Four new compounds, a dibenzylbutane lignin, plasiaticine F (1), an acetylenic glycoside, plasiaticine G (2), an indole alkaloid, plasiaticine H (3), and an ionone derivative, plasiaticine I (4), were isolated from the seeds of Plantago asiatica. The structures of the new compounds were elucidated on the basis of comprehensive analysis of spectroscopic data. Compounds 1–3 were tested for their cytotoxicity, but lacked significant activity.
YinJ.Y., LinH.X., LiJ., WangY.X., CuiS.W., NieS., XieM. (2012) Structural characterization of a highly branched polysaccharide from the seeds of Plantago asiatica L. Carbohydrate Polymers, 87, 2416–2424.
2.
HuangD.F., TangY.F., NieS.P., WanY., XieM.Y., XieX.M. (2009) Effect of phenylethanoid glycosides and polysaccharides from the seed of Plantago asiatica L. on the maturation of murine bone marrow-derived dendritic cells. European Journal of Pharmacology, 620, 105–111.
3.
HarborneJ., WilliamsC.A. (1971) 6-Hydroxyluteolin and scutellarein as phyletic markers in higher plants. Phytochemistry, 10, 367–378.
4.
SalamaHMHS, SaffanS.E.S. (2003) Triterpenoids and flavonoids from the air-dried aerial parts of Plantago amplexicaulis.Kuwait Journal of Science and Engineering, 30, 109–118.
5.
MolgaardP. (1986) Population genetics and geographical distribution of caffeic acid esters in leaves of Plantago major in Denmark. Journal of Ecology, 1127–1137.
6.
NishibeS., TamayamaY., SasaharaM., AndaryC. (1995) A phenylethanoid glycoside from Plantago asiatica.Phytochemistry, 38, 741–743.
LiL., LiuC.M., LiuZ.Q., WangJ. (2008) Isolation and purification of phenylethanoid glycosides from plant extract of Plantago asiatica by high performance centrifugal partition chromatography. Chinese Chemical Letters, 19, 1349–1352.
9.
HandjievaN., SpassovS., BodurovaG., SaadiH., PopovS., PurebO., ZamjansanJ. (1991) Majoroside, an iridoid glycoside from Plantago major.Phytochemistry, 30, 1317–1318.
10.
TaskovaR., HandjievaN., EvstatievaL., PopovS. (1999) Iridoid glucosides from Plantago cornuti, Plantago major and Veronica cymbalaria.Phytochemistry, 52, 1443–1445.
11.
JohnstonJ., BowersM.D., RankerT.A. (1997) Iridoid glycoside and allozyme variation within and among populations of Plantago rhodosperma Decne. (Plantaginaceae). Biochemical Systematics and Ecology, 25, 581–590.
12.
BowersM.D. (1996) Variation in iridoid glycosides in a population of Plantago patagonica Jacq. (Plantaginaceae) in Colorado. Biochemical Systematics and Ecology, 24, 207–210.
13.
RingbomT., SeguraL., NoreenY., PereraP., BohlinL. (1998) Ursolic acid from Plantago major, a selective inhibitor of cyclooxygenase-2 catalyzed prostaglandin biosynthesis. Journal of Natural Products, 61, 1212–1215.
14.
TarvainenM., SuomelaJ.P., KallioH., YangB. (2009) Triterpene acids in Plantago major: Identification, quantification and comparison of different extraction methods. Chromatographia, 71, 279–284.
15.
MuraiM., TamayamaY., NishibeS. (1995) Phenylethanoids in the herb of Plantago lanceolata and inhibitory effect on arachidonic acid-induced mouse ear edema. Planta Medica, 61, 479–480.
16.
ShoyamaY., MatsumotoM., NishiokaI. (1987) Phenolic glycosides from diseased roots of Rehmannia glutinosa var. purpurea. Phytochemistry, 26, 983–986.
17.
Rice-EvansC.A., MillerN.J., PagangaG. (1996) Structure-antioxidant activity relationships of flavonoids and phenolic acids. Free Radicals in Biology and Medicine, 20, 933–956.
AndaryC., WyldeR., LaffiteC., PrivatG., WinternitzF. (1982) Structures of verbascoside and orobanchoside, caffeic acid sugar esters from Orobanche rapum-genistae. Phytochemistry, 21, 1123–1127.
20.
ToyodaM., TanakaK., HoshinoK., AkiyamaH., TanimuraA., SaitoY. (1997) Profiles of potentially antiallergic flavonoids in 27 kinds of health tea and green tea infusions. Journal of Agricultural and Food Chemistry, 45, 2561–2564.
21.
SamuelsenA.B. (2000) The traditional uses, chemical constituents and biological activities of Plantago major L. A review. Journal of Ethnopharmacology, 71, 1–21.
22.
MitsuhashiH. (1988) Illustrated Medicinal Plants of the World in Colour.Hokuryukan, Tokyo, Japan, 493.
23.
HuangD., XieM., YinJ., NieS., TangY., XieX., ZhouC. (2009) Immunomodulatory activity of the seeds of Plantago asiatica L. Journal of Ethnopharmacology, 124, 493–498.
24.
GaoZ.H., KongL.M., ZouX.S., ShiY.M., ShangS.Z., LuoH.R., LiangC.Q., LiX.N., LiY., DuX., XiaoW.L., SunH.D. (2012) Four new indole alkaloids from Plantago asiatica.Natural Products and Bioprospecting, 2, 249–254.
25.
BarltropJ.A., OwenT.C., CoryA.H., CoryJ.G. (1991) 5-(3-Carboxymethoxyphenyl)-2-(4,5-dimethylthiazolyl)-3-(4-sulfophenyl)tetrazolium, inner salt (MTS) and related analogs of 3-(4,5-dimethylthiazolyl)-2,5-diphenyltetrazolium bromide (MTT) reducing to purple water-soluble formazans as cell-viability indicators. Bioorganic and Medicinal Chemistry Letters, 1, 611–614.
26.
ReedL.J., MuenchH. (1938) A simple method of estimating fifty percent endpoints. The American Journal of Hygiene, 27, 493–497.
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