Absolute Configurations and NO Inhibitory Activities of Terpenoids from Curcuma longa

Journal of Agricultural and Food Chemistry

Volumn 63, Issue 24, 2015, Pages 5805-5812

  Xu, Jing ^a   Ji, Feifei ^b   Kang, Jing ^b   Wang, Hao ^a   Li, Shen ^a   Jin, Da Qing ^a   Zhang, Qiang ^c   Sun, Hongwei ^a   Guo, Yuanqiang ^a  

^a NANKAI UNIVERSITY   (China)

^b HARBIN UNIVERSITY OF COMMERCE   (China)

^c NORTHWEST A F UNIVERSITY   (China)

Author keywords

absolute configuration; Curcuma longa; NO inhibitory activity; spice; terpenoids

Indexed keywords

BIOASSAY; LIPIDS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SPICE;

ABSOLUTE CONFIGURATION; CHEMICAL COMPOSITIONS; CHEMICAL CONSTITUENTS; CURCUMA LONGA; FOOD INDUSTRIES; NO INHIBITORY ACTIVITIES; SPECTROSCOPIC DATA; TERPENOIDS;

CHEMICAL COMPOUNDS;

CURCUMA LONGA; MURINAE; ZINGIBERACEAE;

HERBACEOUS AGENT; NITRIC OXIDE; TERPENE;

ANIMAL; ANTAGONISTS AND INHIBITORS; CHEMICAL STRUCTURE; CHEMISTRY; CURCUMA; DRUG EFFECTS; METABOLISM; MICROGLIA; MOUSE; RHIZOME;

ANIMALS; CURCUMA; DRUGS, CHINESE HERBAL; MICE; MICROGLIA; MOLECULAR STRUCTURE; NITRIC OXIDE; RHIZOME; TERPENES;

EID: 84933073819     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/acs.jafc.5b01584     Document Type: Article

References (40)

1. Nanjing University of Chinese Medicine. Dictionary of Chinese Herb Medicines, 2nd ed.; Shanghai Scientific and Technologic Press: Shanghai, China, 2006; pp 2404-2406.
2. Liao, K. K.; Wu, M. J.; Chen, P. Y.; Huang, S. W.; Chiu, S. J.; Ho, C. T.; Yen, J. H. Curcuminoids promote neurite outgrowth in PC12 cells through MAPK/ERK- and PKC-dependent pathways J. Agric. Food Chem. 2012, 60, 433-443 10.1021/jf203290r
3. Chen, J. J.; Tsai, C. S.; Hwang, T. L.; Shieh, P. C.; Chen, J. F.; Sung, P. J. Sesquiterpenes from the rhizome of Curcuma longa with inhibitory activity on superoxide generation and elastase release by neutrophils Food Chem. 2010, 119, 974-980 10.1016/j.foodchem.2009.07.060
4. Dao, T. T.; Nguyen, P. H.; Won, H. K.; Kim, E. H.; Park, J.; Won, B. Y.; Oh, W. K. Curcuminoids from Curcuma longa and their inhibitory activities on influenza A neuraminidases Food Chem. 2012, 134, 21-28 10.1016/j.foodchem.2012.02.015
5. Nishiyama, T.; Mae, T.; Kishida, H.; Tsukagawa, M.; Mimaki, Y.; Kuroda, M.; Sashida, Y.; Takahashi, K.; Kawada, T.; Nakagawa, K.; Kitahara, M. Curcuminoids and sesquiterpenoids in turmeric (Curcuma longa L.) suppress an increase in blood glucose level in type 2 diabetic KK-Ay mice J. Agric. Food Chem. 2005, 53, 959-963 10.1021/jf0483873
6. Lin, X.; Ji, S.; Li, R.; Dong, Y.; Qiao, X.; Hu, H.; Yang, W.; Guo, D.; Tu, P.; Ye, M. Terpecurcumins A-I from the rhizomes of Curcuma longa: absolute configuration and cytotoxic activity J. Nat. Prod. 2012, 75, 2121-2131 10.1021/np300551g
7. Lin, X.; Ji, S.; Qiao, X.; Hu, H.; Chen, N.; Dong, Y.; Huang, Y.; Guo, D.; Tu, P.; Ye, M. Density functional theory calculations in stereochemical determination of terpecurcumins J-W, cytotoxic terpene-conjugated curcuminoids from Curcuma longa L J. Org. Chem. 2013, 78, 11835-11848 10.1021/jo401859u
8. Wright, L. E.; Frye, J. B.; Timmermann, B. N.; Funk, J. L. Protection of trabecular bone in ovariectomized rats by turmeric (Curcuma longa L.) is dependent on extract composition J. Agric. Food Chem. 2010, 58, 9498-9504 10.1021/jf101873f
9. Funk, J. L.; Frye, J. B.; Oyarzo, J. N.; Zhang, H.; Timmermann, B. N. Anti-arthritic effects and toxicity of the essential oils of turmeric (Curcuma longa L.) J. Agric. Food Chem. 2010, 58, 842-849 10.1021/jf9027206
10. Park, S. Y.; Kim, D. S. Discovery of natural products from Curcuma longa that protect cells from beta-amyloid insult: a drug discovery effort against Alzheimer's disease J. Nat. Prod. 2002, 65, 1227-1231 10.1021/np010039x
11. Simon, A.; Allais, D. P.; Duroux, J. L.; Basly, J. P.; Durand-Fontanier, S.; Delage, C. Inhibitory effect of curcuminoids on MCF-7 cell proliferation and structure-activity relationships Cancer Lett. 1998, 129, 111-116 10.1016/S0304-3835(98)00092-5
12. Miriyala, S.; Panchatcharam, M.; Rengarajulu, P. Cardioprotective effects of curcumin Adv. Exp. Med. Biol. 2007, 595, 359-377 10.1007/978-0-387-46401-5-16
13. Park, B. S.; Kim, J. G.; Kim, M. R.; Lee, S. E.; Takeoka, G. R.; Oh, K. B.; Kim, J. H. Curcuma longa L. constituents inhibit sortase A and Staphylococcus aureus cell adhesion to fibronectin J. Agric. Food Chem. 2005, 53, 9005-9009 10.1021/jf051765z
14. Wang, M.; Zhang, Q.; Ren, Q.; Kong, X.; Wang, L.; Wang, H.; Xu, J.; Guo, Y. Isolation and characterization of sesquiterpenes from Celastrus orbiculatus and their antifungal activities against phytopathogenic fungi J. Agric. Food Chem. 2014, 62, 10945-10953 10.1021/jf503735t
15. Xu, J.; Zhang, Q.; Wang, M.; Ren, Q.; Sun, Y.; Jin, D. Q.; Xie, C.; Chen, H.; Ohizumi, Y.; Guo, Y. Bioactive clerodane diterpenoids from the twigs of Casearia balansae J. Nat. Prod. 2014, 77, 2182-2189 10.1021/np5003516
16. Wang, M.; Zhang, Q.; Wang, H.; Ren, Q.; Sun, Y.; Xie, C.; Xu, J.; Jin, D. Q.; Ohizumi, Y.; Guo, Y. Characterization and NO inhibitory activities of chemical constituents from an edible plant Petasites tatewakianus J. Agric. Food Chem. 2014, 62, 9362-9367 10.1021/jf5034224
17. MOE 2013.08; Chemical Computing Group Inc., www.chemcomp.com.
18. Gaussian 09, revision B, 01; Gaussian Inc.: Wallingford, CT, USA, 2010.
19. Autschbach, J.; Nitsch-Velasquez, L.; Rudolph, M. Time dependent density functional response theory for electronic chiroptical properties of chiral molecules Top. Curr. Chem. 2011, 298, 1-98 10.1007/128-2010-72
20. Zhang, Q.; Xiao, J.; Sun, Q. Q.; Qin, J. C.; Pescitelli, G.; Gao, J. M. Characterization of cytochalasins from the endophytic Xylaria sp. and their biological functions J. Agric. Food Chem. 2014, 62, 10962-10969 10.1021/jf503846z
21. Wang, K. B.; Di, Y. T.; Bao, Y.; Yuan, C. M.; Chen, G.; Li, D. H.; Bai, J.; He, H. P.; Hao, X. J.; Pei, Y. H.; Jing, Y. K.; Li, Z. L.; Hua, H. M. Peganumine A, a β-carboline dimer with a new octacyclic scaffold from Peganum harmala Org. Lett. 2014, 16, 4028-4031 10.1021/ol501856v
22. Bruhn, T.; Schaumlöffel, A.; Hemberger, Y.; Bringmann, G. SpecDis, version 1.62; University of Wuerzburg: Germany, 2014.
23. Roth, G. N.; Chandra, A.; Nair, M. G. Novel bioactivities of Curcuma longa constituents J. Nat. Prod. 1998, 61, 542-545 10.1021/np970459f
24. Liu, Y.; Nair, M. G. Curcuma longa and Curcuma mangga leaves exhibit functional food property Food Chem. 2012, 135, 634-640 10.1016/j.foodchem.2012.04.129
25. Xu, J.; Liu, C.; Guo, P.; Guo, Y.; Jin, D. Q.; Song, X.; Sun, Z.; Gui, L.; Ma, Y. Neuroprotective labdane diterpenes from Fritillaria ebeiensis Fitoterapia 2011, 82, 772-776 10.1016/j.fitote.2011.03.009
26. Zeng, Y.; Qiu, F.; Takahashi, K.; Liang, J.; Qu, G.; Yao, X. New sesquiterpenes and calebin derivatives from Curcuma longa Chem. Pharm. Bull. 2007, 55, 940-943 10.1248/cpb.55.940
27. Fujiwara, M.; Yagi, N.; Miyazawa, M. Acetylcholinesterase inhibitory activity of volatile oil from Peltophorum dasyrachis Kurz ex Bakar (yellow batai) and bisabolane-type sesquiterpenoids J. Agric. Food Chem. 2010, 58, 2824-2829 10.1021/jf9042387
28. Imai, S.; Morikiyo, M.; Furihata, K.; Hayakawa, Y.; Seto, H. Turmeronol A and turmeronol B, new inhibitors of soybean lipoxygenase Agric. Biol. Chem. 1990, 54, 2367-2371 10.1271/bbb1961.54.2367
29. Zhang, W. Y.; Wang, H. F.; Cheng, G.; Zhang, O.; Bai, S.; Pei, Y. H. Two new bisabolane sesquiterpenoids from Curcuma longa J. Asian Nat. Prod. Res. 2014, 16, 271-274 10.1080/10286020.2013.875010
30. Li, H. M.; Lei, C.; Luo, Y. M.; Li, X. N.; Li, X. L.; Pu, J. X.; Zhou, S. Y.; Li, R. T.; Sun, H. D. Intermedins A and B; new metabolites from Schisandra propinqua var. intermedia Arch. Pharmacal Res. 2008, 31, 684-687 10.1007/s12272-001-1213-6
31. Uehara, S.; Yasuda, I.; Takeya, K.; Itokawa, H.; Iitaka, Y. New bisabolane sesquiterpenoids from the rhizomes of Curcuma xanthorrhiza (Zingiberaceae) II Chem. Pharm. Bull. 1990, 38, 261-263 10.1248/cpb.38.261
32. Zhu, N.; Kikuzaki, H.; Sheng, S.; Sang, S.; Rafi, M. M.; Wang, M.; Nakatani, N.; DiPaola, R. S.; Rosen, R. T.; Ho, C. T. Furanosesquiterpenoids of Commiphora myrrha J. Nat. Prod. 2001, 64, 1460-1462 10.1021/np010072j
33. Hikino, H.; Sakurai, Y.; Numabe, S.; Takemoto, T. Structure of curcumenol Chem. Pharm. Bull. 1968, 16, 39-42 10.1248/cpb.16.39
34. Firman, K.; Kinoshita, T.; Itai, A.; Sankawa, U. Terpenoids from Curcuma heyneana Phytochemistry 1988, 27, 3887-3891 10.1016/0031-9422(88)83038-3
35. Ohshiro, M.; Kuroyanagi, M.; Ueno, A. Structures of sesquiterpenes from Curcuma longa Phytochemistry 1990, 29, 2201-2205 10.1016/0031-9422(90)83038-3
36. Yin, G. P.; Li, L. C.; Zhang, Q. Z.; An, Y. W.; Zhu, J. J.; Wang, Z. M.; Chou, G. X.; Wang, Z. T. iNOS inhibitory activity of sesquiterpenoids and a monoterpenoid from the rhizomes of Curcuma wenyujin J. Nat. Prod. 2014, 77, 2161-2169 10.1021/np400984c
37. Zhang, C. M.; Fan, P. H.; Li, M.; Lou, H. X. Two new sesquiterpenoids from the rhizomes of Curcuma xanthorrhiza Helv. Chim. Acta 2014, 97, 1295-1300 10.1002/hlca.201300440
38. Lou, Y.; Zhao, F.; He, H.; Peng, K. F.; Zhou, X. H.; Chen, L. X.; Qiu, F. Guaiane-type sesquiterpenes from Curcuma wenyujin and their inhibitory effects on nitric oxide production J. Asian Nat. Prod. Res. 2009, 11, 736-746 10.1080/10286020903042358
39. Chen, H.; Xie, C.; Wang, H.; Jin, D. Q.; Li, S.; Wang, M.; Ren, Q.; Xu, J.; Ohizumi, Y.; Guo, Y. Sesquiterpenes inhibiting the microglial activation from Laurus nobilis J. Agric. Food Chem. 2014, 62, 4784-4788 10.1021/jf501515v
40. Xu, J.; Jin, D. Q.; Liu, C.; Xie, C.; Guo, Y.; Fang, L. Isolation, characterization, and NO inhibitory activities of sesquiterpenes from Blumea balsamifera J. Agric. Food Chem. 2012, 60, 8051-8058 10.1021/jf302530u