Inhibitory effect of diarylheptanoids on nitric oxide production in activated murine macrophages

Jeevan Kumar Prasain, Yasuhiro Tezuka, Kouji Hase, Purusotam Basnet, Hui Dong, Tsuneo Namba, Shigetoshi Kadota

Research output: Contribution to journalArticle

17 Citations (Scopus)

Abstract

Thirteen novel diarylheptanoids bearing a chalcone or a flavanone moiety (1-13), a new curcumin derivative, 1,2-dihydrobis(de-O-methyl)curcumin (14), and two known flavonoids (15 and 16) isolated from the seeds of Alpinia blepharocalyx K. Schum. were tested for their inhibitory effects on nitric oxide (NO) production in lipopolysaccharide (LPS)-activated murine macrophages J774.1 in vitro. All the tested compounds inhibited NO production in a concentration-dependent manner (IC50=36-568 μM). Among the compounds examined, blepharocalyxin B (13) was the most potent inhibitor of NO production (IC50=36 μM). Analysis of the structure activity relationship among these novel diarylheptanoids led to the conclusion that the position of attachment of a chalcone or a flavanone to a diarylheptanoid does not affect their inhibitory potency although their presence in association causes a substantial enhancement of the inhibitory activity. Moreover, a conjugated double bond in a chalcone moiety potentiated the inhibitory activity. On the other hand, hexamethoxydeoxycalyxin A (17) and pentamethoxycalyxin B (18), a methylated product of calyxin A (1) and an epimeric mixture of calyxin B, showed greatly reduced activity suggesting that phenolic hydroxyl groups are involved in the inhibitory activity.

Original languageEnglish
Pages (from-to)371-374
Number of pages4
JournalBiological and Pharmaceutical Bulletin
Volume21
Issue number4
Publication statusPublished - 1998
Externally publishedYes

Fingerprint

Diarylheptanoids
Chalcone
Nitric Oxide
Curcumin
Macrophages
Inhibitory Concentration 50
Alpinia
Structure-Activity Relationship
Flavonoids
Hydroxyl Radical
Lipopolysaccharides
Seeds
flavanone

Keywords

  • Blepharocalyxin
  • Calyxin
  • Diarylheptanoid
  • Macrophage
  • Nitric oxide (NO) production

ASJC Scopus subject areas

  • Molecular Medicine
  • Pharmacology, Toxicology and Pharmaceutics(all)

Cite this

Prasain, J. K., Tezuka, Y., Hase, K., Basnet, P., Dong, H., Namba, T., & Kadota, S. (1998). Inhibitory effect of diarylheptanoids on nitric oxide production in activated murine macrophages. Biological and Pharmaceutical Bulletin, 21(4), 371-374.

Inhibitory effect of diarylheptanoids on nitric oxide production in activated murine macrophages. / Prasain, Jeevan Kumar; Tezuka, Yasuhiro; Hase, Kouji; Basnet, Purusotam; Dong, Hui; Namba, Tsuneo; Kadota, Shigetoshi.

In: Biological and Pharmaceutical Bulletin, Vol. 21, No. 4, 1998, p. 371-374.

Research output: Contribution to journalArticle

Prasain, JK, Tezuka, Y, Hase, K, Basnet, P, Dong, H, Namba, T & Kadota, S 1998, 'Inhibitory effect of diarylheptanoids on nitric oxide production in activated murine macrophages', Biological and Pharmaceutical Bulletin, vol. 21, no. 4, pp. 371-374.
Prasain, Jeevan Kumar ; Tezuka, Yasuhiro ; Hase, Kouji ; Basnet, Purusotam ; Dong, Hui ; Namba, Tsuneo ; Kadota, Shigetoshi. / Inhibitory effect of diarylheptanoids on nitric oxide production in activated murine macrophages. In: Biological and Pharmaceutical Bulletin. 1998 ; Vol. 21, No. 4. pp. 371-374.
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