Two new prenylated flavonoids, 4′,5-dihydroxy-6,7-(2,2-dimethylpyrano)-2′-methoxy-8-γ,γ-dimethylallylflavone 1 and 3′-hydroxycycloartocarpin 2 along with six known flavonoids, 5,7-dihydroxy-4′-methoxy-8-prenylflavanone 3, isobavachalcone 4, pyranocycloartobiloxanthone A 5, artocarpin 6, chaplashin 7 and cycloartocarpin 8 were isolated for the first time from the leaves and the heartwoods of Artocarpus anisophyllus Miq. The structures of isolated flavonoids were elucidated spectroscopically using 1D and 2D NMR, FTIR, MS, UV and also by comparison with literature data. These flavonoids were screened for their antioxidant and tyrosinase inhibitory activities. The dichloromethane and ethyl acetate crude extracts together with 3′-hydroxycycloartocarpin 2, pyranocycloartobiloxanthone A 5 and artocarpin 6 showed DPPH (2,2-diphenyl-1-picrylhydrazyl) radical scavenging activity with SC50 values of 80.2, 40.0, 152.9, 20.2 and 140.0 μg/mL in 30 min, respectively. Pyranocycloartobiloxanthone A 5 exhibited significant tyrosinase inhibitory activity against tyrosinase from mushroom with IC50 values of 60.5 μg/mL.
LimTK. (2012) Edible Medicinal and Non- Medicinal Plants: Fruits, Volume 3, Springer Science+ Business Media B.V., 301–303.
2.
RamliF, RahmaniM, KassimNKHashimNMSukariMAAkimA.Md GoR. (2013) New diprenylated dihydrochalcones from leaves of Artocarpus elasticus. Phytochemistry Letters, 6, 582–585
3.
JamilS, TaherM, SiratHMOthmanNA. (2012) Flavonoids and triterpenes from the leaves of Artocarpus fulvicortex. Natural Product Communications7, 1587–1588
4.
LanWCTzengCWLinCCYenFLKoHH. (2013) Prenylated flavonoids from Artocarpus altilis: Antioxidant activities and inhibitory effects on melanin production. Phytochemistry, 89, 78–88
5.
RenG, XiangHYHuZCLiuRHZhouZWHuangHLShaoF, YangM. (2013) A new isoprenylated flavone from the root bark of Artocarpus styracifolius. Biochemical Systematics and Ecology, 46, 97–100
6.
HashimNMRahmaniM, SukariMAAliAMAlitheenN, GoR, IsmailHBM. (2010) Two new xanthones from Artocarpus obtusus. Journal of Asian Natural Product Research, 12, 106–112
7.
ManeechaiS, De-EknamkulW, UmeharaK, NoguchiH, LikhitwitayawuidK. (2012) Flavonoid and Stilbenoid production in callus cultures of Artocarpus lakoocha. Phytochemistry, 81, 42–49.
8.
HashimNMRahmaniM, EeGCL, SukariMAYahayuM, AminMAM, AliAMGoR. (2012) Antioxidant, antimicrobial and tyrosinase inhibitory activities of xanthones isolated from Artocarpus obtusus F. M. Jarrett. Molecules, 17, 6071–6082
9.
ManuelNGV, OsvaldoSSD, AlejandraRFT, RodolfoAVLucilaAL. (2012) Antimicrobial activity of artocarpesin from Artocarpus heterophyllus Lam. against Methicillin-resistant Staphylococcus aureus (MRSA). Journal of Medicinal Plants Research, 6, 4879–4882
10.
ArungETYoshikawaK, ShimizuK, KondoR. (2010) Isoprenoid-substituted flavonoids from wood of Artocarpus heterophyllus on B16 melanoma cells: Cytotoxic and structural criteria. Fitoterapia, 81, 120–123.
11.
MarkhamKR. (1982) Techniques of Flavonoid Identification. London: Academic Press Inc.36–49
12.
SoekamtoNHAchmadSAGhisalbertiELHakimEHSyahYM. (2004) Prenylated flavones from Artocarpus fretessi Hassk endemic to South Sulawesi. Marina Chimica Acta, 5, 23–28
ParsonsICGrayAIWatermanPG. (1993) New triterpenes and flavonoids from the leaves of Bosistoa brasii. Journal of Natural Products, 56, 46–53
15.
AuziAAHartleyTGWatermanPG. (1997) Distribution of flavonoids, alkaloids, acetophenones and phloroglucinols in the genus Bosistoa (Rutaceae). Biochemical Systematics and Ecology, 25, 611–617
16.
JamilS, SiratHMJantanI, AimiN, KitajimaM. (2008) A new prenylated dihydrochalcone from the leaves of Artocarpus lowii. Journal of Natural Medicine, 62, 321–324
17.
ArungETShimizuK and KondoR. (2006) Inhibitory effect of isoprenoid substituted flavonoids isolated from Artocarpus heterophyllus on melanin biosynthesis. Planta Medica, 72, 847–850
18.
YongHWAiJHLeiC, DaoFCHanDSQinSZBastowKF., NakanishY, XiHWKuoHL. (2004) New isoprenylated flavones, Artochamins A-E and cytotoxic principle from Artocarpus chama. Journal of Natural Products, 67, 757–761
19.
RaoAVRama RathiSSVentakaramanK. (1972) Chaplashin, a flavone containing an oxepine ring from the heartwood of Artocarpus chaplasha. Indian Journal of Chemistry, 10, 905–907
20.
HakimHEAfridaEliza, AchmadSAAimiN, KitajimaM, MakmurL, MujahidinD, SyahYMTakayamaH. (2000) Artoindonesianin D: A new bioactive pyranoflavone derivative and chaplashin from Artocarpus maingayi. ITB Journal, 32, 13–19
21.
RadhakrishnanPVRama RaoAV and VenkataramanK. (1965) Two new flavones from Artocarpus heterophyllus. Tetrahedron Letters, 11, 663–667
22.
BoonphongS, BarameeA, KittakoopP, PuangsombatP. (2007) Antitubercular and antiplasmodial prenylated flavones from the roots of Artocarpus altilis. Chiang Mai Journal of Science, 34, 339–344.
23.
TagashiraM, OhtakeY. (1998) A new antioxidative 1,3-benzodioxole from Melissa officinalis. Planta Medica, 64, 555–558
24.
FengNKZhiJCChunNLCheMT. (1998) Scavenger and antioxidant properties of prenylflavones isolated from Artocarpus heterophyllus. Free Radical Biology and Medicine, 25, 160–168
25.
BatubaraI, DarusmanLKMitsunagaT, RahminiatiM, DjauhariE. (2010) Potency of Indonesian medicinal plants as tyrosinase inhibitor and antioxidant agent. Journal of Biological Sciences, 10, 138–144
26.
ShimizuK, KondoR, SakaiK. (1999) Inhibition of tyrosinase by flavonoids, stilbenes and related 4-substituted resorcinols: structure activity investigations. Planta Medica, 66, 11–15.
