Neopierisoids A and B, two new chlorinated 3,4-seco-grayanane diterpenoids with antifeedant activity from flowers of Pieris japonica

Journal of Agricultural and Food Chemistry

Volumn 61, Issue 30, 2013, Pages 7219-7224

  Li, Yan Ping ^a   Li, Xiao Nian ^b   Gao, Ling Huan ^a   Li, Hai Zhou ^a   Wu, Guo Xing ^c   Li, Rong Tao ^a  

^a KUNMING UNIVERSITY OF SCIENCE AND TECHNOLOGY   (China)

^b KUNMING INSTITUTE OF BOTANY   (China)

^c YUNNAN AGRICULTURAL UNIVERSITY   (China)

Author keywords

antifeedant; chlorinated 3,4 seco grayanane diterpenoids; defensive role; Pieris japonica

Indexed keywords

ANTIFEEDANT; ANTIFEEDANT ACTIVITIES; DEFENSIVE ROLE; DITERPENOIDS; PIERIS JAPONICA; TOXIC PROPERTIES; X-RAY DIFFRACTION DATA;

SPECTROSCOPIC ANALYSIS; X RAY DIFFRACTION;

LIPIDS;

DITERPENE; PLANT EXTRACT;

ANIMAL; ARTICLE; BUTTERFLY; CHEMICAL STRUCTURE; CHEMISTRY; DRUG EFFECT; ERICACEAE; FEEDING BEHAVIOR; FLOWER; ISOLATION AND PURIFICATION; PHYSIOLOGY;

ANIMALS; BUTTERFLIES; DITERPENES; ERICACEAE; FEEDING BEHAVIOR; FLOWERS; MOLECULAR STRUCTURE; PLANT EXTRACTS;

EID: 84881034687     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/jf401921x     Document Type: Article

References (34)

1. Isman, M. Insect antifeedants Pestic. Outlook 2002, 13, 152-157
2. Akhtar, Y.; Isman, M. B.; Niehaus, L. A.; Lee, C.-H.; Lee, H.-S. Antifeedant and toxic effects of naturally occurring and synthetic quinones to the cabbage looper, Trichoplusia ni Crop Prot. 2012, 31, 8-14
3. Kittakoop, P.; Wanasith, S.; Watts, P.; Kramyu, J.; Tanticharoen, M.; Thebtaranonth, Y. Potent antiviral potamogetonyde and potamogetonol, new furanoid labdane diterpenes from Potamogeton malaianus J. Nat. Prod. 2001, 64, 385-388
4. Jaki, B.; Heilmann, J.; Sticher, O. New antibacterial metabolites from the cyanobacterium Nostoc commune (EAWAG 122b) J. Nat. Prod. 2000, 63, 1283-1285
5. Kong, C.; Liang, W.; Xu, X.; Hu, F.; Wang, P.; Jiang, Y. Release and activity of allelochemicals from allelopathic rice seedlings J. Agric. Food. Chem. 2004, 52, 2861-2865
6. Zhang, H. P.; Wang, L. Q.; Qin, G. W. Grayanane diterpenoids from the leaves of Craiobiodendron yunnanense Bioorg. Med. Chem. 2005, 13, 5289-5298
7. Langenheim, J. H. Higher plant terpenoids: A phytocentric overview of their ecological roles J. Chem. Ecol. 1994, 20, 1223-1280
8. Raccuglia, R. A.; Bellone, G.; Loziene, K.; Piozzi, F.; Rosselli, S.; Maggio, A.; Bruno, M.; Simmonds, M. S. J.; Hastifolins, A.-G. Antifeedant neo -clerodane diterpenoids from Scutellaria hastifolia Phytochemistry 2010, 71, 2087-2091
9. Sakakibara, J.; Shirai, N.; Kaiya, T. Diterpene glycosides from Pieris japonica Phytochemistry 1981, 20, 1744-1745
10. Zhong, G.; Hu, M.; Wei, X.; Weng, Q.; Xie, J.; Liu, J.; Wang, W. Grayanane diterpenoids from the flowers of Rhododendron molle with cytotoxic activity against a spodoptera frugiperda cell line J. Nat. Prod. 2005, 68, 924-926
11. Wu, Z. Y.; Li, H. Z.; Wang, W. G.; Li, H. M.; Chen, R.; Li, R. T.; Luo, H. R. Lyonin A, a new 9,10-secograyanotoxin from Lyonia ovalifolia Chem. Biodiversity 2011, 8, 1182-1187
12. Yao, G. M.; Ding, Y.; Zuo, J. P.; Wang, H. B.; Wang, Y. B.; Ding, B. Y.; Chiu, P.; Qin, G. W. Dihydrochalcones from the leaves of Pieris japonica J. Nat. Prod. 2005, 68, 392-396
13. Shirai, N.; Sakakibara, J.; Kaiya, T.; Kobayashi, S.; Hotta, Y.; Takeya, K. Quantitative structure-inotropy relationship applied to substituted grayanotoxins J. Med. Chem. 1983, 26, 851-855
14. Chow, S.; Kress, C.; Albaek, N.; Jessen, C.; Williams, C. M. Determining a synthetic approach to pierisformaside C Org. Lett. 2011, 13, 5286-5289
15. Wang, S.; Lin, S.; Zhu, C.; Yang, Y.; Li, S.; Zhang, J.; Chen, X.; Shi, J. Highly acylated diterpenoids with a new 3,4-secograyanane skeleton from the flower buds of Rhododendron molle Org. Lett. 2010, 12, 1560-1563
16. Isman, M. B; Koul, O.; Luczynski, A.; Kaminski, J. Insecticidal and antifeedant bioactivities of neem oils and their relationship to azadirachtin content J. Agric. Food Chem. 1990, 38, 1406-1411
17. Li, S. H.; Wang, J.; Niu, X. M.; Shen, Y. H.; Zhang, H. J.; Sun, H. D.; Li, M. L.; Tian, Q. E.; Lu, Y.; Cao, P.; Zheng, Q. T. Maoecrystal V cytotoxic diterpenoid with a novel C19 skeleton from Isodon eriocalyx (Dunn.) hara Org. Lett. 2004, 6, 4327-4330
18. Wang, W. G.; Du, X.; Li, X. N.; Wu, H. Y.; Liu, X.; Shang, S. Z.; Zhan, R.; Liang, C. Q.; Kong, L. M.; Li, Y.; Pu, J. X.; Sun, H. D. New bicyclo[3.1.0]hexane unit ent -kaurane diterpene and its seco -derivative from Isodon eriocalyx var. laxiflora Org. Lett. 2012, 14, 302-305
19. Wang, W. G.; Li, X. N.; Du, X.; Wu, H. Y.; Liu, X.; Su, J.; Li, Y.; Pu, J. X.; Sun, H. D. Laxiflorolides A and B, epimeric bishomoditerpene lactones from Isodon eriocalyx J. Nat. Prod. 2012, 75, 1102-1107
20. Nakanishi, K.; Solomon, P. H. Infrared Absorption Spectroscopy, 2 nd ed.; Holden Day: Oakland, 1977; pp 17-44.
21. Breitmaier, E.; Voelter, W. Carbon-13 NMR Spectroscopy, VCH: Weinheim, 1987; pp 183-280.
22. Li, C.-H.; Niu, X.-M.; Luo, Q.; Xie, M.-J.; Luo, S.-H.; Zhou, Y.-Y.; Li, S.-H. Novel polyesterified 3,4- seco -grayanane diterpenoids as antifeedants from Pieris formosa Org. Lett. 2010, 12, 2426-2429
23. Gribble, G. W. The diversity of naturally produced organohalogens Chemosphere 2003, 52, 289-297
24. Blasiak, L. C.; Drennan, C. L. Structural perspective on enzymatic halogenation Acc. Chem. Res. 2009, 42, 147-155
25. Runguphan, W.; Qu, X.; O'Connor, S. E. Integrating carbon-halogen bond formation into medicinal plant metabolism Nature 2010, 468, 461-464
26. Vaillancourt, F. H.; Yeh, E.; Vosburg, D. A.; O'Connor, S. E.; Walsh, C. T. Cryptic chlorination by a non-haem iron enzyme during cyclopropyl amino acid biosynthesis Nature 2005, 436, 1191-1194
27. Vaillancourt, F. H.; Yeh, E.; Vosburg, D. A.; Garneau-Tsodikova, S.; Walsh, C. T. Nature's inventory of halogenation catalysts: Oxidative strategies predominate Chem. Rev. 2006, 106, 3364-3378
28. Allard, P.-M.; Martin, M.-T.; Dau, M.-E. T. H.; Leyssen, P.; Gueritte, F.; Litaudon, M. Trigocherrin A, the first natural chlorinated daphnane diterpene orthoester from Trigonostemon cherrieri Org. Lett. 2012, 14, 342-345
29. Luo, S. H.; Luo, Q.; Niu, X. M.; Xie, M. J.; Zhao, X.; Schneider, B.; Gershenzon, J.; Li, S. H. Glandular trichomes of Leucosceptrum canum harbor defensive sesterterpenoids Angew. Chem., Int. Ed. 2010, 49, 4471-4475
30. Li, C. H.; Jing, S. X.; Luo, S. H.; Shi, W.; Hua, J.; Liu, Y.; Li, X. N.; Schneider, B.; Gershenzon, J.; Li, S. H. Peltate glandular trichomes of Colquhounia coccinea var. mollis harbor a new class of defensive sesterterpenoids Org. Lett. 2013, 15, 1694-1697
31. Hikino, H.; Ohta, T.; Ogura, M.; Ohizumi, Y.; Konno, C.; Takemoto, T. Structure-activity relationship of ericaceous toxins on acute toxicity in mice Toxicol. Appl. Pharmacol. 1976, 35, 303-310
32. Maejima, H.; Kinoshita, E.; Seyama, I.; Yamaoka, K. Distinct sites regulating grayanotoxin binding and unbinding to D4S6 of Na(v)1.4 sodium channel as revealed by improved estimation of toxin sensitivity J. Biol. Chem. 2003, 278, 9464-9471
33. Klocke, J. A.; Mei-Ying, H.; Shin-Foon, C.; Kubo, I. Grayanoid diterpene insect antifeedants and insecticides from Rhododendron molle Phytochemistry 1991, 30, 1797-1800
34. Popescu, R.; Kopp, B. The genus Rhododendron: An ethnopharmacological and toxicological review J. Ethnopharmacol. 2013, 147, 42-62