Planta Med 2006; 72(1): 75-78
DOI: 10.1055/s-2005-873178
Letter
© Georg Thieme Verlag KG Stuttgart · New York

New Cytotoxic 6-Oxygenated 8,9-Dihydrofurocoumarins, Hedyotiscone A - C, from Hedyotis biflora

Yung-Husan Chen1 , Fang-Rong Chang1 , Chin-Chung Wu1 , Ming-Hon Yen1 , Chih-Chuang Liaw1 , Hui-Chi Huang1 , Yao-Haur Kuo2 , Yang-Chang Wu1
  • 1Graduate Institute of Natural Products, Kaohsiung Medical University, Kaohsiung, Taiwan, R.O.C.
  • 2National Research Institute of Chinese Medicine, Taipei, Taiwan, R.O.C.
Further Information

Publication History

Received: March 15, 2005

Accepted: June 20, 2005

Publication Date:
10 November 2005 (online)

Abstract

Using the bioactivity-guided fractionation method, three new 6-oxygenated 8,9-dihydrofurocoumarin-type compounds, hedyotiscones A (1), B (2), and C (3) were isolated from the methanol extract of Hedyotis biflora together with seven known compounds. The structures of all isolated compounds were determined on the basis of mass and spectroscopic evidence. Compounds 1 - 3, oleanolic acid, and 6′-(β-sitosteryl-3-O-β-D-glucopyranosidyl) pentadecanoate showed marginal cytotoxicity against Hep G2 cells (human liver cancer cells) with IC50 values of 14.4, 17.4, 4.9, 8.0, and 9.2 μg/mL, respectively. Ursolic acid showed significant cytotoxicity against MDA-MB-231 cells (human breast carcinoma cells) with an IC50 value of 1.49 μg/mL.

References

  • 1 Yuan Q, Zhao J, Yang J, Li L. Survey on triterpenoids from Hedyotis and their spectroscopic characteristics.  Zhongcaoyao. 2001;  32 754-6
  • 2 Lu P, Dai Q J. Summarization on the chemical constituents of Oldenlandia diffusa Willd.  Beijing Poly Univer. 2000;  26 68-72
  • 3 Kim Y, Park E J, Kim J, Kim S R, Kim Y Y. Neuroprotective constituents from Hedyotis diffusa .  J Nat Prod. 2001;  64 75-8
  • 4 Lu C M, Yang J J, Wang P, Lin C C. A new acylated flavonol glycoside and antioxidant effects of Hedyotis diffusa .  Planta Med. 2000;  66 374-7
  • 5 Peng J N, Feng X Z, Liang X T. Iridoids from Hedyotis hedyotidea .  Phytochemistry. 1998;  47 1657-9
  • 6 Peng J N, Feng X Z, Liang X T. Two new iridoids from Hedyotis chrysotricha .  J Nat Prod. 1999;  62 611-2
  • 7 Hamzah A S, Jasmani H, Ahmad R, Baba A R, Lajis N H, Aimi N. et al . New anthraquinones from the roots of Hedyotis dichotoma .  J Nat Prod. 1997;  60 36-7
  • 8 Lin C C, Ng L T, Yang J J, Hsu Y F. Anti-inflammatory and hepatoprotective activity of Peh-Hue-Juwa-Chi-Cao in male rats.  Am J Chin Med. 2002;  30 225-34
  • 9 Li H L, Liu T S, Huang T C, Koyama T, Devol C E. Flora of Taiwan, 2nd Edition.  Taipei: Editorial Committee of Flora of. Taiwan;  1993 Volume 2, p. 265
  • 10 Uzi A, Aberaham S, Shmuel C. 6,7-Dimethoxycumarin, a citrus phytoalexin conferring resistance against Phytophthora gummosis .  Phytochemistry. 1986;  25 1855-6
  • 11 Sang S, Lapsley K, Rosen R T, Ho C T. New prenylated benzoic acid and other constituents from almond hulls (Prunus amygdalus Batsch).  J Agric Food Chem. 2002;  50 607-9
  • 12 Sidiqui B S, Sultana I, Begum S. Triterpenoidal constituents from Eucalyptus camaldulensis var. obtusa leaves.  Phytochemistry. 2000;  54 861-5
  • 13 Uluelen A, Oksuz S, Mericli A H. Palmitic acid ester of sitosteryl 3β-glucoside from Centaurea regia .  Phytochemistry. 1988;  12 3964-5
  • 14 Chang Y C, Chang F R, Wu Y C. The constituents of Lindera glauca .  J Chin Chem Soc. 2000;  47 913-20
  • 15 Fumiko A, Pongfu C, Tatsuo Y, Hiromu O. Iridiods from the roots of Thevetia peruviana .  Chem Pharm Bull. 1995;  43 499-500
  • 16 Bissoue A N, Muyard F, Bevalot F, Tillequin F, Mercier M F, Armstrong J A. et al . Coumarins from the aerial parts of Chorilaena quercifolia .  Phytochemistry. 1996;  43 877-9
  • 17 Yamaguchi S, Miyakawa R, Yonezawa S, Kawase Y. Acylations of 2-isopropenyl-2,3-dihydrobenzofurans.  Bull Chem Soc Jpn. 1989;  62 3593-7
  • 18 Yamaguchi S, Muro S, Kobayashi M, Miyazawa M, Hirai Y. Absolute structures of some naturally occurring isopropenyl dihydrobenzofurans, remirol, remiridiol, angenomalin, and isoangenomalin.  J Org Chem. 2003;  68 6274-8
  • 19 Lee T T-Y, Kashiwada Y, Huang L, Snider J, Cosentino M, Lee K H. Suksdorfin: an anti-HIV principle from Lomatium suksdorfii, its SAR with related coumarins, and synergistic effects with anti-AIDS nucleoside.  Bioorg Med Chem. 1994;  2 1051-6
  • 20 Tada Y, Shikishima Y, Takaishi Y, Shibata H. Coumarins and γ-pyrone derivatives from Prangos pabularia: antibacterial activity and inhibition of cytokine release.  Phytochemistry. 1988;  12 3964-5
  • 21 Ito C, Katasuno S, Kondo Y, Tan H T-W, Furukawa H. Constituents of Micromelum minutum isolation and structural elucidation of new coumarins.  Chem Pharm Bull. 2000;  48 334-8
  • 22 Sladowski D, Steer S, Clothier R H, Balls M. Chihiro I. An improved MTT assay.  J Immunol Methods. 1993;  157 203-7

Prof. Dr. Yang-Chang Wu

Graduate Institute of Natural Products

Kaohsiung Medical University

100 Shih-Chuan, 1st Road

San Ming District

Kaohsiung 807

Taiwan

Republic of China

Phone: +886-7-3121101 ext. 2197

Fax: +886-7-3114773

Email: yachwu@kmu.edu.tw