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Structure of diarylheptanoids with antiallergic activity from the rhizomes of Curcuma comosa

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Abstract

The methanolic extract from the dried rhizomes of Curcuma comosa cultivated in Thailand was found to inhibit the release of β-hexosaminidase as a maker of degranulation from rat basophil leukemia (RBL-2H3) cells. Two new diarylheptanoids, diarylcomosols IV and V, were isolated from the methanolic extract. The chemical structures of the new compounds were elucidated on the basis of chemical and physicochemical evidence. The isolated diarylheptanoids showed inhibitory activity, and the structural requirements of the active constituents for the inhibition were clarified.

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References

  1. Sodsai A, Piyachaturawat P, Sophasan S, Suksamrarn A, Vongsakul M (2007) Suppression by Curcuma comosa Roxb. of pro-inflammatory cytokine secretion in phorbol-12-myristate stimulated human mononuclear cells. Int Immunopharmacol 7:524–531

    Article  CAS  PubMed  Google Scholar 

  2. Jantaratnotai N, Utaisincharoen P, Piyachaturawat P, Chongthammakun S, Sanvarinda Y (2006) Inhibitory effects of Curcuma comosa on NO production and cytokine in LPS-activated microglia. Life Sci 78:571–577

    Article  CAS  PubMed  Google Scholar 

  3. Qu Y, Xu F, Nakamura S, Matsuda H, Pongpiriyadacha Y, Wu L, Yoshikawa M (2009) Sesquiterpenes from Curcuma comosa. J Nat Med 63:102–104

    Article  CAS  PubMed  Google Scholar 

  4. Nakamura S, Nakashima S, Tanabe G, Oda Y, Yokota N, Fujimoto K, Matsumoto T, Sakuma R, Ohta T, Ogawa K, Nishida S, Miki H, Matsuda H, Muraoka O, Yoshikawa M (2013) Alkaloid constituents from flower buds and leaves of sacred lotus (Nelumbo nucifera, Nymphaeaceae) with melanogenesis inhibitory activity in B16 melanoma cells. Bioorg Med Chem 21:779–787

    Article  CAS  PubMed  Google Scholar 

  5. Matsuda H, Asao Y, Nakamura S, Hamao M, Sugimoto S, Hongo M, Pongpiriyadacha Y, Yoshikawa M (2009) Antidiabetogenic constituents from the Thai traditional medicine Cotylelobium melanoxylon. Chem Pharm Bull 57:487–494

    Article  CAS  PubMed  Google Scholar 

  6. Matsumoto T, Nakamura S, Nakashima S, Fujimoto K, Yoshikawa M, Ohta T, Ogawa K, Matsuda H (2014) Structures of lignan dicarboxylates and terpenoids from the flower buds of Cananga odorata and their inhibitory effects on melanogenesis. J Nat Prod 77:990–999

    Article  CAS  PubMed  Google Scholar 

  7. Matsumoto T, Nakamura S, Fujimoto K, Ohta T, Ogawa K, Yoshikawa M, Matsuda H (2014) Structures of constituents isolated from the flower buds of Cananga odorata and their inhibitory effects on aldose reductase. J Nat Med 68:709–716

    Article  CAS  PubMed  Google Scholar 

  8. Ma J, Jin X, Yang L, Liu ZL (2004) Diarylheptanoids from the rhizomes of Zingiber officinale. Phytochemistry 65:1137–1143

    Article  CAS  PubMed  Google Scholar 

  9. Li J, Liao CR, Wei JQ, Chen LX, Zhao F, Qiu F (2011) Diarylheptanoids from Curcuma kwangsiensis and their inhibitory activity on nitric oxide production in lipopolysaccharide-activated macrophages. Bioorg Med Chem Lett 21:5363–5369

    Article  CAS  PubMed  Google Scholar 

  10. Veith M, Dettner K, Boland W (1996) Stereochemistry of an alcohol oxidase from the defensive secretion of larvae of the leaf beetle Phaedon armoraciae (Coleoptera: Chrysomelidae). Tetrahedron 52:6601–6612

    Article  CAS  Google Scholar 

  11. Li J, Zhao F, Li MZ, Chen LX, Qiu FJ (2010) Diarylheptanoids from the rhizomes of Curcuma kwangsiensis. J Nat Prod 73:1667–1671

    Article  CAS  PubMed  Google Scholar 

  12. Smite E, Lundgren LN, Andersson R (1993) Arylbutanoid and diarylheptanoid glycosides from inner bark of Betula pendula. Phytochemistry 32:365–369

    Article  CAS  Google Scholar 

  13. Shin D, Kinoshita K, Koyama K, Takahashi K (2002) Antiemetic principles of Alpinia officinarum. J Nat Prod 65:1315–1318

    Article  CAS  PubMed  Google Scholar 

  14. Ali MS, Tezuka Y, Awale S, Banskota AH, Kadota S (2001) Six new diarylheptanoids from the seeds of Alpinia blepharocalyx. J Nat Prod 64:289–293

    Article  CAS  PubMed  Google Scholar 

  15. Matsumoto T, Nakamura S, Nakashima S, Yoshikawa M, Fujimoto K, Ohta T, Morita A, Yasui R, Kashiwazaki E, Matsuda H (2013) Diarylheptanoids with inhibitory effects on from the rhizomes of Curcuma comosa in B16 melanoma cells. Bioorg Med Chem Lett 21:5178–5181

    Article  Google Scholar 

  16. Yokosuka A, Mimaki Y, Sakagami H, Sashida Y (2002) New diarylheptanoids and diarylheptanoid glucosides from the rhizomes of Tacca chantrieri and their cytotoxic activity. J Nat Prod 65:283–5181

    Article  CAS  PubMed  Google Scholar 

  17. Kikuzaki H, Kobayashi M, Nakatani N (1991) Constituents of Zingiberaceae. Part 4. Diarylheptanoids from rhizomes of Zingiber officinale. Phytochemistry 30:3647–3651

    Article  CAS  Google Scholar 

  18. Matsuda H, Morikawa T, Ueda K, Managi H, Yoshikawa M (2002) Structural requirements of flavonoids for inhibition of antigen-induced degranulation, TNF-α and IL-4 production from RBL-2H3 cells. Bioorg Med Chem 10:3123–3128

    Article  Google Scholar 

  19. Matsuda H, Morikawa T, Mangi H, Yoshikawa M (2003) Antiallergic principles from Alpinia galanga: structural requirements of phenylpropanoids for inhibition of degranulation and release of TNF-α and IL-4 in RBL-2H3 cells. Bioorg Med Chem Lett 13:3197–3202

    Article  CAS  PubMed  Google Scholar 

  20. Matsuda H, Tewtrakul S, Morikawa T, Nakamura S, Yoshikawa M (2004) Anti-allergic principles from Thai zedoary: structural requirements of curcuminoids for inhibition of degranulation and effect on the release of TNF-α and IL-4 in RBL-2H3 cells. Bioorg Med Chem 12:5891–5989

    Article  CAS  PubMed  Google Scholar 

  21. Yoshikawa M, Shimada H, Komatsu H, Sakurama T, Nishida N, Shimoda H, Matsuda H, Tani T (1997) Medicinal foodstuffs. VI. Histamine release inhibitors from kidney bean, the seeds of Phaseolus vulgaris L.: chemical structures of sandosaponins A and B. Chem Pharm Bull 45:877–882

    Article  CAS  PubMed  Google Scholar 

  22. Yoshizumi S, Murakami T, Kadoya M, Matsuda H, Yoshikawa M (1998) Medicinal foodstuffs. XI. Histamine release inhibitors from wax gourd, the fruits of Benincasa hispida COGN. Yakugaku Zasshi 118:188–192

    CAS  PubMed  Google Scholar 

  23. Matsuda H, Nakamura S, Fujimoto K, Moriuchi R, Kimura Y, Ikoma N, Hata Y, Muraoka O, Yoshikawa M (2010) Medicinal flowers. XXXI. Acylated oleanane-type triterpene saponins, sasanquasaponins I-V, with antiallergic activity from the flower buds of Camellia sasanqua. Chem Pharm Bull 58:1617–1621

    Article  CAS  PubMed  Google Scholar 

  24. Yoshikawa M, Nakamura S, Kato Y, Matsuhira K, Matsuda H (2007) Medicinal flowers. XIV. New acylated oleanane-type triterpene oligoglycosides with antiallergic activity from flower buds of chinese tea plant (Camellia sinensis). Chem Pharm Bull 55:598–605

    Article  CAS  PubMed  Google Scholar 

  25. Morikawa T, Nakamura S, Kato Y, Muraoka O, Matsuda H, Yoshikawa M (2007) Bioactive saponins and glycosides. XXVIII. New triterpene saponins, foliatheasaponins I, II, III, IV, and V, from tencha (the leaves of Camellia sinensis). Chem Pharm Bull 55:293–298

    Article  CAS  PubMed  Google Scholar 

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Acknowledgments

This work was supported in part by JSPS KAKENHI Grant Number 25460144.

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Authors and Affiliations

  1. Department of Pharmacognosy, Kyoto Pharmaceutical University, Misasagi, Yamashina-ku, Kyoto, 607-8412, Japan

    Takahiro Matsumoto, Seikou Nakamura, Katsuyoshi Fujimoto, Tomoe Ohta, Keiko Ogawa, Masayuki Yoshikawa, Eri Onishi, Masashi Fukaya & Hisashi Matsuda

Authors
  1. Takahiro Matsumoto
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  2. Seikou Nakamura
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  3. Katsuyoshi Fujimoto
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  4. Tomoe Ohta
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  5. Keiko Ogawa
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  6. Masayuki Yoshikawa
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  7. Eri Onishi
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  8. Masashi Fukaya
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  9. Hisashi Matsuda
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Correspondence to Hisashi Matsuda.

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Matsumoto, T., Nakamura, S., Fujimoto, K. et al. Structure of diarylheptanoids with antiallergic activity from the rhizomes of Curcuma comosa . J Nat Med 69, 142–147 (2015). https://doi.org/10.1007/s11418-014-0870-8

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  • DOI: https://doi.org/10.1007/s11418-014-0870-8

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