Planta Med 2014; 80(11): 955-958
DOI: 10.1055/s-0034-1382839
Natural Product Chemistry
Letters
Georg Thieme Verlag KG Stuttgart · New York

Monoterpenoid Coumarins from the Peels of Clausena lansium

Hui-Dong Deng*
1   Key Laboratory of Biology and Genetic Resources of Tropical Crops, Ministry of Agriculture (Hainan Key Laboratory for Research and Development of Natural Products from Li Folk Medicine), Institute of Tropical Bioscience and Biotechnology, Chinese Academy of Tropical Agricultural Sciences, Haikou, Hainan, P. R. China
2   Key Laboratory of Protection and Developmental Utilization of Tropical Crop Germplasm Resources, Ministry of Education, College of Horticulture and Landscape Architecture, Hainan University, Haikou, Hainan, P. R. China
,
Wen-Li Mei*
1   Key Laboratory of Biology and Genetic Resources of Tropical Crops, Ministry of Agriculture (Hainan Key Laboratory for Research and Development of Natural Products from Li Folk Medicine), Institute of Tropical Bioscience and Biotechnology, Chinese Academy of Tropical Agricultural Sciences, Haikou, Hainan, P. R. China
,
Zhi-Kai Guo
1   Key Laboratory of Biology and Genetic Resources of Tropical Crops, Ministry of Agriculture (Hainan Key Laboratory for Research and Development of Natural Products from Li Folk Medicine), Institute of Tropical Bioscience and Biotechnology, Chinese Academy of Tropical Agricultural Sciences, Haikou, Hainan, P. R. China
,
Shuai Liu
1   Key Laboratory of Biology and Genetic Resources of Tropical Crops, Ministry of Agriculture (Hainan Key Laboratory for Research and Development of Natural Products from Li Folk Medicine), Institute of Tropical Bioscience and Biotechnology, Chinese Academy of Tropical Agricultural Sciences, Haikou, Hainan, P. R. China
,
Wen-Jian Zuo
1   Key Laboratory of Biology and Genetic Resources of Tropical Crops, Ministry of Agriculture (Hainan Key Laboratory for Research and Development of Natural Products from Li Folk Medicine), Institute of Tropical Bioscience and Biotechnology, Chinese Academy of Tropical Agricultural Sciences, Haikou, Hainan, P. R. China
,
Wen-Hua Dong
1   Key Laboratory of Biology and Genetic Resources of Tropical Crops, Ministry of Agriculture (Hainan Key Laboratory for Research and Development of Natural Products from Li Folk Medicine), Institute of Tropical Bioscience and Biotechnology, Chinese Academy of Tropical Agricultural Sciences, Haikou, Hainan, P. R. China
,
Shao-Peng Li
2   Key Laboratory of Protection and Developmental Utilization of Tropical Crop Germplasm Resources, Ministry of Education, College of Horticulture and Landscape Architecture, Hainan University, Haikou, Hainan, P. R. China
,
Hao-Fu Dai
1   Key Laboratory of Biology and Genetic Resources of Tropical Crops, Ministry of Agriculture (Hainan Key Laboratory for Research and Development of Natural Products from Li Folk Medicine), Institute of Tropical Bioscience and Biotechnology, Chinese Academy of Tropical Agricultural Sciences, Haikou, Hainan, P. R. China
› Author Affiliations
Further Information

Publication History

received 18 November 2013
revised 11 June 2014

accepted 13 June 2014

Publication Date:
21 July 2014 (online)

Abstract

A phytochemical investigation on the peels of Clausena lansium (Lour.) Skeels led to the isolation of two new monoterpenoid coumarins, named clauslactone V (1) and clauslactone W (2), together with three known analogues (35). Their structures were elucidated by spectroscopic techniques (UV, IR, MS, 1D and 2D NMR). All the compounds were evaluated for hypoglycemic activity, and compounds 15 showed α-glucosidase inhibitory activity in vitro.

* These authors contributed equally to this work.


Supporting Information

 
  • References

  • 1 Liu GT, Li WX, Chen YY, Wei HL. Hepatoprotective action of nine constituents isolated from the leaves of Clausena lansium in mice. Drug Develop Res 1996; 39: 174-178
  • 2 Yang ME, Chen YY, Huang L. Three novel cyclic amides from Clausena lansium . Phytochemistry 1988; 27: 445-450
  • 3 Adebajo AC, Iwalewa EO, Obuotor EM, Ibikunle GF, Omisore NO, Adewunmi CO, Obaparusi OO, Klaes M, Adetogun GE, Schmidt TJ, Verspohl EJ. Pharmacological properties of the extract and some isolated compounds of Clausena lansium stem bark: anti-trichomonal, antidiabetic, anti-inflammatory, hepatoprotective and antioxidant effects. J Ethnopharmacol 2009; 122: 10-19
  • 4 Jackobsen HB, Friis P, Kan WS. Mannual of medicinal plants in Taiwan, Volume 2. Taipei: National Research Institute of Chinese Medicine Press; 1972: 372
  • 5 Liu H, Li CJ, Yang JZ, Ning N, Si YK, Li L, Chen NH, Zhao Q, Zhang DM. Carbazole alkaloids from the stems of Clausena lansium . J Nat Prod 2012; 75: 677-682
  • 6 Shen DY, Chao CH, Chan HH, Huang GJ, Hwang TL, Lai CY, Lee KH, Thang TD, Wu TS. Bioactive constituents of Clausena lansium and a method for discrimination of aldose enantiomers. Phytochemistry 2012; 82: 110-117
  • 7 Wisanu M, Thunwadee R, Sarot C, Surat L. Carbazole alkaloids and coumarins from Clausena lansium roots. Phyto Lett 2012; 5: 26-28
  • 8 Uraiwan S, Tula T, Pronsilp Z, Veerapol K, Chantana B, Jinda W, Chavi Y. Antioxidant activity and cytotoxicity against cholangiocarcinoma of carbazoles and coumarins from Clausena harmandiana . Sci Asia 2012; 38: 75-81
  • 9 Zhao Q, Yang JZ, Li CJ, Chen NH, Zhang DM. A new megastigmane glucoside and a new amide alkaloid from the leaves of Clausena lansium (Lour.) Skeels. J Asian Nat Prod Res 2011; 13: 361-366
  • 10 Uraiwan S, Tula T, Chantana B, Chavi Y. Claurailas A–D, cytotoxic carbazole alkaloids from the roots of Clausena harmandiana . J Nat Prod 2011; 74: 208-212
  • 11 Wisanu M, Uma P, Nisakorn S, Surat L. New coumarins from Clausena lansium twigs. J Braz Chem Soc 2010; 21: 665-668
  • 12 Tawannun S, Surat L. Carbazole alkaloids from the stems of Clausena excavata . J Asian Nat Prod Res 2010; 12: 614-617
  • 13 Maneerat W, Laphookhieo S. Antitumoral alkaloids from Clausea lansium . Heterocycles 2010; 81: 1261-1269
  • 14 Nakamura T, Kodama N, Arai Y, Kumamoto T, Higuchi Y, Chaichantipyuth C, Ishikawa T, Ueno K, Yano S. Inhibitory effect of oxycoumarins isolated from the Thai medicinal plant Clausena guillauminii on the inflammation mediators, iNOS, TNF-alpha, and COX-2 expression in mouse macrophage RAW264.7. J Nat Med 2009; 63: 21-27
  • 15 Taufiq-Yap YH, Peh TH, Ee GCL. A new cytotoxic carbazole alkaloid from Clausena excavata . Nat Prod Res 2007; 21: 810-813
  • 16 Kongkathip B, Kongkathip N, Sunthitkawinsakul A, Napaswat C, Yoosook C. Anti-HIV-1 constituents from Clausena excavata: Part II. Carbazoles and a pyranocoumarin. Phytother Res 2005; 19: 728-731
  • 17 Ito C, Katsuno S, Ruangrungsi N, Furukawa H. Structures of clausamine-A, -B, -C, three novel carbazole alkaloids from Clausena anisata . Chem Pharm Bull 1998; 46: 344-346
  • 18 Lakshmi V, Prakash D, Raj K, Kapil RS, Popli SP. Monoterpenoid furanocoumarin lactones from Clausena anisata . Phytochemistry 1984; 23: 2629-2631
  • 19 Khan NU, Naqvi SWI, Ishratullah K. Wampetin, a furocoumarin from Clausena wampi . Phytochemistry 1983; 22: 2624-2625
  • 20 Wu TS, Furukawa H. Constituents of Formosan folk medicine. 13. Biological and phytochemical investigation of Clausena excavata . J Nat Prod 1982; 45: 718-720
  • 21 Yang Y, Zuo WJ, Zhao YX, Dong WH, Mei WL, Dai HF. Indole alkaloids from Kopsia hainanensis and evaluation of their antimicrobial activity. Planta Med 2012; 78: 1881-1884
  • 22 Mosmann T. Rapid colorinetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays. J Immunol Methods 1983; 65: 55-63
  • 23 Jong AN, Bhandari MR, Kawabata J. α-Glucosidase inhibitors from Devil tree (Alstonia scholaris). Food Chem 2007; 103: 1319-1323
  • 24 Cai JN, Basnet P, Wang ZT, Komatsu K, Xu LS, Tani T. Coumarins from the fruits of Cnidium monnieri. J Nat Prod 2000; 63: 485-488