Phytochemical investigation of Garcinia propinqua roots led to the isolation and identification of a new xanthone, doitunggarcinone D (1), together with 15 known compounds (2–16). Their structures were elucidated by intensive analysis of spectroscopic data. Compounds 3, 6, 7, 14, 15 and 16 exhibited strong antibacterial activity against Bacillus subtilis TISTR 088 with MIC values in the range of 1–4 μg/mL. Compounds 3, 7, 10 and 14 also showed good antibacterial activity against B. cereus TISTR 688 with MIC values ranging from 4–8 μg/mL.
MahamodoS, RivièreC, NeutC, AbediniA, RanariveloH, DuhalN, RoumyV, HennebelleT, SahpazS, LemoineA, RazafimahefaD, RazanamahefaB, BailleulF, AndriamihajaB. (2014) Antimicrobial prenylated benzoylphloroglucinol derivatives and xanthones from the leaves of Garcinia goudotiana. Phytochemistry, 102, 162–168;
2.
MohamedGA, IbrahimSRM, ShaabanMIA, RossSA. (2014) Mangostanaxanthones I and II, new xanthones from the pericarp of Garcinia mangostana. Fitoterapia, 98, 215–221;
3.
KomguemJ, LannangAM, TangmouoJG, LouhGN, NgounouFN, LontsiD, ChoudharyMI, SondengamBL. (2006) Polyanxanthone, a xanthone from the stem bark of Garcinia polyantha. Natural Product Communications, 1, 363–365;
4.
FuM, QiuSX, XuY, WuJ, ChenY, YuY, XiaoG. (2013) A new xanthone from the pericarp of Garcinia mangostana. Natural Product Communications, 8, 1733–1734.
5.
KhalidRM, JabitML, AbasF, StanslasJ, ShaariK, LajisNH. (2007) Cytotoxic xanthones from the leaves of Garcinia urophylla. Natural Product Communications, 2, 271–276;
6.
JiF, LiZ, LiuG, NiuS, ZhaoN, LiuX, HuaH. (2012) Xanthones with antiproliferative effects on prostate cancer cells from the stem bark of Garcinia xanthochymus. Natural Product Communications, 7, 53–56.
7.
TantapakulC, PhakhodeeW, RitthiwigromT, CheenprachaS, PrawatU, DeachathaiS, LaphookhieoS. (2012) Rearranged benzophenones and prenylated xanthones from Garcinia propinqua twigs. Journal of Natural Products, 75, 1660–1664;
8.
TrinhDH, HaLD, TranPT, NguyenLHD. (2014) Isoprenylated xanthone and benzophenone constituents of the pericarp of Garcinia planchonii. Natural Product Communications, 9, 1737–1740.
9.
TrisuwanK, RukachaisirikulV, PhongpaichitS, Hutadilok-TowatanaN. (2013) Tetraoxygenated xanthones and biflavanoids from the twigs of Garcinia merguensis. Phytochemistry Letters, 6, 511–513;
10.
KaikaboAA, SamuelBB, EloffJN. (2009) Isolation and activity of two antibacterial biflavonoids from leaf extracts of Garcinia livingstonei (Clusiaceae), Natural Product Communications, 4, 1363–1366.
11.
JamilaN, KhairuddeanM, YaacobNS, KamalNNSNM, OsmanH, KhanSN, KhanN. (2014) Cytotoxic benzophenone and triterpene from Garcinia hombroniana. Bioorganic Chemistry, 54, 60–67.
12.
SriyatepT, ManeeratW, SripisutT, CheenprachaS, MachanT, PhakhodeeW, LaphookhieoS. (2014) Cowabenzophenones A and B, two new tetracyclo[7.3.3.33,11.03,7]tetradecane-2,12,14-trione derivatives, from ripe fruits of Garcinia cowa. Fitoterapia, 92, 285–289.
13.
BabuV, AliSM, SultanaS, IlyasM. (1988) A biflavonoid from Garcinia nervosa. Phytochemistry, 27, 3332–3335;
14.
Al-ShagdariA, AlarcónAB, Cuesta-RubioO, PiccinelliAL, RastrelliL. (2013) Biflavonoids, main constituents from Garcinia bakeriana leaves. Natural Product Communications, 8, 1237–1240;
15.
NgoupayoJ, NoungoueDT, LentaBN, TabopdaTK, KhanSN, NgouelaS, ShaiqMA, TsamoE. (2007) Brevipsidone, a new depsidone and other α-glucosidase inhibitors from Garcinia brevipedicellata (Clusiaceae). Natural Product Communications, 2, 1141–1144;
16.
ItoC, MatsuiT, NodaE, RuangrungsiN, ItoigawaM. (2013) Biphenyl derivatives from Garcinia schom burgkiana and the cytotoxicity of the isolated compounds. Natural Product Communications, 8, 1265–1267.
17.
GunatilakaAAL, De SilvaAMYJ, SotheeswaranS, BalasubramaniamS, WazeerMIM. (1984) Terpenoid and biflavonoid constituents of Calophyllum calaba and Garcinia spicata from Sri Lanka. Phytochemistry, 23, 323–328.
18.
BunyongR, ChaijaroenkulW, PlengsuriyakarnT, Na-BangchangK. (2014) Antimalarial activity and toxicity of Garcinia mangostana Linn. Asian Pacific Journal of Tropical Medicine, 7, 693–698;
LinKW, HuangAM, YangSC, WengJR, HourTC, PuYS, LinCN. (2012) Cytotoxic and antioxidant constituents from Garcinia subelliptica. Food Chemistry, 135, 851–859.
21.
ItoC, MiyamotoY, NakayamaM, KawaiY, RaoKS, FurukawaH. (1997) A novel depsidone and some new xanthones from Garcinia species. Chemical and Pharmaceutical Bulletin, 45, 1403–1413.
22.
NguyenL-HD, VoHT, PhamHD, ConnollyJD, HarrisonLJ. (2003) Xanthones from the bark of Garcinia merguensis. Phytochemistry, 63, 467–470.
23.
BottaB, Delle MonacheG, Delle MonacheF, BettoloGBM, MenichiniF. (1986) Vismione H and prenylated xanthones from Vismia guineensis. Phytochemistry, 25, 1217–1219.
24.
YangNY, HanQB, CaoXW, QiaoCF, SongJZ, ChenSL, YangDJ, YiuH, XuHX. (2007) Two new xanthones isolated from the stem bark of Garcinia lancilimba. Chemical and Pharmaceutical Bulletin, 55, 950–952.
25.
GunasekeraSP, SelliahS, SultanbawaMUS. (1975) Chemical investigation of Ceylonese plants. Part XV. Extractives of Kayea stylosa Thw. (Guttiferae). Journal of the Chemical Society, Perkin Transactions 1, 1539–1544.
26.
WolfromML, KomitskyFJr., FraenkelG, LookerJH, DickeyEE, McWainP, ThompsonA, MundellPM, WindrathOM. (1963) Macluraxanthone and two accompanying pigments from the root bark of the osage orange. Tetrahedron Letters, 4, 749–755.
27.
HouA-J, FukaiT, ShimazakiM, SakagamiH, SunH-D, NomuraT. (2000) Benzophenones and xanthones with isoprenoid groups from Cudrania cochinchinensis. Journal of Natural Products, 64, 65–70.
28.
ThoisonO, CuongDD, GramainA, ChiaroniA, HungNV, SévenetT. (2005) Further rearranged prenylxanthones and benzophenones from Garcinia bracteata. Tetrahedron, 61, 8529–8535.
29.
SomanathanR, SultanbawaMUS. (1974) Chemical investigation of Ceylonese plants. Part VIII. Trapezifolixanthone, a new di-isoprenylated xanthone from the bark of Calophyllum trapezifolium Thw. (Guttiferae). Journal of the Chemical Society, Perkin Transactions 1, 2515–2517.
30.
HanoY, MatsumotoY, ShinoharaK, SunJY, NomuraT. (1991) Structures of four new isoprenylated xanthones, cudraxanthones L, M, N, and O from Cudrania tricuspidata. Planta Medica, 57, 172–175.
31.
FinneganRA, PatelJK, BachmanPL. (1966) Constituents of Mammea americana L. V. Some simple mono- and dihydroxyxanthones. Tetrahedron Letters, 7, 6087–6092.
32.
HayAE, GuiletD, MorelC, LarcherG, MacherelD, Le RayAM, LitaudonM, RichommeP. (2003) Antifungal chromans inhibiting the mitochondrial respiratory chain of pea seeds and new xanthones from Calophyllum caledonicum. Planta Medica, 69, 1130–1135.
33.
ThoisonO, FahyJ, DumontetV, ChiaroniA, RicheC, TriMV, SevenetT. (2000) Cytotoxic prenylxanthones from Garcinia bracteata. Journal of Natural Products, 63, 441–446.
34.
TisdaleEJ, SlobodovI, TheodorakisEA. (2003) Biomimetic total synthesis of forbesione and desoxymorellin utilizing a tandem Claisen/Diels–Alder/Claisen rearrangement. Organic and Biomolecular Chemistry, 1, 4418–4422.
35.
NaZ, HuHB, FanQF. (2010) Three new caged prenylxanthones from Garcinia bracteata. Helvetica Chimica Acta, 93, 958–963.
36.
HenryGE, JacobsH, McLeanS, ReynoldsWF, YangJ-P. (1995) Xerophenones A and B. new isoprenylated derivatives of 11-oxatricyclo[4.3.1.14,10]undecane-7,9-dione from Clusia portlandiana (Guttiferae). Tetrahedron Letters, 36, 4575–4578.
37.
CLSI. (2012) Reference method for dilution antimicrobial susceptibility test for bacteria that grow aerobically; approved standard M07-A9. Clinical and Laboratory Standards Institute; Wayne, PA, USA.
38.
LeeDS, LeeSH. (2001) Genistein, a soy isoflavone, is a potent alpha–glucosidase inhibitor. FEBS Leters, 501, 84–86.
39.
LiGL, HeJY, ZhangA, WanY, WangB, ChenWH. (2011) Toward potent alpha-glucosidase inhibitors based on xanthones: a closer look into the structure-activity correlations. European Journal of Medicinal Chemistry, 46, 4050–4055.
40.
LiuY, LiX, LinG, XiangZ, XiangJ, ZhaoM, ChenJ, YangZ. (2008) Synthesis of catechins via thiourea/AuCl3-catalyzed cycloalkylation of aryl epoxides. Journal of Organic Chemistry, 73, 4625–4629.
41.
LiuY, ZouL, MaL, ChenWH, WangB, XuZL. (2006) Synthesis and pharmacological activities of xanthone derivatives as alpha-glucosidase inhibitors. Bioorganic and Medicinal Chemistry, 14, 5683–5690.
42.
RyuHW, ChoJK, Curtis-LongMJ, YukHJ, KimYS, JungS, KimYS, LeeBW, ParkKH. (2011) alpha-Glucosidase inhibition and antihyperglycemic activity of prenylated xanthones from Garcinia mangostana. Phytochemistry, 72, 2148–2154.
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