C-Glycosylflavonoids are a group of compounds widespread in nature which have gained much interest due to their biological properties. This review focuses on the research of the last ten years concerning detection and structural characterization of C-glycosylflavonoids, their bioactivities and synthesis.
MabryTM, MarkhamKR, ThomasMB. (1970) The Systematic Identification of Flavonoids, Academic Press, London.
3.
MarkhamKR. (1982) Techniques of Flavonoid Identification, Academic Press, London.
4.
MarkhamKR. (1989) Flavones, Flavonols and their Glycosides. In: Methods in Plant Biochemistry, HarborneJB (Ed.). Academic Press, London, 197–235.
5.
JayM. (1994). C-Glycosylflavonoids. In: The Flavonoids: Advances in Research since 1986, HarborneJB (Ed.). Chapman & Hall/CRC, USA, 57–87.
6.
JayM, ViricelM-R, GonnetJ-F. (2006) C-glycosylflavonoids. In: Flavonoids: Chemistry, Biochemistry and Aplications, AndersenOM and MarkhamKR (Eds.). CRC Press, Taylor & Francis, Boca Raton857–916.
7.
McNaughtAD. (1997) Nomenclature of carbohydrates (recommendations 1996)Carbohydrate Research, 297, 1–90.
8.
FossenT, RayyanS, HolmbergMH, NimtzM, AndersenOM. (2007) Covalent anthocyanin-flavone dimer from leaves of Oxalis triangularis.Phytochemistry, 68, 652–662.
9.
BloorSJ. (1999) Novel pigments and copigmentation in the blue marguerite daisy. Phytochemistry, 50, 1395–1399.
10.
FrankeK, HoffmannM, SchmidtJ, PorzelA, ArnoldN, WessjohannL. (2006) 2″-O-Glucosylvitexin, a chemotaxonomic marker for the genus Cryptocoryne (Araceae). Biochemical Systematics and Ecology, 34, 546–548.
11.
WebbyRF, MarkhamKR, MolloyBPJ. (1987) The characterization of New-Zealand Podocarpus hybrids using flavonoid markers. New Zealand Journal of Botany, 25, 355–366.
12.
GrayerRJ, KiteGC, VeitchNC, EckertMR, MarinPD, SenanayakeP, PatonAJ. (2002) Leaf flavonoid glycosides as chemosystematic characters in Ocimum.Biochemical Systematics and Ecology, 30, 327–342.
13.
ChangCS, JeonJI. (2003) Leaf flavonoids in Cotoneaster wilsonii (Rosaceae) from the island Ulleung-do, Korea. Biochemical Systematics and Ecology, 31, 171–179.
14.
MatsumotoS, IwashinaT, KitajimaJ, MitsutaS. (2003) Evidence by flavonoid markers of four natural hybrids among Asplenium normale and related species (Aspleniaceae) in Japan. Biochemical Systematics and Ecology, 31, 51–58.
15.
MimuraMRM, SalatinoA, SalatinoMLF. (2004) Distribution of flavonoids and the taxonomy of Huberia (Melastomataceae). Biochemical Systematics and Ecology, 32, 27–34.
16.
IwashinaT, KitajimaJ, ShiuchiT, ItouY. (2005) Chalcones and other flavonoids from Asarum sensu lato (Aristolochiaceae). Biochemical Systematics and Ecology, 33, 571–584.
17.
van RensenI, VeitM, Rohner-van RensenU, CantoP, VogtH, GreinwaldR, CzyganFC. (1999) Line-scatter plots in chemotaxonomy of Genista L. section Spartioides SPACH in western Europe. Biochemical Systematics and Ecology, 27, 687–708.
18.
WenJ, ShiHM, TuPF. (2006) Chemical constituents of Abrus mollis Hance. Biochemical Systematics and Ecology, 34, 177–179.
19.
OgawaK, KawasakiA, OmuraM, YoshidaT, IkomaY, YanoM. (2001) 3′,5′-di-C-beta-glucopyranosylphloretin, a flavonoid characteristic of the genus Fortunella. Phytochemistry, 57, 737–742.
20.
SuzukiR, OkadaY, OkuyamaT. (2003) A new flavone C-glycoside from the style of Zea mays L. with glycation inhibitory activity. Chemical & Pharmaceutical Bulletin, 51, 1186–1188.
21.
ParkHS, LimJH, KimHJ, ChoiHJ, LeeIS. (2007) Antioxidant flavone glycosides from the leaves of Sasa borealis.Archives of Pharmacal Research, 30, 161–166.
22.
LinCN, KuoSH, ChungMI, KoFN, TengCM. (1997) A new flavone C-glycoside and antiplatelet and vasorelaxing flavones from Gentiana arisanensis. Journal of Natural Products, 60, 851–853.
23.
WuQX, LiY, ShiYP. (2006) Antioxidant phenolic glucosides from Gentiana piasezkii.Journal of Asian Natural Products Research, 8, 391–396.
24.
LiuB, YueME, YangSR, ShiYP. (2005) Determination of phenolic glucosides in Gentiana piasezkii by capillary zone electrophoresis. Chromatographia, 62, 643–647.
25.
CheelJ, TheodulozC, RodriguezJ, Schmeda-HirschmannG. (2005) Free radical scavengers and antioxidants from lemongrass (Cymbopogon citratus (DC.) Stapf.). Journal of Agricultural and Food Chemistry, 53, 2511–2517.
26.
SezikE, AslanM, YesiladaE, ItoS. (2005) Hypoglycaemic activity of Gentiana olivieri and isolation of the active constituent through bioassay-directed fractionation techniques. Life Sciences, 76, 1223–1238.
27.
XieC, VeitchNC, HoughtonPJ, SimmondsMSJ. (2003) Flavone C-glycosides from Viola yedoensis MAKINO. Chemical & Pharmaceutical Bulletin, 51, 1204–1207.
28.
KumarasamyY, ByresM, CoxPJ, DelazarA, JasparsM, NaharL, ShoebM, SarkerSD. (2004) Isolation, structure elucidation, and biological activity of flavone 6-C-glycosides from Alliaria petiolata.Chemistry of Natural Compounds, 40, 122–128.
29.
VoirinB, SportouchM, RaymondO, JayM, BayetC, DanglesO, El HajjiH. (2000) Separation of flavone C-glycosides and qualitative analysis of Passiflora incarnata L. by capillary zone electrophoresis. Phytochemical Analysis, 11, 90–98.
30.
PengJY, FanGR, HongZY, ChaiYF, WuYT. (2005) Preparative separation of isovitexin and isoorientin from Patrinia villosa Juss by high-speed counter-current chromatography. Journal of Chromatography A, 1074, 111–115.
31.
ChengG, BaiYJ, ZhaoYY, TaoJ, LinY, TuGZ, MaLB, LiaoN, XuXJ. (2000) Flavonoids from Ziziphus jujuba Mill var. spinosa. Tetrahedron, 56, 8915–8920.
32.
PicernoP, MencheriniT, LauroMR, BarbatoF, AquinoR. (2003) Phenolic constituents and antioxidant properties of Xanthosoma violaceum leaves. Journal of Agricultural and Food Chemistry, 51, 6423–6428.
33.
KanchanapoomT. (2007) Aromatic diglycosides from Cladogynos orientalis.Phytochemistry, 68, 692–696.
34.
WuJB, ChengYD, SuLL, KuoCW, KuoSC. (1997) A flavonol C-glycoside from Moghania macrophylla.Phytochemistry, 45, 1727–1728.
35.
KawaguchiK, AlvesSD, WatanabeT, KikuchiS, SatakeM, KumazawaY. (1998) Colony stimulating factor-inducing activity of isoflavone C-glucosides from the bark of Dalbergia monetaria.Planta Medica, 64, 653–655.
36.
ColomboR, YariwakeJH, QueirozEF, NdjokK, HostettmannK. (2006) On-line identification of further flavone C- and O-glycosides from sugarcane (Saccharum officinarum L., Gramineae) by HPLC-UV-MS. Phytochemical Analysis, 17, 337–343.
37.
RauterAP, MartinsA, BorgesC, FerreiraJ, JustinoJ, BronzeMR, CoelhoAV, ChoiYH, VerpoorteR. (2005) Liquid chromatography-diode array detection-electrospray ionisation mass spectrometry/nuclear magnetic resonance analyses of the anti-hyperglycemic flavonoid extract of Genista tenera - Structure elucidation of a flavonoid-C-glycoside. Journal of Chromatography A, 1089, 59–64.
38.
TanakaJCA, da SilvaCC, DiasBP, NakamuraCV, de CarvalhoJE, FoglioMA. (2005) Chemical constituents of Luehea divaricata Mart. (Tiliaceae). Quimica Nova, 28, 834–837.
39.
KimJM, LeeYM, LeeGY, JangDS, BaeKH, KimJS. (2006) Constituents of the roots of Pueraria lobata inhibit formation of advanced glycation end products (AGEs). Archives of Pharmacal Research, 29, 821–825.
40.
PrasainJK, ReppertA, JonesK, MooreDR, BarnesS, LilaMA. (2007) Identification of isoflavone glycosides in Pueraria lobata cultures by tandem mass spectrometry. Phytochemical Analysis, 18, 50–59.
41.
BanskotaAH, TezukaY, AdnyanaIK, XiongQB, HaseK, TranKQ, TanakaK, SaikiI, KadotaS. (2000) Hepatoprotective effect of Combretum quadrangulare and its constituents. Biological & Pharmaceutical Bulletin, 23, 456–460.
42.
CaristiC, BelloccoE, GargiulliC, ToscanoG, LeuzziU. (2006) Flavone-di-C-glycosides in citrus juices from southern Italy. Food Chemistry, 95, 431–437.
43.
HsiehPW, ChangFR, LeeKH, HwangTL, ChangSM, WuYC. (2004) A new anti-HIV alkaloid, drymaritin, and a new C-glycoside flavonoid, diandraflavone, from Drymaria diandra.Journal of Natural Products, 67, 1175–1177.
44.
WadaS, HePM, HashimotoI, WatanabeN, SugiyamaK. (2000) Glycosidic flavonoids as rat-liver injury preventing compounds from green tea. Bioscience Biotechnology and Biochemistry, 64, 2262–2265.
45.
JhooJW, AngCYW, HeinzeTM, DeckJ, SchnackenbergLK, BegerRD, DragullK, TangCS. (2007) Identification of C-glycoside flavonoids as potential mutagenic compounds in kava. Journal of Food Science, 72, C120–C125.
46.
HongYJ, Tomas-BarberanFA, KaderAA, MitchellAE. (2006) The flavonoid glycosides and procyanidin composition of Deglet Noor dates (Phoenix dactylifera). Journal of Agricultural and Food Chemistry, 54, 2405–2411.
47.
LuYR, FooLY. (2000) Flavonoid and phenolic glycosides from Salvia officinalis.Phytochemistry, 55, 263–267.
48.
EndaleA, KammererB, Gebre-MariamT, SchmidtPC. (2005) Quantitative determination of the group of flavonoids and saponins from the extracts of the seeds of Glinus lotoides and tablet formulation thereof by high-performance liquid chromatography. Journal of Chromatography A, 1083, 32–41.
49.
CarnatAP, CarnatA, FraisseD, LamaisonJL, HeitzA, WyldeR, TeuladeJC. (1998) Violarvensin, a new flavone di-C-glycoside from Viola arvensis.Journal of Natural Products, 61, 272–274.
50.
SuzukiR, OkadaY, OkuyamaT. (2003) Two flavone C-glycosides from the style of Zea mays with glycation inhibitory activity. Journal of Natural Products, 66, 564–565.
51.
YayliN, BaltaciC, GencH, TerziogluS. (2002) Phenolic and flavone C-glycosides from Scleranthus uncinatus.Pharmaceutical Biology, 40, 369–373.
NorbaekR, AaboerDBF, BleegIS, ChristensenBT, KondoT, BrandtK. (2003). Flavone C-glycoside, phenolic acid, and nitrogen contents in leaves of barley subject to organic fertilization treatments. Journal of Agricultural and Food Chemistry, 51, 809–813.
54.
ZouJH, YangJS, ZhouL. (2004) Acylated flavone C-glycosides from Trollius ledebouri.Journal of Natural Products, 67, 664–667.
55.
GilMI, FerreresF, Tomas-BarberanFA. (1998) Effect of modified atmosphere packaging on the flavonoids and vitamin C content of minimally processed Swiss chard (Beta vulgaris subspecies cycla). Journal of Agricultural and Food Chemistry, 46, 2007–2012.
56.
CaiSQ, WangRF, YangXW, ShangMY, MaCM, ShoyamaY. (2006) Antiviral flavonoid-type C-glycosides from the flowers of Trollius chinensis.Chemistry & Biodiversity, 3, 343–348.
57.
DeachathaiS, MahabusarakamW, PhongpaichitS, TaylorWC. (2005) Phenolic compounds from the fruit of Garcinia dulcis.Phytochemistry, 66, 2368–2375.
58.
de RijkeE, OutP, NiessenWMA, ArieseF, GooijerC, BrinkmanUAT. (2006) Analytical separation and detection methods for flavonoids. Journal of Chromatography A, 1112, 31–63.
59.
IwashinaT, KitajimaJ, KatoT, TobeH. (2005) An analysis of flavonoid compounds in leaves of Japonolirion (Petrosaviaceae). Journal of Plant Research, 118, 31–36.
60.
QueirozEF, IosetJR, NdjokoK, GunternA, FogginCM, HostettmannK. (2005) On-line identification of the bioactive compounds from Blumea gariepina by HPLC-UV-MS and HPLC-UV-NMR, combined with HPLC-micro-fractionation. Phytochemical Analysis, 16, 166–174.
61.
PrasainJK, JonesK, KirkM, WilsonL, Smith-JohnsonM, WeaverC, BarnesS. (2003) Profiling and quantification of isoflavonoids in kudzu dietary supplements by high-performance liquid chromatography and electrospray ionization tandem mass spectrometry. Journal of Agricultural and Food Chemistry, 51, 4213–4218.
62.
MaZZ, WuQL, LeeDYW, TracyM, LukasSE. (2005) Determination of puerarin in human plasma by high performance liquid chromatography. Journal of Chromatography B-Analytical Technologies in the Biomedical and Life Sciences, 823, 108–114.
63.
EdwardsEL, RodriguesJA, FerreiraJ, GoodallDM, RauterAP, JustinoJ, Thomas-OatesJ. (2006) Capillary electrophoresis-mass spectrometry characterisation of secondary metabolites from the antihyperglycaemic plant Genista tenera.Electrophoresis, 27, 2164–2170.
64.
WaridelP, WolfenderJL, NdjokoK, HobbyKR, MajorHJ, HostettmannK. (2001) Evaluation of quadrupole time-of-flight tandem mass spectrometry and ion-trap multiple-stage mass spectrometry for the differentiation of C-glycosidic flavonoid isomers. Journal of Chromatography A, 926, 29–41.
65.
PereiraCAM, YariwakeJH, McCullaghM. (2005) Distinction of the C-glycosylflavone isomer pairs orientin/isoorientin and vitexin/isovitexin using HPLC-MS exact mass measurement and in-source CID. Phytochemical Analysis, 16, 295–301.
66.
LiQM, VandenheuvelH, DillenL, ClaeysM. (1992) Differentiation of 6-C-glycosidic and 8-C-glycosidic flavonoids by positive-Ion Fast-Atom-Bombardment and Tandem Mass-Spectrometry. Biological Mass Spectrometry, 21, 213–221.
67.
MarchRE, LewarsEG, StadeyCJ, MiaoXS, ZhaoXM, MetcalfeCD. (2006) A comparison of flavonoid glycosides by electrospray tandem mass spectrometry. International Journal of Mass Spectrometry, 248, 61–85.
68.
CuyckensF, ClaeysM. (2004) Mass spectrometry in the structural analysis of flavonoids. Journal of Mass Spectrometry, 39, 1–15.
69.
LeeDYW, ZhangW-Y, KarnatiVVR. (2003) Total synthesis of puerarin, an isoflavone C-Glycoside. Tetrahedron Letters, 44, 6857–6859.
70.
KazumaK, TakahashiT, SatoK, TakeuchiH, MatsumotoT, OkunoT. (2000) Quinochalcones and flavonoids from fresh florets in different cultivars of Carthamus tinctorius L. Bioscience Biotechnology and Biochemistry, 64, 1588–1599.
71.
RickettsML, MooreDD, BanzWJ, MezeiO, ShayNF. (2005) Molecular mechanisms of action of the soy isoflavones includes activation of promiscuous nuclear receptors. A review. Journal of Nutritional Biochemistry, 16, 321–330.
72.
ZavodnikLB. (2003) Isoflavone genistein-8-C-glycoside prevents the oxidative damages structure and function of rat liver microsomal membranes. Radiatsionnaya Biologiya. Radioekologiya, 43, 432–438.
73.
CervellatiR, RenzulliC, GuerraMC, SperoniE. (2002) Evaluation of antioxidant activity of some natural polyphenolic compounds using the Briggs-Rauscher reaction method. Journal of Agricultural and Food Chemistry, 50, 7504–7509.
74.
YeH, YuanS, CongXD. (2007) Biotransformation of puerarin into 3′-hydroxypuerarin by Trichoderma harzianum NJ01. Enzyme and Microbial Technology, 40, 594–597.
75.
HanRM, TianYX, BeckerEM, AndersenML, ZhangJP, SkibstedLH. (2007) Puerarin and conjugate bases as radical scavengers and antioxidants: Molecular mechanism and synergism with beta-carotene. Journal of Agricultural and Food Chemistry, 55, 2384–2391.
76.
JiangB, LiuJH, BaoYM, AnLJ. (2003) Hydrogen peroxide-induced apoptosis in PC12 cells and the protective effect of puerarin. Cell Biology International, 27, 1025–1031.
77.
Andrade-CettoA, WiedenfeldH. (2001) Hypoglycemic effect of Cecropia obtusifolia on streptozotocin diabetic rats. Journal of Ethnopharmacology, 78, 145–149.
78.
HsuFL, LiuIM, KuoDH, ChenWC, SuHC, ChengJT. (2003) Antihyperglycemic effect of puerarin in streptozotocin-induced diabetic rats. Journal of Natural Products, 66, 788–792.
79.
YanLP, ChanSW, ChanASC, ChenSL, MaXJ and XuHX. (2006) Puerarin decreases serum total cholesterol and enhances thoracic aorta endothelial nitric oxide synthase expression in diet-induced hypercholesterolemic rats. Life Sciences, 79, 324–330.
80.
YeungDKY, LeungSWS, XuYC, VanhouttePM, ManRYK. (2006) Puerarin, an isoflavonoid derived from Radix puerariae, potentiates endothelium-independent relaxation via the cyclic AMP pathway in porcine coronary artery. European Journal of Pharmacology, 552, 105–111.
81.
BaeHS, KimYS, ChoKH, LeeKS, KimJJ, LeeHU, KimDH. (2003) Hepatoprotective activity of Reduohanxiao-tang (Yuldahanso-tang) is related to the inhibition of beta-glucuronidase. American Journal of Chinese Medicine, 31, 111–117.
82.
ZhangSH, JiG, LiuJW. (2006) Reversal of chemical-induced liver fibrosis in Wistar rats by puerarin. Journal of Nutritional Biochemistry, 17, 485–491.
83.
YuZL, LiWJ. (2006) Induction of apoptosis by puerarin in colon cancer HT-29 cells. Cancer Letters, 238, 53–60.
84.
FurutaT, KimuraT, KondoS, MiharaH, WakimotoT, NukayaH, TsujiK, TanakaK. (2004). Concise total synthesis of flavone C-glycoside having potent anti-inflammatory activity. Tetrahedron, 60, 9375–9379.
85.
NakatsukaT, TomimoriY, FukudaY, NukayaH. (2004) First total synthesis of structurally unique flavonoids and their strong anti-inflammatory effect. Bioorganic & Medicinal Chemistry Letters, 14, 3201–3203.
86.
RezvaniAH, OverstreetDH, PerfumiM, MassiM. (2003) Plant derivatives in the treatment of alcohol dependency. Pharmacology Biochemistry and Behavior, 75, 593–606.
87.
OverstreetDH, KralicJE, MorrowAL, MaZZ, ZhangYW, LeeDY. (2003) NPI-031G (puerarin) reduces anxiogenic effects of alcohol withdrawal or benzodiazepine inverse or 5–HT2C agonists. Pharmacology Biochemistry and Behavior, 75, 619–625.
88.
PrasainJK, JonesK, BrissieN, MooreR, WyssJM, BarnesS. (2004) Identification of puerarin and its metabolites in rats by liquid chromatography-tandem mass spectrometry. Journal of Agricultural and Food Chemistry, 52, 3708–3712.
89.
ChuehFS, ChangCP, ChioCC, LinMT. (2004) Puerarin acts through brain serotonergic mechanisms to induce thermal effects. Journal of Pharmacological Sciences, 96, 420–427.
90.
dos SantosKS, KurtzS, MullerSD, BiavattiMW, de OliveiraR, SantosCAD. (2006) Sedative and anxiolytic effects of methanolic extract from the leaves of Passiflora actinia.Brazilian Archives of Biology and Technology, 49, 565–573.
91.
SorianoIR, AsenstorferRE, SchmidtO, RileyIT. (2004) Inducible flavone in oats (Avena sativa) is a novel defense against plant-parasitic nematodes. Phytopathology, 94, 1207–1214.
92.
ZavodnikLB, ZavodnikIB, LapshinaEA, ShkodichAP, BryszewskaM, BukoVU. (2000) Hypochlorous acid-induced lysis of human erythrocytes. Inhibition of cellular damage by the isoflavonoid genistein-8-C-glucoside. Biochemistry-Moscow, 65, 946–951.
93.
EadeRA, McDonaldFJ, SimesJJH. (1975) Extractives of Australian timbers .15. Synthesis of 7,4′-di-O-methylbayin. Australian Journal of Chemistry, 28, 2011–2018.
94.
EadeRA, PhamHP. (1979) C-Glycosylflavonoids .3. Synthesis of 5,7,4′-tri-O-methylvitexin (8-C-Beta-D-Glucopyranosyl-5,7,4′-Trimethoxyflavone). Australian Journal of Chemistry, 32, 2483–2493.
95.
EadeRA, McDonaldFJ, PhamHP. (1978) C-Glycosylflavonoids .2. Synthesis of 7,4′-Di-O-Methylpuerarin (8-C-Beta-D-Glucopyranosyl-7,4′-Dimethoxyisoflavone). Australian Journal of Chemistry, 31, 2699–2706.
96.
HarborneJB, MabryTJ. (1982) The flavonoids: Advances in research, Chapman & Hall, London, 449–503.
97.
TschescheR, WideraW. (1982) C-Glycosylflavonoids .1. Synthesis of 4′,7-Di-O-Methylisobayin [6-(beta-D-glucopyranosyl)-7-methoxy-2-(4-methoxyphenyl)-4H-1-benzopyran -4-one]. Liebigs Annalen Der Chemie, 902–907.
98.
FrickW, SchmidtRR. (1989) Convenient synthesis of C-beta-D-glucopyranosyl arenes - Synthesis of 5,7,4′-tri-O-methylvitexin. Liebigs Annalen der Chemie, 565–570.
99.
MahlingJA, JungKH, SchmidtRR. (1995) Glycosyl imidates .69. Synthesis of flavone C-glycosides vitexin, isovitexin, and isoembigenin. Liebigs Annalen der Chemie, 461–466.
100.
KumazawaT, MinatogawaT, MatsubaS, SatoS, OnoderaJ. (2000) An effective synthesis of isoorientin: the regioselective synthesis of a 6-C-glucosylflavone. Carbohydrate Research, 329, 507–513.
101.
PintoDCGA, SilvaAMS, CavaleiroJAS. (1994) Synthesis of 6,8-(dibromo or diiodo)-5-hydroxy-2-(phenyl or styryl)chromonesTetrahedron Letters, 35, 9459–9460.
102.
OyamaK, KondoT. (2004) Total synthesis of flavocommelin, a component of the blue supramolecular pigment from Commelina communis, on the basis of direct 6-C-glycosylation of flavan. Journal of Organic Chemistry, 69, 5240–5246.
WangZX, RenZH, YanJ, XuX, ShiXX, ChenGR. (2006) Total synthesis of glycosylflavone Parkinsonin B. Chinese Journal of Organic Chemistry, 26, 1254–1258.
105.
SatoS, HiroeK, KumazawaT, OnoderaJ. (2006) Total synthesis of two isoflavone C-glycosides: genistin and orobol 8-C-glucopyranosides. Carbohydrate Research, 341, 1091–1095.
106.
ZhangQ, BottingNP. (2004) The synthesis of [2,3,4-13C3]glycitein. Tetrahedron, 60, 12211–12216.
SatoS, AkiyaT, NishizawaH, SuzukiT. (2006) Total synthesis of three naturally occurring 6,8-di-C-glycosylflavonoids: phloretin, naringenin and apigenin bis-C-β-D-glucosides. Carbohydrate Research, 341, 964–970.
109.
SatoS, AkiyaT, SuzukiT, OnoderaJ. (2004) Environmentally friendly C-glycosylation of phloroacetophenone with unprotected D-glucose using scandium(III) trifluoromethanesulfonate in aqueous media: key compounds for the syntheses of mono- and di-C-glucosylflavonoids. Carbohydrate Research, 339, 2611–2614.
