Advertisement

Journal of Natural Medicines

, Volume 60, Issue 3, pp 161–184 | Cite as

Prenylated flavonoids and related compounds of the Indonesian Artocarpus (Moraceae)

  • Euis H. Hakim
  • Sjamsul A. Achmad
  • Lia D. Juliawaty
  • Lukman Makmur
  • Yana M. Syah
  • Norio Aimi
  • Mariko Kitajima
  • Hiromitsu Takayama
  • Emilio L. Ghisalberti
Review

Abstract

Several species of the genus Artocarpus (Moraceae) have been investigated in our laboratories during the last decade. Over 60 phenolic constituents have been discovered and characterized, including 27 new compounds from 13 Indonesian taxa of Artocarpus, namely A. champeden, A. lanceifolius, A. teysmanii, A. scortechinii, A. rotunda, A. maingayi, A. kemando, A. bracteata, A. altilis, A. fretessi, A. gomezianus, A. reticulatus and A. glaucus. The principal and the most pronounced features of these phenolic constituents are the assembly of an isoprenyl substituent at C-3 of a flavone skeleton by closure of an ether bridge or a carbon-carbon linkage with the B ring of the skeleton, which may further rearrange into xanthone to produce various classes of natural products. The structures of the new and unusual natural products are presented. Many of the metabolites also exhibit cytotoxic effect against murine leukemia P388 cells.

Keywords

Artocarpus Moraceae Phenolic constituent Flavonoid Prenylflavone Cytotoxicity 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1.
    Verheij EWM, Coronel RE (Eds) (1992) Plant resources of South-East Asia, No. 2, edible fruits and nuts. PROSEA, Bogor, Indonesia, pp 79–96Google Scholar
  2. 2.
    Heyne K (1987) The useful Indonesian plants. Research and Development Agency, The Ministry of Forestry, Jakarta, pp 659–703Google Scholar
  3. 3.
    Perry LM (1980) Medicinal plants of East and Southeast Asia: attributed properties and uses. MIT Press, Cambridge, pp 269–276Google Scholar
  4. 4.
    Venkataraman K (1972) Wood phenolics in the chemotaxonomy of the Moraceae. Phytochemistry 11:1571–1586CrossRefGoogle Scholar
  5. 5.
    Nomura T (1988) Phenolic compounds of the mulberry tree and related plants. Fortschr Chem Org Naturst 53:87–201PubMedGoogle Scholar
  6. 6.
    Nomura T, Hano Y (1994) Isoprenoid-substituted phenolic compounds of moraceous plants. Nat Prod Rep 11:205–218CrossRefPubMedGoogle Scholar
  7. 7.
    Nomura T, Hano Y, Aida M (1998) Isoprenoid-substituted flavonoids from Artocarpus plants (Moraceae). Heterocycles 47:1179–1205CrossRefGoogle Scholar
  8. 8.
    Hakim EH, Juliawaty LD, Syah YM, Achmad SA (2005) Molecular diversity of Artocarpus champeden (Moraceae): a species endemic to Indonesia. Mol Divers 9: 149–158CrossRefPubMedGoogle Scholar
  9. 9.
    Achmad SA, Hakim EH, Makmur L, Mujahidin D, Juliawaty LD, Syah YM (2002) Discovery of natural products from Indonesian tropical rainforest plants: chemodiversity of Artocarpus (Moraceae). In: Sener B (ed) Biodiversity: biomolecular aspects of biodiversity and innovative utilization. Kluwer Academic/Plenum, London, pp 91–99CrossRefGoogle Scholar
  10. 10.
    Achmad SA, Hakim EH, Juliawaty LD, Makmur L, Syah YM (2005) Indonesian rainforest plants-chemodiversity and bioactivity. Malaysian J Sci 24:7–16Google Scholar
  11. 11.
    Meyer N, Ferrigini NR, Putnam JE, Jacobsen DE, Nichols DE, McLaughlin JL (1982) Brine shrimp: a convenient general bioassay for active plant constituents. Planta Med 45:31–34CrossRefGoogle Scholar
  12. 12.
    Anonym (1995) Medicinal herb index in Indonesia. PT Eisai Indonesia, pp 135–138Google Scholar
  13. 13.
    Djakaria YK ( 1999) Artocarpanone, a flavanone derivative from root trunk of Artocarpus champeden Spreng. PhD Thesis, Department of Chemistry, Bandung Institute of TechnologyGoogle Scholar
  14. 14.
    Lin CN, Lu CM, Huang PL (1995) Flavonoids from Artocarpus heterophyllus. Phytochemistry 39:1447–1451CrossRefGoogle Scholar
  15. 15.
    Hakim EH, Aripin A, Achmad SA, Aimi N, Kitajima M, Makmur L, Mujahidin D, Syah YM, Takayama H (2001) Artoindonesianin E, a new flavanone derivative from Artocarpus champeden. Proc ITB (Indonesia) 33:69–73Google Scholar
  16. 16.
    Lu CM, Lin CN (1993) Two 2′,4′,6′-trioxygenated flavanones from Artocarpus heterophyllus. Phytochemistry 33:909–911CrossRefGoogle Scholar
  17. 17.
    Hakim EH, Achmad SA, Aimi N, Kitajima M, Makmur L, Mujahidin D, Syah YM, Takayama H (1999) Artoindonesianin and its derivatives from Artocarpus champeden. In: Proceedings of the National Seminar on Natural Product Chemistry, Jakarta, Indonesia, pp 49–53Google Scholar
  18. 18.
    Mabry TJ, Markham KR, Thomas MB (1970) The systematic identification of flavonoids. Springer, Berlin Heidelberg New YorkCrossRefGoogle Scholar
  19. 19.
    Ferlinahayati, Hakim EH, Achmad SA, Aimi N, Kitajima M, Makmur L (1999) Norartocarpetin and artonin E, two phenolic compounds from Artocarpus scortechinii King. In: Proceedings of the National Seminar on Natural Product Chemistry, Jakarta, Indonesia, pp 162–167Google Scholar
  20. 20.
    Suhartati T, Achmad SA, Aimi N, Hakim EH (2000) Isolation of flavonoid compounds from Artocarpus kemando Miq. In: Proceedings of the Joint Chemistry Seminar, Bandung Institute of Technology-National University of Malaysia, Indonesia. pp 58–64Google Scholar
  21. 21.
    Kurniadewi F. Hakim EH, Achmad SA, Makmur L, Mujahidin D, Syah YM (2001) Oxyresveratrol and norartocarpetin from Artocarpus gomezianus Wall. In: Proceedings of the National Seminar on Natural Product Chemistry, Jakarta, Indonesia, pp 467–470Google Scholar
  22. 22.
    Syah YM, Achmad SA, Ghisalberti EL, Hakim EH, Makmur L, Mujahidin D (2002) Artoindonesianins Q-T, four new isoprenylated flavones from Artocarpus champeden Spreng. (Moraceae). Phytochemistry 61:949–953CrossRefPubMedGoogle Scholar
  23. 23.
    Syah YM, Achmad SA, Ghisalberti EL, Hakim EH, Mujahidin D (2004) Two new cytotoxic isoprenylated flavones, artoindonesianins U and V, from the heartwood of Artocarpus champeden Spreng. (Moraceae). Fitoterapia 75: 134–140CrossRefPubMedGoogle Scholar
  24. 24.
    Hano Y, Matsumoto Y, Shinohara K, Sun JY, Nomura T (1990) Cudraflavones C and D, two new prenylflavones from the root bark of Cudrania tricuspidata. Heterocycles 31: 1339–1344CrossRefGoogle Scholar
  25. 25.
    Hakim EH, Fahriyati, Kau MS, Achmad SA, Makmur L, Ghisalberti EL, Nomura T (1999) Artoindonesianins A and B, two new prenylated flavones from the root bark of Artocarpus champeden. J Nat Prod 62:613–615CrossRefPubMedGoogle Scholar
  26. 26.
    Fahriyati A (1998) Artonin A, a flavonoid derivatives from the root bark of Artocarpus champeden. PhD Thesis, Department of Chemistry, Bandung Institute of TechnologyGoogle Scholar
  27. 27.
    Erwin, Achmad SA, Syah YM, Aimi N, Hakim EH, Kitajima M, Makmur L, Mujahidin D, Takayama H (2001) Artoindonesianin B, a cytotoxic compound against P388 tumor cells from Artocarpus altilis. Bull Soc Nat Prod Chem (Indonesia) 1:20–27Google Scholar
  28. 28.
    Nomura T, Fukai T, Yamada S, Katayanagi M (1978) Studies on the constituents of the cultivated mulberry tree. II. Photooxidative cyclization of morusin. Chem Pharm Bull 26:1431–1436CrossRefGoogle Scholar
  29. 29.
    Achmad SA, Hakim EH, Juliawaty LD, Makmur L, Suyatno (1996) A new prenylated flavone from Artocarpus champeden. J Nat Prod 59:878–879CrossRefGoogle Scholar
  30. 30.
    Lin CN, Shieh WL (1992) Pyranoflavonoids from Artocarpus communis. Phytochemistry 31:2922–2924CrossRefGoogle Scholar
  31. 31.
    Rao AYR, Varadan M, Venkataraman K (1971) Coloring matters of the wood of Artocarpus heterophyllus. VI. Cycloheterophyllin, a flavone linked to three isoprenoid groups. Indian J Chem 9:7–13Google Scholar
  32. 32.
    Ajizah A (2001) Some flavonoids from the heartwood of Artocarpus champeden. PhD Thesis, Department of Chemistry, Bandung Institute of TechnologyGoogle Scholar
  33. 33.
    Hano Y, Aida M, Shiina M, Nomura T, Kawai T, Ohe H, Kagei K (1989) Artonins A and B, two new prenylflavones from the root bark of Artocarpus heterophyllus Lamk. Heterocycles 29:1447–1453CrossRefGoogle Scholar
  34. 34.
    Sultanbawa MUS, Surendrakumar S (1989) Two pyranodihydrobenzoxanthones from Artocarpus nohilis. Phytochemistry 28:599–605CrossRefGoogle Scholar
  35. 35.
    Syah YM, Achmad SA, Ghisalberti EL, Hakim EH, Makmur L, Mujahidin D (2002) Artoindonesianin M, a new prenylated flavone from Artocarpus champeden. Bull Soc Nat Prod Chem (Indonesia) 2:31–36Google Scholar
  36. 36.
    Hakim EH, Eliza, Kusumawati Y, Achmad SA, Makmur L, Aimi N, Takayama H, Kitajima M (1999) Some phenolic compounds from genus Artocarpus. J Mat Sci (Indonesia) 4:199–205Google Scholar
  37. 37.
    Hakim EH, Fahriyati A, Achmad SA, Makmur L, Mujahidin D, Nomura T, Syah YM (2000) Artonin A, a furanodihydrobenzoxanthone derivative from Artocarpus champeden. J Kimia Andalas (Indonesia) 6:72–76Google Scholar
  38. 38.
    Lemmens RHMJ, Soerianegara I, Wong WC (eds) (1995) Plant resources of South-East Asia, No. 4 (2), Timber trees: Minor commercial timbers. PROSEA, Bogor, Indonesia, pp 65–71Google Scholar
  39. 39.
    Syah YM, Achmad SA, Ghisalberti EL, Hakim EH, Makmur L, Mujahidin D (2001) Artoindonesianins G-I, three new isoprenylated flavones from Artocarpus lanceifolius. Fitoterapia 72:765–773CrossRefPubMedGoogle Scholar
  40. 40.
    Kijjoa A, Cidade HM, Gonzales MJTG, Afonso CM, Silva AMS, Herz W (1998) Further prenylflavonoids from Artocarpus elasticus. Phytochemistry 47:875–878CrossRefGoogle Scholar
  41. 41.
    Kijjoa A, Cidade HM, Pinto MMM, Gonzales MJTG, Anantachoke C, Gedris TE, Herz W (1996) Prenylflavonoids from Artocarpus elasticus. Phytochemistry 43:691–69CrossRefGoogle Scholar
  42. 42.
    Kumar SN, Pavanasasivam G, Sultanbawa MUS, Mageswaran R (1977) Chemical investigation of Ceylonese plants. Part 24. New chromenoflavonoids from the bark of Artocarpus nohilis Thw. (Moraceae). J Chem Soc Perkin Trans I:1243–1251CrossRefGoogle Scholar
  43. 43.
    Hakim EH, Asnizar, Kurniadewi F, Ghofar TA, Achmad SA, Aim N, Kitajima M, Makmur L, Mujahidin D, Takayama H. Tamin R (1999) Pyranoflavone and furanodihydrobenzoxanthone derivatives from Artocarpus lanceifolius. Proc ITB (Indonesia) 31:57–62Google Scholar
  44. 44.
    Mujahidin D, Achmad SA, Syah YM, Aimi N, Hakim EH, Kitajima M, Makmur L, Takayama H, Tamin R (2000) Artelastochromene, a diprenylpyranoflavone and β-resorcylaldehyde from the wood trunk of Artocarpus lanceifolius. Proc ITB (Indonesia) 32:41–46Google Scholar
  45. 45.
    Hakim EH, Asnizar, Yurnawilis, Aimi N, Kitajima M, Takayama H (2002) Artoindonesianin P, a new prenylated flavone with cytotoxicity from Artocarpus lanceifolius. Fitoterapia 73:668–673CrossRefPubMedGoogle Scholar
  46. 46.
    Aida M, Shinomiya K, Hano Y, Nomura T (1994) Artonin J, K and L, three new isoprenylated flavones from the root bark of Artocarpus heterophyllus Lamk. Heterocycles 36:575–583Google Scholar
  47. 47.
    Syah YM, Achmad SA, Aimi N, Hakim. EH, Juliawaty LD, Takayama H (2005) Two prenylated flavones from the tree bark of Artocarpus lanceifolius. Z Naturforsch (in press)Google Scholar
  48. 48.
    Achmad SA, Hakim EH, Juliawaty LD, Makmur L. Syah YM (2005) New natural products from Indonesian Moraceae. International Science Congress, Kuala Lumpur, MalaysiaGoogle Scholar
  49. 49.
    Cao S, Butler MS, Buss A (2002) Flavonoids from Artocarpus lanceifolius. Nat Prod Res 17:79–81CrossRefGoogle Scholar
  50. 50.
    Makmur L, Syamsurizal, Tukiran, Achmad SA, Aimi N, Hakim EH, Kitajima M, Takayama H (2000) Artoindonesianin C, a new xanthone derivative from Artocarpus teysmanii. J Nat Prod 63:243–244CrossRefPubMedGoogle Scholar
  51. 51.
    Aida M, Shinomiya K, Hano Y, Nomura T (1993) Artonins J, K, and L three new isoprenylated flavones from the root bark of Artocarpus heterophyllus Lamk. Heterocycles 36:575–580CrossRefGoogle Scholar
  52. 52.
    Makmur L, Syamsurizal, Tukiran, Syamsu Y, Achmad SA, Aimi N, Hakim EH, Kitajima M, Mujahidin D, Takayama H (1999) Artonol B and cycloartobiloxanthone from Artocarpus teysmanii Miq. Proc ITB (Indonesia) 31:63–68Google Scholar
  53. 53.
    Tukiran, Achmad SA, Makmur L, Hakim EH, Juliawaty LD (1999) Cycloartobiloxanthone and artonin J from the tree bark of Artocarpus teysmanii Miq. (Moraceae). J Mat Sci (Indonesia) 4: 156–163Google Scholar
  54. 54.
    Aida M, Shinomiya K, Matsuzawa K, Hano Y, Nomura T (1994) Constituents of the Moraceae plants. 19. Artonins Q, R, S, T, and U, five new isoprenylated phenols from the bark of Artocarpus heterophyllus Lamk. Heterocycles 39:847–858CrossRefGoogle Scholar
  55. 55.
    Hano Y, Yamagami Y, Kobayashi M, Isohata R, Nomura T (1990) Artonin E and F, two new prenylflavones from the bark of Artocarpus communis Forst. Heterocycles 31:877–882CrossRefGoogle Scholar
  56. 56.
    Ferlinahayati EH, Hakim EH, Achmad SA, Aimi N, Kitajima M, Makmur L (1999) Artonin E and norartocarpin, two phenolic compounds from Artocarpus scortechinii King. In: Proceedings on the National Seminar on Chemistry of Natural Products ′99, Jakarta, Indonesia, November 16–17, pp 162–1Google Scholar
  57. 57.
    Armin HA, Hakim EH, Achmad SA, Ghisalberti EL, Makmur L, Syah YM (1999) Two flavonoids from the West Sumateran plants. In: Proceedings on the National Seminar on Chemistry of Natural Products ′99, Jakarta, Indonesia, November 16–17, pp 140–147Google Scholar
  58. 58.
    Suhartati T, Achmad SA, Aimi N, Hakim EH, Kitajima M, Takayama H, Takeya K (2001) Artoindonesianin L, a new prenylated flavone with cytotoxic activity from Artocarpus rotunda. Fitoterapia 72:912–918CrossRefPubMedGoogle Scholar
  59. 59.
    Suhartati T, Achmad SA, Aimi N, Hakim EH (1999) Artonin E, a flavonoid from Artocarpus rotunda. J Mat Sci (Indonesia) 4:178–184Google Scholar
  60. 60.
    Hano Y, Inami R, Nomura T (1993) Components of the bark of Artocarpus rigida Bl. Structures of four new isoprenylated flavone derivatives artonins M, N, 0 and P. Heterocycles 35:1341–1350CrossRefGoogle Scholar
  61. 61.
    Hakim EH, Afrida, Eliza, Achmad SA, Aimi N, Kitajima M, Makmur L, Mujahidin D, Syah YM, Takayama H (2000) Artoindonesianin D a new bioactive pyranoflavone derivative and chaplasin from Artocarpus maingayii. Proc ITB (Indonesia) 32:13–19Google Scholar
  62. 62.
    Hano Y, Matsumoto Y, Shinohara K, Sun JY, Nomura T (1990c) Cudraflavones C and D two new prenylflavones from the root bark of Cudrania tricuspidata (Carr.) Bur. Heterocycles 37:1339–1344Google Scholar
  63. 63.
    Hakim EH, Eliza, Kusumawati Y, Achmad SA, Makmur L, Aimi N, Takayama H, Kitajima K (1999d) Some phenolic compounds from the genus Artocarpus. J Mat Sci (Indonesia) 4:199–205Google Scholar
  64. 64.
    Suhartati T, Achmad SA, Aimi N, Hakim EH (2000) Isolation of flavonoid compounds from Artocarpus kemando Miq. In: Proceedings of Joint Chemistry Seminar, Bandung Institute of Technology-National University of Malaysia, Indonesia, pp 58–64Google Scholar
  65. 65.
    Ersam T, Achmad SA, Ghisalberti EL, Hakim EH, Makmur L, Syah YM (2002) A new isoprenylated chalcone, artoindonesianin J, from the root and tree bark of Artocarpus bracteata. J Chem Res (S) 186–187Google Scholar
  66. 66.
    Hano Y, Itoh N, Hanaoka A, Nomura T (1995) Constituents of the Moraceae plants. 25. Paratocarpins F-L, seven new isoprenoid-substituted flavonoids from Paratocarpus venenosa Zoll. Heterocycles 41:2313–2326CrossRefGoogle Scholar
  67. 67.
    Abegaz BW, Ngajui BT, Dongo E, Tamboue H (1998) Prenylated chalcones and flavones from the leaves of Dorstenia kameruniana. Phytochemistry 49: 1147–1150CrossRefGoogle Scholar
  68. 68.
    Ersam T, Achmad SA, Ghisalberti EL, Hakim EH, Tamin R (1999) An isoprenylated flavonoid from Artocarpus bracteata Hook. J Mat Sci (Indonesia) 4: 172–177Google Scholar
  69. 69.
    Picker K, Ritchie E, Taylor WC (1976) The chemical constituents of Australian Flidera species. XXI: An examination of the bark and the leaves of F. laevicarpa. Aust J Chem 29:2023–2026CrossRefGoogle Scholar
  70. 70.
    Hakim EH, Adimurti A, Makmur L, Achmad SA, Aimi N, Kitajima M, Mujahidin D, Syah YM, Takayama H (2001) A prenylated stilbene from the root trunk of Artocarpus altilis. Proc ITB (Indonesia) 33:75–80Google Scholar
  71. 71.
    Hano Y, Inami R, Nomura T (1994) A new flavone artonin V from root bark of Artocarpus altilis. J Chem Res (S) 348–349Google Scholar
  72. 72.
    Erwin, Hakim EH, Achmad SA, Syah YM, Aimi N, Kitajima M, Makmur L, Mujahidin D, Takayama H (2001) Artoindonesianin B, a cytotoxic compound against P 388 cell lines from Artocarpus altilis. Bull Soc Nat Prod Chem (Indonesia) I:20–27Google Scholar
  73. 73.
    Ersam T, Achmad SA, Ghisalberti EL, Hakim EH, Tamin R (1999) Two isoprenylated flavones from the root bark of Artocarpus altilis (Parkinson) Fosberg. In: Proceedings National Seminar on Natural Products Chemistry, Jakarta, Indonesia, pp 97–103Google Scholar
  74. 74.
    Kurdi VA (2001) Artoindonesianin Z, a new 2-arylbenzofuran derivative from the root wood of Artocarpus altilis (Park.) Fosb. PhD Thesis, Department of Chemistry, Bandung Institute of TechnologyGoogle Scholar
  75. 75.
    Soekamto NH, Achmad SA, Ghisalberti EL, Hakim EH, Syah YM (2003) Artoindonesianins X and Y, two isoprenylated 2-arylbenzofurans from Artocarpus fretessi (Moraceae). Phytochemistry 64:831–834CrossRefPubMedGoogle Scholar
  76. 76.
    Soekamto NH, Achmad SA, Ghisalberti EL, Hakim EH, Syah YM (2002) Mulherin and mulberochromene two bioactive compounds from Artocarpus fretessi. Bull Soc Nat Prod Chem (Indonesia) 2:45–50Google Scholar
  77. 77.
    Deshpande VH, Parthasarathy PC, Venkataraman K (1968) Four analogs of artocarpin and cycloartocarpin from Marus alba. Tetrahedron Lett 1715–1719Google Scholar
  78. 78.
    Achmad SA, Murniana, Udjiana SS, Aimi N, Hakim EH, Makmur L (1998) Three flavan-3-ol compounds from Artocarpus reticulatus. Proc ITB (Indonesia) 30:1–7Google Scholar
  79. 79.
    Hakim EH, Ulinnuha UZ, Syah YM, Ghisalberti EL (2002) Artoindonesianins N and 0, new prenylated stilbene and prenylated arylbenzofuran derivatives from Artocarpus gomezianus. Fitoterapia 73:597–603CrossRefPubMedGoogle Scholar
  80. 80.
    Kurniadewi F, Hakim EH (2003) Three phenolic compounds from the tree bark of Artocarpus gomezianus (Moraceae). Bull Soc Nat Prod (Indonesia) 3:78–83Google Scholar
  81. 81.
    Christensen LP, Jorgen L (1989) Excelsaoctaphenol, a stilbene dimer from Chlorophora excelsa. Phytochemistry 28:917–918CrossRefGoogle Scholar
  82. 82.
    Dewick PM (1982) In: Harborne JB, Mabry TJ (eds) The flavonoids: advances in research, Chapter 10. Chapman and Hall, London, p 535CrossRefGoogle Scholar
  83. 83.
    Takasugi M, Nagao S, Ueno S, Masamune T, Shirata A, Takahashi K (1978) Studies on phytoalexins of the Moraceae. 2. Moracin C and D, new phytoalexins from diseased mulberry. Chem Lett 1239–1240Google Scholar
  84. 84.
    Agustini DM, Makmur L, Achmad SA, Ghisalberti EL, Hakim EH, Syah YM (1999) Cudraflavone C and catechin from tiwu landu. In: Proceedings of the National Seminar on Natural Products Chemistry, Jakarta, Indonesia, pp 198–204Google Scholar
  85. 85.
    Aida M, Yamagami Y, Hano Y, Nomura T (1996) Formation of dihydrobenzoxanthone skeleton from 3-isoprenylated 2′,4′,5′-trioxygenated flavone. Heterocycles 43:2561–2565CrossRefGoogle Scholar
  86. 86.
    Aida M, Yamaguchi N, Hano Y, Nomura T (1997) Artonols A, B, C, D and E, five new isoprenylated phenols from the bark of Artocarpus communis Forst. Heterocycles 45:163–175CrossRefGoogle Scholar
  87. 87.
    Giordana B, Parenti P (1994) Determination for the activity of the neutral amino acid /K+ symport in Leptidopteran larval midgut. J Exp Biol 196: 145PubMedGoogle Scholar
  88. 88.
    Leonardi MO, Cappellozza S, Ianne P, Cappellozza L, Parenti P, Giordana B (1996) Effects of topical application of an insect growth regulator (fenoxycarb) on some physiological parameters in the fifth instar larvae of the silkworm Bombyx mori. Comp Biochem Physiol 113B:361CrossRefGoogle Scholar
  89. 89.
    Parenti P, Pizzigoni A, Hanozet G, Hakim EH, Makmur L, Achmad SA, Giordana B (1998) A new prenylated flavone from Artocarpus champeden inhibits the K+-dependent amino acid transport in Bombyx mori midgut. Biochem Biophys Res Commun 244:445–448CrossRefPubMedGoogle Scholar
  90. 90.
    Forcella M, Hanozet G, Pugliese A, Achmad SA, Hakim EH, Makmur L, Parenti P (1999) Structure-activity relatioships of substrats for the neutral amino acid transport in Bombyx mori anterior midgut. In: Italian Biochemical Society XIV Meeting (Proteine ′99), Rome, ItalyGoogle Scholar
  91. 91.
    Kanzaki S, Yonemori K, Sugiura A, Subhadrabandhu S (1997) Phylogenetic relationships between the jackfruit, the breadfruit and nine other Artocarpus spp. From RFLP analysis of an amplified region of cpDNA. Sci Hort 70:57–66CrossRefGoogle Scholar

Copyright information

© The Japanese Society of Pharmacognosy and Springer-Verlag 2006

Authors and Affiliations

  • Euis H. Hakim
    • 1
  • Sjamsul A. Achmad
    • 1
  • Lia D. Juliawaty
    • 1
  • Lukman Makmur
    • 1
  • Yana M. Syah
    • 1
  • Norio Aimi
    • 2
  • Mariko Kitajima
    • 2
  • Hiromitsu Takayama
    • 2
  • Emilio L. Ghisalberti
    • 3
  1. 1.Natural Products Research Group, Department of ChemistryBandung Institute of TechnologyBandungIndonesia
  2. 2.Graduate School of Pharmaceutical SciencesChiba UniversityInage-ku, ChibaJapan
  3. 3.Chemistry, School of Biomedical and Chemical SciencesThe University of Western AustraliaCrawleyAustralia

Personalised recommendations