Flavanones are one of the most interesting naturally occurring flavonoids in view of their structural pattern as well as biological and pharmacological potentials. The present review deals with natural flavanones reported from 1998 to mid 2007, along with their biological and pharmacological activities. The review includes more than 160 new naturally occurring flavanones from 135 references. The reported flavonoids belong to thirty-six plant families.
ReddyMK, ReddyMVB, JayakrishnaG, GunasekarD, CauxC, BodoB. (2003) Two new flavonoids from Andrographis rothii. Chemical and Pharmaceutical Bulletin, 51, 191–193.
5.
AhmedE, ImranM, MalikA, AshrafM. (2006) Antioxidant activity with flavonoidal constituents from Aerva perisca. Archives of Pharmacal Research, 29, 343–347.
6.
AhmedMS, GalalAM, RossSA, FerreiraD, ElsohlyMA, IbrahimA-RS, MossaJS, El-FeralyFS. (2001) A weakly antimalarial biflavanone from Rhus retinorrhoea. Phytochemistry, 58, 599–602.
7.
WangS, ZhangPC, ChenRY, WangYH, HeWY, YuDQ. (2002), A Novel Dihydroflavone from the Roots of Uvaria macrophylla. Chinese Chemical Letters, 13, 857–858.
8.
ZhangH, WangS, ChengR, YuD. (2002) Studies on chemical constituents of Uvaria macrophylla. Yaoxue Xuebao, 37, 124–127.
9.
TewtrakulS, NakamuraN, HattoriM, FujiwaraT, SupavitaT. (2002) Flavanone and flavonol glycosides from the leaves of Thevetia peruviana and their HIV-1 reverse transcriptase and HIV-1 integrase inhibitory activities. Chemical and Pharmaceutical Bulletin, 50, 630–635.
10.
ZhangSX, TaniT, YamajiS, MaCM, WangMC, CaiSQ, ZhaoYY. (2003) Glycosyl flavonoids from the roots and rhizomes of Asarum longerhizomatosum. Journal of Asian Natural Products Research, 5, 25–30.
11.
FlaggML, WachterGA, DavisAL, MontenegroG, TimmermannBN. (2000) Two Novel Flavanones from Greigia sphacelata. Journal of Natural Products, 63, 1689–1691.
12.
EmamAM, EliasR, MoussaAM, FaureR, DebrauwerL, BalansardG. (1998) Two flavonoid triglycosides from Buddleja madagascariensis. Phytochemistry, 48, 739–742.
13.
AliMS, AhmedF, PervezMK, AzharI, IbrahimSA. (2005) Parkintin: A new flavanone with epoxy-isopentyl moiety from Parkinsonia aculeata Linn. (Caesalpiniaceae). Natural Product Research, 19, 53–56.
14.
DengY, LeeJP, RamamonjyMT, SnyderJK, Des EtagesSA, KanadaD, SnyderR, TurnerCJ. (2000) New antimicrobial flavanones from Physena madagascariensis. Journal of Natural Products, 63, 1082–1089.
15.
BracaA, BiliaAR, MendezJ, MorelliI. (1999) Three flavonoids from Licania densiflora. Phytochemistry, 51, 1125–1128.
16.
SrivastavaSK, SrivastavaSD, ChoukseyBK. (1999) New constituents of Terminalia alata. Fitoterapia, 70, 390–394.
17.
SrivastavaSK, SrivastavaSD. (2004) New biologically active constituents from Terminalia chebula stem bark. Indian Journal of Chemistry, 43B, 2731–1733.
18.
ChanphenR, ThebtaranonthY, WanauppathamkulS, YuthavongY. (1998) Antimalarial principles from Artemisia indica. Journal of Natural Products, 61, 1146–1147.
19.
LiS, KuangHX, OkadaY, OkuyamaT. (2005) New flavanone and chalcone glucosides from Bidens bipinnata Linn. Journal of Asian Natural Products Research, 7, 67–70.
20.
MatsudaH, MorikawaT, ToguchidaI, HarimaS, YoshikawaM. (2002) Medicinal Flowers. VI. Absolute Stereostructures of Two New Flavanone Glycosides and a Phenylbutanoid Glycoside from the Flowers of Chrysanthemum indicum L.: Their Inhibitory Activities for Rat Lens Aldose Reductase. Chemical and Pharmaceutical Bulletin, 50, 972–975.
21.
YadavaRN, SinghSK. (2006) New anti-inflammatory active flavanone glycoside from the Echinops echinatus Roxb. Indian Journal of Chemistry, 45B, 1004–1008.
22.
de CarvalhoMG, de CostaFM, Dos Santos AbrenH. (1999), Flavanones from Vernonia diffusa. Journal of Brazilian Chemical Society, 10, 163–166.
23.
CalanasanCA, MacLeodJK. (1998) A phloroglucinol derivative from cell suspension cultures of Hypericum patulum. Phytochemistry, 47, 1041–1043.
24.
MaverM, QueirozEF, WolfenderJL, HostettmannK. (2005) Flavonoids from the stem of Eriophorum scheuchzeri. Journal of Natural Products, 68, 1094–1098.
TakahashiH, HirataS, MinamiH, FukuyamaY. (2001) Triterpene and flavanone glycoside from Rhododendron simsii. Phytochemistry, 56, 875–879.
27.
JangDS, CuendetM, HawthorneME, KardonoLBS, KawanishiK, FongHHS, MehtaRG, PezzutoJM, KinghornAD. (2002) Prenylated flavonoids of the leaves of Macaranga conifera with inhibitory activity against cyclooxygenase-2. Phytochemistry, 61, 867–872.
28.
TsengMH, ChouCH, ChenYM, KuoYH. (2001) Allelopathic prenylflavanones from the fallen leaves of Macaranga tanarius. Journal of Natural Products, 64, 827–828.
29.
PhommartS, sutthivaivakitP, ChimnoiN, RuchirawatS, SutthivaivakitS. (2005) Constituents of the leaves of Macaranga tanarius. Journal of Natural Products, 68, 927–930.
30.
ZhangYJ, AbeT, TanakaT, YangCR, KounoT. (2002) Two new acylated flavanone glycosides from the leaves and branches of Phyllanthus emblica. Chemical and Pharmaceutical Bulletin, 50, 841–843.
31.
BarakatHH, SoulemanAM, HusseinSAM, IbrahiemOA, NawwarMAM. (1999) Flavonoid galloyl glucosides from the pods of Acacia farnesiana. Phytochemistry, 51, 139–142.
32.
El-ShafaeAM, El-DomiatyMM. (1998) Flavonoidal constituents of the flowers of Acacia saligna. Zagazig Journal of Pharmaceutical Science, 7, 48–53.
YadavaRN, MathewsSR, JainN. (1997) Naringenin-4′-O-alpha-L-rahmnopyranoside: A novel flavanone glycoside from the stem of Crotalaria DC. Journal of the Indian Chemical Society, 74, 426–427.
38.
NanayakkaraNPD, BurandtCLJr., JacobMR. (2002) Flavonoids with activity against methicillin-resistant Staphylococcus aureus from Dalea scandens var. paucifolia. Planta Medica, 68, 519–522.
39.
KanokmedhakulS, KanokmedhakulK, NambuddeeK, KongsaereeP, (2004) New bioactive prenylflavonoids and dibenzocycloheptene derivative from roots of Dendrolobium lanceolatum. Journal of Natural Products, 67, 968–972.
40.
MahidolC, PrawatH, KaweetripobW, RuchirawatS. (2002) Two new pyranoflavanones from the stems of Derris reticulata. Heterocycles, 57, 1287–1292.
41.
BhattacharyyaJ, MajetichG, JenkinsTM, AltmidaRN. (1998) Dioflorin, a minor flavonoid from Dioclea grandiflora. Journal of Natural Products, 61, 413–414.
42.
JenkinsT, BhattacharyyaJ, MajetichG, TangQ, de FatimaAM, AltmidaRN. (1999) Flavonoids from the root-bark of Dioclea grandiflora. Phytochemistry, 52, 723–730.
43.
YenesewA, MidiwoJO, MiessnerM, HeydenreichM, PeterMG. (1998) Two prenylated flavanones from stem bark of Erythrina burttii. Phytochemistry, 48, 1439–1443.
44.
ChachaM, Bojase–MoletaG, MajindaRRT. (2005) Antimicrobial and radical scavenging flavonoids from the stem wood of Erythrina latissima. Phytochemistry, 66, 99–104.
45.
YenesewA, InduliM, DereseS, MidiwoJO, HeydenreichM, PeterMG, AkalaH, WanguiJ, LiyalaP, WatersNC. (2004) Anti-plasmodial flavonoids from the stem bark of Erythrina abyssinica. Phytochemistry, 65, 3029–3032.
46.
YenesewA, MidiuoJO, MiessnerM, HeydenreichM, PeterMG. (1998) Two prenylated flavanones from stem bark of Erythrina burttii. Phytochemistry, 48, 1439–1443.
47.
LoWL, ChangFR, HsiehTJ, WuYC. (2002) Coumaronochromones and flavanones from Euchresta formosana roots. Phytochemistry, 60, 839–845.
48.
WächterGA, HoffmannJJ, FurbacherT, BlakeME, TimmermannBN. (1999) Antibacterial and antifungal flavanones from Eysenhardtia texana. Phytochemistry, 52, 1469–1471.
49.
RukachaisirikulT, InnokP, AroonreokN, BoonamnkaylapN, LimrangsunS, BoonyonC, WoonjinaU, SukumaranA. (2007) Antibacterial pterocarpans from Erythrina subumbrans. Journal of Ethnopharamacology, 110, 171–175.
CaoS, SchillingJK, MillerJS, AndriantsiferanaR, RasamisonVE, KingstonDGI. (2004) Cytotoxic compounds from Mundulea chapelieri from the Madagascar rainforest. Journal of Natural Products, 67, 454–456.
60.
Carcache-BlancoEJ, KangYH, ParkEJ, SuBN, KardonoLBS, RiswanS, FongHHS, PezzutoJM, KinghornAD. (2003) Constituents of the stem bark of Pongamia pinnata with the potential to induce quinone reductase. Journal of Natural Products, 66, 1197–1202.
61.
KangSS, KimJS, SouKH, ChangHW, KimHP. (2000) A new prenylated flavanone from the roots of Sophora flavescens. Fitoterapia, 71, 511–515.
62.
KuroyanagiM, ArakawaT, HirayamaY, HayashiT. (1999) Antibacterial and antiandrogen flavonoids from Sophora flavescens. Journal of Natural Products, 62, 1595–1599.
JangDS, ParkEJ, KangYH, HawthorneME, VigoJS, GrahamJG, CabiesesF, FongHHS, MehtaRG, PezzutoJM, KinghornAD. (2003) Potential cancer chemopreventive flavonoids from the stems of Tephrosia toxicaria. Journal of Natural Products, 66, 1166–1170.
65.
Es-SafiN-E, KhlifiS, KerhoasL, KollmannA, El AbbouyiA, DucrotP-H. (2005) Antioxidant constituents of the aerial parts of Globularia alypum growing in Morocco. Journal of Natural Products, 68, 1293–1296.
66.
MoulariB, PellequerY, LboutounneH, GirardC, ChaumontJP, MilletJ, MuyardF. (2006) Isolation and in vitro antibacterial activity of astilbin, the bioactive flavanone from the leaves of Harungana madagascariensis Lam. ex Poir (Hypericaceae). Journal of Ethnopharmacology, 106, 272–278.
67.
StevensJF, IvancicM, DeinzerML, WollenweberE. (1999) A novel 2-hydroxyflavanone from Collinsonia canadensis. Journal of Natural Products, 62, 392–394.
68.
AliMS, SaleemM, AhmadW, ParvezM, YamdagniR. (2002) A chlorinated monoterpene ketone, acylated β-sitosterol glycosides and a flavanone glycoside from Mentha longifolia (Lamiaceae). Phytochemistry, 59, 889–895.
69.
AhmedI, AnisI, MalikA, NawazSA, ChoudharyMI. (2003) Cholinesterase Inhibitory Constituents from Onosma hispida. Chemical and Pharmaceutical Bulletin, 51, 412–414.
70.
ZhangZ, El-SohlyHN, LiXC, KhanSI, BroedelSEJr., RaulliRE, CihlarRL, WalkerLA. (2003) Flavanone glycosides from Miconia trillii. Journal of Natural Products, 66, 39–41.
71.
MatsudaH, NishidaN, YoshikawaM. (2002) Antidiabetic principles of natural medicines. V. Aldose reductase inhibitors from Myrcia multiflora DC. (2): structures of myrciacitrins III, IV, and V. Chemical and Pharmaceutical Bulletin, 50, 429–431.
72.
NgadjuiBT, DongoE, AbegazBM, FotsoS, TamboueH. (2002) Dinklagins A, B and C: three prenylated flavonoids and other constituents from the twigs of Dorstenia dinklagei. Phytochemistry, 61, 99–104.
73.
NgadjuiBT, AbegazBM, DongoE, TamboueH, FogueK. (1998) Geranylated and prenylated flavonoids from the twigs of Dorstenia mannii. Phytochemistry, 48, 349–354.
74.
NgadjuiBT, KouamSF, DongoE, KapcheGWF, AbegazBM. (2000) Prenylated flavonoids from the aerial parts of Dorstenia mannii. Phytochemistry, 55, 915–919.
75.
NgadjuiBT, DongoE, TamboueH, FogueK, AbegazBM. (1999) Prenylated flavanones from the twigs of Dorstenia mannii. Phytochemistry, 50, 1401–1406.
HuangYL, YehPY, ShenCC, ChenCC. (2003) Antioxidant flavonoids from the rhizomes of Helminthostachys zeylanica. Phytochemistry, 64, 1277–1283.
85.
YiJ, ZhangG, LiBG. (2002), Studies on the chemical constituents of Pseudotsuga sinensis. Acta Pharmacologica Sinica, 37, 352–354.
86.
HsiehYL, FangJM, ChengYS. (1998) Terpenoids and flavonoids from Pseudotsuga wilsoniana. Phytochemistry, 47, 845–850.
87.
ZhouY, ZhangGL, LiBG, ChenYZ. (2001) Three new compounds from Oxyria digyna (L.) Hill. Indian Journal of Chemistry, 40B, 1219–1222.
88.
KoorbanallyNA, RandrianarivelojosiaM, MulhollandDA, Quarles van UffordL, van den BergAJJ. (2002) Bioactive constituents of Cedrelopsis microfoliata. Journal of Natural Products, 65, 1349–1352.
89.
KimHK, JeonWK, KoBS. (2000) Flavanone glycoside from the fruits of Chaenomeles sinensis. Natural Product Science, 6, 79–81.
90.
RoemmeltS, ZimmermannN, RademacherW, TreutterD. (2001) Triterpene and flavanone glycoside from Rhododendron simsii. Phytochemistry, 56, 875–879.
91.
KimHK, JeonWK, KoBS. (2001) Flavanone glycosides from Citrus junos and their anti-influenza virus activity. Planta Medica, 67, 548–549.
92.
IwaseY, TakahashiM, TakemuraY, Jun-IchiM, ItoC, FurukawaH, YanoM. (2001) Isolation and identification of two new flavanones and a chalcone from Citrus kinokuni. Chemical and Pharmaceutical Bulletin, 49, 1356–1358.
93.
ChenJ, MontanariAM. (1998) Isolation and identification of new polymethoxyflavonoids from Dancy tangerine Leaves. Journal of Agriculture and Food Chemistry, 46, 1235–1238.
94.
RahmanMM, GrayAI. (2002) Antimicrobial constituents from the stem bark of Feronia limonia. Phytochemistry, 59, 73–77.
95.
WattanapiromsakulC, WatermanPG. (2000) Flavanone, triterpene and chromene derivatives from the stems of Paramignya griffithii. Phytochemistry, 55, 269–273.
96.
ShetgiriNP, RegeLN. (1998) Phytosterol and flavanone from roots of Zanthoxylum budrunga. Asian Journal of Chemistry, 10, 848–851.
97.
MurphyBT, CaoS, NorrisA, MillerJS, RatovosonF, AndriantsiferanaR, RasamisonVE, KingstonDGI. (2005) Cytotoxic Flavanones of Schizolaena hystrix from the Madagascar Rainforest. Journal of Natural Products, 68, 417–419.
ChenJJ, LeeHH, DuhCY, ChenIS. (2005) Cytotoxic chalcones and flavonoids from the leaves of Muntingia calabura. Planta Medica, 71, 970–973.
100.
AnamEM. (1997) Novel flavones and chalcone glycosides from Clerodendron phlomidis. Indian Journal of Chemistry, 36B, 897–900.
101.
AnamEM. (1999), Novel flavanone and chalcone glycosides from Clerodendron phlomidis (Verbenaceae). Indian Journal of Chemistry, 38B, 1307–1310.
102.
ChouCJ, KoHC, LinLC. (1999) Flavonoid Glycosides from Viscum alniformosanae. Journal of Natural Products, 62, 1421–1422.
103.
LinJH, ChiouYN, LinYL. (2002) Phenolic Glycosides from Viscum angulatum. Journal of Natural Products, 65, 638–640.
104.
YaoH, LiaoZX, WuQ, LeiGQ, LinZJ, ChenDF, ChenJK, ZhouTS. (2006) Antioxidative flavanone glycosides from the branches of leaves of Viscum coloratum. Chemical and Pharmaceutical Bulletin, 54, 133–135.
105.
RajnarayanaK, Sripal ReddyM, ChaluvadiMR, KrishnaDR. (2001) Bioflavonoids classification, pharmacological, biochemical effects and therapeutic potentials. Indian Journal of Pharmacology, 33, 2–16.
106.
AresJJ, OuttPE. (1998) Gastroprotective agents for the prevention of NSAID-induced gastropathy. Current Pharmaceutical Design, 4, 17–36.
107.
BrahmachariG. (2006) Antioxidants of Flowering Plants. In: Floriculture, Ornamental and Plant Biotechnology: Advances and Topical Issues (1st Edition), Vol. IV, Chapter 41, Teixeira da SilvaJA (Ed.), Global Science Books, London, UK, PP-373–378.
108.
LissiEA, ModakB, TorresR, EscoberJ, UrzuaA. (1999) Total antioxidant potential of resinous exudates from Heliotropium Species. Free Radical Research, 30, 471–477.
109.
Al-BurtamaniSKS, FatopeMO. (2004) IUPAC International conference on biodiversity and natural products chemistry and medicinal applications, New Delhi, January 26–31, 29.
110.
RattyAK. (1988) Effects of flavonoids on non enzymatic lipid peroxidation: structure activity relationship. Biochemical Medicine and Metabolic Biology, 39, 67–69.
111.
NjamenD, MbaforJT, FomumZT, KamanylA, MbanyaJC, RecloMC, GinerRM, ManezS, RiosJL. (2004) Anti-inflammatory activities of two flavanones, sigmoidin A and sigmoidin B, from Erythrina sigmoidea. Planta Medica, 70, 104–107.
112.
CholbiMR, PayaM, AlcarazMJ. (1991) Inhibitory effects of phenolic compounds on CCl4-induced microssomal lipid peroxidation. Experientia, 47, 195–199.
113.
LeuYL, HwangTL, ChungYM, HengPY. (2006) The inhibition of superoxide anion generation in human neutrophils by Viscum coloratum. Chemical and Pharmaceutical Bulletin, 54, 1063–1066.
114.
MartinMJ, MarhuendaE, Perez-GuerreroC, FrancoJM. (1994) Antiulcer effect of naringin on gastric lesions induced by ethanol in rats. Pharmacology, 49, 144–150.
115.
HosseinimehrSJ. (2004) Determination of flavanone content and antioxidant activity of Citrus aurantium. Chemistry: An Indian Journal, 1, 635–638.
116.
HeoHJ, KimD-O, ShinSC, KimMJ, KimBG, ShinD-H. (2004) Effect of antioxidant flavanone, naringenin, from Citrus junos on neuroprotection. Journal of Agriculture and Food Chemistry, 52, 1520–1525.
117.
GorinsteinS, LeontowiczM, KrzeminskiR, GralakM, JastrzebskiZ, ParkYS, JungST, KangSG, TrakhtenbergS. (2007) Effect of hesperidin and naringin on the plasma lipid profile and plasma antioxidant activity in rats fed a cholesterol-containing diet. Journal of the Science of Food and Agriculture, 87, 1257–1262.
118.
HabtemariamS. (1997) Flavonoids as inhibitors or enhancers of the cytotoxicity of tumor necrosis factor-▪ in L-929 tumor cells. Journal of Natural Products, 60, 775–778.
119.
HahmER, ParkS, YangCH. (2003) 7,8-Dihydroxyflavanone, as an inhibitor for Jun-Fos-DNA complex formation and its cytotoxic effect on cultured human cancer cells. Natural Products Research, 17, 431–436.
120.
LodishH, BaltimoreD, BerkA, ZipurskySL, MatsudairaP, DarnellJ. (1995) Regulation of transcription initiation. In: Molecular Cell Biology, 3rd ed. (DarnellJ, LodishH and BaltimoreD, eds.), Scientific American Books, New York, PP- 405–481.
121.
WeinbergRA. (1989) Oncogenes and the Molecular Origins of Cancer, Cold Spring Harbour Laboratory Press, New York, 176.
122.
DelmulleL, BellahceneA, DhoogeW, ComhaireF, RoelensF, HuvaereK, HeyerickA, CastronovoV, De keukeleireD. (2006) Anti-proliferative properties of prenylated flavonoids from hops (Humulus lupulus L.) in human prostate cancer cell lines. Phytomedicine, 13, 732–734.
123.
NakaharaK, RoyMK, OnoH, MaedaI, KameyamaOM, YoshidaM, TrakoontivakornG. (2003) Prenylated flavanones isolated from flowers of Azadirachta indica (the Neem Tree) as antimutagenic constituents against heterocyclic amines. Journal of Agriculture and Food Chemistry, 51, 64566460.
124.
ZierauO, MorriseyC, WatsonW, SchwabP, KolbaS, MetzD, VollmerG. (2003) Antiandrogenic activity of the phytoestrogens naringenin, 6-(1,1-dimethylallyl)naringenin and 8-prenylnaringenin. Planta Medica, 69, 856–858.
125.
ZierauO, GeisRB, SchwabP, MetzP, VollmerG. (2004) Uterine effects of the phytoestrogen 6-(1,1-dimethylallyl)naringenin in rats. Planta Medica, 70, 590–593.
126.
WildC, FaselJ. (1969) Effect of a flovonoid on the capillary resistance of the rectal mucosa in hepatic cirrhosis. American Journal of Proctology, 20, 60–62.
127.
HergertHL. (1962) In The Chemistry of Flavonoid Compounds, (ed. GeissmanT. A.), pp. 553–592.
128.
BelofskyG, PercivillD, LewisK, TegosGP, EkartJ. (2004) Phenolic metabolites of Dalea versicolor that enhance antibiotic activity against model pathogenic bacteria. Journal of Natural Products, 67, 481–484.
129.
EdenharderR, von PetersdorffI, RauscherR. (1993), Antimutagenic effects of flavonoids, chalcones and structurally related compounds on the activity of 2-amino-3-methylimidazo[4,5-f]quinoline (IQ) and other heterocyclic amine mutagens from cooked food. Mutation Research, 287, 261–274.
130.
KawaguchiK, KikuchiS, HasunumaR, MaruyamaH, RyllR, KumazawaY. (2004) Suppression of infection-induced endotoxin shock in mice by a Citrus flavanone naringin. Planta Medica, 70, 17–22.
131.
BrahmachariG, GoraiD. (2006) Recent developments in the research of naturally occurring flavonoids: An overview. In: Chemistry of Natural Products: Recent Trends & Developments, Chapter 4, GoutamBrahmachari (Ed.), Research Singpost, Trivandrum, Kerala, India, PP-61–159.
KumarN, SinghB, KaulVK. (2006) Flavonoids from Rosa damascene Mill. Natural Product Communications, 1, 623–626.
134.
CuendetM, OtehamCP, MoonRC, PezzutoJM (2006) Quinone reductase induction as a biomarker for cancer chemoprevention. Journal of Natural Products, 69, 460–463.