Journal of Natural Products
Article
Caspase-3 Activity Assay. For compounds 1 and 21, the
caspase-3 activity was carried out following the methods described by
Xu et al.28
ASSOCIATED CONTENT
* Supporting Information
The Supporting Information is available free of charge on the
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S
Additional figures and a table (PDF)
AUTHOR INFORMATION
Corresponding Authors
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Figure 7. Caspase-3 activity of SH-SY5Y cells treated with H2O2 and/
or compounds 1 and 21. Data are presented as the means SDs.
***P < 0.001 compared with control; ##P < 0.01 compared with
H2O2-treated cells.
ORCID
Notes
(4S,5S,7R,8S,9S,10S,11S,12S,13S,14R)-Kumulactone B (2): white
The authors declare no competing financial interest.
powder, [α]2D0 +32 (c 0.4, MeOH); UV (MeOH) λmax (log ε) 271
(0.911) nm; ECD (MeOH, Δε) λmax 259 (−3.89), 308 (+0.67) nm;
IR (KBr) νmax 3444, 2984, 1708, 1606, 1492, 1396, 1371, 1273, 1238,
ACKNOWLEDGMENTS
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This project was funded by the National Nature Science
Foundation (81872767) of China and the Career Develop-
ment Support Plan for Young and Middle-aged Teachers in
Shenyang Pharmaceutical University (ZQN2018006).
1
1174, 1115 cm−1; H and 13C NMR, see Tables 1 and 2; HRESIMS
m/z 431.2054 [M + Na]+ (calcd for C22H32NaO7, 431.2040).
(4S,5S,7R,8R,9S,10S,11S,12S,13R)-Kumulactone C (3): white pow-
der, [α]2D0 −8 (c 0.8, MeOH); UV (MeOH) λmax (log ε) 261 (1.12) nm;
ECD (MeOH, Δε) λmax 227 (−6.92) nm; IR (KBr) νmax 3425, 2964,
2938, 2881, 1721, 1706, 1632, 1450, 1371, 1355, 1260, 1239, 1114,
REFERENCES
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1
1036 cm−1; H and 13C NMR, see Tables 1 and 2; HRESIMS m/z
(1) Xu, J.; Xiao, D.; Song, W.; Chen, L.; Liu, W.; Xie, N.; Feng, F.;
Qu, W. Fitoterapia 2016, 110, 13−19.
(2) Xu, J.; Xiao, D.; Lin, Q.; He, J.; Liu, W.; Xie, N.; Feng, F.; Qu,
W. J. Nat. Prod. 2016, 79, 1899−1910.
411.1789 [M + Na]+ (calcd for C22H28NaO6, 411.1778).
(5R,7R,8S,9S,10R,11S,12S,13R,14S)-Kumulactone D (4): white
powder, [α]2D0 +33 (c 0.2, MeOH); UV (MeOH) λmax (log ε) 262
(1.12) nm; ECD (MeOH, Δε) λmax 257 (+6.67) nm; IR (KBr) νmax
3431, 2986, 1608, 1492, 1441, 1400, 1367, 1173, 1006, 799 cm−1; 1H
and 13C NMR, see Tables 1 and 2; HRESIMS m/z 457.1808 [M + Na]+
(calcd for C23H30NaO8, 457.1833).
(3) Jiao, W.; Chen, G.-D.; Gao, H.; Li, J.; Gu, B.; Xu, T.; Yu, H.; Shi,
G.; Yang, F.; Yao, X.; Lin, H. J. Nat. Prod. 2014, 77, 2707−2712.
(4) Yoshikawa, K.; Sugawara, S.; Arihara, S. Phytochemistry 1995, 40,
253−256.
(5) Polonsky, J. Fortschr. Chem. Org. Naturst. 1985, 47, 221−264.
(6) Polonsky, J. Fortschr. Chem. Org. Naturst. 1973, 30, 101−150.
(7) Guo, Z.; Vangapandu, S.; Sindelar, R. W.; Walker, L. A.;
Sindelar, R. D. Curr. Med. Chem. 2005, 12, 173−190.
(8) Koreeda, M.; Harada, N.; Nakanishi, K. J. Am. Chem. Soc. 1974,
96, 266−268.
(5R,7R,8S,9S,10R,11S,12S,13R,14S,16S)-Picrasinoside I (5): yellow
powder, [α]2D0 −1 (c 0.1, MeOH); UV (MeOH) λmax (log ε) 260
(1.30) nm; ECD (MeOH, Δε) λmax 261 (+5.33) 323 (−1.60) nm; IR
(KBr) νmax 3427, 2986, 1611, 1492, 1441, 1400, 1366, 1173, 1006,
1
799 cm−1; H and 13C NMR, see Tables 1 and 2; HRESIMS m/z
621.2540 [M + Na]+ (calcd for C29H42NaO13, 621.2518).
(9) Hikino, H.; Ohta, T.; Takemoto, T. Phytochemistry 1975, 14,
2473−2481.
(4S,5S,7R,8R,9S,10S,11S,13S,14R,16S)-Picrasinoside K (6): white
powder, [α]2D0 −6 (c 0.4, MeOH); UV (MeOH) λmax (log ε) 269
(1.13) nm; ECD (MeOH, Δε) λmax 256 (−8.02) 300 (+2.83) nm; IR
(KBr) νmax 3416, 2984, 2929, 1728, 1673, 1632, 1614, 1492, 1442,
(10) Daido, M.; Fukamiya, N.; Okano, M.; Tagahara, K. J. Nat. Prod.
1992, 55, 1643−1647.
(11) Daido, M.; Fukamiya, N.; Okano, M.; Tagahara, K. J. Nat. Prod.
1995, 58, 605−608.
(12) Yang, S.; Yue, J. Helv. Chim. Acta 2004, 87, 1591−1600.
(13) Pescitelli, G.; Di Bari, L. Chirality 2017, 29, 476−485.
(14) Pescitelli, G.; Di Bari, L. J. Nat. Prod. 2017, 80, 2855−2859.
(15) Murae, T.; Tsuyuki, T.; Nishihama, T.; Masuda, S.; Takahashi,
T. Tetrahedron Lett. 1969, 10, 3013−3016.
(16) Koike, K.; Ishii, k.; mitsunaga, k.; Ohmoto, T. Chem. Pharm.
Bull. 1991, 39, 2021−2023.
(17) Dou, J.; McChesney, J.; Sindelar, R.; Goins, D. K.; Khan, I.;
Walker, L. Int. J. Pharmacogn. 1996, 34, 349−354.
(18) Barbetti, P.; Grandolini, G.; Fardella, G.; Chiappini, I.
Phytochemistry1993, 32, 1007−1013.
(19) Murae, T.; Sugie, A.; Tsuyuki, T.; Takahashi, T. Chem. Pharm.
Bull. 1975, 23, 2188−2190.
(20) Lang’at-Thoruwa, C.; Kirby, G. C.; Phillipson, J. D.; Warhurst,
D. C.; Watt, R. A.; Wright, C. W. J. Nat. Prod. 2003, 66, 1486−1489.
(21) Jiao, W.; Gao, H.; Zhao, F.; He, F.; Zhou, G.; Yao, X. Chem.
Biodiversity 2011, 8, 1163−1169.
(22) Robins, R. J.; Rhodes, M. J. J. Chromatogr. A 1984, 283, 436−
440.
1
1396, 1368, 1237, 1172, 1122, 1040, 1024 cm−1; H and 13C NMR,
see Tables 1 and 2; HRESIMS m/z 579.2392 [M + Na]+ (calcd for
C27H40NaO12, 579.2412).
(4S,5S,7R,8R,9S,10S,11S,13S,14R,16S)-Picrasinoside J (7): light
yellow powder, [α]2D0 −3 (c 0.3, MeOH); UV (MeOH) λmax (log ε)
275 (1.02) nm; ECD (MeOH, Δε) λmax 256 (−2.89) 303 (+2.00)
nm; IR (KBr) νma1x 3428, 2986, 1611, 1492, 1441, 1400, 1367, 1173,
1007, 799 cm−1; H and 13C NMR, see Tables 1 and 2; HRESIMS
m/z 621.2506 [M + Na]+ (calcd for C29H42NaO13, 621.2518).
(4S,5S,7R,8S,9S,10S,12R,13R,14S)-Kumulactone E (8): yellow
powder, [α]2D0 −46 (c 0.3, MeOH); UV (MeOH) λmax (log ε) 263
(1.27) nm; ECD (MeOH, Δε) λmax 256 (−5.32) nm; IR (KBr) νmax
3424, 2986, 1611, 1492, 1441, 1399, 1367, 1173, 1006, 799 cm−1;
1H and 13C NMR, see Tables 1 and 2; HRESIMS m/z 399.1763
[M + Na]+ (calcd for C21H28NaO6, 399.1778).
Neuroprotective Activity Assay. The protective activities of
the 23 quassinoids toward SH-SY5Y cells damaged by H2O2 were
examined following the reported procedures.26
Apoptosis Analysis. The apoptosis analysis was carried out by an
annexin V-FITC/PI double staining assay as described previously.27
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