Planta Med 2013; 79(06): 487-491
DOI: 10.1055/s-0032-1328297
Natural Product Chemistry
Original Papers
Georg Thieme Verlag KG Stuttgart · New York

Flavonoids and 3-Arylcoumarin from Pterocarpus soyauxii

Zushang Su
1   National Center for Pharmaceutical Crops, Arthur Temple College of Forestry and Agriculture, Stephen F. Austin State University, Nacogdoches, TX, USA
,
Ping Wang
1   National Center for Pharmaceutical Crops, Arthur Temple College of Forestry and Agriculture, Stephen F. Austin State University, Nacogdoches, TX, USA
,
Wei Yuan
1   National Center for Pharmaceutical Crops, Arthur Temple College of Forestry and Agriculture, Stephen F. Austin State University, Nacogdoches, TX, USA
,
Shiyou Li
1   National Center for Pharmaceutical Crops, Arthur Temple College of Forestry and Agriculture, Stephen F. Austin State University, Nacogdoches, TX, USA
› Author Affiliations
Further Information

Publication History

received 27 November 2012
revised 30 January 2013

accepted 05 February 2013

Publication Date:
11 March 2013 (online)

Abstract

Phytochemical study on the constituents of the heartwood of Pterocarpus soyauxii led to the isolation of five new isoflavonoids and one new 3-arylcoumarin, pterosonins A–F (16), together with 17 known analogues, among which 8, 9, and 18 were reported as natural products for the first time. Structure elucidation was achieved by way of spectroscopic measurements as well as by comparison with literature data. Only Compound 6 showed potent cytotoxicity against human non-small cell lung cancer (A549), pancreatic cancer (Panc-28), and colon carcinoma (HCT-116) cells with GI50 values at 7.39, 25, and 19.17 µM, respectively; the other isolates showed no cytotoxicity against the above tested cell lines with GI50 values > 50 µM.

Supporting Information

 
  • References

  • 1 MacLachlan IR, Gasson P. PCA of cites listed Pterocarpus santalinus (Legminosae) wood. IAWA J 2010; 31: 121-131
  • 2 Prakash E, Khan PSSV, Rao TJVS, Meru ES. Micropropagation of red sanders (Pterocarpus santalinus L.) using mature nodal explants. J For Res 2006; 11: 329-335
  • 3 Wu SF, Hwang TL, Chen SL, Wu CC, Ohkoshi E, Lee KH, Chang FR, Wu YC. Bioactive components from the heartwood of Pterocarpus santalinus . Bioorg Med Chem Lett 2011; 21: 5630-5632
  • 4 Wu SF, Chang FR, Wang SY, Hwang TL, Lee CL, Chen SL, Wu CC, Wu YC. Anti-inflammatory and cytotoxic neoflavonoids and benzofurans from Pterocarpus santalinus . J Nat Prod 2011; 74: 989-996
  • 5 Bremaud I, Amusant N, Minato K, Gril J, Thibaut B. Effect of extractives on vibrational properties of African Padauk (Pterocarpus soyauxii Taub). Wood Sci Technol 2011; 45: 461-472
  • 6 Tchamadeu MC, Dzeufiet PD, Nana P, Kouambou Nouga CC, Ngueguim Tsofack F, Allard J, Blaes N, Siagat R, Zapfack L, Girolami JP, Tack I, Kamtchouing P, Dimo T. Acute and sub-chronic oral toxicity studies of an aqueous stem bark extract of Pterocarpus soyauxii Taub (Papilionaceae) in rodents. J Ethnopharmacol 2011; 133: 329-335
  • 7 Saha JBT, Abia D, Dumarcay S, Ndikontar MK, Gerardin P, Ngamveng Noah J, Perrin D. Antioxidant activities, total phenolic contents and chemical compositions of extracts from four Cameroonian woods: Padouk (Pterocarpus soyauxii Taubb), tali (Erythrophleum suaveolens), moabi (Baillonella toxisperma), and movingui (Distemonanthus benthamianus). Indian Crops Prod 2013; 41: 71-77
  • 8 Loris R, Imberty A, Beeckmans S, Van Driessche E, Read JS, Bouckaert J, De Greve H, Buts L, Wyns L. Crystal structure of Pterocarpus angolensis lectin in complex with glucose, sucrose, and turanose. J Biol Chem 2003; 278: 16297-16303
  • 9 Barend CB, Brandt BEV. Flavonoid analogs from Pterocarpus species. Phytochemistry 1987; 26: 531-535
  • 10 Wang P, Ownby S, Zhang ZZ, Yuan W, Li SY. Cytotoxicity and inhibition of DNA topoisomerase I of polyhydroxylated triterpenoids and triterpenoid glycosides. Bioorg Med Chem Lett 2010; 20: 2790-2796
  • 11 Umehara K, Nemoto K, Matsushita A, Terada E, Monthakantirat O, De-Eknamkul W, Miyase T, Warashina T, Degawa M, Noguchi H. Flavonoids from the heartwood of the Thai medicinal plant Dalbergia parviflora and their effects on estrogenic-responsive human breast cancer cells. J Nat Prod 2009; 72: 2163-2168
  • 12 Jurd L, Stevens K, Manners G. Isoflavones of the heartwood of Dalbergia retusa . Phytochemistry 1972; 11: 2535-2540
  • 13 Kinjo J, Uemura H, Nohara T, Yamashita M, Marubayashi N, Yoshihira K. Studies on the constituents of leguminous plants. 47. Novel yellow pigment from Pterocarpus santalinus: biogenetic hypothesis for santalin analogs. Tetrahedron Lett 1995; 36: 5599-5602
  • 14 Ollis WD, Sutherland IO, Alves HM, Gottlieb OR. Duartin, an isoflavan from Machaerium opacum . Phytochemistry 1978; 17: 1401-1403
  • 15 Shoukry MM, Darwish NA, Morsi MA. Synthesis of 2′,4′-dimethoxy-3′,6,7-trihydroxy-3-isoflavene, a constituent of Baphia nitida . Gazz Chim Ital 1982; 112: 289-291
  • 16 Chen WH, Wang R, Shi YP. Flavonoids in the poisonous plant Oxytropis falcata . J Nat Prod 2010; 73: 1398-1403
  • 17 Rong H, Stevens JF, Deinzer ML, Cooman LD, Keukeleire DD. Identification of isoflavones in the roots of Pueraria lobata . Planta Med 1998; 64: 620-627
  • 18 Ferreira MA, Moir M, Thomson RH. New pterocarpenes from Brya ebenus . J Chem Soc [Perkin I] 1974; 2429-2435
  • 19 Miyase T, Sano M, Nakai H, Muroka M, Nakazawa M, Suzuki M, Yoshino K, Nishihara Y, Tanai J. Antioxidants from Lespedeza homoloba (II). Phytochemistry 1999; 52: 311-319
  • 20 Engler TA, Reddy JP, Combrink KD, Velde DV. Formal 2 + 2 and 3 + 2 cycloaddition reactions of 2H-chromenes with 2-alkoxy-1,4-benzoquinones: regioselective synthesis of substituted pterocarpans. J Org Chem 1990; 55: 1248-1254
  • 21 Umehara K, Nemoto K, Kimijima K, Matsushita A, Terada E, Monthakantirat O, De-Eknamkul W, Miyase T, Warashina T, Degawa M, Noquchi H. Estrogenic constituents of the heartwood of Dalbergia parviflora . Phytochemistry 2008; 69: 546-552
  • 22 Amesty A, Burqueno-Tapia E, Joseph-Nathan P, Ravelo AG, Estevez-Braun A. Benzodihydrofurans from Cyperus teneriffae . J Nat Prod 2011; 74: 1061-1065
  • 23 Aziz-ur-Rehman. Malik AR, Riaz N, Ahmad H, Nawaz SA, Choudhary MI. Lipoxygenase inhibiting flavonoids from Indigofera hetrantha . Heterocycles 2004; 63: 359-366
  • 24 Ali MS, Ali MI, Ahmed Z, Onocha PA. Two new prenylflavanones from Erythrina sigmoidea . Nat Prod Commun 2011; 6: 1099-1102