RSS-Feed abonnieren
DOI: 10.1055/a-0828-9831
Cytotoxic Prenylated Xanthones from the Leaves of Garcinia bracteata
Publikationsverlauf
received 28. Juni 2018
revised 23. Dezember 2018
accepted 27. Dezember 2018
Publikationsdatum:
16. Januar 2019 (online)
![](https://www.thieme-connect.de/media/plantamedica/201906/lookinside/thumbnails/10-1055-a-0828-9831_pmc0509-1.jpg)
Abstract
Six new prenylated xanthones (1–6) and seventeen known xanthones were isolated from extracts of Garcinia bracteata leaves. Their structures were determined by extensive NMR and MS spectroscopic data analysis. The inhibitory activities of the isolates were assayed on HeLa, A549, PC-3, HT-29, and WPMY-1 cell lines. Compounds 1 and 15–17 showed moderate inhibitory effects on tumor cell growth, with IC50s ranging from 3.7 to 14.7 µM.
* These two authors contributed equally to this work.
Supporting Information
- Supporting Information I
- Supporting Information II
HRMS, UV, IR, and NMR spectra of compounds 1–6 are available as Supporting Information I, and the dose-response curves of compounds in [Table 3] are available as Supporting Information II.
-
References
- 1 Li X, Li J, Stevens PF. Garcinia Linnaeus. In: Wu Z, Raven P, Zhang L. eds. Flora of China, Illustrations Volume 13, Clusiaceae through Araliaceae. St. Louis: Missouri Botanical Garden Press; 2008: 40-47
- 2 Hemshekhar M, Sunitha K, Santhosh MS, Devaraja S, Kemparaju K, Vishwanath BS, Niranjana SR, Girish KS. An overview on genus Garcinia: phytochemical and therapeutical aspects. Phytochem Rev 2011; 10: 325-351
- 3 Anantachoke N, Tuchinda P, Kuhakarn C, Pohmakotr M, Reutrakul V. Prenylated caged xanthones: chemistry and biology. Pharm Biol 2012; 50: 78-91
- 4 Negi JS, Bisht VK, Singh P, Rawat MSM, Joshi GP. Naturally occurring xanthones: chemistry and biology. J App Chem 2013; 2013: 621459
- 5 Wu SB, Long C, Kennelly EJ. Structural diversity and bioactivities of natural benzophenones. Nat Prod Rep 2014; 31: 1158-1174
- 6 Li P, Yue GGL, Kwok HF, Long CL, Lau CBS, Kennelly EJ. Using ultra-performance liquid chromatography quadrupole time of flight mass spectrometry-based chemometrics for the identification of anti-angiogenic biflavonoids from edible Garcinia species. J Agric Food Chem 2017; 65: 8348-8355
- 7 Xia ZX, Zhang DD, Liang S, Lao YZ, Zhang H, Tan HS, Chen SL, Wang XH, Xu HX. Bioassay-guided isolation of prenylated xanthones and polycyclic acylphloroglucinols from the leaves of Garcinia nujiangensis . J Nat Prod 2012; 75: 1459-1464
- 8 Zhang H, Zhang DD, Lao YZ, Fu WW, Liang S, Yuan QH, Yang L, Xu HX. Cytotoxic and anti-inflammatory prenylated benzoylphloroglucinols and xanthones from the twigs of Garcinia esculenta . J Nat Prod 2014; 77: 1700-1707
- 9 Fu W, Wu M, Zhu L, Lao Y, Wang L, Tan H, Yuan Q, Xu H. Prenylated benzoylphloroglucinols and biphenyl derivatives from the leaves of Garcinia multiflora Champ. RSC Adv 2015; 5: 78259-78267
- 10 Tang YX, Fu WW, Wu R, Tan HS, Shen ZW, Xu HX. Bioassay-guided isolation of prenylated xanthone derivatives from the leaves of Garcinia oligantha . J Nat Prod 2016; 79: 1752-1761
- 11 Xu D, Lao Y, Xu N, Hu H, Fu W, Tan H, Gu Y, Song Z, Cao P, Xu H. Identification and characterization of anticancer compounds targeting apoptosis and autophagy from Chinese native Garcinia species. Planta Med 2015; 81: 79-89
- 12 Thoison O, Fahy J, Dumontet V, Chiaroni A, Riche C, Tri MV, Sevenet T. Cytotoxic prenylxanthones from Garcinia bracteata . J Nat Prod 2000; 63: 441-446
- 13 Niu SL, Li DH, Li XY, Wang YT, Li SG, Bai J, Pei YH, Jing YK, Li ZL, Hua HM. Bioassay- and chemistry-guided isolation of scalemic caged prenylxanthones from the leaves of Garcinia bracteata . J Nat Prod 2018; 81: 749-757
- 14 Niu SL, Li ZL, Ji F, Liu GY, Zhao N, Liu XQ, Jing YK, Hua HM. Xanthones from the stem bark of Garcinia bracteata with growth inhibitory effects against HL-60 cells. Phytochemistry 2012; 77: 280-286
- 15 Yang Y, Li L, Lou J. Isoprenylated flavones from Garcinia bracteata and their anti-tobacco mosaic virus activity. Heterocycles 2015; 91: 375-380
- 16 Li Y, Wang Z, Wu X, Yang Y, Qin Y, Xia C, Meng Y, Li M, Gao XM, Hu Q. Biphenyl derivatives from the twigs of Garcinia bracteata and their biological activities. Phytochem Lett 2015; 11: 24-27
- 17 Niu SL, Li DH, Wang YT, Wang KB, Lin B, Jing YK, Hua HM, Bai J, Li ZL. Neobraclactones A–C, three unprecedented chaise longue-shaped xanthones from Garcinia bracteata . Org Biomol Chem 2017; 15: 4901-4906
- 18 Nkengfack AE, Azebaze GA, Vardamides JC, Fomum ZT, van Heerden FR. A prenylated xanthone from Allanblackia floribunda . Phytochemistry 2002; 60: 381-384
- 19 Bayma JC, Arruda MSP, Neto MS. A prenylated xanthone from the bark of symphonia globulifera . Phytochemistry 1998; 49: 1159-1160
- 20 Nomura T, Hano Y, Okamoto T, Suzuki K, Negishi M. Components of the root bark of Morus insignis Bur. 3. structures of three new isoprenylated xanthones morusignins I, J, and K and an isoprenylated flavone morusignin L. Heterocycles 1993; 36: 1359-1366
- 21 Ghazali SAISM, Lian GEC, Ghani KDA. Chemical constituent from roots of Garcinia mangostana (Linn.). Int J Chem 2010; 2: 134-142
- 22 Zhang X, Li X, Ye S, Zhang Y, Tao L, Gao Y, Gong D, Xi M, Meng H, Zhang M, Gao W, Xu X, Guo Q, You Q. Synthesis, SAR and biological evaluation of natural and non-natural hydroxylated and prenylated xanthones as antitumor agents. Med Chem 2012; 8: 1012-1025
- 23 Nguyen LH, Venkatraman G, Sim KY, Harrison LJ. Xanthones and benzophenones from Garcinia griffithii and Garcinia mangostana . Phytochemistry 2005; 66: 1718-1723
- 24 Hou A, Fukai T, Shimazaki M, Sakagami H, Sun H, Nomura T. Benzophenones and xanthones with isoprenoid groups from Cudrania cochinchinensis . J Nat Prod 2001; 64: 65-70
- 25 Shen YC, Wang LT, Khalil AT, Chiang LC, Cheng PW. Bioactive pyranoxanthones from the roots of Calophyllum blancoi . Chem Pharm Bull 2005; 53: 244-247
- 26 Botta B, Delle Monache G, Delle Monache F, Bettolo GBM, Menichini F. Vismione H and prenylated xanthones from Vismia guineensis . Phytochemistry 1986; 25: 1217-1219
- 27 Chang CH, Lin CC, Kawata Y, Hattori M, Namba T. Prenylated xanthones from Cudrania cochinchinensis . Phytochemistry 1989; 28: 2823-2826
- 28 Ito C, Miyamoto Y, Nakayama M, Kawai Y, Koyyalamudi S, Furukawa H. A novel depsidone and some new xanthones from Garcinia species. Chem Pharm Bull 1997; 45: 1403-1413
- 29 Wang R, Chen R, Li J, Liu X, Xie K, Chen D, Peng Y, Dai J. Regiospecific prenylation of hydroxyxanthones by a plant flavonoid prenyltransferase. J Nat Prod 2016; 79: 2143-2147
- 30 Otsuka H. Triptexanthosides A–E: xanthone glycosides from aerial parts of Tripterospermum japonicum . Chem Pharm Bull 1999; 47: 962-965
- 31 Oger JM, Morel C, Helesbeux JJ, Litaudon M, Séraphin D, Dartiguelongue C, Larcher G, Richomme P, Duval O. First 2-hydroxy-3-methylbut-3-enyl substituted xanthones isolated from plants: structure elucidation, synthesis and antifungal activity. Nat Prod Res 2003; 17: 195-199
- 32 Helesbeux JJ, Duval O, Dartiguelongue C, Séraphin D, Oger JM, Richomme P. Synthesis of 2-hydroxy-3-methylbut-3-enyl substituted coumarins and xanthones as natural products. Application of the Schenck ene reaction of singlet oxygen with ortho-prenylphenol precursors. Tetrahedron 2004; 60: 2293-2300
- 33 Sia GL, Bennett GJ, Harrison LJ, Sim KY. Minor xanthones from the bark of cratoxylum cochinchinense . Phytochemistry 1995; 38: 1521-1528
- 34 Jin SL, Wang NL, Zhang X, Dai Y, Yao XS. A new xanthone from Cratoxylum cochinchinense . Chinese Trad Herb Drugs 2009; 40: 341-344
- 35 Johnson OO, Zhao M, Gunn J, Santarsiero BD, Yin ZQ, Ayoola GA, Coker HA, Che CT. alpha-Glucosidase inhibitory prenylated anthranols from Harungana madagascariensis . J Nat Prod 2016; 79: 224-229
- 36 Costes N, Michel S, Tillequin F, Koch M, Pierré A, Atassi G. Chiral dihydroxylation of acronycine: absolute configuration of natural cis-1,2-dihydroxy-1,2-dihydroacronycine and cytotoxicity of (1R,2R)- and (1S,2S)-1,2-diacetoxy-1,2-dihydroacronycine. J Nat Prod 1999; 62: 490-492
- 37 Ren Y, Matthew S, Lantvit DD, Ninh TN, Chai H, Fuchs JR, Soejarto DD, de Blanco EJ, Swanson SM, Kinghorn AD. Cytotoxic and NF-kappa B inhibitory constituents of the stems of Cratoxylum cochinchinense and their semisynthetic analogues. J Nat Prod 2011; 74: 1117-1125
- 38 Iinuma M, Tosa H, Toriyama N, Tanaka T, Ito T, Chelladurai V. Six xanthones from Calophyllum austroindicum . Phytochemistry 1996; 43: 681-685
- 39 Chin YW, Jung HA, Chai H, Keller WJ, Kinghorn AD. Xanthones with quinone reductase-inducing activity from the fruits of Garcinia mangostana (Mangosteen). Phytochemistry 2008; 69: 754-758
- 40 Ha LD, Hansen PE, Vang O, Duus F, Pham HD, Nguyen LH. Cytotoxic geranylated xanthones and O-alkylated derivatives of alpha-mangostin. Chem Pharm Bull 2009; 57: 830-834
- 41 Kaennakam S, Siripong P, Tip-Pyang S. Kaennacowanols A–C, three new xanthones and their cytotoxicity from the roots of Garcinia cowa . Fitoterapia 2015; 102: 171-176
- 42 Ruan J, Zheng C, Liu Y, Qu L, Yu H, Han L, Zhang Y, Wang T. Chemical and biological research on herbal medicines rich in xanthones. Molecules 2017; 22: 1698