Download PDF
Planta Med 2012; 78(2): 154-159
DOI: 10.1055/s-0031-1280338
Natural Product Chemistry
Original Papers
© Georg Thieme Verlag KG Stuttgart · New York

Phosphodiesterase I-Inhibiting Diels-Alder Adducts from the Leaves of Morus mesozygia

Christian D. A. Fozing1 , 2 , Zulfiqar Ali2 , 3 , Bonaventure T. Ngadjui1 , M. Iqbal Choudhary2 , 4 , Gilbert D. W. F. Kapche5 , Berhanu M. Abegaz6 , Ikhlas A. Khan3
  • 1Department of Organic Chemistry, Faculty of Science, University of Yaounde I, Yaounde, Cameroon
  • 2H. E. J. Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi, Pakistan
  • 3National Center for Natural Products Research, School of Pharmacy, University of Mississippi, University, MS, USA
  • 4Department of Chemistry, College of Science, King Saud University, Riyadh, Saudi Arabia
  • 5Department of Chemistry, Higher Teacher Training College, University of Yaounde I, Yaounde, Cameroon
  • 6Department of Chemistry, Faculty of Science, University of Botswana, Gaborone, Botswana
Further Information

Publication History

received May 29, 2011 revised Sept. 13, 2011

accepted October 11, 2011

Publication Date:
14 November 2011 (online)

    Permissions and Reprints

Abstract

A new 2-arylbenzofuran derivative, (+)-dimethylsmoracin O (1), and three new Diels-Alder type adducts, mesozygins A–C (2–4), in addition to eight known compounds, artonin I (5), chalcomaracin (6), norartocarpetin (7), moracin L (8), mulberrofuran F (9), moracin M (10), moracin C (11), and morachalcone A (12), were isolated from the leaves of Morus mesozygia Stapf. Structures were elucidated by spectroscopic data analyses. Compounds 2–7 displayed a potent phosphodiesterase I inhibitory activity.

Key words

Morus mesozygia - Moraceae - Diels-Alder adducts - (+)-dimethylsmoracin O - mesozygins A–C - phosphodiesterase I inhibition

Supporting Information

References

  • 1 Fashing P J. Feeding ecology of guereza in the Kakamega forest, Kenya: the importance of Moraceae fruit in their diet.  Int J Primatol. 2001;  22 579-609
    Google Scholar
  • 2 Amala S. Management of diabetes in African traditional medicines, traditional herbal medicines for modern times: antidiabetic plants. New York: CRC Press; 2006: 214-215
    Google Scholar
  • 3 Burkill H M. The useful plants of west tropical Africa: Families M – R. Vol. 4 Richmond: Royal Botanic Gardens Kew; 1997: 969
    Google Scholar
  • 4 Kapche G D W F, Fozing D C, Donfack J H, Fotso G W, Amadou D, Tchana A N, Bezabih M, Moundipa P F, Ngadjui B T, Abegaz B M. Prenylated arybenzofuran derivatives from Morus mesozygia with antioxidant activity.  Phytochemistry. 2009;  70 216-221
    Google Scholar
  • 5 Kuete V, Fozing D C, Kapche G D W F, Mbaveng A T, Kuiate J R, Ngadjui B T, Abegaz B M. Antimicrobial activity of the methanolic extract and compounds from Morus mesozygia stem bark.  J Ethnopharmacol. 2009;  124 551-555
    Google Scholar
  • 6 Kapche G D W F, Amadou D, Waffo-Teguo P, Donfack J H, Fozing C D, Harakat D, Tchana A N, Mérillon J M, Moundipa P F, Ngadjui B T, Abegaz B M. Hepatoprotective and antioxidant arylbenzofurans and flavonoids from the twigs of Morus mesozygia.  Planta Med. 2011;  77 1044-1047
    Google Scholar
  • 7 Choudhary M I, Fatima N, Abbasi M A, Jalil S, Ahmad V U, Atta-ur-Rahman. Phenolic glyscosides, a new class of human recombinant nucleotide pyrophosphatase phosphodiesterase-1 inhibitors.  Bioorg Med Chem. 2004;  12 5793-5798
    Google Scholar
  • 8 Ahmad V U, Abbasi M A, Hussain H, Akhtar M N, Farooq U, Fatima N, Choudhary M I. Phenolic glycosides from Symplocos racemosa: natural inhibitors of phosphodiesterase.  Phytochemistry. 2003;  63 217-220
    Google Scholar
  • 9 Peluso M R. Flavonoids attenuate cardiovascular disease, inhibit phosphodiesterase, and modulate lipid homeostasis in adipose tissue and liver.  Exp Biol Med. 2006;  231 1287-1299
    Google Scholar
  • 10 Dat N T, Jin X, Lee K, Hong Y S, Kim Y H, Lee J J. Hypoxia-inducible factor-1 inhibitory benzofurans and chalcone-derived Diels-Alder adducts from Morus species.  J Nat Prod. 2009;  72 39-43
    Google Scholar
  • 11 Arnone A, Assante G, Bava A, Dallavalle S, Nasini S, Acremines H. Novel prenylated polyketide metabolites produced by a strain of Acremonium byssoides.  Tetrahedron. 2009;  65 786-791
    Google Scholar
  • 12 Su C R, Kuo P C, Wang M L, Liou M J, Damu A G, Wu T S. Acetophenone derivatives from Acronychia pedunculata.  J Nat Prod. 2003;  66 990-993
    Google Scholar
  • 13 Torres-Valencia J M, Chávez-Ríos O E, Cerda-García-Rojas C M, Burgueño-Tapia E, Joseph-Nathan P. Dihydrofurochromones from Prionosciadium thapsoides.  J Nat Prod. 2008;  71 1956-1960
    Google Scholar
  • 14 Ferrari F, Monache F D. Constituents of Morus multicaulis roots.  Fitoterapia. 1998;  69 554-555
    Google Scholar
  • 15 Xia Y, Jin Y, Kaur N, Choi Y, Lee K. HIF-1α inhibitors: Synthesis and biological evaluation of novel moracin O and P analogues.  Eur J Med Chem. 2011;  46 2386-2396
    Google Scholar
  • 16 Zhang Q J, Tang Y B, Chen R Y, Yu D Q. Three new cytotoxic Diels-Alder type adducts from Morus australis.  Chem Biodivers. 2007;  4 1533-1540
    Google Scholar
  • 17 Hano Y, Suzuki S, Kohno H, Nomura T. Absolute configuration of kuwanon L, a natural Diels-Alder type adduct from the Morus root bark.  Heterocycles. 1988;  27 75-81
    Google Scholar
  • 18 Hano Y, Suzuki S, Nomura T, Iitaka Y. Absolute configuration of natural Diels-Alder type adducts from the Morus root bark.  Heterocycles. 1988;  27 2315-2324
    Google Scholar
  • 19 Hano Y, Aida M, Nomura T, Ueda S. A novel way of determining the structure of artonin I, an optically active Diels-Alder type adduct, with the aid of an enzyme of Morus alba cultures.  J Chem Soc Chem Commun. 1992;  1177-1178
    Google Scholar
  • 20 Takasugi M, Nagao S, Masamune T, Shirata A, Takahashi K. Chalcomoracin, a natural Diels-Alder adduct from diseased mulberry.  Chem Lett. 1980;  9 1573-1576
    Google Scholar
  • 21 Lin C, Lu C, Huang P. Flavonoids from Artocarpus heterophyllus.  Phytochemistry. 1995;  39 1447-1451
    Google Scholar
  • 22 Matsuyama S, Kuwahara Y, Suzuki T. A new 2-arylbenzofuran, ω-hydroxymoracin N, from mulberry leaves.  Agric Biol Chem. 1991;  55 1409-1410
    Google Scholar
  • 23 Matsuyama S, Kuwahara Y, Nakamura S, Suzuki T. Oviposition stimulants for the lesser mulberry pyralid, Glyphodes pyloalis (Walker), in mulberry leaves; rediscovery of phytoalexin components as insect kairomones.  Agric Biol Chem. 1991;  55 1333-1341
    Google Scholar
  • 24 Fukai T, Hano Y, Hirakura K, Nomura T, Uzawa J, Fukushima K. Structures of two natural hypotensive Diels-Alder type adducts, mulberrofurans F and G, from the cultivated mulberry tree (Morus ihou Koidz.).  Chem Pharm Bull. 1985;  33 3195-3204
    Google Scholar
  • 25 Basnet P, Kadota S, Terashima S, Shimizu M, Namba T. Two new 2-arylbenzofuran derivatives from hypoglycemic activity-bearing fractions of Morus insignis.  Chem Pharm Bull. 1993;  41 1238-1243
    Google Scholar
  • 26 Takasugi M, Nagao S, Ueno S, Masamune T, Shirata A, Takahashi K. Studies on phytoalexins of the Moraceae. 2. Moracins C and D, new phytoalexins from diseased mulberry.  Chem Lett. 1978;  7 1239-1240
    Google Scholar
  • 27 Gunawan C, Rizzacasa M A. Mulberry Diels-Alder adducts: synthesis of chalcomoracin and mulberrofuran C methyl ethers.  Org Lett. 2010;  12 1388-1391
    Google Scholar

Dr. Zulfiqar Ali

National Center for Natural Products Research
School of Pharmacy
University of Mississippi

University, MS 38677

USA

Phone: +1 66 29 15 78 61

Email: zulfiqar@olemiss.edu

Dr. Gilbert D. W. F. Kapche

Department of Chemistry
Higher Teacher Training College
University of Yaounde I

P. O. Box 47

Yaounde 237

Cameroon

Phone: +2 37 77 66 49 73

Email: dkapche2002@yahoo.com

>