Two new compounds, baccataxinine (1) and baccalignan (2), were isolated from the Taxus baccata, together with 16 known ones. Their structures were elucidated by comprehensive spectroscopic analyses of HR-ESI-MS, NMR and IR. Compound 1 is a taxane diterpenoid possessing a rare dioxolane ring between C-1 and C-2, while 2 is the first benzofuran neolignan from this species. Furthermore, they were also evaluated for their α-glucosidase inhibitory activity, but none of them showed considerable inhibitory effects.
WangY.F., ShiQ.W., DongM., KiyotaH., GuY.C., CongB. (2011) Natural taxanes: developments since 1828. Chemical Reviews, 111, 7652–7709.
2.
TopcuG., DemirkiranO. (2007) Bioactive Heterocycles V. Topics in Heterocyclic Chemistry, 11, 103–144.
3.
LouisH.D., JenniskensL.H.D., RozendaalE.L.V., T.A.V. (1996) Identification of six taxine alkaloids from Taxus baccata Needles. Journal of Natural Products, 59, 117–123.
4.
LucasH. (1856) Ueber ein in den Blattern von Taxus baccata L. enhaltenes Alkaloid (das Taxin). Archiv der Pharmazie, 135, 145.
5.
WaniM.C., TaylorH.L., WallM.E., CoggonP., McPhailA.T. (1971) The isolation and structure of taxol, a novel antileukemic and antitumor agent from Taxus breoifolia.Journal of the American Chemical Society, 93, 2325–2326.
6.
DangP.H., NguyenH.H.T., TruongH.T.T., DoT.N.V., NguyenH.X., NguyenM.T.T., AbeM., TakagiR., NguyenN.T. (2017) Two ring opened oxetane taxoids containing a C-20 benzoyloxy group from the roots of Taxus wallichiana Zucc.Tetrahedron Letters, 58, 3897–3900.
7.
DangP.H., NguyenH.X., NguyenH.H.T., VoT.D., LeT.H., PhanT.H.N., NguyenM.T.T., NguyenN.T. (2017) Lignans from the roots of Taxus wallichiana and their α-glucosidase inhibitory activities. Journal of Natural Products, 80, 1876–1882.
8.
DangP.H., NguyenH.X., DuongT.T.T., TranT.K.T., NguyenP.T., VuT.K.T., VuongH.C., PhanN.H.T., NguyenM.T.T., NguyenN.T., AwaleS. (2017) α-Glucosidase inhibitory and cytotoxic taxane diterpenoids from the stem bark of Taxus wallichiana.Journal of Natural Products, 80, 1087–1095.
9.
ThomasP.A., PolwartA. (2003) Taxus baccata L. Journal of Ecology, 91, 489–524.
10.
MalikS., CusidóR.M., MirjaliliM.H., MoyanoE., PalazónJ., BonfillM. (2011) Production of the anticancer drug taxol in Taxus baccata suspension cultures: A review. Process Biochemistry, 46, 23–34.
11.
AsifM., RizwaniG.H., ZahidH., KhanZ., QasimR. (2016) Pharmacognostic studies on Taxus baccata L.: A brilliant source of Anti-cancer agents. Pakistan Journal of Pharmaceutical Sciences, 29, 105–109.
12.
ShiQ.W., LedermanZ., SauriolF., MccollumR.S., ZamirL.O. (2004) A yew in Israel, new taxane derivatives. Journal of Natural Products, 67, 168–173.
ShenY.C., ChenC.Y., HungM.C. (2000) Taxane diterpenoids from seeds of Taxus mairei.Chemical and Pharmaceutical Bulletin, 48, 1344–1346.
15.
LunB.S., ShaoL.W., WangY., LiC.C., YuH., WangC.H., ZhuY. (2017) Taxanes from Taxus wallichiana var. mairei cultivated in the southern area of the Yangtze River in China. Natural Product Research, 31, 2341–2347.
16.
PetzkeT.L., ShiQ.W., SauriolF., MamerO., ZamirL.O. (2004) Taxanes from rooted cuttings of Taxus canadensis.Journal of Natural Products, 67, 1864–1869.
17.
ZamirL.O., ZhangJ.Z., KuttererK., SauriolF., (1998) 5-epi-Canadensene and other novel metabolites of Taxus canadensis.Tetrahedron, 54, 15845–15860.
18.
ShiQ.W., OritaniT.HoriguchiT., SugiyamaT., MurakamiR., YamadaT. (2000) Four novel taxane diterpenoids from the needles of Japanese yew, Taxus cuspidata. Bioscience, Biotechnology, and Biochemistry, 63, 924–929.
19.
FujiK., TanakaK., LiB. (1993) Novel diterpenoids from Taxus chinensis.Journal of Natural Products, 56, 1520–1531.
20.
FujiK., TanakaK., LiB. (1995) Structures of nine new diterpenoids from Taxus Chinese.Tetrahedron, 51, 10175–10188.
21.
ShiQ.W., OritaniT., KiyotaH., ZhaoD. (2000) Taxane diterpenoids from Taxus yunnanensis and Taxus cuspidata.Phytochemistry, 54, 829–834.
22.
SatoK., AkaiS., SugitaN., OhsawaT., KogureT., ShojiH., YoshimuraJ. (2005) Novel and stereocontrolled synthesis of (+/-)-tetrodotoxin from myo-inositol. Journal of Organic Chemistry, 70, 7496–7504.
23.
GopalaiahK., KavithaJ., KanumuriR.V., RajasekharD., SubbarajuG.V. (2001) Two new lignans from Justicia neesii Ramamoorthy (white flower variety). Indian Journal of Chemistry, Section B., 40B, 596–600.
24.
RehmanN.U., KhanA., Al-HarrasiA., HussainH., WadoodA., RiazM., Al-AbriZ. (2018) New alpha-glucosidase inhibitors from the resins of Boswellia species with structure-glucosidase activity and molecular docking studies. Bioorganic Chemistry, 79, 27–33.
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