [67]Cp 7 [38]Cp 8 [68]Cp 9 [69]Cp 10 [70]Cp 11 [24]Cp 12 [70]
δCδHδCδHδCδHδCδHδCδHδCδHδCδH
2159.6—161.2—160.91—160.4—160.6—160.7—160.5—
3114.76.3112.66.28113.546.23112.86.26114.76.30114.76.37114.76.34
4145.418.0139.28.16140.158.10139.38.10144.47.70144.57.78144.37.74
4a116.4—106.5—108.11—107.6—116.5—116.5—116.4—
5110.3no data149.6—150.34—144.3—113.27.29113.47.38113.27.34
5-OMe——60.14.2762.314.2561.64.16——————
6125.7—112.7—115.20—114.8—125.9—125.9—125.8—
7147.21—158.4—158.61—150.0—148.6—148.7—148.7—
8130.2—93.97.14143.12—128.2—131.7—131.6—131.5—
8-OMe————60.84.14——————
8a139.81—152.7—152.80—143.7—143.8—143.9—143.9—
2′145.037.4144.87.60145.187.59145.17.61146.77.62146.77.70146.67.66
3′106.876.95105.07.02105.626.99105.16.99106.76.75106.76.82106.76.79
1″————————70.24.9470.15.0370.15.01
2″————————119.85.54120.15.67119.45.57
3″————————139.8—142.8—143.2—
4″————————18.21.6536.42.27, 2.1339.51.98
5″————————25.91.6729.21.55, 1.4226.31.99
6″——————————77.73.27123.74.98
7″——————————73.0—131.7—
8′——————————26.41.1725.61.61
9″——————————23.01.1317.61.54
10″——————————16.51.7116.51.67
Acetyl-Me——————————————
Acetyl(C═O)——————————————
Table 5

13C and 1H NMR chemical shift data (δ, ppm) of furanocoumarins isolated from genus Casimiroa

Carbon no.Cp 13 [29]Cp 14 [71]Cp 15 [24]Cp 16 [72]Cp 17 [29]Cp 18 [30]Cp 19 [33]
δCδHδCδHδCδHδCδHδCδHδCδHδCδH
2160.43—160.5—160.7160.84—160.42160.7—160.4—
3114.837.77112.86.27112.76.28113.046.27 112.916.28112.826.27112.96.27
4144.276.38 139.48.12139.58.13139.718.11 139.558.12139.7 8.11139.3 8.10
4a116.54—107.5—107.5—107.78107.61—107.7—107.6—
5113.817.37144.3—144.5—144.67— 144.26—150.7—144.5—
5-OMe——60.74.1760.74.1861.024.1660.794.1860.8 4.1660.84.16
6125.95—114.5—114.5—114.73—114.61—114.6—114.6—
7148.32—150.8—150.9—151.18—150.57—Abs—150.5—
8131.39—126.8—126.7—126.99—136.51—Abs—126.6—
8-OMe——————————————
8a143.67—144.3—144.4—144.70125.63—143.1—144.2
2′146.767.69145.17.62145.1 7.63145.347.61 145.167.64145.3 7.61145.17.60
3′106.766.82105.06.98105.17.00105.366.98 105.126.99105.36.98105.16.97
1″69.125.0970.44.8370.34.8870.534.8769.364.9169.34.8669.34.90
2″125.135.86119.85.59120.25.66119.705.58125.275.86122.2 5.71125.25.84
3″136.57—139.7—142.6—143.41—136.51Abs—136.5
4″62.794.6625.81.7336.42.26, 2.1239.851.99 62.784.6621.5 1.8521.4 1.79
5″21.421.8118.01.6929.21.55, 1.3826.631.99 21.411.8061.8δ 4.2462.8 4.62
6″————77.63.24124.075.01 ——————
7″————73.0—131.98———————
8′————26.41.1717.921.56 ——————
9″————23.0 1.1325.931.64 ——————
10″————16.31.6816.771.66 ——————
Acetyl-Me20.832.04——————20.842.03——20.92.02
Acetyl(C═O)170.85——————170.84——170.8—

5 Alkaloids

More than 12,000 alkaloids have been isolated from the plant kingdom, and this number is increasing exponentially. Based on their structure, alkaloids may be classified as indole, tropane, piperidine, purine, imidazole, pyrrolizidine, pyrrolidine, quinolizidine, and isoquinoline alkaloids [73,74,75]. They are well known for their pharmacological activities such as antioxidant [76,77] antidiabetic [76], antimicrobial [77], anti-inflammatory [78], anticancer [79], and amoebicidal properties [80]. The structures of various alkaloids isolated from Casimiroa and their biological activities are described in the following section. Genus Casimiroa are famous for different alkaloids like furoquinoline, quinolinone, and quinolone. In 1999, seven active alkaloids, proline (20), N-methylproline (21), N-monomethylhistamine (22), N,N-dimethylhistamine (23), synephrine acetonide (24), γ-amino-butyric acid (25), and synephrine acetonide, (26) have been derived from the seeds of C. edulis (data not reported) [35]. Iriarte et al. and Ito et al. found the presence of 4-methoxy-1-methyl-2(1H)-quinolinone (27), edulitine (28) (no NMR data), casimiroin (29), dictamnine (30), γ-Fagarine (31), and skirnmianine (32) from various parts (seeds, bark, trunk, and root bark) of C. edulis [23,24]. A quinolone alkaloid, 1-methyl-2-phenyl-4-quinolone (33) was identified from the seeds of C. tetrameria [33]. Other researchers reported the presence of quinolone alkaloids: edulein (no NMR data) (34), seven quinolinone alkaloids: 5-hydroxy-1-methyl-2-phenyl-4-quinolone (35), 5,6-dimethoxy-2-(3-methoxyphenyl)-1H-quinolin-4-one (36), 5,6-dimethoxy-2-(3,4-dimethoxyphenyl)-1H-quinolin-4-one (37), 5,6-dimethoxy-2-(2,5,6-tri-methoxyphenyl)-1H-quinolin-4-one (38), 5,8-dimethoxy-2-(3′-methoxy-phenyl)-3-propyl-1H-quinolin-4-one (39), 5,8-dimethoxy-2-(3′,4′-di-methoxyphenyl)-3-propyl-1H-quinolin-4-one (40), and 2-(2′-hydroxy-4′-methoxy-phenyl)-5,8-dimethoxy-3-propyl-1H-quinolin-4-one (41) from the various parts (leaves, fruits, seeds, trunk, and root bark) of C. edulis [23,24,27,28]. The chemical structures of various alkaloids are shown in Figures 3–5, and their NMR (1H NMR and 13C NMR) data are presented in Tables 8, 9, 10, 12, and 13.

Figure 3 Structures of alkaloids from Casimiroa.
Figure 3

Structures of alkaloids from Casimiroa.

Figure 4 Structures of quinolone alkaloids from Casimiroa.
Figure 4

Structures of quinolone alkaloids from Casimiroa.

Figure 5 Structures of quinolinone and quinolone alkaloids from Casimiroa.
Figure 5

Structures of quinolinone and quinolone alkaloids from Casimiroa.

Table 8

13C and 1H NMR chemical shift data (δ, ppm) of alkaloid isolated from genus Casimiroa

Carbon no.Cp 27 [81]
δCδH
1-NMe29.033.70
2163.82—
396.496.06
4162.64—
4-OMe55.793.97
4a116.50—
5131.187.35
6121.617.60
7123.347.24
8114.017.99
8a139.75—
Table 9

13C and 1H NMR chemical shift data (δ, ppm) of alkaloid isolated from genus Casimiroa

Carbon no.Cp 29 [24]
δCδH
1-NMe29.13.84
2164.1—
394.65.89
4162.7—
4-OMe55.83.91
5118.07.53
6104.36.78
7149.9—
8133.5—
9101.06.04
4a113.0—
8a126.5—
Table 10

13C and 1H NMR chemical shift data (δ, ppm) of furoquinoline alkaloids isolated from genus Casimiroa

Carbon no.Cp 30 [82]Cp 31 [83]Cp 32 [84]
δCδHδCδHδCδH
2168.9—163.2—164.4—
3103.7—103.9—102.0—
4157.0—156.9—157.2—
4a119.0—119.7—114.9—
4-OMe59.14.4559.04.4258.94.42
5122.48.27114.17.82118.28.01
6123.87.45123.47.34112.17.23
7129.67.68107.57.04152.2—
7-OMe————56.84.03
8128.08.01154.6—142.0—
8a145.9—137.5—141.5—
8-OMe——56.04.0661.74.12
2′143.77.08143.97.62143.07.58
3′104.87.69104.57.05104.67.03
Table 12

13C and 1H NMR chemical shift data (δ, ppm) of quinolinone and quinolone alkaloids isolated from genus Casimiroa

Carbon no.Cp 33 [85]Cp 35 [24,86]Cp 36 [28]Cp 37 [28]Cp 38 [28]Cp 39 [27]
δCδHδCδHδCδHδCδHδCδHδCδH
2154.8—155.5—164.0—163.0—161.6—164.21—
3112.7 6.31 104.66.22112.76.74112.66.65107.76.20113.41—
3-Propyl————————24.63, 21.92, 13.940.96, 1.58, 2.45
4177.6—181.7—180.1—182.0—180.2—179.10—
4a126.8—113.9—no data—119.0—118.0—117.31—
5126.88.51 162.8—151.8—151.8—151.4—152.32—
6123.87.45 110.97.48No data—No data—149.0—152.927.81
5-OMe——62.03.8862.03.9362.03.9261.103.83
6-OMe——57.33.8861.43.9161.83.88——
7132.37.73 134.37.56120.97.49121.07.37120.97.39120.947.95
8115.97.57 109.87.56115.07.56115.07.47115.07.54115.14—
8-OMe59.733.79
8a141.9—142.7—No data—No data—No data—116.81—
1′135.9—135.3—133.0—129.9—119.0—130.41—
2′128.57.42 128.96.81118.47.57–7.44116.97.18153.0—119.257.15
3′128.87.52 128.47.69161.8—153.0—115.16.81152.92—
4′129.67.52 129.9—131.27.13155.0—117.07.14131.127.14
5′128.87.52 128.4—108.27.57–7.44121.67.20148.3—122.47.25
6′128.57.42 128.97.19119.67.57–7.44125.67.33153.4—126.147.31
2′-OMe————————57.43.85——
3′-OMe————55.93.9357.43.85——56.113.71
4′-OMe——————56.63.85————
5′-OMe————————57.03.81——
6′-OMe————————56.73.75——
N-Me37.33.62 37.93.60————————
Table 13

13C and 1H NMR chemical shift data (δ, ppm) of quinolinone and quinolone alkaloids isolated from genus Casimiroa

Carbon no.Cp 40 [27]Cp 41 [27]
δCδHδCδH
2158.79—163.9—
3113.31—113.31—
3-Propyl24.63, 21.92, 13.940.96, 1.58, 2.4524.63, 21.92, 13.940.96, 1.58, 2.45
4178.56—178.3—
4a117.83—117.31—
5149.77—152.32—
6145.296.88No data6.81
5-OMe61.903.9861.903.92
7147.127.95121.347.97
8114.94—114.94—
8-OMe56.773.9757.133.85
8a116.51—116.81—
1′147.79—133.4—
2′119.617.56119.21—
3′No data—162.17.49
4′151.781—131.12—
5′108.147.39108.147.29
6′120.147.49120.147.26
2′-OMe————
3′-OMeNo data3.93——
4′-OMe56.773.9356.113.85
5′-OMe————
6′-OMe————
N-Me————

6 Flavonoids

Flavonoids are a large group of plant metabolites. They are divided into several subgroups. Among them, flavones, flavonols, flavanones, flavanonols, flavanols or catechins, antocyanins, and chalcones are almost always in the plant kingdom. They have been isolated from fruits, nuts seeds, stem, flowers, wine, and other vegetal tissues of large number of plants [87]. Flavonoids are known for their pharmacological properties such as antioxidants [88,89,90], antibacterial [90], antiviral [91], anti-inflammatory [92,93], antiallergic [93], antidiabetic [94], and anticancer activities [95]. Twenty flavonoids, namely, 6,7-dimethoxyflavone (42), 6-hydroxy-5-methoxyflavone (43), zapotinin (44), 5,6,2′-trimethoxyflavone (45), 5,6,3′-trimethoxyflavone (46), 5,6,2′,3′-trimethoxyflavone (47), 5,7,3′,5′-tetramethoxy-flavone (48), 5,6,3′,5′-tetramethoxy-flavone (49), zapotin (50), zapotinin acetate (51), 5,6,2′,3′,4′-pentamethoxyflavone (52), 5,6,2′,3′,6′-pentamethoxy-flavone (53), 5,6,2′,3′,4′,6′-hexamethoxy-flavone (54), 5,6,2′,3′,5′,6′-hexamethoxy-flavone (55), 5-methoxyflavone 6-O-β-d-glucoside (56), quercetin (57), quercetin 3-O-rutinoside (58), kaempferol 3-O-rutinoside (59), quercetin 3-O-glucoside (60), and kaempferol 3-O-glucoside (61) were isolated from various parts (stem bark, leaves, and seeds) of C. edulis, C. pubescens, Casimiroa sapota, and C. tetrameria. The structures of flavonoids are shown in Figure 6, and their NMR (1H NMR and 13C NMR) data are presented in Tables 15–17.

Figure 6 Structures of flavonoids from genus Casimiroa.
Figure 6

Structures of flavonoids from genus Casimiroa.

Table 15

13C and 1H NMR chemical shift data (δ, ppm) of flavonoids isolated from genus Casimiroa

Carbon no.Cp 42 [37]Cp 43 [26]Cp 45[38]Cp 46 [66]Cp 47 [97]
δCδHδCδHδCδHδCδHδCδH
2161.6—164.18—159.1—ND—ND—
36.69108.196.75113.16.98ND6.6311.256.82
4178.0—180. 29—178.4—ND—ND—
4a119.3—119.48—119.1—ND—ND—
5113.47.32149.10—158.0—ND—ND—
6148.0—148.57—149.7—ND—147.29—
7150.0—125.637.72113.47.30ND7.307.58119.53
8119.17.32115.287.45119.27.27ND7.30113.657.45
8a151.6—154.19—151.9—ND—150.11—
5-OMe——62.463.9057.33.93ND3.9960.003.94
6-OMe57.23.94——55.73.93ND3.9255.973.96
7-OMe61.93.98————ND——
1′131.7—132.49—120.8—NDND—
2′126.17.89127.397.98147.9—ND7.42ND—
3′129.07.51130.267.54111.77.03ND—ND—
4′131.47.51133.17.54132.27.46ND7.03115.467.25
5′129.07.51130.267.54120.77.09ND7.42124.287.24
6′126.17.89127.397.98129.17.85ND7.42120.237.39
2′-OMe————61.93.98ND—60.663.92
3′-OMe——————3.8755.23.91
4′-OMe——————————
5′-OMe——————————
6′-OMe——————————
Acetyl(C═O)——————————
Acetyl-Me——————————

ND = no data reported.

Table 16

13C and 1H NMR chemical shift data (δ, ppm) of flavonoids isolated from genus Casimiroa

Carbon no.Cp 50 [99]Cp 52 [32]Cp 53 [30]Cp 55 [30]Cp 56 [26]
δCδHδCδHδCδHδCδHδCδH
2158.9160.6—158.5—158.6—164.18—
3115.26.26110.96.84115.26.27114.5 6.29108.19 6.75
4178.2—178.4—178.0—177.8—180.29—
4a119.4—118.9—119.5—119.5—119.48—
5148.0—147.8—148.6—148.1—149.10—
6149.6—149.9—149.8—149.9—149.28—
7119.17.28119.37.30113.7 7.26113.6 7.26125.637.72
8113.77.20 113.37.25119.1 7.18119.2 7.17115.287.45
8a152.7—151.7—152.6—152.4—154.19—
5-OMe61.83.9856.2 3.9862.0 3.9762.0 3.9862.53.9
6-OMe57.3 3.9261.33.9357.4 3.9157.3 3.91——
1′111.4—118.5———101.7—132.49—
2′158.6—153.3—147.15—140.9—127.46δ 7.98
3′104.06.63142.7—132.1—149.2—130.287.54
4′132.0 7.39 156.5—115.0 6.98114.5 6.67133.04δ 7.54
5′104.06.63107.46.79106.3 6.65149.2—130.287.54
6′158.6—124.27.5151.8140.9—127.467.98
2′-OMe56.03.7957.23.9561.63.8361.83.75——
3′-OMe——62.03.9156.73.8556.73.88——
4′-OMe——61.03.94——————
5′-OMe——————56.73.88——
6′-OMe56.03.7961.33.9357.43.9157.33.91——
Acetyl(C═O)——————————
Acetyl-Me——————————
1″————————103.384.96
2″————————75.05—
3″————————78.11—
4″————————71.343–3.9
5″————————78.4—
6″————————62.74—
Table 17

13C and 1H NMR chemical shift data (δ, ppm) of flavonoids isolated from genus Casimiroa

Carbon no.Cp 57 [100]Cp 58 [101]Cp 59 [101]Cp 60 [102]Cp 61 [102]
δCδHδCδHδCδHδCδHδCδH
2147.8—158.22—155.98—158.4—156.4—
3136.89.44134.52—134.58—135.6—133.3—
4176.9—178.39—177.23—179.1—177.4—
4a103.9—105.32—104.79—105.7—104.1—
5161.912.54162.48—162.04—163.0—161.3—
698.86.2299.726.1098.886.2298.06.1699.16.30
7165.010.85166.58—163.31—168.4—164.2—
894.06.4494.906.2893.986.3395.66.3893.86.50
8a157.4—158.91—156.82—160.0—156.5—
1′123.1—122.77—121.39—121.2—121.0—
2′115.77.71117.377.64130.768.19115.97.47131.08.05
3′146.2—144.32—113.406.92146.5—115.26.95
4′148.7—150.23—160.92—151.4—160.0—
5′116.26.92115.466.85114.876.92116.96.79115.26.95
6′120.67.57122.477.63131.038.19121.37.64131.08.05
1″——103.634.96102.115.02104.4ND101.25.48
2″——74.64—74.83—75.7ND74.33.32
3″——77.81—75.48—78.1ND76.53.55
4″——71.123.20–3.9069.233.15–3.9071.2ND69.93.20
5″——78.09—77.65—78.4ND77.63.21
6″——68.37—67.08—62.6ND60.93.58, 3.72
1‴——101.924.50100.104.45————
2‴——71.32—70.89—————
3‴——72.13—72.23—————
4″——73.733.20–3.9073.463.20–3.90————
5‴——68.91—67.88—————
6‴——18.841.1218.121.09————
3-OH——————————
5-OH——————————
7-OH——————————
3′-OH——————————
4′-OH——————————

ND = no data reported.

7 N-Benzoyltyramide derivatives

Four N-benzoyltyramide derivatives 62–65 (Table 18), were reported from the genus Casimiroa. Compounds 62 and 63 contain isopropylidene moiety in their O-alkyl side chains. Likewise, compound 62 contains monoterpenic moiety in O-alkyl side chain. The structures of N-benzoyltyramide derivatives are shown in Figure 7, and their NMR (1H NMR and 13C NMR) data are presented in Table 19.

Table 18

Pharmacological properties of benzoyltyramide derivatives isolated from Casimiroa species

Compound (Cp)Biological activitiesPlantPart usedRef.
Pubesamide A (62)Solid tumor selective cytotoxicityC. tetrameria & C. pubescensSeeds[33,34]
Pubesamide B (63)Solid tumor selective cytotoxicityC. tetrameria & C. pubescensSeeds[33,34]
Pubesamide C (64)—C. pubescensSeeds[34]
Tetrahydropubesamide A (65)—C. pubescensSeeds[34]
Figure 7 Structures of N-benzoyltyramide derivatives from Casimiroa.
Figure 7

Structures of N-benzoyltyramide derivatives from Casimiroa.

Table 19

13C and 1H NMR chemical shift data (δ, ppm) of N-benzoyltyramide derivatives isolated from genus Casimiroa

Atom no.Cp 61 [34]Cp 62 [34]Cp 63 [34]Cp 64 [34]
δCδHδCδHδCδHδCδH
141.33.69 41.3 3.69 41.33.67 41.2 3.69
234.8 2.87 34.8 2.86 34.8 2.86 34.8 2.87
3131.2—130.7—131.3—130.8—
4129.8 7.14 129.7 7.13 129.87.14 129.7 7.15
5114.96.85 114.8 6.86 114.9 6.85 114.7 6.85
6157.5—157.7—157.2—157.7—
7167.4—167.4—167.4—167.4—
8134.7—134.7—134.6—134.7—
9126.8 7.69 126.1 7.68 126.8 7.68 126.8 7.69
10128.5 7.45 128.5 7.45128.5 7.41 128.5 7.38
11131.4 7.38 131.4 7.41 131.4 7.47 131.6 7.45
1265.9 4.09 67.2 4.16 65.4 4.12 66.0 3.97
13a40.6 2.59 33.7 3.06 40.9 2.14 36.0 1.78
13b————40.9 1.97 36.0 1.67
14154.9—155.0—72.7—26.4 2.26
15126.2 6.08127.4 6.08 136.6 5.63 50.6 2.41
16191.4—190.8—124.5 6.52 210.4—
17127.4 6.13126.0 6.13 124.3 5.82 52.3 2.26
18153.0—153.0—135.5—24.5 2.15
1927.8 1.8827.8 1.89 18.3 1.73 22.6 0.90
2020.6 2.17 20.6 2.15 26.0 1.76 22.6 0.91
2119.3 2.22 26.8 2.01 29.0 1.37 19.9 0.97

8 Pharmacological activities

Several pharmacological reports have confirmed the wide variety of biological activities of the genus Casimiroa. For example, Mora et al. [16] reported the effect on central nervous system by the extract of hydroalcoholic leaves of C. edulis, using different behavioral tests and animal models of depression and anxiety. The extract exhibited sedative and antidepressant properties in rodents. The leaves and seeds extracts of C. edulis also showed the anticonvulsant activity in vivo [15,17]. Esposito et al. [20] studied the HIV-1 reverse transcriptase-associated activities of the hydroalcoholic extract of C. edulis seeds, using HIV-1 RT RDDP assay and HIV-1 RT RNase H assay. The extract exhibited the ability to inhibit both RDDP (IC50 0.27 μg mL−1) and RNase H (IC50 2.0 μg mL−1) activities in a dose-dependent manner. The extract was also displayed dose-dependent cytotoxicity on K562 (CC50 3.1 mg mL−1) cell line. The antimutagenic activity of several compounds (9, 11, 14, 15, 27, 29, 31, 35, 45, and 48) were evaluated against Salmonella typhimurium strain TM677, using the antimutagenicity assay. Compounds 15 and 29 were found to have the most significant antimutagenic activity against S. typhimurium strain TM677. Compounds 29 and 45 were also inhibited the formation of DMBA-induced preneoplastic lesions in the mouse mammary gland [24]. Awaad et al. [25] reported not only the antimicrobial activity of ethyl acetate, butanol, ether, and chloroform fractions but also anticoagulant activity of ethanol extract and compounds 1, 2, 6, and 10 from the leaves of C. edulis. Another important study was performed on the antioxidant activity of fractions and isolated compounds (43, 54, 55, and 56) from leaves of C. edulis. Ethanol fraction was exhibited the more potent antioxidant activity (842 μM Trolox equivalents/g dry weight) [26]. According to the study by Awaad et al. [27], compounds 38–39 and fruit extracts of C. edulis were tested for the antihypertensive activity using male dogs. All compounds showed the antihypertensive activity at doses of 50, 100, 200, and 300 mg/kg, and the ethanolic and total alkaloids (in chloroform) extracts were found to possess important antihypertensive properties at doses of 500 and 200 mg/kg, respectively. Nagai et al. [29] reported the functions of glucose and lipid metabolism activities with 3T3-L1 adipocytes on two furocoumarins (13 and 17) and two polymethoxyflavones (45 and 53) from leaves of C. edulis. It was clear that the addition of furanocoumarin increased the glucose uptake and lipid accumulation in 3T3-L1 adipocyte. Bertin et al. [31] reported vasodilation and radical-scavenging activity of imperatorin and selected coumarinic and flavonoid compounds (3, 10, 12, and 50) from seeds of C. edulis and C. pubescens. Ya-ming et al. [33] evaluated solid tumor selective cytotoxicity of extract, fractions, and compounds (19, 33, 45, 46, 48, 61, and 62) from C. tetrameria. Compounds 48, 61, and 62 were active against solid tumor cell line C38 and a leukemia cell line L1210. Cardiovascular activities for compounds 20–27 were also reported [35]. Ubaldo-suarez et al. [36] evaluated antidepressant-like effect of hexane, ethyl acetate, and methanol roots extracts of C. pubescens, using the forced swim test. The result showed antidepressant-like activity on hexane extract. Further studies reported antidiabetic and antioxidant activities of compounds 7, 9, 42, and 45, isolated from C. edulis using the DPPH radical scavenging assay and the yeast α-glucosidase assay [37,38]. Moreover, the leaves, seeds, and nonedible fruit’s parts extracts of C. edulis have been studied for their biological effects, including antihypertensive, vasorelaxant, antioxidant, anti-inflammatory, antitumor, relaxant, and contractile effect in vitro [18,103,104]. Landaverde et al. [105] noted that essential oils extracted from C. pringlei displayed significant sedative and anxiolytic properties in rats. However, there is still a lack of biological and other phytochemical research to prove medicinal uses of genus Casimiroa like Casimiroa watsonii, Casimiroa tomentosa, C. sapota Var. Villosa, Casimiroa calderoniae, Casimiroa dura, Casimiroa emarginata, Casimiroa greggii, and Casimiroa microcarpa.

9 Concluding remarks

Casimiroa genus is a rich of diverse plant metabolites, with important biological activities. Their potential as drug leads is yet to be explored. Several Casimiroa species have not yet been chemically studied. Therefore, it is necessary to carry out these studies to contribute to the taxonomic classification and medicinal chemistry. In this article, the emphasis has been on the NMR data of compounds obtained from the genus, and pharmaceutically most of these compounds were reported in 1968s, and during that time, the data were either incomplete or unavailable. In this review, we have presented the NMR data and its description of compounds isolated from the genus Casimiroa. In addition, the information concerning different skeletons of the compounds is also provided.

tel: +62-31-5936501, fax: +62-31-5936502

Acknowledgments

The authors are grateful to Airlangga Development Scholarship (ADS) and RISET MANDAT GRANT of Universitas Airlangga, Surabaya, Indonesia. The appreciation is also conveyed to Prof. M. Iqbal Choudhary from H. E. J. Research Institute of Chemistry, International Center of Chemical and Biological Sciences, University of Karachi, Karachi-75270, Pakistan, for his help in improving this review article.

  1. Conflict of interest: The authors have no conflict of interest.

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Received: 2020-01-30
Revised: 2020-05-08
Accepted: 2020-05-20
Published Online: 2020-07-02

© 2020 Khun Nay Win Tun et al., published by De Gruyter

This work is licensed under the Creative Commons Attribution 4.0 International License.

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  104. A new phenyl alkyl ester and a new combretin triterpene derivative from Combretum fragrans F. Hoffm (Combretaceae) and antiproliferative activity
  105. Erratum
  106. Erratum to: A one-step incubation ELISA kit for rapid determination of dibutyl phthalate in water, beverage and liquor
  107. Review Articles
  108. Sinoporphyrin sodium, a novel sensitizer for photodynamic and sonodynamic therapy
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  110. Plant description, phytochemical constituents and bioactivities of Syzygium genus: A review
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  148. A study on the bacterial adhesion of Streptococcus mutans in various dental ceramics: In vitro study
  149. Corrosion study of copper in aqueous sulfuric acid solution in the presence of (2E,5E)-2,5-dibenzylidenecyclopentanone and (2E,5E)-bis[(4-dimethylamino)benzylidene]cyclopentanone: Experimental and theoretical study
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  160. Topical Issue on Applications of Mathematics in Chemistry
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https://doi.org/10.1515/chem-2020-0128
Keywords for this article
aromatic compounds; Casimiroa; NMR spectral data; Rutaceae
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BY 4.0

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