Plant description, phytochemical constituents and bioactivities of Syzygium genus: A review

Ei Ei Aung; Alfinda Novi Kristanti; Nanik Siti Aminah; Yoshiaki Takaya; Rico Ramadhan

doi:10.1515/chem-2020-0175

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Plant description, phytochemical constituents and bioactivities of Syzygium genus: A review

Ei Ei Aung , Alfinda Novi Kristanti , Nanik Siti Aminah , Yoshiaki Takaya und Rico Ramadhan

Veröffentlicht/Copyright: 13. Oktober 2020

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Abstract

This article attempts to report native growth, plant description, phytochemical constituents and bioactivities of Syzygium aqueum, S. aromaticum, S. cumini, S. guineense and S. samarangense. Those are the large public species in the Syzygium genus and some of them have been used as traditional medicines. Different parts (leaves, seeds, fruits, barks, stem barks and flower buds) of each species plant are rich in phytochemical constituents such as flavonoids, terpenoids, tannins, glycosides and phenolics. Antioxidant, antidiabetic, anticancer, toxicity, antimicrobial, anti-inflammatory and anthelmintic activities are reported in various extracts (methanol, ethanol and aqueous) from different parts of Syzygium sp. The bioactivities were studied by using 1,1-diphenyl-2-picrylhydrazyl and ferric reducing antioxidant power assays for antioxidant, 5-(3-carboxymethoxyphenyl)-2-(4,5-dimethyl-thiazoly)-3-(4-sulfophenyl) tetrazolium and 3-(4,5-dimethylthiazol-2-yl)-2-5-diphenyltetrazolium bromide assays for anticancer, α-glucosidase and α-amylase inhibition assays for antidiabetic, agar well diffusion method for antimicrobial and brine shrimp lethality assay for toxicity. Moreover, this review shows that phytochemical constituents of each species significantly presented various bioactivities. Therefore, this review suggests that there is great potential for obtaining the lead drug from these species.

Keywords: Myrtaceae; Syzygium aqueum; S. aromaticum; S. cumini; S. guineense; S. samarangense; flavonoid; chromone; terpenoid; steroid; tannin; phenol; acylphloroglucinol

1 Introduction

Natural products are resources derived from living organisms, such as plants, animals and microorganisms. The chemicals produced by plants may be defined as “phytochemicals” [1,2]. Phytochemicals in plants have undoubtedly been a resource of medicinal treatment for human diseases for a long time. They played a key role in primary health care of nearly 75–80% of the world’s population according to the World Health Organization [3]. Phytochemicals in a plant can be explored by using various methods such as extraction, separation, purification, identification, structure elucidation, determination of physical and chemical properties, biosynthesis and quantification [4]. The phytochemicals could be classified as primary and secondary metabolites. Primary metabolites involved natural sugars, amino acids, proteins, purines and pyrimidines of nucleic acids and chlorophyll. Secondary metabolites are the remaining plant chemicals such as glycosides, alkaloids, terpenoids, flavonoids, lignans, steroids, curcumines, saponins and phenolics [5].

The secondary metabolites are primary for plants to protect themselves from environmental hazards such as pollution, UV exposure, stress, drought and pathogenic attack, as well as researchers have reported that phytochemicals can protect them from human diseases [5,6]. The secondary metabolites have biological properties such as antioxidant activity, anticancer property, antimicrobial effect, anti-inflammatory and stimulant to the immune system [7]. Bioactive secondary metabolites, more than a thousand known and many unknown, come from all parts of plants such as stems, fruits, roots, flowers, seeds, barks and pulps. [7,8]

The eighth-largest family in herbal plants is Myrtaceae that comprised about 140 genera and 3,800–5,800 species [9]. Syzygium is the 16th largest genus of flowering plants in Myrtaceae family [10] that includes high diversity cultivated for many purposes such as colorful, edible and fleshy fruits [11,12]. There are 1,100–1,200 species of Syzygium [13,14,15,16]. Species of Syzygium are distributed in the tropical and sub-tropical regions of the world [17,18]. They have a native range that extends from Africa and Madagascar through southern East Asia and the Pacific [13,17]. The enormous diversity of species takes place in South East Asia such as Indonesia, Malaysia, East India [11], Myanmar, Philippines and Thailand [13]. The Syzygium genus is widely grown in rainforests such as coastal forests, swamp forests, resembled monsoons, bamboo forests and peat swamp forests [14].

Syzygium genus contains abundant secondary metabolites such as terpenoids, chalcones, flavonoids, lignans, alkyl phloroglucinols, hydrolysable tannins and chromone derivatives [19], which exhibits bioactivities such as antidiabetic, antifungal, anti-inflammatory, antibacterial, antioxidant, cytotoxic [20], anti-HIV, antidiarrheal, anthelmintic and antivirus activities [16]. S. aqueum, S. aromaticum, S. cumini, S. guineense and S. samarangense are five large public species in this genus [14]. Some of them have been used as a traditional medicine to treat several disorders (such as hemorrhage, dysentery and gastrointestinal disorders), diabetes, inflammation such as antifungal, antimicrobial, antihypertensive, analgesic and antiviral [15] bronchitis, thirst, dysentery and ulcers [16].

Most researchers have reported their rich sources of phytochemical constituents and bioactivities. Native growth and plant description of five species have been already reviewed by many reviewers [21,22,23,24,25]. S. cumini, one known species, has been overviewed by some authors [26,27]. And then, phytochemical constituents and bioactivities of both S. aromaticum [28,29] and S. cumini [30,31] have been already reported in review articles. However, phytochemical constituents and bioactivities of S. aqueum, S. guineense and S. samarangense have not yet been discussed by any reviewers. Moreover, most of the authors have reviewed only phytochemicals or bioactivities of one species in each review article.

Therefore, this review aims to provide detailed reports of five large public species in Syzygium genus. Rich phytochemicals and bioactivities of five species have been recorded by reviewing many international public articles and most of the review articles by authors. All of native growths, plant descriptions, phytochemical constituents and bioactivities from different parts of plants (five species) are studied in this review article (Table 1).

Table 1

Common name and distribution of five Syzygium species

Species name	Family	Genus	Common name	Distribution	Ref.
S. aqueum	Myrtaceae	Syzygium	Water apple, bell fruit, water cherry and water rose apple	India, Malaysia, Asia and Philippines	[13,32,33]
S. samarangense	Myrtaceae	Syzygium	Java apple, markopa, Java rose apple, Samarang apple, wax jambu and wax apple	Malaysia, Indonesia, Thailand, Cambodia, Laos, Vietnam, India, Australia and Taiwan	[13,34,35]
S. aromaticum	Myrtaceae	Syzygium	Clove, Lavang and Laung (Hindi)	Indonesia, Madagascar, Pakistan, India, Sri Lanka and China	[13,28,36]
S. cumini	Myrtaceae	Syzygium	Jambul, Jambolan, black plum, duhat plum and Java plum	India, Malaysia, Myanmar, Philippines, Sri Lanka and Thailand	[13,30,37]
S. guineense	Myrtaceae	Syzygium	Water berry, water boom and woodland Roof of Africa	Australia, Asia and Horn of Africa	[13,38]

2 Description of plants

2.1 Syzygium aqueum

The tree of S. aqueum is cultivated well in heavy and fertile soils and is sensitive to frost. It grows up to a height of 8–10 m with branching near the base. Leaves are 4.5–23 cm long, 1.5–11 cm wide and oblong to elliptic. The leafstalk is 1–5 mm long. Flowers are yellowish-white or pinkish and are 2–3 cm long. They produced terminal or axillary cymes and moreover the flowering season occurs in February–March and fruits mature during May–June. Fruits are pale rose or white. They are watery, small bell-shaped with shinning skin, spongy and slightly fragrant. They are about 1 inch long and are ½ inch wide [39,40,41].

2.2 Syzygium samarangense

The tree of S. samarangense is grown in a rather long dry period and relatively moist tropical sea level area up to 1,200 m. It grows up to a height of 3–15 m with branching near the base. Leaves are 10–25 cm × 5–12 cm, petiole is thick and the shape of leaves is opposite and oblong to elliptic. Flowers are white to yellowish-white, 2.5 cm in diameter and the flowering season is early or late in the dry period. Fruits are bell-shaped, oval and their sizes are 3.5–5.5 cm × 4.5–5.5 cm. The skin color of fruits splits from white to pale green to dark green, from pink to red to pink-red [21,22].

2.3 Syzygium aromaticum

S. aromaticum is also known as clove, which is an aromatic dried flower bud of a plant in the Myrtaceae family. The clove is composed of buds and leaves (the commercial part of the plant). The flowering bud production begins 4 years after plantation, and they are collected by hand or using a natural phytohormone in the pre-flowering period [29,42].

2.4 Syzygium cumini

S. cumini is an evergreen tree and the height is 25 m. Leaves are slightly leathery and from oblong-ovate to elliptical or obovate-elliptic. The length of leaf is 6–12 cm long and the stalk of a leaf is 3 cm long. Flowers are fragrant, white to pink or greenish-white, about 1 cm in cross, branched clusters at the stem tips. The calyx is about 4 mm long, four toothed and funnel-shaped. The very numerous stamens are as long as the calyx. The ovoid fruits are 1.5–3.5 cm long berries, dark purple or nearly black, dark purplish-red, shiny, with white to lavender flesh. The fruit contains a single large seed, 2 cm long [17,23,37].

2.5 Syzygium guineense

S. guineense prefers moist soils on high water tables in lowland riverine forest or wooded grassland and lower montane forests, from sea level to 2,100 m. It is a sizeable evergreen tree in the forest and the height is from 10 to 15 m or 25 m. It has a broad trunk and fluted with dense rounded thick crown, branches drooping. The more the age of the plant, the more the bark is rough and flaking. Leaves are opposite, smooth on both surfaces, shiny and with short stalks. The color of leaves is from purple-red to dark green. Flowers have white, showy stamens, with fragrant smell and in dense clusters. Fruits are oval shaped, 3 cm long, shiny, purple-black in color and one-seeded [24].

3 Phytochemical constituents

3.1 Flavonoids

Phloretin (1), myrigalone-G (2), myrigalone B (3) [43], 2′,4′-dihydroxy-6′-methoxy-3′-methyldihydrochalcone (4), 2′-hydroxy-4′,6′-dimethoxy-3′-methyldihydrochalcone (5), 2′,4′-dihydroxy-6′-methoxy3′,5′-dimethyldihydrochalcone (6) [46,47], 2′,4′-dihydroxy-6′-methoxy-3′-methylchalcone or stercurensin (7), 2′-hydroxy-4′,6′-dimethoxy-3′-methylchalcone (8) [46,47], 2′,4′-dihydroxy-6′-methoxy-3′,5′dimethylchalcone (9) [44], 2′,4′-dihydroxy-3′,5′-dimethyl-6′-methoxychalcone (10), 2′,4′-dihydroxy-6′-methoxchalcone or cardamonin (11) [51], pinocembrin (12), (−)-strobopinin (13), 8-methylpinocembrin (14), demethoxymatteutcinol (15), 7-hydroxy-5-methoxy-6,8-dimethylfoavanone (16) [48], 7,8,3′,4′-tetrahydroxy-3,5-dimethoxyflavone (17) [45], 7-hydroxy-5-methoxy-6,8-dimethylflavanone (18), quercetin (19) [49,50], kaempferol (20) [54], gallocatechin (21), myricetin (22) [51], (−)-epigallocatechin (23), (−)-epigallocatechin 3-O-gallate (24), samarangenin A (25), samarangenin B (26), prodelphinidin B-2 3″-O-gallate (27) and prodelphinidin B-2 3,3″-O-gallate (28) [52] are presented in Figure 1.

Figure 1

Flavonoids from various parts of S. aqueum, S. samarangense, S. aromaticum, S. cumini and S. guineense.

3.2 Flavonoid glycosides

Myricetin-3-O-rhamnoside (29) [43,45], europetin-3-rhamnoside (30) [43], mearnsitrin (31) [53], reynoutrin (32), hyperin (33), quercitrin (34), guaijaverin (35) [49], tamarixetin 3-O-β-d-glucopyranoside (36), ombutin 3-O-β-d-glucopyranoside (37) [50], quercetin 3-O-α-l-rhamnopyranoside (38), kaempferol 3-O-β-d-glucuronopyranoside (39), myricetin 3-O-β-d-glucuronopyranoside (40), mearnsetin 3-O-(4″-O-acetyl)-α-l-rhamnopyranoside (41), myricetin 3-O-(4″-O-acetyl)-α-l-rhamnopyranoside (42), myricetin 4′-methyl ether 3-O-α-l-rhamnopyranoside (43), myricetrin 4″-O-acetyl-2″-O-gallate (44) [54], myricetin-3-O-glucoside (45), myricetin-3-O-rhamnoside (46), myricetin-3-O-glucoronide (47) and myricetin-3-O-β-d-(6″-galloyl) galactoside (48) [51] are shown in Figure 2.

Figure 2

Flavonoid glycosides from various parts of S. aqueum, S. samarangense, S. aromaticum, S. cumini and S. guineense.

3.3 Chromone glycosides

Biflorin (49), isobiflorin (50), 6-C-β-d-(6′-O-galloyl) glucosylnoreugenin (51) and 8-C-β-d-(6′-O-galloyl)glucosylnoreugenin (52) [55] are shown in Figure 3.

Figure 3

Chromone glycosides from various parts of S. aromaticum.

3.4 Terpenoids

Sysamarin A (53), sysamarin B (54), sysamarin C (55), sysamarin D (56), sysamarin E (57) [56], lupenyl stearate (58) [57], lupeol (59) [46,57], betulin (60), betulinic acid (61) [46,63], oleanolic acid (62) [55,58,59], arjunolic acid (63) [58,61,62], corosolic acid (64) [58] asiatic acid (65) [58,61,62], maslinic acid (66) [55], 12-oleanen-3-ol-3β acetate (67) [60], 2-hydroxyoleanolic acid (68), 2-hydroxyursolic acid (69), terminolic acid (70), 6-hydroxy asiatic acid (71) [61,62], limonin (72) [50], caryolane-1,9β-diol (73), clovane-2,9β-diol (74), α-humulene (75), humulene epoxide α (76), β-caryophyllene (77) and β-caryophyllene oxide (78) [55] are shown in Figure 4.

Figure 4

Terpenoids and steroids from various parts of S. samarangense, S. aromaticum, S. cumini and S. guineense.

3.5 Steroids

Lupenyl stearate cycloartenyl stearate (79), β-sitosteryl stearate (80), 24-methylenecycloartenyl stearate (81) [57], β-sitosterol (82) [57,59] and stigmasterol (83) [60] are shown in Figure 5.

Figure 5

Steroids from various parts of S. aromaticum and S. cumini.

3.6 Steroid glycoside and terpenoid glycosides

β-Sitosterol-3-O-β-d-glucoside (84) [55], arjunolic acid 28-β-glycopyranosyl ester (85) and asiatic acid 28-β-glycopyranosyl ester (86) [61,62] are displayed in Figure 6.

Figure 6

Steroid glycosides and terpenoid glycosides from various parts of S. aromaticum and S. guineense.

3.7 Tannins

3,3′,4′-Tri-O-methylellagic acid (87) [55], ellagic acid (88) [49,64], ellagitannin-3-O-methylellagic acid 3′-O-β-d-glucopyranoside (89), ellagic acid 4-O-α-l-2″-acetylhamnopyranoside (90) [64], 3-O-methylellgic acid 3′-O-α-l-rhamnopyranoside (91), gallotannins 1,2,3,6-tetra-O-galloyl-β-d-glucose (92), 1,2,3,4,6-penta-O-galloyl-β-d-glucose (93), casuarictin (94) and casuarinin (95) [51] are depicted in Figure 7.

Figure 7

Tannins from various parts of S. aromaticum, S. cumini and S. guineense.

3.8 Phenols

Hydroxybenzaldehyde (96) [43], gallic acid (97) [49,64], ferulic aldehyde (98) [50], eugenol (99), eugenyl acetate (100), trans-coniferylaldehyde (101), 3-(4-hydroxy-3-methoxy-phenyl) propane-1,2-diol (102), 1-O-methyl-guaiacylglycerol (103), epoxiconiferyl alcohol (104) [55], 7-hydroxycalamenene (105) and methyl-β-orsellinate (106) [59] are shown in Figure 8.

Figure 8

Phenyls of S. aqueum, S. samarangense and S. aromaticum.

3.9 Phenyl glycosides

2,4,6-Trihydroxy-3-methylacetophenone-2-O-β-d-glycoside (107) and 2,4,6-trihydroxy-3-methylaceto-phenone-2-C-β-d-glycoside (108) [55] are shown in Figure 9.

Figure 9

Phenyl glycosides of S. aromaticum.

3.10 Acylphloroglucinol derivatives

Samarone A (109), samarone B (110), samarone C (111), jambone G (112), samarone D (113), jambone E (114), jambone F (115), jamunone B (116) and 2-pentadecyl-5,7-didydroxychromone (117) [65] are illustrated in Figure 10.

Figure 10

Acylphloroglucinol derivatives from S. samarangense.

4 Bioactivities

4.1 Antioxidant activity

Antioxidant activity of methanol extract of S. aqueum leaves was investigated by using β-carotene bleaching and 2,2′-azinobis(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS) free radical scavenging assays. Fresh and dried leaves of sample were extracted with methanol:water (1:10). The percentage of antioxidant activity of the fresh sample was higher than that of the dried sample for both β-carotene bleaching and ABTS assays [32].

Fruits of S. aqueum were mashed with citrate buffer, pH 4.2. Then, the extract was investigated using 1,1-diphenyl-2-picrylhydrazyl (DPPH) assay. Vitamin C was used as a positive control. The absorbance was measured at 517 nm. IC₅₀ (µg/mL) values of both standard and sample were nearly the same, and they had powerful antioxidant activity because the IC₅₀ value was less than 50 µg/mL [66].

S. aqueum leaves were extracted with 50% acetone (v/v). The extract was investigated by using DPPH radical scavenging and ferric reducing antioxidant power (FRAP) assays. In the DPPH assay, the percentage scavenging of acetone extract was higher than that of water extract. In the FRAP assay, µM Fe(ii)/g of water extract was higher than that of acetone extract [67].

Leaves of S. aqueum were extracted with 100% methanol. The antioxidant activity of the extract was investigated using DPPH radical scavenging, FRAP, ABTS radical scavenging and total antioxidant capacity assays. (epi) Gallocatechin gallate (EGCG) and vitamin C were used as standards when compared with the sample for all assay methods. Radical scavenging activity (µg/mL) of the extract is nearly the same as standards for all methods [33].

S. samarangense seeds were extracted with methanol, and then the antioxidant activity of the extract was determined using DPPH and FRAP assays. Gallic acid was selected as a positive control. The methanol extract showed moderate activity by the DPPH assay as well as by the FRAP assay [49].

The antioxidant activity of fruits of each S. samarangense tree cultivar (red, pink and green) was studied using DPPH radical scavenging. Ascorbic acid was used as a standard. The red cultivar showed the highest antioxidant activity and the green cultivar exhibited the lowest antioxidant activity [68].

Extraction of the roots of S. samarangense was carried out with three kinds of solvents (ethyl acetate, methanol and water) using the Soxhlet extraction method. The antioxidant activity of root extracts was evaluated using DPPH radical scavenging and ascorbic acid was used as a standard. The highest percentage of scavenging was shown by the methanol extract [69].

S. aromaticum (clove) was extracted with methanol and distilled water. The antioxidant activity of two extracts was determined using the DPPH assay and quercetin was chosen as a positive control. The highest percent scavenging was shown by quercetin, followed by the distilled water extract and the methanol extract was the lowest. [70].

S. aromaticum flower buds were extracted with ethanol and distilled water. The sample was also extracted to obtain the essential oil. Different percentages of oil (0.1%, 0.5% and 1%) and dried ethanol extract (5.0%) were dissolved in aqueous ethanol solu-tion (1:1). The antioxidant activities of ethanol extract, distilled water extract and three different percentages of essential oil in aqueous ethanol were determined using the DPPH assay. Ascorbic acid was used as a standard. The best inhibition was presented by the ethanol extract which had the EC₅₀ (µg/mL) value nearly the same as that of the standard [71].

S. cumini leaves were extracted with ethanol. The antioxidant activity of the extract was determined using the DPPH assay, and the result showed that IC₅₀ = 9.85 ± 0.51 µg/mL. Ascorbic acid was used as a positive control [72].

S. cumini seeds were extracted with methanol. The antioxidant activity of the extract was determined using DPPH and FRAP assays. Vitamin C, butylated hydroxyanisole (BHA) and quercetin were used as positive controls. This methanol extract expressed strong antioxidant activity. At certain concentration, this extract showed a stronger percentage of DPPH scavenging than that of BHA. Likewise with the reducing power in the FRAP assay, vitamin C showed weaker antioxidant activity than the methanol extract. The authors stated that the high tannins present in the methanol extract contributed to the strong antioxidant activity [73].

S. cumini leaves were extracted with methanol. The antioxidant activity of the extract was determined using the DPPH assay. Butyl hydroxyl toluene (BHT) and ascorbic acid were used as standards. The IC₅₀ value of the extract obtained showed a potent scavenging activity when compared with BTH and ascorbic acid [74].

S. guineense leaves were extracted with 80% methanol. The antioxidant activity of the extract was determined using the DPPH assay. The leaf extract did not show the antioxidant activity [75].

The essential oil was extracted from S. guineense leaves by using the hydro-distillation method. The antioxidant activity of essential oil was determined using the DPPH radical scavenging assay. BHT was used as a standard. The authors reported that this essential oil exhibited the high antioxidant activity [76].

4.2 Anticancer activity

S. aqueum leaves were extracted with methanol for the determination of cytotoxicity using sulforhodamine B (SRB) assay. The activity was tested on human breast cancer cell (MDA-MB-231) and compared with that of doxorubicin (standard cytotoxic drug). The extract was less toxic on cancer cell line (IC₅₀ > 100 µg/mL) [86].

Pulp of S. samarangense was extracted with methanol and then the extract was tested on SW-480 human colon cancer cell line using the MTT (3-(4,5-dimethylthiazol-2-yl)-2-5-diphenyltetrazolium bromide) assay. EGCG was treated as a positive control. Methanolic extract and EGCG were highly toxic on cancer cell line according to data [49].

S. cumini seeds were extracted with ethyl acetate. The extract was separated using column chromatography with an eluent mixture of chloroform:ethyl acetate:methanol (30:50:20) to obtain a single compound, flavopiridol. The anticancer activity of the isolated compound was evaluated on MCF7, A2780, PC-3 and H460 cell lines using the MTS (5-(3-carboxymethoxyphenyl)-2-(4,5-dimethyl-thiazoly)-3-(4-sulfophenyl) tetrazolium) assay. Flavopiridol was used as a positive control. The S. cumini seed extract proved the highest activity against A2780 cell line (IC₅₀ = 49 μg/ml), whereas showed the least activity against H₄₆₀ cell line [77].

S. guineense’s leaves and bark were extracted with ethanol, water and the mixture of ethanol–water. All extracts were tested on HeLa cell line and SiHa cell line for anticancer activity using the SRB assay. Adriamycin was used as a positive control on both cell lines. The aqueous extract of bark showed the best inhibition of cancer cell growth on both cell lines. The ethanol extract of leaves exhibited more efficient inhibition than other leaf extracts on both cell lines [78].

The ethanol leaf extract of S. cumini was tested on human keratinocyte cells (HaCaT cell line) by using the MTT assay. From this study, it was known that the ethanol extract was not toxic at concentrations of 500–250 µg/mL [72].

S. aqueum leaves were extracted with methanol. The cytotoxicity of the extract was detected on breast cancer cell line MCF-7 using the SRB assay. Doxorubicin was used as the standard. The results showed that the extract had high activity against MCF-7 cell line (IC₅₀ < 100 µg/mL). This activity is caused by the content of phenolic compounds which act as phytoestrogens in the Syzygium extract under study [86].

4.3 Antimicrobial activity

S. samarangense fruits were extracted by using three solvents (petroleum ether, ethyl acetate and methanol). All extracts were tested against certain bacterial and fungal strains using the disc diffusion method. Gram-positive bacteria (Bacillus cereus, Staphylococcus aureus and Candida albicans) and Gram-negative bacteria (Escherichia coli, Pseudomonas aeruginosa and Klebsiella pneumoniae) were used in this study. Ampicillin, kanamycin, tetracycline and vancomycin were used as standards. The method used was a microdilution using a 96-well microtiter plate. The result of this study showed that the Gram-positive and Gram-negative bacteria were sensitive to fruit extracts. Among the three extracts, the methanol extract showed a higher activity than other extracts [79].

The ethanol extract of S. samarangense leaves was examined for antibacterial activity by using the broth microdilution method. The extract was tested against E. coli, B. cereus, Enterobacter aerogenes, Salmonella enterica and Kocuria rhizophila. The minimum inhibitory concentration (MIC) value was determined to be the lowest concentration of the extract capable of inhibiting microorganism growth. The leaf extract of the sample was more effective against B. cereus and S. enterica than others when compared with chloramphenicol [35].

Leaves, bark and fruits of S. samarangense tree cultivars (red, pink and green) were extracted with methanol and ethanol. All extracts were evaluated against four bacteria, including two Gram-positive (B. cereus and S. aureus) and two gram-negative bacteria (E. coli and P. aeruginosa), by using the disc diffusion method. Tetracycline was used as a positive control. All the extracts showed the antimicrobial activity. However, the ethanolic extracts showed higher antimicrobial activities than the methanolic extracts. All the bark extracts of three cultivars exhibited higher antimicrobial activities followed by fruit and leaf extracts [68].

S. samarangense root was extracted by using three kinds of solvents (ethyl acetate, methanol and water) by using the Soxhlet extraction method. The root extracts were evaluated against Salmonella typhi, E. coli, P. aeruginosa and Bacillus subtilis by using the agar well diffusion method. The methanolic extract presented high inhibitory effect on S. typhi, the ethyl acetate extract showed potent inhibitory effect on P. aeruginosa and the aqueous extract exhibited strong inhibitory effect on S. typhi [69].

The antibacterial and antifungal activities of S. aromaticum oil were determined by using the agar well diffusion method against S. aureus, E. coli and P. aeruginosa bacteria and C. albicans, Aspergillus flavus and Penicillium. Ciprofloxacin and ketoconazole were used as positive controls. S. aromaticum oil had a high inhibitory effect on bacteria and fungi when compared with positive control [70].

S. aromaticum (clove) was extracted with 70% ethanol and 80% methanol. The two extracts were tested on S. aureus, P. aeruginosa and E. coli in comparison with the selected antibiotic (tetracycline) using the agar well diffusion method. The highest activity against P. aeruginosa was presented by the ethanol extract and against S. aureus was shown by the methanol extract. [80].

S. aromaticum (cloves) was extracted with 80% methanol. The 1% of six metals (Zn⁺⁺, Cu⁺⁺, Pb⁺⁺, Ca⁺⁺, Mg⁺⁺ and Fe⁺⁺) was added in the extract and the antibacterial properties were tested using the agar well diffusion method. For S. aureus, the maximum zone of inhibition was presented by zinc, for E. coli by magnesium and for P. aeruginosa by lead [80].

S. cumini seeds were extracted with ethyl acetate. The extract was separated and purified to obtain a single compound. This compound showed antibacterial activity against E. coli, P. aeruginosa, S. aureus and B. subtilis using the agar cup method. The largest zone of inhibition was observed in E. coli [77].

S. cumini (leaves, pulps and seeds) was extracted with methanol. The extract was examined against E. coli and S. aureus using the agar well diffusion assay. Leaf extract exhibited antibacterial activity both on E. coli and S. aureus, whereas pulp and seed extracts did not show any antibacterial activity [81].

The essential oil was isolated from S. guineense leaves by using the hydrodistillation method. The MIC of essential oil on microorganisms (P. aeruginosa, K. pneumonia, E. coli, S. aureus, C. albicans and Mycobacterium bovis [BCG]) was determined using the microbroth dilution method. Essential oil of S. guineense exhibited strong antimicrobial activities against the tested microorganisms when compared with ciprofloxacin, fluconazole and isoniazid [76].

S. guineense seeds were extracted with ethanol. The MIC on microorganisms (E. coli, K. pneumonia, S. typhi, S. aureus and C. albicans) of the extract was determined by using the broth microdilution method. Gentamicin sulfate and fluconazole were used as standard drugs. The extract showed weak to moderate antibacterial activity and lower than standard drugs [82].

4.4 Antidiabetic activity

S. samarangense root was extracted by using three kinds of solvents (ethyl acetate, methanol and water) by using the Soxhlet extraction method. The antidiabetic activity of all extracts was determined using alpha-amylase inhibition. Water extract showed the highest percentage of alpha-amylase inhibition, followed by methanol and ethyl acetate extracts [69].

S. cumini seeds were extracted with methanol. The antidiabetic activity of extract was determined by using alpha-amylase enzyme. The percentage of inhibition varied from 38.6% to 95.4%. It was concluded that the sample possessed significant antidiabetic activity [84].

S. guineense leaves were extracted with 80% methanol. The antidiabetic activity of the extract was determined using alpha-glucosidase enzyme. IC₅₀ obtained from that study was 6.15 μg/mL, which was the best inhibition for antidiabetic activity [75].

4.5 Toxicity

The toxicity of the ethanolic leaf extract of S. cumini was tested by using the brine shrimp lethality assay. Thymol was used as a standard. Ten brine shrimp larvae were added in each concentration of extract (1,000–10 μg/mL). The absence of brine shrimp death in the sample was calculated to obtain the LC₅₀ value. The result of the test showed that the extract did not have high toxicity compared to thymol as a standard [72].

S. guineense seeds were extracted with ethanol and the toxicity of the obtained was tested using the brine shrimp lethality assay. Cyclophosphamide was used as a standard. Ten brine shrimps larvae were added in different concentrations of extract (240, 120, 80, 40 and 24 μg/mL). The absence of brine shrimp death in the sample was calculated to obtain the LC₅₀ value. The extract did not have the toxicity (LC₅₀ value was above100 µg/mL) [85].

4.6 Anti-inflammatory activity

The anti-inflammatory activity of the methanolic extract of S. aqueum leaves was determined. For this study, the ability of the extract to inhibit lipoxygenase (LOX) using an LOX inhibitor screening assay kit was established as well as ovine COX-1 and COX-2 inhibition using an enzyme immunoassay kit. Celecoxib, indomethacin and diclofenac were used as standards. The extract showed more potent inhibitory effect than diclofenac on COX-2 as well as on LOX. Celecoxib was less active than the extract on COX-1 [33].

Different kinds of solvents (ethyl acetate, methanol and water) were used for extraction of S. samarangense root. All extracts of root were evaluated for anti-inflammatory activity by the albumin denaturation assay. The methanol extract showed the highest percentage of albumin denaturation, followed by water and ethyl acetate extracts [69].

4.7 Anthelmintic activity

S. guineense seeds were extracted with ethanol. The anthelmintic activity of the extract was tested on adult roundworms (Ascaris suum) by using the protocol described by Nilani’s team. Albendazole was received as a standard drug. All tested concentrations of the extract required a longer time to cause paralysis and death than albendazole. To give the 100% death effect, the time requirement of the extract was slightly higher than that of negative control (normal saline) at concentrations of 50 and 30 mg/mL, but at a concentration of 100 mg/mL, the time requirement was 6% higher than that of the standard drug. This study resulted in a conclusion that at higher concentration, the extract exhibits reasonably high anthelmintic activity compared to albendazole [82]. Another paper gave a similar result (Table 2) [85].

Table 2

Isolated compounds and their bioactivities reported from Syzygium genus

No	Compound name	Bioactivities	Plant species (parts of plant)	Ref.
1	Phloretin	Antidiabetic activity (EC₅₀ µM)	S. aqueum (leaves)	[43,83]
1	Phloretin	(20 ± 2.2) for α-glucosidase inhibition and (31 ± 5.5) for α-amylase inhibition, positive control (acarbose)-(43 ± 1.6) for α-glucosidase and (19 ± 1.6) for α-amylase	S. aqueum (leaves)	[43,83]
2	Myrigalone-G	Antidiabetic activity (EC₅₀ µM)	S. aqueum (leaves)	[43,83]
2	Myrigalone-G	(7 ± 1.4) for α-glucosidase inhibition and (33 ± 6.6) for α-amylase inhibition, positive control (acarbose)-((43 ± 1.6) for α-glucosidase and (19 ± 1.6) for α-amylase	S. aqueum (leaves)	[43,83]
3	Myrigalone B	Antidiabetic activity (EC₅₀ µM)	S. aqueum (leaves)	[43,83]
3	Myrigalone B	(19 ± 1.0) for α-glucosidase inhibition and (8.3 ± 1.3) for α-amylase inhibition, positive control (acarbose) – ((43 ± 1.6) for α-glucosidase and (19 ± 1.6) for α-amylase	S. aqueum (leaves)	[43,83]
4	2′,4′-Dihydroxy-6′-methoxy-3′-methyldihydrochalcone	Trypsin inhibition assay	S. samarangense (leaves)	[46,47]
		IC₅₀ 31.9 ± 0.25 mM to compared with Leupeptin (IC₅₀ 0.026 ± 0.001 µM)
		Thrombin inhibition assay
		IC₅₀ 14.9 ± 0.25 mM to compared with Leupeptin (IC₅₀0.045 ± 0.003 µM)
		Prolyl endopeptidase inhibition assay
		IC₅₀ 12.5 ± 0.2 µM to compared with Bacitracin (IC₅₀ 129.26 ± 3.28 µM)
5	2′-Hydroxy-4′,6′-dimethoxy-3′-methyldihydrochalcone	Trypsin inhibition assay	S. samarangense (leaves)	[46,47]
		IC₅₀ 2.7 ± 0.5 mM to compared with Leupeptin (IC₅₀ 0.026 ± 0.001 µM)
		Thrombin inhibition assay
		IC₅₀ 10.0 ± 0.5 mM to compared with Leupeptin (IC₅₀0.045 ± 0.003 µM)
		Prolyl endopeptidase inhibition assay
		IC₅₀ 158.5 ± 0.1 µM to compared with Bacitracin (IC₅₀ 129.26 ± 3.28 µM)
6	2′,4′-Dihydroxy-6′-methoxy3′,5′-dimethyldihydrochalcone	Trypsin inhibition assay	S. samarangense (leaves)	[46,47]
		IC₅₀ 38.2 ± 0.25 mM to compared with Leupeptin (IC₅₀0.045 ± 0.003 µM)
		Thrombin inhibition assay
		IC₅₀ 62.1 ± 0.25 mM to compared with Leupeptin (IC₅₀ 0.026 ± 0.001 µM)
		Prolyl endopeptidase inhibition assay
		IC₅₀ 98.3 ± 0.8 µM to compared with Bacitracin (IC₅₀ 129.26 ± 3.28 µM)
7	2′,4′-Dihydroxy-6′-methoxy-3′-methylchalcone or stercurensin	Trypsin inhibition assay	S. samarangense (fruit and leaves)	[46,47,49]
		IC₅₀ 5.6. ± 0.125 mM to compared with Leupeptin (IC₅₀ 0.026 ± 0.001 µM)
		Prolyl endopeptidase inhibition assay
		IC₅₀ 37.5 ± 1.0 µM to compared with Bacitracin (IC₅₀ 129.26 ± 3.28 µM)
		Anticancer activity (MTT assay)
		IC₅₀ 35 µM for compound and IC₅₀ 50 µM for EGCG as positive control on SW-480 human colon cancer cell line
		Antioxidant activity
		(IC₅₀ 141 ± 2.3 µM) by DPPH assay and (IC₅₀ 191 ± 0.1 µM) by FRAP assay
		IC₅₀ 25.0 ± 0.1 µM for gallic acid (positive control) by DPPH
8	2′-Hydroxy-4′,6′-dimethoxy-3′-methylchalcone	Trypsin inhibition assay	S. samarangense (leaves)	[46,47]
		IC₅₀ 15.8 ± 0.25 mM to compared with Leupeptin (IC₅₀ 0.026 ± 0.001 µM)
		Thrombin inhibition assay
		IC₅₀ 30.7 ± 0.25 mM to compared with Leupeptin (IC₅₀0.045 ± 0.003 µM)
		Prolyl endopeptidase inhibition assay
		IC₅₀ > 200 µM to compared with Bacitracin (IC₅₀ 129.26 ± 3.28 µM)
9	2′,4′-Dihydroxy-6′-methoxy-3′,5′ dimethylchalcone	Anticancer activity (IC₅₀ µM)	S. aqueum (leaves) and S. samarangense (leaves)	[44,46,47]
		Inhibition of the proliferation of the breast cancer (MCF-7) cell lines by using MTT assay, IC₅₀ values 270 µM (24 h) and 250 µM (48 hr)
		Thrombin inhibition assay
		IC₅₀ 1.8 ± 0.25 mM to compared with Leupeptin (IC₅₀0.045 ± 0.003 µM)
		Prolyl endopeptidase inhibition assay
		IC₅₀ 149.8 ± 7.1 µM to compared with Bacitracin (IC₅₀ 129.26 ± 3.28 µM)
10	2′,4′-Dihydroxy-3′,5′-dimethyl-6′-methoxychalcone	Anticancer activity (MTT assay)	S. samarangense (fruits)	[49]
		IC₅₀10 µM for compound and IC₅₀ 50 µM for EGCG as positive control on SW-480 human colon cancer cell line
		Antioxidant activity
		(IC₅₀ 205 ± 1.2 µM) by DPPH assay and (IC₅₀ 196 ± 0.0 µM) by FRAP assay
		IC₅₀ 25.0 ± 0.1 µM for gallic acid (positive control) by DPPH
11	2′,4′-Dihydroxy-6′-methoxchalcone or cardamonin	Anticancer activity (MTT assay)	S. samarangense (fruits)	[49]
		IC₅₀ 35 µM for compound and IC₅₀ 50 µM for EGCG as positive control on SW-480 human colon cancer cell line
		Antioxidant activity
		(IC₅₀ 141 ± 3.4 µM) by DPPH assay and (IC₅₀ 173 ± 0.0 µM) by FRAP assay
		IC₅₀ 25.0 ± 0.1 µM for gallic acid (positive control) by DPPH
12	Pinocembrin	Anticancer activity (MTT assay)	S. samarangense (fruit and leaves)	[48,49]
		IC₅₀ 60 µM for compound and IC₅₀ 50 µM for EGCG as positive control on SW-480 human colon cancer cell line
		Antioxidant activity
		(IC₅₀ 199 ± 0.8 µM) by DPPH assay and (IC₅₀ 196 ± 0.0 µM) by FRAP assay
		IC₅₀ 25.0 ± 0.1 µM for gallic acid (positive control) by DPPH
13	(—)-Strobopinin	—	S. samarangense (leaves)	[48]
14	8-Methylpinocembrin	—	S. samarangense (leaves)	[48]
15	Demethoxymatteutcinol	—	S. samarangense (leaves)	[48]
16	7-Hydroxy-5-methoxy-6,8-dimethyl-foavanone	—	S. samarangense (leaves)	[48]
17	7,8,3′,4′-Tetrahydroxy-3,5-dimethoxyflavone	Antioxidant activity (EC₅₀ µg/mL)	S. samarangense (leaves)	[45]
		(3.89 µg/mL) for DPPH assay whenby compared~~ing~~ with ascorbic acid (2.94 µg/mL)
		(21.08 µg/mL) for FRAP assay whenby compared~~ing~~ with quercetin (23.18 µg/mL)
18	7-Hydroxy-5-methoxy-6,8-dimethylflavanone	Trypsin inhibition assay	S. samarangense (leaves)	[46,47]
		IC₅₀ 7.4 ± 0.1 mM to compared with Leupeptin (IC₅₀ 0.026 ± 0.001 µM)
		Prolyl endopeptidase inhibition assay
		13.9% inhibition at 0.5 mM to compared with Bacitracin (IC₅₀ 129.26 ± 3.28 µM)
19	Quercetin	—	S. samarangense (fruits) and S. aromaticum (flower buds)	[49,50]
20	Kaempferol	—	S. cumini (leaves)	[54]
21	Gallocatechin	Antioxidant (DPPH)	S. guineense (leaves)	[51]
		IC₅₀ 17 ± 3 µM for compound and IC₅₀ 12± 0.2 µM for quercetin (positive control)
		15-lipoxygenase (15-LO) inhibition
		IC₅₀ 112 ± 4 µM for compound and IC₅₀ 72±7 µM for quercetin (positive control)
		Xanthine oxidase (OX) inhibition
		IC₅₀>167 µM for compound and IC₅₀ 3.0±0.6 µM for quercetin (positive control)
22	Myricetin	Antioxidant (DPPH)	S. guineense (leaves)	[51]
		IC₅₀ 41±6 µM for compound and IC₅₀ 12±0.2 µM for quercetin (positive control)
		15-Lipoxygenase (15-LO) inhibition
		IC₅₀>83 µM for compound and IC₅₀ 72±7 µM for quercetin (positive control)
		Xanthine oxidase (OX) inhibition
		IC₅₀ 8±1 µM for compound and IC₅₀ 3.0±0.6 µM for quercetin (positive control)
23	(—)-Epigallocatechin	—	S. aqueum (leaves) and S. samarangense (leaves)	[52]
24	(—)-Epigallocatechin 3-O-gallate	—	S. aqueum (leaves) and S. samarangense (leaves)	[52]
25	Samarangenins A	—	S. aqueum (leaves) and S. samarangense (leaves)	[52]
26	Samarangenins B	—	S. aqueum (leaves) and S. samarangense (leaves)	[52]
27	Prodelphinidin B-2 3″-O-gallate	—	S. aqueum (leaves) and S. samarangense (leaves)	[52]
28	Prodelphinidin B-2 3,3″-O-gallate	—	S. aqueum (leaves) and S. samarangense (leaves)	[52]
29	Myricetin-3-O-rhamnoside	Antidiabetic activity (EC₅₀ µM)	S. aqueum (leaves) and S. samarangense (leaves)	[43,45,83]
		(1.1 ±0.06 µM) for compound and (43±1.6 µM) for acarbose by using α-glucosidase (1.9 ± 0.02 µM) for compound and (19± 1.6 µM) for acarbose by using α-amylase
		Antioxidant activity (EC₅₀ µg/mL)
		(3.21 µg/mL) for DPPH assay whenby compared~~ing~~ with ascorbic acid (2.94 µg/mL), (22.9 µg/mL) for FRAP assay bywhen compared~~ing~~ with quercetin (23.18 µg/mL)
30	Europetin-3-Orhamnoside	Antidiabetic activity (EC₅₀ µM)	S. aqueum (leaves)	[43,84]
30	Europetin-3-Orhamnoside	(1.9 ± 0.06) for α-glucosidase inhibition and (2.3 ± 0.04) for α-amylase inhibition, (43 ± 1.6) for α-glucosidase inhibition and (19± 1.6) for α-amylase inhibition in the positive control (acarbose)	S. aqueum (leaves)	[43,84]
31	Mearnsitrin	—	S. samarangense (leaves)	[53]
32	Reynoutrin	—	S. samarangense (fruits)	[49]
33	Hyperin	—	S. samarangense (fruits)	[49]
34	Quercitrin	—	S. samarangense (fruits)	[49]
35	Guaijaverin	—	S. samarangense (fruits)	[49]
36	Tamarixetin 3-O-β-D-glucopyranoside	—	S. aromaticum (flower buds)	[50]
37	Ombutin 3-O-β-d glucopyranoside	—	S. aromaticum (flower buds)	[50]
38	Quercetin 3-O-α-l-rhamnopyranoside~~rhamnopyronside~~	—	S. cumini (leaves)	[54]
39	Kaempferol 3-O-β-d-glucuronopyranoside	—	S. cumini (leaves)	[54]
40	Myricetin 3-O-β-d-glucuronopyranoside	—	S. cumini (leaves)	[54]
41	Mearnsetin 3-O-(4″-O-acetyl)-α-l-rhamnopyranoside	—	S. cumini (leaves)	[54]
42	Myricetin 3-O-(4″-O-acetyl) -α-l-rhamnopyranoside	—	S. cumini (leaves)	[54]
43	Myricetin 4′-methyl ether 3-O-α-l-rhamnopyranoside	—	S. cumini (leaves)	[54]
40	Myricetrin 4″-O-acetyl-2″-O-gallate	—	S. cumini (leaves)	[54]
45	Myricetin-3-O-glucoside	Antioxidant (DPPH)	S. guineense (leaves)	[51]
		IC₅₀ 11±2 µM for compound and IC₅₀ 12±0.2 µM for quercetin (positive control)
		15-Lipoxygenase (15-LO) inhibition
		IC₅₀ 42±4 µM for compound and IC₅₀ 72± 7 µM for quercetin (positive control)
		Xanthine oxidase (OX) inhibition
		IC₅₀ 38 ± 4 µM for compound and IC₅₀ 3.0 ± 0.6 µM for quercetin (positive control)
46	Myricetin-3-O-rhamnoside	Antioxidant (DPPH)	S. guineense (leaves)	[51]
		IC₅₀ 28 ± 3 µM for compound and IC₅₀ 12 ± 0.2 µM for quercetin (positive control)
		15-Lipoxygenase (15-LO) inhibition
		IC₅₀ 138 ± 11 µM for compound and IC₅₀ 72± 7 µM for quercetin (positive control)
		Xanthine oxidase (OX) inhibition
		IC₅₀ > 167 µM for compound and IC₅₀ 3.0 ± 0.6 µM for quercetin (positive control)
47	Myricetin-3-O-glucoronide	Antioxidant (DPPH)	S. guineense (leaves)	[51]
		IC₅₀ 85 ± 33 µM for compound and IC₅₀ 12 ± 0.2 µM for quercetin (positive control)
		15-lipoxygenase (15-LO) inhibition
		IC₅₀ > 83 µM for compound and IC₅₀ 72 ± 7 µM for quercetin (positive control)
		Xanthine oxidase (OX) inhibition
		IC₅₀ > 83 µM for compound and IC₅₀ 3.0 ± 0.6 µM for quercetin (positive control)
48	Myricetin-3-O-β-d-(6″-galloyl) galactoside	Antioxidant (DPPH)	S. guineense (leaves)	[51]
		IC₅₀ 10 ± 3 µM for compound and IC₅₀ 12 ± 0.2 µM for quercetin (positive control)
		15-Lipoxygenase (15-LO) inhibition
		IC₅₀ 75 ± 7 µM for compound and IC₅₀ 72 ± 7 µM for quercetin (positive control)
		Xanthine oxidase (OX) inhibition
		IC₅₀ > 167 µM for compound and IC₅₀ 3.0 ± 0.6 µM for quercetin (positive control)
49	Biflorin	Cytotoxicity (MTT assay)	S. aromaticum (cloves)	[55]
49	Biflorin	IC₅₀ > 100 µM against human ovarian cancer cells (A2780) whenby compared~~ing~~ with Cisplatin (IC₅₀ 6.96 ± 2.60 µM) as positive control	S. aromaticum (cloves)	[55]
50	Isobiflorin	Cytotoxicity (MTT assay)	S. aromaticum (cloves)	[55]
50	Isobiflorin	(IC₅₀ > 100 µM) against human ovarian cancer cells (A2780) whenby compared~~ing~~ with Cisplatin (IC₅₀ 6.96 ± 2.60 µM) as positive control	S. aromaticum (cloves)	[55]
51	6-C-β-d-(6′-O-galloyl) glucosylnoreugenin	Cytotoxicity (MTT assay)	S. aromaticum (cloves)	[55]
51	6-C-β-d-(6′-O-galloyl) glucosylnoreugenin	(IC₅₀ 66.78 ± 5.49 µM) against human ovarian cancer cells (A2780) whenby compared~~ing~~ with Cisplatin (IC₅₀ 6.96 ± 2.60 µM) as positive control	S. aromaticum (cloves)	[55]
52	8-C-β-d-(6′-O-galloyl) glucosylnoreugenin	Cytotoxicity (MTT assay)	S. aromaticum (cloves)	[55]
52	8-C-β-d-(6′-O-galloyl) glucosylnoreugenin	(IC₅₀ 87.50 ± 1.56 µM) against human ovarian cancer cells (A2780) whenby compared~~ing~~ with Cisplatin (IC₅₀ 6.96 ± 2.60 µM) as positive control	S. aromaticum (cloves)	[55]
53	Sysamarin A	—	S. samarangense (leaves)	[56]
54	Sysamarin B	—	S. samarangense (leaves)	[56]
55	Sysamarin C	—	S. samarangense (leaves)	[56]
56	Sysamarin D	—	S. samarangense (leaves)	[56]
57	Sysamarin E	—	S. samarangense (leaves)	[56]
58	Lupenyl stearate	—	S. samarangense (leaves)	[57]
57	Lupeol	Thrombin inhibition assay	S. samarangense (leaves) and S. cumini (leaves)	[46,57,60]
		IC₅₀ 49.2 ± 0.2 mM to compared with Leupeptin (IC₅₀ 0.026 ± 0.001 µM)
		Prolyl endopeptidase inhibition assay
		IC₅₀ 65.0 ± 3.2 µM to compared with Bacitracin (IC₅₀ 129.26 ± 3.28 µM)
60	Betulin	Trypsin inhibition assay	S. samarangense (leaves) and S. guineense(stem bark)	[46,57,63]
		IC₅₀ 24.4 ± 0.125 mM to compared with Leupeptin (IC₅₀0.045 ± 0.003 µM)
		Prolyl endopeptidase inhibition assay
		IC₅₀ 101.6 3.2 µM to compared with Bacitracin (IC₅₀ 129.26 ± 3.28 µM)
		Antibacterial activity~~Minimum Inhibition Concentration~~
61	Betulinic acid	(Prolyl endopeptidase inhibition assay	S. samarangense (leaves) and S. guineense(stem bark)	[46,63]
		64.4% inhibition at 0.5 mM to compared with Bacitracin (IC₅₀ 129.2 6 ± 3.28 µM) Antibacterial activity
		~~Minimum Inhibition Concentration~~
62	Oleanolic acid	(Cytotoxicity (MTT assay)	S. aromaticum (flower buds) and S. cumini (seeds)	[55,58,59]
62	Oleanolic acid	(IC₅₀ 24.30 ± 0.30 µM) against on human ovarian cancer cells (A2780) by when compared~~ing~~ with Cisplatin (IC₅₀ 6.96 ± 2.60 µM) as positive control	S. aromaticum (flower buds) and S. cumini (seeds)	[55,58,59]
63	Arjunolic acid	Antibacterial activity	S. aromaticum (flower buds) and S. guineense (leaves and roots)	[58,61,62]
		(IC₅₀ 3 µg/mL) against Escherichia coli, (IC₅₀ 0.5 µg/mL) against Bacillus subtilis, and (IC₅₀ 30 µg/mL) against Shigella saonnei
		Chloramphenicol as Ppositive control against Escherichia coli (IC₅₀ 0.3 µg/mL), Bacillus subtilis (IC₅₀0.1 µg/mL) and Shigella soannei (IC₅₀ 2 µg/mL)
64	Corosolic acid	—	S. aromaticum (flower buds)	[58]
65	Asiatic acid	Antibacterial activity	S. aromaticum (flower buds) and S. guineense (leaves and roots)	[58,61,62]
		(IC₅₀ 5 µg/mL) against Escherichia coli, (IC₅₀ 0.75 µg/mL) against Bacillus subtilis, and (IC₅₀ 30 µg/mL) against Shigella saonnei
		Chloramphenicol as Ppositive control against Escherichia coli (IC₅₀ 0.3 µg/mL), Bacillus subtilis (IC₅₀0.1 µg/mL) and Shigella saonnei (IC₅₀ 2 µg/mL)
66	Maslinic acid	Cytotoxicity (MTT assay)	S. aromaticum (flower buds)	[55]
66	Maslinic acid	(IC₅₀ 29.61 ± 4.68 µM) against human ovarian cancer cells (A2780) whenby compared~~ing~~ with Cisplatin (IC₅₀ 6.96 ± 2.60 µM) as positive control	S. aromaticum (flower buds)	[55]
67	12-Oleanen-3-ol-3β acetate	—	S. cumini (leaves)	[60]
68	2-Hydroxyoleanolic acid	Not observed Aantibacterial activity (Escherichia coli and Bacillus subtilis)	S. guineense (leaves and roots)	[61,62]
69	2-Hydroxyursolic acid	Not observed Aantibacterial activity (Escherichia coli and Bacillus subtilis)	S. guineense (leaves and roots)	[61,62]
70	Terminolic acid	Antibacterial activity	S. guineense (leaves and roots)	[61,62]
		(IC₅₀ 6 µg/mL) against Escherichia coli, (IC₅₀ 3 µg/mL) against Bacillus subtilis, and (IC₅₀ 50 µg/mL) against Shigella saonnei
		Chloramphenicol as Ppositive control against Escherichia coli (IC₅₀ 0.3 µg/mL), Bacillus subtilis (IC₅₀0.1 µg/mL) and Shigella saonnei (IC₅₀ 2 µg/mL)
71	6-Hydroxy asiatic acid	—	S. guineense (leaves and roots)	[61,62]
72	Limonin	—	S. aromaticum (flower buds)	[50]
73	Caryolane-1,9β-diol	Cytotoxicity (MTT assay)	S. aromaticum (cloves)	[55]
73	Caryolane-1,9β-diol	(IC₅₀ > 100 µM) against human ovarian cancer cells (A2780) whenby compared~~ing~~ with Cisplatin (IC₅₀ 6.96 ± 2.60 µM) as positive control	S. aromaticum (cloves)	[55]
74	Clovane-2,9-β-diol	Cytotoxicity (MTT assay)	S. aromaticum (cloves)	[55]
74	Clovane-2,9-β-diol	(IC₅₀ > 100 µM) against human ovarian cancer cells (A2780) whenby compared~~ing~~ with Cisplatin (IC₅₀ 6.96 ± 2.60 µM) as positive control	S. aromaticum (cloves)	[55]
75	α-Humulene	Cytotoxicity (MTT assay)	S. aromaticum (cloves)	[55]
75	α-Humulene	(IC₅₀ 21.03 ± 5.53 µM) against human ovarian cancer cells (A2780) whenby compared~~ing~~ with Cisplatin (IC₅₀ 6.96 ± 2.60 µM) as positive control	S. aromaticum (cloves)	[55]
76	Humulene epoxide α	Cytotoxicity (MTT assay)	S. aromaticum (cloves)	[55]
76	Humulene epoxide α	(IC₅₀ > 100 µM) against human ovarian cancer cells (A2780) whenby compared~~ing~~ with Cisplatin (IC₅₀ 6.96 ± 2.60 µM) as positive control	S. aromaticum (cloves)	[55]
77	β-Caryophyllene	Cytotoxicity (MTT assay)	S. aromaticum (cloves)	[55]
77	β-Caryophyllene	(IC₅₀ 60.70 ± 1.44 µM) against human ovarian cancer cells (A2780) whenby compared~~ing~~ with Cisplatin (IC₅₀ 6.96 ± 2.60 µM) as positive control	S. aromaticum (cloves)	[55]
78	β-Caryophyllene oxide	Cytotoxicity (MTT assay)	S. aromaticum (cloves)	[55]
78	β-Caryophyllene oxide	(IC₅₀ > 100 µM) against human ovarian cancer cells (A2780) whenby compared~~ing~~ with Cisplatin (IC₅₀ 6.96 ± 2.60 µM) as positive control	S. aromaticum (cloves)	[55]
79	Lupenyl stearate cycloartenyl stearate	—	S. samarangense (leaves)	[57]
80	β-Sitosteryl stearate	—	S. samarangense (leaves)	[57]
81	24-Methylenecycloartenyl stearate	—	S. samarangense (cloves)	[57]
82	β-Sitosterol	—	S. samarangense and S. cumini (leaves and seeds)	[57,59,60]
83	Stigmasterol	—	S. cumini (leaves)	[60]
84	β-Sitosterol-3-O-β-d-glucoside	Cytotoxicity (MTT assay)	S. aromaticum (flower buds)	[55]
84	β-Sitosterol-3-O-β-d-glucoside	(IC₅₀ > 100 µM) against human ovarian cancer cells (A2780) whenby compared~~ing~~ with Cisplatin (IC₅₀ 6.96 ± 2.60 µM) as positive control	S. aromaticum (flower buds)	[55]
85	Arjunolic~~Arjulonic~~ acid 28-β-glycopyranosyl ester	Not observed Aantibacterial activity (Escherichia coli and Bacillus subtilis)	S. guineense (leaves and roots)	[61,62]
86	Asiatic acid 28-β-glycopyranosyl ester	Not observed Aantibacterial activity (Escherichia coli and Bacillus subtilis)	S. guineense (leaves and roots)	[61,62]
87	3,3′,4′-Tri-O-methylellagic acid	Cytotoxicity (MTT assay)	S. aromaticum (flower buds)	[55]
87	3,3′,4′-Tri-O-methylellagic acid	(IC₅₀ 87.64 ± 1.70 µM) against human ovarian cancer cells (A2780) by when compared~~ing~~ with Cisplatin (IC₅₀ 6.96 ± 2.60 µM) as positive control	S. aromaticum (flower buds)	[55]
88	Ellagic acid	—	S. samarangense (fruits) and S. cumini (stem bark)	[49,64]
89	Ellagitannin-3-O-methylellagic acid 3′-O-β-d-glucopyranoside	—	S. cumini (stem bark)	[64]
90	Ellagic acid 4-O-α-l-2″-acetylhamnopyranoside	—	S. cumini (stem bark)	[64]
91	3-O-Methylellgic acid 3′-O-α-l-rhamnopyranoside	—	S. cumini (stem bark)	[64]
92	Gallotannins 1,2,3,6-tetra-O-galloyl-β-d-glucose	—	S. guineense (leaves)	[51]
93	1,2,3,4,6-Penta-O-galloyl-β-d-glucose	Antioxidant (DPPH)	S. guineense (leaves)	[51]
		IC₅₀ 5 ± 1 µM for compound and IC₅₀ 12 ± 0.2 µM for quercetin (positive control)
		15-lipoxygenase (15-LO) inhibition
		IC₅₀ 25 ± 4 µM for compound and IC₅₀ 72 ± 7 µM for quercetin (positive control)
		Xanthine oxidase (OX) inhibition
		IC₅₀ 8 ± 1 µM for compound and IC₅₀ 3.0 ± 0.6 µM for quercetin (positive control)
94	Casuarictin	Antioxidant (DPPH)	S. guineense (leaves)	[51]
		IC₅₀ 3.9 ± 0.1 µM for compound and IC₅₀ 12 ± 0.2 µM for quercetin (positive control)
		15-lipoxygenase (15-LO) inhibition
		IC₅₀ 36 ± 3 µM for compound and IC₅₀ 72 ± 7 µM for quercetin (positive control)
		Xanthine oxidase (OX) inhibition
		IC₅₀ 86 ± 3 µM for compound and IC₅₀ 3.0 ± 0.6 µM for quercetin (positive control)
95	Casuarinin	Antioxidant (DPPH)	S. guineense (leaves)	[51]
		IC₅₀ 4.5 ± 0.3 µM for compound and IC₅₀ 12 ± 0.2 µM for quercetin (positive control)
		15-lipoxygenase (15-LO) inhibition
		IC₅₀ 39 ± 2 µM for compound and IC₅₀ 72 ± 7 µM for quercetin (positive control)
		Xanthine oxidase (OX) inhibition
		IC₅₀ 105 ± 3 µM for compound and IC₅₀ 3.0 ± 0.6 µM for quercetin (positive control)
96	4-Hydroxybenzaldehyde	Antidiabetic activity (EC₅₀ µM)	S. aqueum (leaves)	[43,83]
96	4-Hydroxybenzaldehyde	(9 ± 4.9) for α-glucosidase inhibition and (20 ± 8.2) for α-amylase inhibition, (43 ± 1.6) for α-glucosidase inhibition and (19 ± 1.6) for α-amylase inhibition in the positive control (acarbose)	S. aqueum (leaves)	[43,83]
97	Gallic acid	—	S. cumini (stem bark) and S. samarangense (fruits)	[49,64]
98	Ferulic aldehyde	—	S. aromaticum (cloves)	[50]
99	Eugenol	Cytotoxicity (MTT assay)	S. aromaticum (cloves)	[55]
99	Eugenol	(IC₅₀ > 100 µM) against human ovarian cancer cells (A2780) whenby compared~~ing~~ with Cisplatin (IC₅₀ 6.96 ± 2.60 µM) as positive control	S. aromaticum (cloves)	[55]
100	Eugenyl acetate	Cytotoxicity (MTT assay)	S. aromaticum (cloves)	[55]
100	Eugenyl acetate	(IC₅₀ > 100 µM) against human ovarian cancer cells (A2780) bywhen compared~~ing~~ with Cisplatin (IC₅₀ 6.96 ± 2.60 µM) as positive control	S. aromaticum (cloves)	[55]
101	trans-Coniferylaldehyde	Cytotoxicity (MTT assay)	S. aromaticum (cloves)	[55]
101	trans-Coniferylaldehyde	(IC₅₀ 78.45 ± 5.01 µM) against human ovarian cancer cells (A2780) whenby compared~~ing~~ with Cisplatin (IC₅₀ 6.96 ± 2.60 µM) as positive control	S. aromaticum (cloves)	[55]
102	3-(4-Hydroxy-3-methoxy-phenyl) propane-1,2-diol	Cytotoxicity (MTT assay)	S. aromaticum (cloves)	[55]
102	3-(4-Hydroxy-3-methoxy-phenyl) propane-1,2-diol	(IC₅₀ > 100 µM) against human ovarian cancer cells (A2780) whenby compared~~ing~~ with Cisplatin (IC₅₀ 6.96 ± 2.60 µM) as positive control	S. aromaticum (cloves)	[55]
103	1-O-Methyl-guaiacylglycerol	Cytotoxicity (MTT assay)	S. aromaticum (cloves)	[55]
103	1-O-Methyl-guaiacylglycerol	(IC₅₀ > 100 µM) against human ovarian cancer cells (A2780) whenby compared~~ing~~ with Cisplatin (IC₅₀ 6.96 ± 2.60 µM) as positive control	S. aromaticum (cloves)	[55]
104	Epoxy iconiferyl alcohol	Cytotoxicity (MTT assay)	S. aromaticum (cloves)	[55]
104	Epoxy iconiferyl alcohol	(IC₅₀ > 100 µM) against human ovarian cancer cells (A2780) whenby compared~~ing~~ with Cisplatin (IC₅₀ 6.96 ± 2.60 µM) as positive control	S. aromaticum (cloves)	[55]
105	7-Hydroxycalamenene	—	S. cumini (seeds)	[59]
106	Methyl-β-orsellinate	—	S. cumini (seeds)	[59]
107	2,4,6-Trihydroxy-3-methylacetophenone-2-O-β-d-glycoside	Cytotoxicity (MTT assay)	S. aromaticum (cloves)	[55]
107	2,4,6-Trihydroxy-3-methylacetophenone-2-O-β-d-glycoside	(IC₅₀ > 100 µM) against human ovarian cancer cells (A2780) whenby compared~~ing~~ with Cisplatin (IC₅₀ 6.96 ± 2.60 µM) as positive control	S. aromaticum (cloves)	[55]
108	2,4,6-Trihydroxy-3-methylacetophenone-2-C-β-glycoside	Cytotoxicity (MTT assay)	S. aromaticum (cloves)	[55]
108	2,4,6-Trihydroxy-3-methylacetophenone-2-C-β-glycoside	(IC₅₀ > 100 µM) against human ovarian cancer cells (A2780) whenby compared~~ing~~ with Cisplatin (IC₅₀ 6.96 ± 2.60 µM) as positive control	S. aromaticum (cloves)	[55]
109	Samarone A	Cytotoxicity (MTT assay)	S. samarangense (leaves)	[65]
		(IC₅₀ 32.90 ± 3.17 µM) against HepG2 whenby compared~~ing~~ with Doxorubicin (IC₅₀ 0.30 ± 0.023 µM) as positive control
		(IC₅₀ 26.57 ± 2.16 µM) against on MDA-MB-231 whenby compared~~ing~~ with Doxorubicin (IC₅₀ 1.53 ± 0.13 µM) as positive control
110	Samarone B	Cytotoxicity (MTT assay)	S. samarangense (leaves)	[65]
		(IC₅₀ 3.9 ± 3.17 µM) against HepG2 whenby compared~~ing~~ with Doxorubicin (IC₅₀ 0.30 ± 0.023 µM) as positive control
		(IC₅₀ 27.57 ± 4.76 µM) against on MDA-MB-231 whenby compared~~ing~~ with Doxorubicin (IC₅₀ 1.53 ± 0.13 µM) as positive control
111	Samarone C	Cytotoxicity (MTT assay)	S. samarangense (leaves)	[65]
		(IC₅₀ 5.56 ± 1.17 µM) against HepG2 by when compared~~ing~~ with Doxorubicin (IC₅₀ 0.30 ± 0.023 µM) as positive control
		(IC₅₀ 28.26 ± 4.52 µM) against on MDA-MB-231 bywhen compared~~ing~~ with Doxorubicin (IC₅₀ 1.53 ± 0.13 µM) as positive control
112	Jambones G	Cytotoxicity (MTT assay)	S. samarangense (leaves)	[65]
		(IC₅₀ 1.73 ± 0.66 µM) against HepG2 whenby compared~~ing~~ with Doxorubicin (IC₅₀ 0.30 ± 0.023 µM) as positive control
		(IC₅₀ 4.02 ± 0.87 µM) against on MDA-MB-231 whenby compared~~ing~~ with Doxorubicin (IC₅₀ 1.53 ± 0.13 µM) as positive control
113	Samarone D	—	S. samarangense (Leaves)	[65]
114	Jambone E	Cytotoxicity (MTT assay)	S. samarangense (leaves)	[65]
		(IC₅₀ 7.78 ± 1.78 µM) against HepG2 by when ~~comparing~~ compared with Doxorubicin (IC₅₀ 0.30 ± 0.023 µM) as positive control
		(IC₅₀ 28.26 ± 3.15 µM) against on MDA-MB-231 by when ~~comparing~~ compared with Doxorubicin (IC₅₀ 1.53 ± 0.13 µM) as positive control
115	Jambone F	Cytotoxicity (MTT assay)	S. samarangense (leaves)	[65]
		(IC₅₀ 7.70 ± 1.78 µM) against HepG2 by when ~~comparing~~ compared with Doxorubicin (IC₅₀ 0.30 ± 0.023 µM) as positive control
		(IC₅₀ 12.01 ± 1.31 µM) against on MDA-MB-231 by when ~~comparing~~ compared with Doxorubicin (IC₅₀ 1.53 ± 0.13 µM) as positive control
116	Jamunone B	Cytotoxicity (MTT assay)	S. samarangense (leaves)	[65]
		(IC₅₀ 13.55 ± 2.33 µM) against HepG2 by when ~~comparing~~ compared with Doxorubicin (IC₅₀ 0.30 ± 0.023 µM) as positive control
		(IC₅₀ 37.83 ± 3.42 µM) against on MDA-MB-231 by when ~~comparing~~ compared with Doxorubicin (IC₅₀ 1.53 ± 0.13 µM) as positive control
117	2-Pentadecyl-5,7-didydroxychromone	Cytotoxicity (MTT assay)	S. samarangense (leaves)	[65]
		(IC₅₀ 14.00 ± 1.68 µM) against HepG2 by when ~~comparing~~ compared with Doxorubicin (IC₅₀ 0.30 ± 0.023 µM) as positive control
		(IC₅₀ 7.196 ± 1.75 µM) against on MDA-MB-231 by when ~~comparing~~ compared with Doxorubicin (IC₅₀ 1.53 ± 0.13 µM) as positive control

5 Conclusion

The information of Syzygium species was collected from global publication papers and review articles. S. aqueum, S. aromaticum, S. cumini, S. guineense and S. samarangense are rich sources of phytochemical constituents. Various parts (leaves, seeds, fruits, barks, stem barks and flower buds) of Syzygium species are reported for the treatment of antioxidant, anticancer, toxicity, antimicrobial and antidiabetic activities. The review highlights on the information about plant native growth, botanical description, phytochemical constituents and bioactivities of five known species of Syzygium genus. According to the literature, Syzygium genus is a source of bioactivity in the Myrtaceae family. Therefore, this review suggests that there is great potential for obtaining the lead drug from phytochemical constituents with various bioactivities from those species, whose benefits have been widely used since ancient times without knowing their chemical components.

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Acknowledgments

This study was supported by ADS (Academic Development Scholarship) scholarship form Faculty of Science and Technology, Universitas Airlangga in Indonesia.

Conflict of interest: The authors declare no conflict of interest.

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Received: 2020-05-27

Revised: 2020-08-26

Accepted: 2020-08-29

Published Online: 2020-10-13

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

Artikel in diesem Heft

https://doi.org/10.1515/chem-2020-0175

Schlagwörter für diesen Artikel

Myrtaceae; Syzygium aqueum; S. aromaticum; S. cumini; S. guineense; S. samarangense; flavonoid; chromone; terpenoid; steroid; tannin; phenol; acylphloroglucinol

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