Jurnal Kedokteran dan Kesehatan

Indonesian Journal of Medicine and Health

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Chemical compounds and antibacterial activity of dulcis (Roxb)kurz. Hady Anshory Tamhid*1 1Department of Pharmacy, Faculty of Mathematics and Natural Sciences, Universitas Islam Indonesia, Yogyakarta, Indonesia Article Review ABSTRACT ARTICLE INFO Garcinia dulcis is a medicinal used traditionally to treat various Keywords: diseases including infections of wounds and ulcers. The antibacterial Garcinia dulcis, activity of this plant has also been widely reported, but the most potent antibacterial, compounds as an antibacterial agent are not widely reported, even chemical compounds, xanthones, though the compounds contained in this plant is well known. This paper reviews the compounds contained in G. dulcis and their potential benzophenone as antibacterial agents. Each part of this plant, such as leaves, , *Correspondingflavonoids, author: [email protected] are potential antibacterial agents. Here are described the compounds DOI : 10.20885/JKKI.Vol10.Iss1.art11 flowers, seeds, stems, and roots, contains secondary metabolites which History: contained in each part of the plant, such as xanthones, the most Received: February 4, 2019 Accepted: April 4, 2019 triterpenoid. Their antibacterial activity is also described, especially those Online: April 30, 2019 thatdominant have strong compounds, activity then against flavonoids, bacteria. benzophenones, The molecular structure chromones, and and the Copyright @2019 Authors. possibilities of how the antibacterial mechanism are also discussed. Eleven This is an open access article compounds that have the potential to be used as antibacterial agents for distributed under the terms of the Creative Commons At- tribution-NonCommercial 4.0 (54) are compounds that have the most vigorous activity against S. aureus International Licence (http:// andthe treatmentMRSA compared of infectious to the diseases. other Garcigerincompounds. A (27)The Compoundsand α-mangostin that creativecommons.org/licences/ have strong activity can be used as antibacterial agents for anti-infective by-nc/4.0/). therapy, although they must go through various further studies. Garcinia dulcis merupakan tanaman obat yang digunakan secara tradisional untuk mengobati berbagai macam penyakit termasuk infeksi luka dan bisul. Aktivitas antibakteri dari tanaman ini juga sudah banyak dilaporkan. Namun senyawa aktif dari tanaman ini yang paling bertanggung jawab memberikan efek antibakteri belum pernah dilaporkan, padahal kandungan senyawa dalam tanaman ini sudah banyak diketahui. Paper ini mereview senyawa-senyawa yang terkandung dalam tanaman G.dulcis serta potensinya sebagai agen antibakteri. Setiap bagian dari tanaman ini, seperti daun, buah, bunga, biji, batang dan akar mengandung senyawa metabolit sekunder yang berpotensi sebagai agen antibakteri. Hasil review menunjukkan senyawa yang paling banyak terdapat dalam tiap bagian tanaman ini adalah golongan santon, kemudian golongan flavonoid, benzofenon, kromon, dan triterpenoid. Aktivitas antibakteri dari senyawa-senyawa ini juga diuraikan, terutama yang memiliki aktivitas antibakteri yang kuat. Struktur senyawa dan mekanisme aksinya sebagai antibakteri juga dibahas. Terdapat sebelas senyawa yang dengan aktivitas yang kuat dan berpotensi sebagai agen antibakteri untuk mengobati penyakit infeksi. Senyawa garcigerin (27) dan α-mangostana (54) adalah dua senyawa yang memiliki aktivitas antibakteri yang paling kuat terhadap S.aureus dan MRSA dibanding dengan senyawa-senyawa lain yang diperoleh dari tanaman ini. Kedua senyawa ini sangat berpotensi digunakan sebagai agen antibakteri untuk terapi penyakit infeksi, namun perlu dilakukan penelitian lanjut secara invivo maupun klinis untuk melihat efektivitas, farmakokinetk, dan farmakodinamiknya.

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INTRODUCTION riverside in the areas of Java, Sulawesi and The use of medicinal plants as an alternative Maluku.17 Garcinia dulcis is known to contain therapy is now overgrowing, starting from the various kinds of secondary metabolites including use of fresh plants, dry plants, extract, and active compound isolates. In Asian, including Indonesia, chromones, xanthones and triterpenoids. In the use of plants as traditional medicine is so high thisbenzophenones, article, we will flavonoids,discuss the compounds bioflavonoids, that that almost every country has clear regulations have been successfully isolated from Garcinia regarding the use of medicinal plants as herbal dulcis along with chemical structure and their therapy.1 The use of medicinal plants as a therapy antibacterial activity. for diseases is extensive, including infectious diseases, especially those caused by bacteria. Classification and Botanical It has been reported that 69% of antibiotics Garcinia dulcis is also known as Garcinia currently are from a natural product.2 But only elliptica Choisy, Garcinia longifolia Blume, a few are sourced from plants, even though it is Stalagmites dulcis, Xanthochymus dulcis Roxb, known that the potential of medicinal plants as and Xanthochymus javanensis, Blume. Some an anti-infective agent is enormous. A chemical regions in Indonesia recognise this plant with the compound of plantssuch as phenolic groups, name mundu, also calls this plant the name mundu, while Thailand calls it the name shown to have vigorous antibacterial activity.3 On Ma Phut.18 This species originated from Java, theflavonoids, other hand, terpenoids, infectious and diseases alkaloids (especially have been Malaysia, Thailand, Borneo and . The by bacteria) are one of the highest causes of death in Indonesia.4 One more fact that bacterial below:18 resistance to antibiotics used today is increasing.5 taxonomic Kingdom classification : Plant of this plant is shown Based on these, the study of antibacterial Division : Spermatophyte compounds from medicinal plants needs to be Subdivision : Magnoliophyta improved so that it is not impossible that the Class : Magnoliopsida active compounds can be used as an alternative Order : Theales drug which more effective and safer to common Family : drugs used today. Genus : Garcinia Garcinia dulcis or mundu is one of the Species : Garcinia dulcis (Roxb.) Kurz. medicinal plants that is believed by the people These plants have a height of about 10-13 to cure various diseases, such as ulcer and meters, the stem is brown or dark grey, and the wound infections,6 besides that it is traditionally branches are green. The leaves are green to dark also believed to treat struma, lymphangitis, green, ovoid, oval, rounded with a length of 10-30 and parotitis.7 cm and a width of 3-15 cm. Flowers are small seeds are known to have antibacterial and and dense with yellowish green or yellowish antioxidant activity, Scientifically,8,9 the thebarks flowers have and an white petals. The is slightly oval-shaped antimalarial effect,10 and the leaves and fruits round with a diameter of 5-8 cm, the surface are effective as antibacterial, antioxidant, and of the fruit is smooth green, and when ripe it anticholesterol.11–13 Its fruit extract is effective as an anti-cancer in liver cells,14 besides it can also reduce LDL levels and increase HDL cholesterol Thewill seedsbe yellow are brownto dark with yellow. a length The fruitof about flesh 2.5 is in mice,15 and can provide vasorelaxant effects in cm.slightly17,18 This fibrous plant but produces soft with one a sweet-sour period in a taste. year hypertensive rats.16 Indonesian people recognise in July-September,19 20 this plant with the name 'mundu' and include it from the garcinia family. This plant grows the stems shown in and Figure flowering 1. in April-May. in primary forests, lowland forests or on the The shape of the , leaves, fruit, flowers, and

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Figure 1. Morphology of Garcinia dulcis. (A) Tree, (B)

and seed appearance, (E) leaves, (F) freshly grown fruit,flowers and that (G) haven’t stem. (These bloomed images yet, are(C) authorbranch, collection (D) fruit pictures)

Phytochemical Compound Secondary metabolites contained in a plant was found, it is 16 compounds. Triterpenoid is are very numerous, as well as those found in onlyand flowers.found in oneEven compound, in its roots, that only is in xanthonethe leaves the plant G.dulcis. Based on table 1, 68 types of and stems. The most common compound group compounds reported have been successfully G. dulcis. These chromone and triterpenoids respectively. The subsectionis xanthones, below then will flavonoids, discuss eachbenzophenone, compound isolated and identified from and their structure based on the class of xanthones,compounds areand grouped triterpenoids. into five typesThe xanthone of groups, compounds we have categorised. groupthat is benzophenones,was the major compound chromones, in flavonoids, this plant with 46 compounds, followed by 16 compounds a) Benzophenone The type of benzophenone group obtained chromone and triterpenoid groups are three, from the plant is a benzophenone-isoprenylation, twoof the and flavonoid one compound group. While respectively. the benzophenone, Every where this compound belongs to the phenol part of the plant is known to contain various group. Benzophenone-isoprenylation is a kinds of compounds. Garcinia dulcis leaves compound that is widely distributed in Garcinia sp, including G. dulcis.21 There are three types of triterpenoids. The primary compound of its benzophenone-isoprenylation which have been contain flavonoids, chromones, xanthones and reported to be successfully isolated from this predominantly in the stem, roots, fruit, seeds, plant, namely garcinol (1), cambogin (2) and leaves is flavonoid, whereas xanthones are found

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xantochymol (3). These three compounds have d) Xanthone also been reported in other Garcinia genus.22–25 Xanthones are the most abundant group of Compounds 1 and 2 were isolated from the compounds found in Garcinia plants.31–33 The fruits while compound 3 was isolated from the xanthone compounds are also known to have 8,12 many biological activities, such as antioxidants, flowers.b) Flavonoid and antihyperlipid.34–37 In this review, there are Flavonoids are a type of secondary metabolite 46antimicrobials, types of xanthone anti-inflammatory, compounds whichanti-cancer have that is very common in all kinds of plants. Sixteen been reported to have been isolated from the plant and more than half of them are prenylated to have been successfully isolated from G.dulcis. xanthones. This is in accordance with a previous flavonoid compounds that have been reported study which stated that the primary type of xanthone compounds in the Guttiferae family Flavonoid compounds of 6 and 7 are flavon and (G. dulcis) is prenylated xanthones.34 compoundsflavan respectively, 15 - 17 compound are chalcon 8-9 istypes. isoflavone, More of these compounds are new xanthone that was compounds 4, 5, and 10-14 are biflavonoid, and found in this plant, namely dulciol A-E Twenty-five (22-26), dulcisxanthone A-L (39 - 50), and dulxanthone than half of the types of flavonoids found are inbiflavonoids. the family plantsAccording of Guttiferae to Iwashina (Clusiaceae), (2000), especiallybiflavonoid the is genusindeed Garcinia. most commonly26 Therefore found it is theirA-H (55 structure - 62). isChromatographic also related. Flavonoids profiles are of frequentlyxanthones foundare similar in plants. to that Meanwhile, of flavonoids xanthone and in Garcinia dulcis is obtained in a limited number of families.34 10reasonable - 14 obtained if biflavonoids from leaves, are while very compounds dominant 4 and 5 were obtained.biflavonoid from the compounds stems. There were are e) The triterpenoid Triterpenoid compounds that were obtained to be successfully isolated from the plants, from this plant are friedelin (68). This compound five new compounds that have been reported is not only present in G.dulcis plants but is isolated from the fruits,12 widely distributed in various other plants.38–40 (14)namely which dulcisflavan are isolated (7) andfrom dulcisisoflavon the leaves,27 and (8) Compound 68 was found in the stems and leaves Dulcisbiflavonoid A of G. dulcis.29,41 Friedelin has an antibacterial isolated from green stems or twigs.28 While other effect on Gram-positive bacteria. However, its Dulcisbiflavonoid B (15) and C (16) which are activity is not strong with a MIC value of more have been previously known. than 128 µg/mL.42 Friedelin also has antioxidant flavonoid compounds reported from this plant and liver protective effects,43 hypolipidemic c) Chromone effect,44 and anti-diarrheal activity.45 There are two types of chromone compounds which are reported to have been isolated from G.dulcis G.dulcis . The first is the dulcinone (20), a new 3,compound II-8) -chromon isolated (21) from obtained the flowers from the of leaves.29 Dulcinon[8], and the (20) other is is a the hydroxycromones Penta (Ome) flavonone type (I-of preventive effect of myocardial ischemia, and effectcromones of increasing that has melanin anti-inflammatory synthesis.30 effect,

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Table 1. Chemical compounds of Garcinia dulcis (Group, Structure, and Plant parts) Group Structure Compound name (code) Plant parts (sources) Benzophenone

Garcinol (1) Fruit12

Cambogin (2) Fruit12

Xanthochymol (3) Fruit8

Flavonoid

Biapigenin (4) Stem41

Stem,41 Flower8

Podocarpusflavone (5)

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Dulcinosida (6) Fruit12

Fruit12

Dulcisflavan (7)

Fruit12

Dulcisisoflavon (8)

Lupalbigenin (9) Fruit12

GB-2a (10) Leaves,27 Flower,8 Stem28

Leaves,27 Flower,8 Stem28

R=H : Volkensiflavon (11)

Leaves,27 Seed,9 Flower,8 Stem28

R=OH : Morelloflavon (12)

Leaves,27 Stem28

Amentoflavone (13)

Leaves27

Dulcisbiflavonoid A (14)

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Branch28

Dulcisbiflavonoid B (15)

Branch28

Dulcisbiflavonoid C (16)

R1=Me, R2 = H : Loureirin Seed9 A (17) R1=Me, R2=OMe : Seed9 Loureirin B (18) R1 dan R2=H : Loureirin Seed9 C (19) Chromone

Dulcinone (20) Flower8

Leaves29 II-8)-kromon (21) Penta (Ome) flavanon (I-3,

Xanthone

Biapigenin (4) Stem41

Stem41, Flower 8

Podocarpusflavone (5)

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Dulciol C (24) Root46

Dulciol D (25) Root46

Dulciol E (26) Root46

Garcigerrin A (27) Root bark10 , Stem bark47

Garciniaxanthone A (28) Root46

Garciniaxanthone B (29) Root46

Garciniaxanthone D (30) Root46

Globuxanthone (31) Root46

R1 = R2 =OH : Root46 Subelliptenone C (32) R2 = R1 =OH : Root46 Subelliptenone D (33)

Subelliptenone F (34) Root46

Toxyloxanthone B (35) Root bark46

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1,3,4,5,8-pentahydroxy Root bark46 xanthone (36)

1,4,5,7-tetrahydroxy-2- (1,1-dimetilalil) xanthone Root bark46 (37)

BR-xanthone (38) Fruit12 ,Flower8

Dulcisxanthone A (39) Fruit12

Dulcisxanthone B (40) Fruit12

Dulcisxanthone C (41) Flower8

Dulcisxanthone D (42) Flower8

Dulcisxanthone E (43) Flower8

Dulcisxanthone F (44) Flower8

Dulcisxanthone G (45) Seed9

Dulcisxanthone H (46) Branch48

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Dulcisxanthone I (47) Branch48

Dulcisxanthone J (48) Stem bark47

Dulcisxanthone K (49) Stem bark47

Dulcisxanthone L (50) Stem bark47

Garcinone B (51) Fruit12, Flower8

Garcinone D (52) Fruit12

Cowanin (53) Fruit12

Fruit12

Flower8 α - Mangostin (54) R1= R3=OH, R2=H Stem bark49 Dulxanthone A (55) R1 = R2=OH, R3 = H : Stem bark49 Dulxanthone B (56) R1=H, R2=OMe, R3 = Stem bark49 Dulxanthone C (57)

Dulxanthone D (58) Stem bark49

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R1=R3=OMe, R2=H : Leaves50,51 Dulxanthone E (59) R1=OH,R2=OMe,R3=H : Leaves50,51 Dulxanthone F (60) R1=OH, R2=R3=OMe : Leaves50,51 Dulxanthone G (61) R1=R3=OH, R2=H : Stem bark49 Ugaxanthone (63) R1=R2=OH, R3=H : Stem bark10 Symphoxanthone (64) R1=Ome,R2=OH,R3-H : 1-O-metylsympoxanthone Stem bark10 (65)

Euxanthone (66) Stem bark10, Seed9

Garciniaxanthone (67) Stem bark10

Triterpen

Friedelin (68) Stem41, Leaves29

Antibacterial Activity isolated compounds should be avoided, whereas According to Redulovic et al. (2013), the the presence of activity is exciting in the case of antibacterial activity of a plant extract that concentrations below 100 µg/ml for extracts and categorised of high potent if the Minimum 10 µg/ml for isolated compounds.52 Therefore we Inhibitory Concentration (MIC) value is less than here focus on discussing about compounds that 1000 µg/mL, while for plant isolates less than have antibacterial activity with MIC values less 100 µg/mL.3 On the other hand, Rios and Recio than 100 µg/mL. There are eleven compounds (2005) said that experiments with quantities from all compounds of G.dulcis in this review higher than 1 mg/ml for extracts or 0.1 mg/ml for which have strong antibacterial activity, namely

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garcinol (1), cambogin (2), xanthochymol (3), of bacteria such as S. aureus, Pseudomonas lupalbigenin (9) GB-2a (10), garcigerine A (27), aeruginosa, Salmonella typhimurium, Bacillus dulcisxanthone J (48), garcinon B (51), garcinon subtilis, Klebsiella sp., Proteus sp., and Escherichia coli.55 Also, the compound 54 is active against All of eleven compounds that have antibacterial Mycobacterium tuberculosis with MIC 6.25 µg activity,D (52), cowaninonly one type(53), is and really α-mangostin a new compound (54) . / mL,56 as well as against Vancomycin-Resistant produced from its bark, namely dulcisxanthone Enterococci (VRE) with the same MIC value.57 J (48),47 while the others are already known and found not only in G.dulcis. for the secondary metabolites of plants to Garcinol (1), cambogin (2), and xanthochymol killThere or inhibit are at bacterial least five growth, possible which mechanisms disrupt (3) compounds are benzophenone compounds the function and structure of bacterial cell which have antibacterial activity against membranes, interfere with the synthesis and Staphylococcus aureus and Methicilin Resistant function of DNA / RNA, disrupt cell metabolism, Staphylococcus aureus (MRSA) with MICs cause coagulation in the cell cytoplasm, and between 8-128 µg/mL.8,12 These three compounds interfere with intercellular communication.3 are prenylated benzophenone compounds which Benzophenone found in this plant are phenol have phenol groups, so this class of compounds compounds, where the antibacterial mechanism is also often categorized as phenol compounds. Compound 1 is also known to have antibacterial existing phenol groups. The mechanism that activity against MRSA bacteria with MIC 16 µg/ mightof this occurcompound is to isdamage strongly the influenced cell membrane by the mL, besides that it has also activities against permeability. Besides that, the phenol group Helicobacter pylori bacteria with higher activity is also known to inhibit protein synthesis, than clarithromycin antibiotics.53 inhibit ATP synthesis and interfere with cell Other compounds that have antibacterial metabolism.3 The hydroxyl groups in the phenol activity are lupalbigenin (9) and GB-2a (10), compound can also bind to proteins or other where both of these compounds belong to molecules, such as lipoteikoic acid, on the cell wall, causing damage to the bacterial cell wall.58 compound 9 against bacteria S. aureus and Flavonoids are known to increase the MRSAthe flavonoid is quite group. strong Antibacterial with MIC values activity 8 µg/ of permeability of bacterial cell membranes and mL,12 whereas compound 10 is weaker with interfere with bacterial DNA gyrase synthesis.3 MIC 128 µg/mL against S. aureus and 64 µg/mL against MRSA bacteria. From other studies, it is is known to interfere with DNA / RNA synthesis known that compound 9 isolated from plants ofCompound Vibrio Harvey 9 is an. 59isoflavonoid While santon compound compounds which Derris scandens has weak antibacterial activity against Bacillus subtilis, Bacillus sphaericus, and membranes by hydrophobic interactions with klebsiella aerugenes.54 membrane(α-mangostin) lipids canresulting cause in diffusion damage of to water cell The compounds group of xanthones which passing through the membrane and causing strong antibacterial activity are Garcigerin A (27), membrane deformation and ultimately bacterial dulcisxanthone J (48), garcinon B (51), garcinon death.58,60

Compounds 27 and 52 are the two compounds Conclusion thatD (52), have cowanin the strongest (53), and antibacterial α- mangostin activity (54). A total of 68 types of compounds that have against S.aureus and MRSA compared to the other compounds in this plant. The MIC value on various literature that we reviewed from this of these two compounds is 4 µg / mL.12,47 The reviewbeen successfully illustrate isolatedthat the andcompound identified content based in G.dulcis varies greatly. The benzophenones, antibacterial activity against various types α-mangostin (54) are known to have extensive flavonoids and xanthones show antibacterial

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activity with varying strengths. The presence tibacterial testing of medicinal plants used of phenol groups in each compound plays an by the Bulu and inland Kaulong of Papua important role in its activity as an antibacterial, New Guinea. J Ethnopharmacol 2012; 139: but the structural differences greatly affect its 497–503. activity. There are eleven compounds that have 7. Kasahara S, Henmi S. Medicine Herb Index the potential to be used as antibacterial agents for in Indonesia. In: Eisai Indonesia. Jakarta, the treatment of infectious diseases. Garcigerin A 1986, p. 92. 8. Deachathai S, Mahabusarakam W, Phong- have the most potent activity against S.aureus paichit S, et al. Phenolic compounds from and(27) MRSAand α-mangostin compared to(54) the are other compounds compounds, that - istry 2006; 67: 464–469. but it is possible to have different effects when 9. Deachathaithe flowers ofS, Garcinia Phongpaichit dulcis. Phytochem S, Ma- used clinically, therefore further research on the habusarakam W. Phenolic compounds from active compounds of this plant, especially as an the seeds of Garcinia dulcis. Nat Prod Res 2008; 22: 1327–1332. needs to be carried out continuously. 10. Likhitwitayawuid K, Chanmahasathien W, antibacterial agent to fight infectious diseases, Ruangrungsi N, et al. Xanthones with anti- CONFLICT OF INTEREST malarial activity from Garcinia dulcis. Plan- The authors declare that there are no potential ta Med 1998; 64: 281–282. 11. Tuansulong K, Hutadilok-towatana N, Ma-

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