ˇ
T. Rezanka et al. / Phytochemistry 70 (2009) 1049–1054
1
054
Stratmann, Yazyev, O., Austin, A.J., Cammi, R., Pomelli, C., Ochterski, J.W., Ayala,
Ramesh, C., Ravindranath, N., Ram, T.S., Das, B., 2003. Arylnaphthalide lignans from
Cleistanthus collinus. Chem. Pharm. Bull. 51, 1299–1300.
Reynaud, J., Couble, A., Raynaud, J., 1988. Flavonoids from Acanthus mollis L.
(Acanthaceae). Pharmazie 43, 373–374.
Rezanka, T., Dembitsky, V.M., 2006. The colleflaccinosides, two chiral
bianthraquinone glycosides with antitumor activity from the lichen Collema
flaccidum collected in Israel and Russia. Nat. Prod. Res. 20, 969–980.
Rezanka, T., Sigler, K., 2007. Hirtusneanoside, an unsymmetrical dimeric
tetrahydroxanthone from the lichen Usnea hirta. J. Nat. Prod. 70, 1487–1491.
Rezanka, T., Rezanka, P., Sigler, K., 2008. A biaryl xanthone derivative having axial
chirality from Penicillium vinaceum. J. Nat. Prod. 71, 820–823.
P.Y., Morokuma, K., Voth, G.A., Salvador, P., Dannenberg, J.J., Zakrzewski, V.G.,
Dapprich, S., Daniels, A.D., Strain, M.C., Farkas, O., Malick, D.K., Rabuck, A.D.,
Raghavachari, K., Foresman, J.B., Ortiz, J.V., Cui, Q., Baboul, A.G., Clifford, S.,
Cioslowski, J., Stefanov, B.B., Liu, G., Liashenko, A., Piskorz, P., Komaromi, I.,
Martin, R.L., Fox, D.J., Keith, T., Al-Laham, M.A., Peng, C.Y., Nanayakkara, A.,
Challacombe, M., Gill, P.M.W., Johnson, B., Chen, W., Wong, M.W., Gonzalez, C.,
Pople, J.A., 2004. Gaussian 03, Revision C.02. Gaussian, Inc., Wallingford, CT.
Gordaliza, M., Castro, M.A., del Corral, J.M.M., San Feliciano, A., 2000. Antitumor
properties of podophyllotoxin and related compounds. Curr. Pharm. Des. 6,
1
811–1839.
Innocenti, G., Puricelli, L., Piacente, S., Caniato, R., Filippini, R., Cappelletti, E.M.,
002. Patavine, a new arylnaphthalene lignan glycoside from shoot cultures of
Susplugas, S., Van Hung, N., Bignon, J., Thoison, O., Kruczynski, A., Sevenet, T.,
2
Gueritte, F., 2005. Cytotoxic arylnaphthalene lignans from a Vietnamese
Haplophyllum patavinum. Chem. Pharm. Bull. 50, 844–846.
acanthaceae, Justicia patentiflora. J. Nat. Prod. 68, 734–738.
Johnson, D.A., Liu, H.W., 1999. Deoxysugars: occurrence, genetics and mechanisms
of biosynthesis. In: Barton, D., Nakanishi, K., Meth-Cohn, O. (Eds.),
Comprehensive Natural Products Chemistry, vol. 3. In: Pinto, B.M. (vol. Ed.),
Carbohydrates and Their Derivatives Including Tannins, Cellulose and Related
Lignins. Elsevier, Amsterdam, pp. 311–362.
Therien, M., Fitzsimmons, B.J., Scheigetz, J., Macdonald, D., Choo, L.Y., Guay, J.,
Falgueyret, J.P., Riendeau, D., 1993. Justicidin E: a new leukotriene biosynthesis
inhibitor. Bioorg. Med. Chem. Lett. 3, 2063–2066.
Ukita, T., Nakamura, Y., Kubo, A., Yamamoto, Y., Takahashi, M., Kotera, J., Ikeo, T.,
1999. 1-Arylnaphthalene lignan: a novel scaffold for type 5 phosphodiesterase
inhibitor. J. Med. Chem. 42, 1293–1305.
Umezawa, T., 2003. Diversity in lignan biosynthesis. Phytochem. Rev. 2, 371–390.
Ward, R.S., 1999. Lignans, neolignans and related compounds. Nat. Prod. Rep. 16,
75–96 (and proceedings papers published in this series).
Kanchanapoom, T., Kamel, M.S., Kasai, R., Yamasaki, K., Picheansoonthon, C., Hiraga,
Y., 2001. Lignan glucosides from Acanthus ilicifolius. Phytochemistry 56, 369–
3
72.
Lamidi, M., Rondi, M.L., Faure, R., Debrauwer, L., Nze-Ekekang, L., Balansard, G.,
Ollivier, E., 2006. Flavonoid glycosides from Sclerochiton vogelii. Compt. Rend.
Chem. 9, 1309–1313.
Weng, J.R., Ko, H.H., Yeh, T.L., Lin, H.C., Lin, C.N., 2004. Two new arylnaphthalide
lignans and antiplatelet constituents from Justicia procumbens. Arch. Pharm.
337, 207–212.
Leroux, F., 2004. Atropisomerism, biphenyls, and fluorine:
rotational barriers and twist angles. ChemBioChem 5, 644–649.
Liu, G.R., Wu, J., Si, J.Y., Wang, J.M., Yang, M.H., 2008. Complete assignments of 1H
a comparison of
0
0
Wolf, R.B., Spencer, G.F., Plattner, R.D., 1985. Benzoxazolinone, 2,4-dihydroxy-1,4-
benzoxazin-3-one, and its glucoside from Acanthus mollis seeds inhibit
velvetleaf germination and growth. J. Nat. Prod. 48, 59–63.
13
and
C NMR data for three new arylnaphthalene lignan from Justicia
procumbens. Magn. Reson. Chem. 46, 283–286.
Wolf, C., Pirkle, W.H., Welch, C.J., Hochmuth, D.H., Konig, W.A., Chee, G.L., Charlton,
J.L., 1997. Determination of the enantiomerization barrier of arylnaphthalene
lignans by cryogenic subcritical fluid chromatography and computer
simulation. J. Org. Chem. 62, 5208–5210.
Wu, S.J., Wu, T.S., 2006. Cytotoxic arylnaphthalene lignans from Phyllanthus
oligospermus. Chem. Pharm. Bull. 54, 1223–1225.
Wu, J., Zhang, S., Li, Q., Huang, J., Xiao, Z., Long, L., 2004. Two new cyclolignan
glycosides from Acanthus ilicifolius. Z. Naturforsch. B: J. Chem. Sci. 59, 341–344.
Yeo, H., Li, Y., Fu, L., Zhu, J.L., Gulden, E.A., Dutschman, G.E., Lee, Y., Chung, R., Huang,
E.S., Austin, D.J., Cheng, Y.C., 2005. Synthesis and antiviral activity of
helioxanthin analogues. J. Med. Chem. 48, 534–546.
Mabberley, D.J., 1987. The Plant-Book. A Portable Dictionary of the Higher Plants.
Cambridge University Press, Cambridge, UK.
Podlasek, C.A., Wu, J., Stripe, W.A., Bondo, P.B., Serianni, A.S., 1995. [13C]-enriched
1
3
1
methyl aldopyranosides: structural interpretations of C– H spin-coupling
constants and 1H chemical shifts. J. Amer. Chem. Soc. 117, 8635–8644.
Pratt, K., Kumar, P., Chilton, W.S., 1995. Cyclic hydroxamic acids in dicotyledonous
plants. Biochem. System. Ecol. 23, 781–785.
Rajasekhar, D., Vanisree, M., Subbaraju, G.V., 1999. Justicia lignans: part 4 two new
arylnaphthalide lignans from Justicia neesii Ramamoorthy. Indian J. Chem. Sect.
B – Org. Chem. Incl. Med. Chem. 38, 713–717.