This paper presents a review of the occurrence of tricetin and its methyl ethers, with respect to their occurrence in the free state. In addition to literature data, our tabulated survey also includes a dozen unpublished results. The review indicates that 5,7,3′,4′,5′-pentahydroxyflavone and its methyl derivatives are more widespread than was known so far. Their presence as aglycones has been proved in a good number of plant species belonging to unrelated families.
AndersonJA, PerkinAG. (1931) The yellow colouring matter of khapli wheat, Triticum dicoccum. Journal of the Chemical. Society, 2624–2625.
2.
HarborneJB. (1967) Comparative biochemistry of the flavonoids. IV. Correlation between chemistry, pollen morphology and systematics in the family Plumbaginaceae. Phytochemistry, 6, 1415–1428.
3.
HarborneJB. (1975) The biochemical systematics of flavonoids. In The flavonoids.HarborneJB, MabryTJ, MabryH. (Eds). Chapman and Hall, London. 1056–1095.
4.
LamerE, MelcherE, GrimshawJ (1968) Identification of 3′,4′,5′,5,7-pentahydroxyflavone and its 3′-monoglucoside. Tetrahedron Letters, 12, 1419–1421.
5.
BeckmannS, GeigerH. (1968) Inhaltsstoffe von Metasequoia glyptostroboides – II. Flavon- und Flavonolglykoside. Phytochemistry, 7, 1667–1671.
6.
CamposMG, MarkhamKR, MitchellKA, da CunhaAP. (1997) An approach to the characterization of bee pollens via their flavonoid/phenolic profiles. Phytochemical Analysis, 8, 181–185.
7.
CamposMG, WebbyRF, MarkhamKR. (2002) The unique occurrence of the flavone aglycone tricetin in Myrtaceae pollen. Zeitschrift für Naturforschung, 57C, 944–946.
8.
MartosI, FerreresF, Tomás-BarberánFA. (2000) Identification of flavonoid markers for the botanical origin of Eucalyptus honey. Journal of Agriculture and Food Chemistry, 48, 1498–1502.
9.
YaoL, JiangYM, SinganusongR, D'ArcyB, DattaN, CaffinN, RaymontK. (2004) Flavonoids in Australian Melaleuca, Guioa, Lophostemon, Banksia and Helianthus honey and their potential floral authentication. Food Research International, 37, 166–174.
10.
ChungS-K, KimY-C, TakayaY, TerashimaK, NiwaM. (2004) Novel flavonol glycoside, 7-O-methyl mearnsitrin, from Sageretia theezans. Journal of Agriculture and Food Chemistry, 52, 4664–4668.
11.
VoirinB, JayM, HautevilleM. (1976) Selgine, nouvelle flavone isolée de Huperzia selago. Phytochemistry, 15, 840–841.
12.
LiuY-L, MabryTJ. (1982) Flavonoids from Artemisia ludoviciana var. ludoviciana. Phytochemistry, 21, 209–214.
13.
UlubelenA, MabryTJ, DellamonicaG, ChopinJ. (1984) Flavonoids from Passiflora palmeri. Journal of Natural Products, 47, 384–385.
14.
WollenweberE, WehdeR, DörrM, StevensJF. (2002) On the occurrence of exudate flavonoids in the borage family (Boraginaceae). Zeitschrift für Naturforschung, 57C, 445–448.
15.
WollenweberE, and co-workers, unpublished.
16.
ReutrakulV, KrachangchaengC, TuchindaP, PohmakotrM, JaipetchT, YoosookC, KasisitJ, SophasanS, SujaritK, SantisukT. (2004) Cytotoxic and anti-HIV-1 constituents from leaves and twigs of Gardenia tubifera. Tetrahedron, 60, 1517–1523.
RofiRD, PomilioAB. (1985) 5,7,3′-Trihydroxy-4′,5′-dimethoxyflavone and other phenolics form Poa hueca. Phytochemistry, 24, 2131–2132.
19.
Silva LucianoJH, Sousa LimaMA, de SouzaEB, SilveiraER. (2004) Chemical constituents of Alibertia myrciifolia. Biochemical Systematics and Ecology, 32, 1227–1229.
20.
WollenweberE. (2007) Flavonoids occurring in the sticky resin on Roridula dentata and Roridula gorgonias (Roridulaceae). Carnivorous Plants Newsletter, 36, 77–80.
21.
ZhouJ-M, FukushiY, WollenweberE, IbrahimRK. (2008) Characterization of two O-methyltransferase-like genes in barley and maize. Pharmaceutical Biology46, 26–34.
22.
GripenbergJ. (1962) Flavones. In: The chemistry of flavonoid compounds. GeissmanTA. (Ed). Pergamon Press, Oxford. London. New York. Paris. 406–440.
23.
HarborneJB. (1967) Comparative Biochemistry of the Flavonoids. Academic Press, London, New York, 1–383.
24.
KanetaM, SugiyamaN. (1973) Identification of flavone compounds in eighteen Gramineae species. Agricultural and Biological Chemistry, 37, 2663–2665.
25.
SwainT. (1976) Flavonoids. In Chemistry and Biochemistry of Plant Pigments. GoodwinTW. (Ed). Vol. 1. Academic Press, London, 166–206.
26.
ZahirA, JossangA, BodoB, ProvostJ, CossonJ-P, SévenetT. (1996) DANN topoisomerase I inhibitors: cytotoxic flavones from Lethedon tannaensis. Journal of Natural Products, 59, 701–703.
27.
YamazakiK, IwashinaT, KitajimaJ, GamouY, YoshidaA, TannowaT. (2007) External and internal flavonoids from Madagascarian Uncarina species (Pedaliaceae). Biochemical Systematics and Ecology, 35, 743–749.
28.
MarinPD, GrayerRJ, Grujic-JavanovicS, KiteGC, VeitchNC. (2004) Glycosides of tricetin methyl ethers as chemosystematic markers in Stachys subgenus Betonica. Phytochemistry, 65, 1247–1253.
29.
JoshiBS, RaneDF. (1967) The structure and synthesis if corymbosin, a flavone from Webera corymbosa Willd. Tetrahedron Letters, 46, 4579–4581.
30.
FraserAW, LewisJR. (1974) Flavonoids from Merrillia caloxylon. Phytochemistry, 13, 1561–1564.
31.
Valant-VetscheraKM, FischerR, WollenweberE. (2003) Exudate flavonoids in species of Artemisia (Asteraceae-Anthemideae): new results and chemosystematic interpretation. Biochemical Systematics and Ecology, 31, 487–498.
32.
TóthL, BulyákiM, BujtásGY. (1981) über die Flavonoide von Rhinanthus angustifolius Gmel. Em. Soó. Pharmazie, 36, 577.
33.
DesaiHK, GawadDH, GovindachariTR, JoshiBS, ParthasarathyPC, RamachandranKS, RavindranathKR, SidhayeAR, VisawathanN. (1976) Chemical investigation of some Indian plants: Part IX. Indian Journal of Chemistry, 14B, 473–476.
34.
GarciaR, MarcoJA, SoaneE, TortajadaA. (1981) Triterpenes, waxes and tricin in Phoenix canariensis. Journal of Natural Products, 44, 111–113
35.
EbertM, MerfortI, WilluhnG. (1988) Flavonoid distribution in Arnica subgenera montana and austromontana. Phytochemistry, 27, 3849–3851.
36.
LiuY-L, MabryTJ. (1981) Flavonoids from Artemisia frigida. Phytochemistry, 20, 1389–1395.
37.
JacobsH, BunburyM, McLeanS. (1986) Tricin from Vernonia remotiflora. Journal of Natural Products, 49, 1158–1159.
38.
YuS, FangN, MabryTJ. (1987) Flavonoid aglycones from Xanthocephalum gymnospermoides var. gymnospermoides. Phytochemistry, 26, 2131–2133.
39.
GuoB-L, KuW-K, YuJ-G, XiaoP-G. (1996) Brevicornin, a flavonol from Epimedium brevicornum. Phytochemistry, 41, 991–992.
40.
WuF-E, KoikeK, NikaidoT, IshiK, OhmotoT, IkedaK. (1990) Terpenoids and flavonoids from Arenaria kansuensis. Chemical and Pharmaceutical Bulletin, 38, 2281–2282.
41.
KuwabaraH, MouriK, OtsukaH, KasalR, YamasakiK. (2003) Tricin from a Malagasy Connariaceous plant with potent antihistaminic activity. Journal of Natural Products, 66, 1273–1275.
42.
SalmenkalloM, McCormickS, MabryTJ, DellamonicaG, ChopinJ. (1982) The flavonoids of Trichophorum cespitosum. Phytochemistry, 21, 2990–2991.
43.
Braz-FilhoB, GottliebOR, Vieira PinhoSL, Queiroz MonteFJ, da RochaAI. (1973) Flavonoids from Amazonian Leguminosae. Phytochemistry, 12, 1184–1186.
44.
PopoviciG, WeissenböckG, BouillantM.-L, DellamonicaG, ChopinJ. (1977) Isolation and characterization of flavonoids from Avena sativa L. Zeitschrift fuer Pflanzenphysiologie, 85, 103–115.
45.
BenavidesA, BassarelloC, MontoroP, VilegasW, PiacenteS, PizzaC. (2007) Flavonoids and isoflavonoids from Gynerium sagittatum. Phytochemistry, 68, 1277–1284.
46.
KongC, XuX, ZhouB, HuF, ZhangC, ZhangM. (2004) Two compounds from allelopathic rice accesssion and their inhibitory activity on weeds and fungal pathogens. Phytochemistry, 65, 1123–1128.
47.
WollenweberE, DörrM. (2008) Flavonoid aglycones from the lipophilic exudates of some species of Rosaceae. Biochemical Systematics and Ecology, 36, 481–483.
48.
WollenweberE, DörsamM, DörrM, RoitmanJN, Valant-VetscheraKM. (2005) Chemodiversity of surface flavonoids in Solanaceae. Zeitschrift für Naturforschung, 60C, 661–670.
49.
LeeK-H, TagaharaK, SuzukiH, WuR-Y, HarunaM, HallIH, HuangH-C, ItoK, IidaT, LaiJ-S. (1981) Antitumor agents. 49. Tricin, kaempferol-3-O-β-D-glucopyranoside and (+)-nortrachelogenin, antileukemic principles form Wikstroemia indica. Journal of Natural Products, 44, 530–535.
50.
AkkalS, BenayacheF, BenayacheS, JayM. (1997) Flavonoids from Centaurea incana. Biochemical Systematics and Ecology, 25, 361–362.
51.
KobzarAJ, NikonovGK. (1986) Flavonoids from overground parts of Betonica officinalis. Khimiya Prirodnykh Soedinenii, 636–637.
52.
WollenweberE, DörrM, BohmBA, RoitmanJN. (2004) Exudate flavonoids of eight species of Ceanothus (Rhamnaceae). Zeitschrift für Naturforschung, 59C, 459–462.
53.
CitogluGS, YilmazBS, TarikahyaB, TipirdamazR. (2005) Chemotaxonomy of Ballota species. Chemistry of Natural Compounds, 41, 299–302.
KinoshitaT, FirmanK. (1997) Myricetin-5,7,3′,4′,5′-pentamethylether and other methylated flavonoids from Murraya paniculata. Phytochemistry, 45, 179–181.
