Phytochemicals from bryophytes: Structures and biological activity Review
Main Article Content
Abstract
Little attention has been paid to the bryophytes as sources for human diet despite the presence of 23,000 species in the world. Some mosses contain Vitamin B1, tocopherols, prostaglandin-like highly unsaturated fatty acids and phenolic compounds. On the other hand, liverworts contain enantiomeric mono-, sesqui- and diterpenoids similar to those found in vascular plants. Additionally, they possess bibenzyls, bis-bibenzyls and polyketides, many of them showing various bioactivity, such as antimicrobial, antiviral, anti-inflammatory, cytotoxicity against cancer cell lines, muscle relaxing, antioxidant and others. In this paper, the structures of phytochemicals from bryophytes and their biological activities are discussed.
Downloads
Metrics
Article Details
This work is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License.
Authors retain copyright and grant the journal right of first publication with the work simultaneously licensed under a Creative Commons Attribution license 4.0 that allows others to share the work with an acknowledgement of the work's authorship and initial publication in this journal.
References
Y. Asakawa, in Progress in the Chemistry of Organic Natural Products, G. W. Kirby, H.Grisebach, W. Herz, Eds., Springer, Vienna, 1982, p. 1 (https://doi.org/10.1007/978-3-7091-8677-0_1)
Y. Asakawa, in Progress in The Chemistry of Organic Natural Products, C. Tamm, R. E. Moore, W. Herz, W. B. Kirby, W. Steglich, Eds., Springer, Vienna, 1995, p. 1
C. Suire, M. Toyota, N. Tokunaga, T. Takemoto, Y. Asakawa, J. Hatt. Bot. Lab. 45 (1979) 395
A. Ludwiczuk, Y. Asakawa, Heterocycles 86 (2012) 891 (https://dx.doi.org/10.3987/REV-12-SR(N)5)
A. Ludwiczuk, F. Nagashima, Y. Asakawa, Phytochemistry 55 (2013) 55 (https://doi.org/10.1016/j.phytochem.2012.04.012)
A. Ludwiczuk, F. Nagashima, Y. Asakawa, in Progress in the Chemistry of Organic Natural Products, D. A. Kinghorn, H. Falk, J. Kobayashi, Eds., Springer, Vienna, 2013, p. 1 (https://doi.10.1007/978-3-7091-1084-3)
A. Ludwiczuk, Y. Asakawa, Rośliny Lecznicze w Polsce i na Świecie (Medical Plants in Poland and in the World) 2 (2008) 33
A. Ludwiczuk, Y. Asakawa, Rośliny Lecznicze w Polsce i na Świecie (Medical Plants in Poland and in the World) 3/4 (2008) 43
A. Ludwiczuk, Y. Asakawa, J. Nat. Prod. 81 (2018) 641 (https://doi.org/10.1021/acs.jnatprod.6b01046)
Y. Asakawa, A. Ludwiczuk, M. Novakovic, D. Bukvicki, K. Y. Anchang, J. Nat. Prod. (2021) in press (https://doi.org/10.1021/acs.jnatprod.1c00302)
A. Matsuo, H. Ando, in Advances in Bryology, W. J. Schultze-Motel, Ed., Cramer, Vaduz, Liechtenstein, 1984, p. 133
G. Bezanger-Beauquensne Debraux, H. Garnier, Resources Medicinales de la Flore Francaise, Tome 1, Vigot Freres, Paris, 1961
Y. Asakawa, M. Toyota, M. Tori, T. Hashimoto, Spectroscopy 14 (2000) 149
Y. Asakawa, in Phytochemicals in Human Health Protection, Nutrition, and Plant Defense, J. Romeo, Ed., Kluwer Academic/Plenum Publishers, New York, 1999, p. 319 (https://doi.org/10.1007/978-1-4615-4689-4_12)
Y. Asakawa, in Bioactive Natural Products: Detection, Isolation, and Structural Determination, R. J. Molyneux, S. M. Colegate, Eds., Press, Boca Raton, FL, 1993, p. 319
Y. Asakawa, Pure Appl. Chem. 66 (1994) 2193 (https://doi.org/10.1351/pac199466102193)
Y. Asakawa, Phytochemistry 56 (2001) 29 (https://doi.org/10.1016/s0031-9422(00) 00454-4)
Y. Asakawa, Phytochemistry 65 (2004) 623 (https://doi.org/10.1016/j.phytochem.2004.01.003)
Y. Asakawa, Aroma Research 5 (2004) 204 (https://doi.org/10.1016/j.phytochem.2004.01.003)
Y. Asakawa, Chenia 9 (2007) 73
A. Ludwiczuk, Y. Asakawa, Malaysian J. Sci. 28 (2009) 229
Y. Asakawa, A. Ludwiczuk, F. Nagashima, M. Toyota, T. Hashimoto, M. Tori, Y. Fukuyama, L. Harinantenaina, Heterocycles 77 (2009) 99 (https://doi.org/10.1002/chin.200917258)
Y. Asakawa, M. Toyota, M. Tori, T. Hashimoto, Spectroscopy 14 (2000) 149 (https://doi.org/10.1155/2000/570265)
H. Inoue, Kagaku Asahi 8 (1988) 116
Y. Asakawa, J. Hattori Bot. Lab. 5 (1985) 284
Bryology in the New Millenium, H. Mohamed, B. B. Baki, A. Nasrulhaq-Boyce, P. K. Y. Lee (Eds.), University of Malaya, Kuala Lumpur, 2008. p. 1
S. H. von Reuβ, W. A. König, Phytochemistry 65 (2004) 3113 (https://doi.10.1016/j.phytochem.2004.10.002)
Y. Asakawa, M. Toyota, H. Tanaka, T. Hashimoto, D. Joulain. J. Hattori Bot. Lab. 78 (1995) 183 (https://doi.org/10.18968/jhbl.78.0_183)
A. Ludwiczuk, I. Komala, A. Pham, J.-P. Bianchini, P. Raharivelomanana, Y. Asakawa, Nat. Prod. Commun. 4 (2009) 1387 (https://doi.org/10.1177/1934578X0900401015)
S. Sugawa, Hikobia 2 (1960) 119
Y. Asakawa, in Bryophyte Development: Physiology and Biochemistry, R. N. Chopra, S. C. Bhatla, Eds., CRC Press, Boca Raton, FL, 1990, p. 259
Y. Asakawa, in Bryophytes: Their Chemistry and Chemical Taxonomy, D. H. Zinsmeister, R. Mues, Eds., Oxford University Press, Oxford, 1990, p. 369
D. Takaoka, H. Nozaki, H. Udaka, K. Hamazaki, N. Nishimura, N. Takashima, in Proceedins of 15th International Botanical Congress, 1993, Yokohama, Japan, p. 370
M. Nishiki, M. Toyota, Y. Asakawa, in Proceedings of 51st Symposium on Chemistry of Terpenes, 2007, Nagahama, Japan, Essential Oils and Aromatics, p. 260
Y. Asakawa, F. Nagashima, A. Ludwiczuk, J. Nat. Prod. 83 (2020) 756 (https://doi.org/10.1021/acs.jnatprod.9b01132)
K. Kondo, K. Sakai, K. Yamada, M. Namikawa, T. Ichikawa, Tetrahedron Lett. 24 (1983) 3337 (https://doi.org/10.1016/S0040-4039(00)86263-2)
T. Ichikawa, K. Yamada, M. Namikawa, K. Sakai, K. Kondo, J. Hattori Bot. Lab. 56 (1984) 209
H. H. T. Prins, Oikos 38 (1981) 374
S. C. Bhatla, S. Dhingra-Babbar, in Bryophyte development: Physiology and biochem¬istry, R. N. Chopra, S. C, Bhatla, Eds., CRC press, Boca Raton, FL, 1990, p. 79
T. L. Wang, D. J. Cove, P. Beutelmann, E. Hartmann, Phytochemistry 19 (1980) 1103 (https://doi.org/10.1016/0031-9422(80)83064-0)
Y. Asakawa, Bryol. Res. 9 (2007) 198 (https://doi.org/10.24474/bryologicalresearch.9.6_198)
S. Hayashi, T. Kami, A. Matsuo, H. Ando, T. Seki, Proc. Bryol. Soc. Jap. 2 (1977) 38
M. Mizutani, Misc. Bryol. Lichenol. 6 (1972) 64
M. Toyota, Y. Asakawa, Flav. Fragr. J. 9 (1994) 237 (https://doi.org/10.1002/ffj.2730090507)
M. Toyota, H. Koyama, Y. Asakawa, Phytochemistry 44 (1997) 1261 (https://doi.org/10.1016/S0031-9422(96)00722-4)
Y. Asakawa, M. Sono, M. Wakamatsu, K. Kondo, S. Hattori, M. Mizutani, Phytochemistry 30 (1991) 2295 (https://doi.org/10.1016/0031-9422(91)83633-V)
M. Sono, Ph.D. Thesis, Tokushima Bunri University, Tokushima, 1991, p. 1
M. Tori, M. Sono, Y. Nishigaki, K. Nakashima, Y. Asakawa, J. Chem. Soc. Perkin Trans. 1 (1991) 435 (https://doi.org/10.1039/P19910000435)
M. Toyota, T. Saito, J. Matsunami, Y. Asakawa, Phytochemistry 44 (1997) 1265 (https://doi.org/10.1016/S0031-9422(96)00723-6)
J. D. Connolly, Rev. Latinoam. Quim. 12 (1982) 121
J. D. Connolly, in Bryophytes, Their Chemistry and Chemical Taxonomy, H. D. Zinsmeister, R. Mues, Eds., Oxford University Press, Oxford, 1990, p. 41
M. Toyota, Y. Asakawa, J.-T. Frahm, Phytochemistry 29 (1990) 2334 (https://doi.org/10.1016/0031-9422(90)83066-A)
J. Spörle, Ph.D. Thesis, Universität des Saarlandes, Saarbrcken, 1990, p. 1
S. Huneck, J. D. Connolly, A. A. Freer, D. S. Rycroft, Phytochemistry 27 (1988) 1405 (https://doi.org/10.1016/0031-9422(88)80204-8)
Y. Asakawa, M. Toyota, A. Cheminat, Phytochemistry 25 (1986) 2555 (https://doi.org/10.1016/s0031-9422(00)84508-2)
W. Geis, H. Becker, Flavour Fragr. J. 16 (2001) 422 (https://doi.org/10.1002/ffj.1030)
F. Cullmann, H. Becker, J. Hattori Bot. Lab. 84 (1998) 285 (https://doi.org/10.18968/jhbl.84.0285)
Y. Asakawa, Bryol. Res. 9 (2007) 227 (https://doi.org/10.24474/bryologicalresearch.9.7_227)
H. Inoue, Koke no Sekai (World of Bryophytes), Idemitsu Ltd., Tokyo, 1978, p. 1
C. Suire, M. Toyota, S. Huneck, T. Takemoto, Y. Asakawa, J. Hattori Bot. Lab. 46 (1979) 163
Y. Asakawa, A. Ludwiczuk, L. Harinantenaina, M. Toyota, M. Nishiki, A. Bardon, K. Nii, Nat. Prod. Commun. 7 (2012) 685 (https://doi.org/10.1177/1934578X1200700601)
T. Hashimoto, Y. Okumura, K. Suzuki, S. Takaoka, Y. Kan, M. Tori, Y. Asakawa, Chem. Pharm. Bull. 43 (1995) 2030 (https://doi.org/10.1248/cpb.43.2030)
L. J. Harrison, M. Toyota, Y. Asakawa, Phytochemistry 24 (1985) 261 (https://doi.org/10.1016/S0031-9422(00)83533-5)
K. Ono, M. Toyota, Y. Asakawa, Phytochemistry 31 (1992) 1249 (https://doi.org/10.1016/0031-9422(92)80270-O)
K. Ono, H. Tanaka, T. Sakamoto, Y. Asakawa, Flav. Fragr. J. 11 (1996) 53
(https://doi.org/10.1002/(SICI)1099-1026(199601)11:1<53::AID-FFJ535>3.0.CO;2-8)
T. Hashimoto, H. Tanaka, Y. Asakawa, Chem. Pharm. Bull. 42 (1994) 1542 (https://doi.org/10.1248/cpb.42.1542)
A. Ueda, M. Toyota, Y, Asakawa, Phytochemistry 30 (1991) 567 (https://doi.org/10.1016/0031-9422(91)83728-4)
M. Toyota, I. Omatsu, J. Braggins, Y. Asakawa, Chem. Pharm. Bull. 57 (2009) 1015 (https://doi.org/10.1248/cpb.57.1015)
F. Nagashima, M. Toyota, Y. Asakawa, Phytochemistry 29 (1990) 1619 (https://doi.org/10.1016/0031-9422(90)80133-2)
D. S. Rycroft, in Bryophytes: Their Chemistry and Chemical Taxonomy, Zinsmeister, D. H., Mues, R. Eds., Oxford University Press, Oxford, 1990, p. 109
D. S. Rycroft, G. Ferguson, J. D. Connolly, L. J. Harrison, M. Parvez, R. Joseph, S. Huneck, W. Phillip, J. Chem. Res. (S) (1986) 162
Y. Asakawa, T. Masuya, M. Tori, E. O. Campbell, Phytochemistry 26 (1987) 735 (https://doi.org/10.1016/S0031-9422(00)84775-5)
Z.-Q. Lu, P.-H. Fan, M. Ji, H.-X. Lou, J. Asian Nat. Prod. Res. 8 (2006) 187 (https://doi.org/10.1080/1028602042000325537)
M. Toyota, K. Tanimura, Y. Asakawa, Planta Med. 64 (1998) 462 (https://doi.org/10.1055/s-2006-957484)
J. C. Aponte, H. Yang, A. J. Vaisberg, D. Castillo, E. Malaga, M. Verastegui, L. K. Casson, N. Stivers, P. J. Bates, R. Rojas, I. Fernandez, W. H. Lewis, C. Sarasara, M. Sauvain, R. H. Gilman, G. B. Hammond, Planta Med. 76 (2010) 705 (https://doi.10.1055/s-0029-1240681)
Y.-F. Shu, H.-C. Wei, C.-L. Wu, Phytochemistry 37 (1994) 773 (https://doi.org/10.1016/S0031-9422(00)90356-X)
I. Komala, T. Ito, F. Nagashima, Y. Yagi, M. Kawahata, K. Yamaguchi, Y. Asakawa, Phytochemistry 71 (2010) 1387 (https://doi.10.1016/j.phytochem.2010.04.023)
Y. Wang, L. J. Harrison, B. C. Tan, Tetrahedron 65 (2009) 4035 (https://doi.org/10.1016/j.tet.2009.03.026)
F. Nagashima, I. Komala, T. Ito,Y. Asakawa, Y. Yagi, in Proceedings of 53rd Symposium on Chemistry of Terpenes, Essential Oils and Aromatics, 2009, Nara, Japan, p. 266
C. Wu, A. A. L. Gunatilaka, F. L. Mc Cabe, R. K. Johnson, R.W. Spjut, D. G. I. Kingston, J. Nat. Prod. 60 (1997) 1281 (https://doi.org/10.1021/np970251u)
H. Baek, N. B. Perry, S. D. Lorimer, J. Chem. Res. (S) (2003) 14 (https://doi.org/10.3184/030823403103172977)
Y. C. Kim, V. da S. Bolzani, N. Baj, A. A. L. Gunatilaka, D. G. I. Kingston, Planta Med. 62 (1996) 61 (https://doi.org/10.1055/s-2006-957800)
J. Burgess, L. Larsen, N. B. Perry, J. Nat. Prod. 63 (2000) 537 (https://doi.org/10.1021/np990492x)
N. B. Perry, L. M. Foster, J. Nat. Prod. 58 (1995) 1131 (https://doi.org/10.1021/np50121a027)
I. Komala, T. Ito, F. Nagashima, Y. Yagi, Y. Asakawa, J. Nat. Med. 64 (2010) 417 (https://doi.org/10.1007/s11418-010-0423-8)
J. M. Scher, E. J. Burgess, S. D. Lorimer, N. B. Perry, Tetrahedron 58 (2002) 7875 (https://doi.org/10.1016/S0040-4020(02)00899-2)
S. D. Lorimer, N. B. Perry, E. J. Burgess, L. M. Foster, J. Nat. Prod. 60 (1997) 421 (https://doi.org/10.1021/np960733q)
N. B. Perry, E. J. Burgess, R. S. Tangney, Tetrahedron Lett. 37 (1996) 9387 (https://doi.org/10.1016/S0040-4039(97)82971-1)
N. B. Perry, E. J. Burgess, S.-H. Baek, R. T. Weavers, W. Geis, A. B. Mauger, Phytochemistry 50 (1999) 423 (https://doi.org/10.1016/s0031-9422(98)00602-5)
F. Nagashima, M. Kondoh, T. Uematsu, A. Nishiyama, S. Saito, M. Sato, Y. Asakawa, Chem. Pharm. Bull. 50 (2002) 808 (https://doi.org/10.1248/cpb.50.808)
N. B. Perry, E. J. Burgess, L. M. Foster, P. J. Gerard, M. Toyota, Y. Asakawa, J. Nat. Prod. 71 (2008) 258 (https://doi.org/10.1021/np070644l)
N. B. Perry, E. J. Burgess, S.-H. Baek, R. T. Weavers, Org. Lett. 3 (2001) 4243 (https://doi.org/10.1021/ol0169224)
M. Neves, R. Morais, S. Gafner, K. Hostettmann, Phytotherapy Res. 12 (1998) 21 (https://doi.org/10.1002/(SICI)1099-1573(1998)12:1+3.0.CO;2-1)
S. M. Wong, Y. Oshima, J. M. Pezzuto, H. H. S. Fong, N. R. Farnsworth, J. Pharm. Sci. 75 (1986) 317 (https://doi.org/10.1002/jps.2600750324)
I. Komala, T. Ito, F. Nagashima, Y. Yagi, Y. Asakawa, Nat. Prod. Commun. 6 (2011) 303 (https://doi.org/10.1177/1934578X1100600301)
Y. Asakawa, Nat. Prod. Commun. 12 (2017) 1335 (https://doi.org/10.1177/1934578X1701200845)
Y. Asakawa, R. Matsuda, Phytochemistry 21 (1982) 2143 (https://doi.org/10.1016/0031-9422(82)83073-2)
S. Friederich, U. H. Maier, B. Deus-Meumann, Y. Asakawa, M. H. Zenk, Phytochemistry 50 (1999) 589 (https://doi.org/10.1016/S0031-9422(98)00557-3)
S. Friederich, M. Rueffer, Y. Asakawa, M. H. Zenk, Phytochemistry 52 (1999) 1195
H. Morita, Y. Tomizawa, T. Tsuchiya, Y. Hirasawa, T. Hashimoto, Y. Asakawa, Bioorg. Med. Chem. Lett. 19 (2009) 493 (https://doi.org/10.1016/j.bmcl.2008.11.036)
M. Novakovic, D. Bukvicki, B. Andjelkovic, T. Ilic-Tomic, M.Veljic, V. Tesevic, Y. Asakawa, J. Nat. Prod. 82 (2019) 694 (https://doi.org/10.1021/acs.jnatprod.8b00390)
I. Opsenica, J. Nikodinovic-Runic, L. Koracak, M. Novakovic, M. Zlatovic, S. Simic,T. Ilic Tomic, Y. Asakawa, Fitoterapia 142 (2020) 10452 (https://doi.org/10.1016/j.fitote.2020.104520)
W.-J. Huang, C.-L. Wu, C.-W. Lin, L.-L. Chi, P.-Y. Chen, C.-J. Chiu, C.-Y. Huang, C.-N. Chen, Cancer Lett. 291 (2010) 108 (https://doi.org/10.1016/j.canlet.2009.10.006)
C.-F. Xie, J.-B. Qu, X.-Z. Wu, N. Liu, M. Ji, H.-X. Lou, Nat. Prod. Res. 24 (2010) 515 (https://doi.org /10.1080/14786410802271587)
Y.-Q. Shi, J.-X. Liao, X.-J. Qu, H.-Q. Yuan, S. Li, J.-B. Qu, H.-X. Lou, Cancer Lett. 262 (2008) 173 (https://doi.org /10.1016/j.canlet.2007.12.014)
Y.-Q. Shi, X.-J. Qu, Y.-X. Liao, C.-F. Xie, Y.-N. Cheng, S. Li, H.-X. Lou, Eur. J. Pharmacol. 584 (2008) 66 (https://doi.org /10.1016/j.ejphar.2008.01.039)
A. Speicher, M. Groh, J. Zapp, A. Shaumloffel, M. Knauer, G. Bringmann, Synlett 11 (2009) 1852 (https://doi.org/10.1055/s-0029-1217510)
S. D. Lorimer, N. B. Perry, Planta Med. 60 (1994) 386 (https://doi.org/10.1055/s-2006-959511)
B. C. H. May, E. Nakaishi, L. M. Foster, M. Toyota, N. B. Perry, R. T. Weavers, S. D. Lorimer, Y. Asakawa, J. Nat. Prod. 59 (1996) 729 (https://doi.org/10.1021/np9603378)
S. H. Baek, H. J. Oh, J. A. Lim, H. J. Chun, H. O. Lee, J. W. Ahn, N. B. Perry, H. M. Kim, Bull. Korean Chem. Soc. 25 (2004) 195 (https://doi.org/10.5012/bkcs.2004.25.2.195)
F. Nagashima, W. Kasai, M. Kondoh, M. Fujii, Y. Watanabe, J. E. Braggins, Y. Asakawa, Chem. Pharm. Bull. 51 (2003) 1189 (https://doi.org/10.1248/cpb.51.1189)
F. Nagashima, M. Kondoh, M. Fujii, S. Takaoka, Y. Watanabe, Y. Asakawa, Tetrahedron 61 (2005) 4531 (https://doi.org/10.1016/j.tet.2005.03.010)
F. Nagashima, M. Kondoh, M. Kawase, S. Simizu, H. Osada, M. Fujii, Y. Watanabe, M. Sato, Y. Asakawa, Planta Med. 69 (2003) 377 (https://doi.org/10.1055/s-2003-38888)
M. Kondoh, I. Suzuki, M. Sato, F. Nagashima, S. Simizu, M. Harada, M. Fujii, H. Osada, Y. Asakawa, Y. Watanabe, J. Pharmacol. Exp. Ther. 311 (2004) 115 (https://doi.org/10.1124/jpet.104.069690)
I. Suzuki, M. Kondoh, M. Harada, N. Koizumi, M. Fujii, F. Nagashima, Y. Asakawa, Y. Watanabe, Planta Med. 70 (2004) 723 (https://doi.org/10.1055/s-2004-827202)
I. Suzuki, M. Kondoh, F. Nagashima, M. Fujii, Y. Asakawa, Y. Watanabe, Planta Med. 70 (2004) 401 (https://doi.org/10.1055/s-2004-818966)
M. Kondoh, F. Nagashima, I. Suzuki, M. Harada, M. Fujii, Y. Asakawa, Y. Watanabe, Planta Med. 71 (2005) 1005 (https://doi.org/10.1055/s-2005-873133)
M. Kondoh, I. Suzuki, M. Harada, F. Nagashima, M. Fujii, Y. Asakawa, Y. Watanabe, Planta Med. 71 (2005) 275 (https://doi.org/10.1055/s-2005-837830)
I. Shunsuke, N. Yosuke, T. Osamu, H. Toshifumi, Chem. Let. 26 (1997) 837 (https://doi.org/10.1246/cl.1997.837)
D.-X. Guo, Y. Du, Y.-Y. Wang, L.-M. Sun, J.-B. Qu, X.-N. Wang, H.-X. Lou Nat. Prod. Commun. 4 (2009) 1319 (https://doi.org/10.1177/1934578X0900401001)
H. Nozaki, K.-I. Hayashi, N. Nishimura, H. Kawaide, A. Matsuo, D. Takaoka, Biosci. Biotechnol. Biochem.71 (2007) 3127 (https://doi.org/10.1271/bbb.70625)
S.-J. Kim, H.-R. Park, E. Park, S.-C. Lee, J. Agric. Food Chem. 55 (2007) 1702 (https://doi.org/10.1021/jf062020b)
G.-Q. Zheng, D. K. Ho, P. J. Elder, R. E. Stephens, C. E. Cottrell, J. M. Cassady, J. Nat. Prod. 57 (1994) 32 (https://doi.org/10.1021/np50103a005)
P. Fu, S. Lin, L. Shan, Y.-H. Shen, J. Tang, R.-H. Liu, X. Zhang, R.-L. Zhu, W.-D. Zhang, J. Nat. Prod. 72 (2009) 1335 (https://doi.org/10.1021/np800830v)
F. Nagashima, Y. Ohi, T. Nagai, M. Tori, Y. Asakawa, S. Huneck, Phytochemistry 33 (1993) 1445 (https://doi.org/10.1016/0031-9422(93)85107-3)
A. C. Figueiredo, M. Sim-Sim, J. G. Barroso, L. G. Pedro, P. A. G. Santos, S. S. Fontinha, J. Schripsema, S. G. Deans, J. J. C. Scheffer, J. Essent. Oil Res. 14 (2002) 439 (https://doi.org/10.1080/10412905.2002.9699915)
X.-L. Guo, P. Leng. Y. Yeng, L.-G. Yu, H.-X. Lou. J. Appl. Microbiol. 104 (2008) 831 (https://doi.org/10.1111/j.1365-2672.2007.03617.x)
X.-Z. Wu, A.-X., Cheng, L.-M. Sun, H.-X. Lou, Acta Pharmacol. Sin. 29 (2008) 1478 (https://doi.org/10.1111/j.1745-7254.2008.00900.x)
X.-Z. Wu, A.-X. Cheng, L.-M. Sun, S.-J. Sun, H.-X. Lou, Biochim. Biophys. Acta 1790 (2009) 770 (https://doi.org/10.1016/j.bbagen.2009.05.002)
X.-Z. Wu, W.-Q. Chang, A.-X. Cheng, L.-M. Sun, H.-X. Lou, Biochim. Biophys. Acta 1800 (2010) 439 (https://doi.org/10.1016/j.bbagen.2010.01.001)
C. Niu, J.-B. Qu, H.-X. Lou, 2006. Chem. Biodivers. 3 (2006) 34 (https://doi.org/10.1002/cbdv.200690004)
J. Qu, C. Xie, H. Guo, W. Yu, H. Lou, Phytochemistry 68 (2007) 1767 (https://doi.org/10.1016/j.phytochem.2007.04.036)
J. M. Scher, J.-B. Speakman, J. Zapp, H. Becker, Phytochemistry 65 (2004) 2583 (https://doi.org/10.1016/j.phytochem.2004.05.013)
Y. Iwai, K. Murakami, Y. Gomi, T. Hashimoto, Y. Asakawa, Y. Okuno, T. Ishikawa, D. Hatakeyama, N. Echigo, T. Kuzuhara, PLoS ONE 6 (2011) 1 (https://doi.org/10.1371/journal.pone.0019825)
L. Harinantenaina, Y. Asakawa, Chem. Pharm. Bull. 52 (2004) 1382 (https://doi.org/10.1248/cpb.52.1382)
A. Matsuo, K. Ono, K. Hamasaki, H. Nozaki, Phytochemistry 42 (1996) 427 (https://doi.org/10.1016/0031-9422(96)00017-9)
H. J. M. Gijsen, J. B. P. A.Wijnberg, G. A. Stork, A. De Groot, M. A. De Waard, J. G. M. Van Nistelrooy, Tetrahedron 48 (1992) 2465 (https://doi.org/10.1016/S0040-4020(01)88765-2)
R. S. Burden, M. S. Kemp, Phytochemistry 22 (1983) 1039 (https://doi.org/10.1016/ doi.org/0031-9422(83)85056-0)
M. Neves, R. Morais, S. Gafner, H. Stoeckli-Evans, K. Hostettmann, Phytochemistry 50 (1999) 967 (https://doi.org/10.1016/S0031-9422(98)00648-7)
C. Labbé, F. Faini, C. Villagran, J. Coll, D. S. Rycroft, J. Nat. Prod. 70 (2007) 2019 (https://doi.org/10.1021/np070192c)
C. Labbé, F. Faini, C. Villagran, J. Coll, D. S. Rycroft, J. Agric. Food Chem. 53 (2005) 247 (https://doi.org/10.1021/jf048935c)
S. H. Baek, R. K. Phipps, N. B. Perry, J. Nat. Prod. 67 (2004) 718 (https://doi.org/10.1021/np030455c)
J. M. Scher, A. Schinkovitz, J. Zapp, Y. Wang, S. G. Franzblau, H. Becker, D. C. Lankin, G. F. Pauli, J. Nat. Prod. 73 (2010) 656 (https://doi.org/10.1021/np900806j)
T. Yoshida, T. Hashimoto, S. Takaoka, Y. Kan, M. Tori, Y. Asakawa, J. Pezzuto, T. Pengsuparp, G. Cordell Tetrahedron 52 (1996) 14487 (https://doi.org/10.1016/0040-4020(96)00889-7).