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Chan, Popplewell, Bokesch, McKee, and Gustafson: Five New Stilbenes from the Stem Bark of Artocarpus communis
Original Article

Natural Product Sciences 2018;24(4):266-271.

Published online: 17 December 2018

DOI: https://doi.org/10.20307/nps.2018.24.4.266

Five New Stilbenes from the Stem Bark of Artocarpus communis

Susanna T. S. Chan1, 2, Wendy L. Popplewell1, 3, Heidi R. Bokesch1, 4, Tawnya C. McKee1, 5, Kirk R. Gustafson1, ∗

1Molecular Targets Program, Center for Cancer Research, National Cancer Institute, Frederick, Maryland, USA, 21702

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

∗Author for correspondence Gustafson, Molecular Targets Program, Center for Cancer Research, National Cancer Institute, Frederick, Maryland, USA, 21702 Tel: +1-301-846-5197; E-mail: gustafki@mail.nih.gov

Received 28 June 2018       Revised 20 July 2018       Accepted 20 July 2018

Copyright © 2018 The Korean Society of Pharmacognosy

This is an Open Access article distributed under the terms of the Creative Commons Attribution Non-Commercial License (http://creativecommons.org/licenses/by-nc/3.0) which permits unrestricted non-commercial use, distribution, and reproduction in any medium, provided the original work is properly cited.

Abstract

Five new prenylated stilbenes (1–5), along with the known compounds cudraflavone C, trans-4-isopentenyl-3,5,2′,4′-terahydroxystilbene, trans-4-(3-methyl-E-but-1-enyl)-3,5,2′,4′-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.

Keywords: Artocarpus communis, Artocarpus altilis, Moraceae, stilbene

REFERENCES

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Fig. 1.
Structures of compounds 1–5 isolated from Artocarpus communis.
nps-24-266f1.tif
Fig. 2.
Key HMBC correlations for compounds 1–5.
nps-24-266f2.tif
Table 1.
1 H NMR Assignments (600 MHz, CD3 OD) for compounds 1–5
  1 2 3 4 5
position δH (J in Hz) δH (J in Hz) δH (J in Hz) δH (J in Hz) δH (J in Hz)
1          
2     7.04, s   7.03, d (2.1)
3          
4          
5          
6 7.08, s 7.14, s 7.04, s 7.11, s 7.11, d (2.1)
7 3.41, d (7.0) 6.71, d (9.9) 3.33, m 6.64, d (9.7) 6.38, d (9.70)
8 5.20, br t (7.3) 5.63, d (10.0) 5.34, br t (7.3) 5.68, d (10.0) 5.70, d (9.6)
9          
10 1.80, s 1.39, s 1.75, s 1.45, s 1.41, s
11 1.68, s 1.39, s 1.77, s 1.45, s 1.41, s
12 3.27, d (7.3) 3.20, d (7.3) 3.33, m 6.35, d (8.9) 3.27, d (7.5)
13 5.33, br t (7.3) 5.26, m 5.34, br t (7.3) 5.60, d (9.0) 5.28, tt (1.6, 7.5)
14          
15 1.75, s 1.76, s 1.75, s 1.42, s 1.74, s
16 1.77, s 1.73, s 1.77, s 1.42, s 1.76, s
α 7.32, d (16.2) 7.32, d (16.3) 6.85, d (16.5) 7.24, d (16.2) 6.92, d (16.2)
β 6.71, d (16.2) 6.76, d (16.3) 6.68, d (16.6) 6.87, d (16.4) 6.80, d (16.2)
1′          
2′ 6.46, d (2.2) 6.47, d (2.1) 6.46, s 6.45, s 6.45, d (2.3)
3′          
4′ 6.14, br t (2.2) 6.15, t (2.1)   6.16, m 6.16, t (2.2)
5′          
6′ 6.46, d (2.2) 6.47, d (2.1) 6.46, s 6.45, s 6.45, d (2.3)
4′-CH3     2.03, s    
Table 2.
13C NMR Assignments (150 MHz, CD3 OD) for compounds 1–5
  1 2 3 4 5
position δC, type δC, type δC, type δC, type δC, type
1 119.6, C 119.6, C 130.8, C 119.3, C 131.2, C
2 152.5, C 149.9, C 126.2, CH 152.2, C 123.2, CH
3 118.8, C 112.0, C 130.1, C 111.2, C 122.6, C
4 154.2, C 152.2, C 153.5, C 149.6, C 151.6, C
5 122.5, C 122.9, C 130.1, C 116.0, C 130.4, C
6 124.6, CH 127.2, CH 126.2, CH 124.1, CH 128.8, CH
7 24.0, CH2 118.6, CH 29.7, CH2 117.7, CH 123.6, CH
8 124.3∗, CH 129.8, CH 123.9, CH 130.3, CH 132.0, CH
9 132.3, C 76.3, C 133.4, C 77.5, C 77.4, C
10 18.0, CH3 27.9, CH3 18.0, CH3 28.2, CH3 28.2, CH3
11 26.0, CH3 27.9, CH3 26.0, CH3 28.2, CH3 28.2, CH3
12 29.4, CH2 29.1, CH2 29.7, CH2 123.2, CH 29.4, CH2
13 124.2∗, CH 124.8, CH 123.9, CH 129.4, CH 124.1, CH
14 133.2, C 132.0, C 133.4, C 77.9, C 132.7, C
15 17.9, CH3 18.0, CH3 18.0, CH3 28.4, CH3 18.0, CH3
16 26.0, CH3 26.0, CH3 26.0, CH3 28.4, CH3 26.0, CH3
α 125.0, CH 124.6, CH 128.8, CH 123.5, CH 129.3, CH
β 127.2, CH 127.4, CH 127.0, CH 127.7, CH 127.5, CH
1′ 141.9, C 141.9, C 137.4, C 141.7, C 141.2, C
2′ 105.8, CH 105.8, CH 105.5, CH 105.7, CH 105.8, CH
3′ 159.8, C 159.6, C 157.6, C 159.7, C 159.8, C
4′ 102.6, CH 102.5, CH 111.6, C 102.6, CH 102.8, CH
5′ 159.8, C 159.6, C 157.6, C 159.7, C 159.8, C
6′ 105.8, CH 105.8, CH 105.5, CH 105.7, CH 105.8, CH
4′-CH3     8.6, CH3    

∗ interchangeable

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