Nat Prod Sci.  2018 Dec;24(4):266-271. 10.20307/nps.2018.24.4.266.

Five New Stilbenes from the Stem Bark of Artocarpus communis

Affiliations
  • 1Molecular Targets Program, Center for Cancer Research, National Cancer Institute, Frederick, Maryland, USA, 21702. gustafki@mail.nih.gov
  • 2Current Address: The Ferrier Research Institute of Victoria, University of Wellington, Lower Hut, New Zealand.
  • 3Current Address: Institute of Environmental Science and Research Ltd., Kenepuru Science Centre, Porirua, New Zealand.
  • 4Basic Science Program, Leidos Biomedical Research, Inc, Frederick National Laboratory for Cancer Research sponsored by the National Cancer Institute, Frederick, Maryland, USA 21702.
  • 5Current Address: Diagnostic Biomarkers and Technology Branch, Cancer Diagnosis Program, National Cancer Institute, Rockville, Maryland, USA 20850-9728.

Abstract

Five new prenylated stilbenes (1 - 5), along with the known compounds cudraflavone C, trans-4-isopentenyl-3,5,2"²,4"²-terahydroxystilbene, trans-4-(3-methyl-E-but-1-enyl)-3,5,2"²,4"²-tetrahydroxystilbene, pannokin G, cycloartobiloxanthone, artonin P, morusin, artocarpin, artonin E, kuwanon C, artobiloxanthone, and artoindonesianin C (6 - 17) were isolated from the stem bark of the tropical tree Artocarpus communis. The structures were established by NMR spectroscopic analysis, MS studies, and comparison with spectral data reported in the literature.

Keyword

Artocarpus communis; Artocarpus altilis; Moraceae; stilbene

MeSH Terms

Artocarpus*
Moraceae
Stilbenes*
Trees
Stilbenes

Figure

  • Fig. 1. Structures of compounds 1–5 isolated from Artocarpus communis.

  • Fig. 2. Key HMBC correlations for compounds 1–5.


Reference

(1). Jagtap U. B., Bapat V. A. J.Ethnopharmacol. 2010; 129:142–166.
(2). Sikarwar M. S., Hui B. J., Subramaniam K., Valeisamy B. D., Yean L. K., Balaji K. J.Appl. Pharm. Sci. 2014; 4:91–97.
(3). McKee T. C., Rabe D., Bokesch H. R., Grkovic T., Whitson E. L., Diyabalanage T., Van Wyk A. W. W., Marcum S. R., Gardella R. S., Gustafson K. R., Linehan W. M., McMahon J. B., Bottaro D. P. J.Nat. Prod. 2012; 75:1632–1636.
(4). Löfstedt T., Fredlund E., Holmquist-Mengelbier L., Pietras A., Ovenberger M., Poelinger L., Pahlman S.Cell Cycle. 2007; 8:919–926.
(5). Bokesch H. R., Gardella R. S., Rabe D. C., Bottaro D. P., Linehan W. M., McMahon J. B., McKee T. C.Chem. Pharm. Bull. 2011; 59:1178–1179.
(6). McCloud T. G.Molecules. 2010; 15:4526–4563.
(7). Toume K., Habu T., Arai M. A., Koyano T., Kowithayakorn T., Ishibashi M. J.Nat. Prod. 2015; 78:103–110.
(8). Pacher T., Seger C., Engelmeier D., Vajrodaya S., Hofer O., Greger H. J.Nat. Prod. 2002; 65:820–827.
(9). Kostecki K., Engelmeier D., Pacher T., Hofer O., Vajrodaya S., Greger H.Phytochemistry. 2004; 65:99–106.
(10). Hano Y.Heterocycles. 1990; 31:1339–1344.
(11). Takasugi M, Muñoz L., Masamune T., Shirata A., Takahashi K.Chem. Lett. 1978; 7:1241–1242.
(12). Boonlaksiri C., Oonanant W., Kongsaeree P., Kittakoop P., Tanticharoen M., Thebtaranonth Y.Phytochemistry. 2000; 54:415–417.
(13). Sultanbawa M. U. S., Surendrakumar S.Phytochemistry. 1989; 28:599–605.
(14). Hano Y., Inami R., Nomura T.Heterocycles. 1993; 35:1341–1350.
(15). Nomura T., Fukai T., Yamada S., Katayanagi M.Chem. Pharm. Bull. 1976; 24:2898–2900.
(16). Nomura T., Fukai T.Heterocycles. 1979; 12:1289–1295.
(17). Lin C. N., Lu C. M., Huang P. L.Phytochemistry. 1995; 39:1447–1451.
1451.(18) Sato M.., Fujiwara S.., Tsuchiya H.., Fujii T.., Iinuma M.., Tosa H.., Ohkawa Y. J.Ethnopharmacol. 1996. 54:171–176.
(19). Hano Y., Yamagami Y., Kobayashi M., Isohata R., Nomura T.Heterocycles. 1990; 31:877–882.
(20). Nomura T., Fukai T., Katayanagi M.Chem. Pharm. Bull. 1977; 25:529–532.
(21). Makmur L., Syamsurizal S., Tukiran T., Achmad S. A., Aimi N., Hakim E. H., Kitajima M., Takayama H. J.Nat. Prod. 2000; 63:243–244.
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