Planta Med 2014; 80(08/09): 688-694
DOI: 10.1055/s-0034-1368456
Natural Product Chemistry
Original Papers
Georg Thieme Verlag KG Stuttgart · New York

Horsfiequinones A–F, Dimeric Diarylpropanoids from Horsfieldia tetratepala

Qin Ma
1   School of Chemistry and Chemical Engineering, Yunnan Normal University, Chenggong New Development Area, Kunming, Yunnan, China
,
Kang Min
2   Diqing Institute of Agricultural Science, Shangrila, Yunnan, China
,
Hao-Liang Li
1   School of Chemistry and Chemical Engineering, Yunnan Normal University, Chenggong New Development Area, Kunming, Yunnan, China
,
Jin-He Jiang
1   School of Chemistry and Chemical Engineering, Yunnan Normal University, Chenggong New Development Area, Kunming, Yunnan, China
,
Ying Liu
1   School of Chemistry and Chemical Engineering, Yunnan Normal University, Chenggong New Development Area, Kunming, Yunnan, China
,
Rui Zhan
1   School of Chemistry and Chemical Engineering, Yunnan Normal University, Chenggong New Development Area, Kunming, Yunnan, China
,
Ye-Gao Chen
1   School of Chemistry and Chemical Engineering, Yunnan Normal University, Chenggong New Development Area, Kunming, Yunnan, China
› Author Affiliations
Further Information

Publication History

received 06 January 2014
revised 10 April 2014

accepted 14 April 2014

Publication Date:
22 May 2014 (online)

Abstract

A new diarylpropanoid, horsfiequinone A (1), and five new dimeric diarylpropanoids with 1,4-p-benzoquinone residue, horsfiequinones B–F (26), along with a known compound, combrequinone B (7), were isolated from Horsfieldia tetratepala. Their structures were elucidated by means of spectroscopic analysis. Horsfiequinones B–F (26), isolated as enantiomer mixtures with unequal proportions, were verified by analysis on a chiral OD-H HPLC column. Cytotoxicity evaluation against five human tumor lines showed selective inhibitory effects on HL-60 for several compounds tested with IC50 values ranging from 3.18 ± 0.67 to 6.61 ± 0.08 µM.

Supporting Information

 
  • References

  • 1 Teo L, Pachiaper G, Chan K, Hadi H, Weber J, Deverre J, David B, Sevenet T. A new phytochemical survey of Malaysia V. Preliminary screening and plant chemical studies. J Ethnopharmacol 1990; 28: 63-101
  • 2 Waruruai J, Sipana B, Koch M, Barrows LR, Matainaho TK, Rai PP. An ethnobotanical survey of medicinal plants used in the Siwai and Buin districts of the Autonomous Region of Bougainville. J Ethonpharmacol 2011; 138: 564-577
  • 3 Khan M, Kihara M, Omoloso A. Antimicrobial activity of Horsfieldia helwigii and Melia azedarach . Fitoterapia 2001; 72: 423-427
  • 4 Xu YL, Cai NH, Wu Y, Duan AA. Fatty acid composition of several plants of Horsfieldia . China Oil Fat 2012; 37: 80-82
  • 5 Pinto MM, Kijjoa A, Tantisewiet B, Yoshida M, Gottlieb OR. Arylalkanones from Horsfieldia glabra . Phytochemistry 1988; 27: 3988-3989
  • 6 Tillekeratne L, Jayamanne D, Weerasuria K, Gunatilaka A. Lignans of Horsfieldia iryaghedhi . Phytochemistry 1982; 21: 476-478
  • 7 Gunatilaka A, De Silva A, Sotheeswaran S, Tillekeratne L. Horsfieldin, a lignan and other constituents from Horsfieldia iryaghedhi . Phytochemistry 1982; 21: 2719-2723
  • 8 Gonzalez MJ, Pinto MM, Kijjoa A, Kengthong S, Mondanondra I, Silva A, Eaton G, Herz W. 5, 7-Dihydroxychromones and 8-hydroxytetrahydrochromones from Horsfieldia irya . Phytochemistry 2002; 61: 995-998
  • 9 Al-Mekhlafi NA, Shaaria K, Abas F, Jeyaraj EJ, Stanslas J, Khalivulla SI, Lajis NH. New flavan and alkyl alpha, beta-lactones from the stem bark of Horsfieldia superba . Nat Prod Commun 2013; 8: 447-451
  • 10 Jossang A, Jossang P, Hadi HA, Sevenet T, Bodo B. Horsfiline, an oxindole alkaloid from Horsfieldia superba . J Org Chem 1991; 56: 6527-6530
  • 11 Lu ZY, Van Wagoner RM, Pond CD, Pole AR, Jensen JB, Blankenship DA, Grimberg BT, Kiapranis R, Matainaho TK, Barrows LR, Ireland CM. Myristicyclins A and B: antimalarial procyanidins from Horsfieldia spicata from Papua New Guinea. Org Lett 2014; 16: 346-349
  • 12 Editorial Committee of Flora of China, Chinese Academy of Sciences. Flora of China, Volume 30 (2). Beijing: Science Press; 1979: 197
  • 13 Wu MM, Wang LQ, Hua Y, Chen YG, Wang YY, Li XY, Li Y, Li T, Yang XY, Tang ZR. New chalcone and dimeric chalcones with 1, 4-p-benzoquinone residue from Combretum yunnanense . Planta Med 2011; 77: 481-484
  • 14 Moosophon P, Kanokmedhakul S, Kanokmedhakul K. Diarylpropanes and an arylpropyl quinone from Combretum griffithii . J Nat Prod 2011; 74: 2216-2218
  • 15 Morimoto S, Nonaka GI, Nishioka I, Ezaki N, Takizawa N. Tannins and related compounds. XXIX. Seven new methyl derivatives of flavan-3-ols and a 1, 3-diarylpropan-2-ol from Cinnamomum cassia, C. obtusifolium and Lindera umbellate var. membranacea . Chem Pharm Bull 1985; 33: 2281-2286
  • 16 Zhao Y, Shong GQ, Guo YW. Rotundifolinol, a new 1, 3-diarylpropan-2-ol from bark of Litsea rotundifolia var. oblongifolia . J Asian Nat Prod Res 2003; 5: 273-277
  • 17 Ko RK, Kang MC, Jin YJ, Choi HM, Kim BS, Han JH, Kim GO, Lee NH. A new diarylpropane from the stem bark of Lindera erythrocarpa Makino. Bull Korean Chem Soc 2010; 31: 739-741
  • 18 Huh GW, Park JH, Shrestha S, Lee YH, Ahn EM, Kang HC, Kim YB, Baek NI. New diarylpropanoids from Lindera glauca B1. heartwood. Holzforschung 2012; 66: 585-590
  • 19 Monks A, Scudiero D, Skehan P, Shoemaker R, Paull K, Vistica D, Hose C, Langley J, Cronise P, Vaigro-Wolff A, Gray-Goodrich M, Campbell H, Mayo J, Boyd M. Feasibility of a high-flux anticancer drug screen using a diverse panel of cultured human tumor cell lines. J Natl Cancer Inst 1991; 83: 757-766
  • 20 Alley MC, Scudiero DA, Monks A, Hursey ML, Czerwinski MJ, Fine DL, Abbott BJ, Mayo JG, Shoemaker RH, Boyd MR. Feasibility of drug screening with panels of human tumor cell lines using a microculture tetrazolium assay. Cancer Res 1988; 48: 589-601
  • 21 Reed LJ, Muench H. A simple method of estimating fifty percent endpoints. Am J Hyg 1938; 27: 493-497