Inhibitors of nitric oxide production and new sesquiterpenes, 4-epi-curcumenol, neocurcumenol, gajutsulactones A and B, and zedoarolides A and B from zedoariae rhizoma

Heterocycles

Volumn 55, Issue 5, 2001, Pages 841-846

  Matsuda, Hisashi ^a   Morikawa, Toshio ^a   Toguchida, Iwao ^a   Ninomiya, Kiyofumi ^a   Yoshikawa, Masayuki ^a  

^a KYOTO PHARMACEUTICAL UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

4 EPICURCUMENOL; GAJUTSULACTONE A; GAJUTSULACTONE B; NEOCURCUMENOL; NITRIC OXIDE; NITRIC OXIDE SYNTHASE; NITRIC OXIDE SYNTHASE INHIBITOR; SESQUITERPENE DERIVATIVE; UNCLASSIFIED DRUG; ZEDOAROLIDE A; ZEDOAROLIDE B;

ARTICLE; CHEMICAL STRUCTURE; CIRCULAR DICHROISM; DRUG ISOLATION; HERBAL MEDICINE; NUCLEAR OVERHAUSER EFFECT; PERITONEUM MACROPHAGE; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; STEREOISOMERISM; STRUCTURE ANALYSIS;

EID: 0035337349     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/com-01-9178     Document Type: Article

References (24)

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3. c) H. Matsuda, T. Morikawa, K. Ninomiya, and M. Yoshikawa, Bioorg. Med. Chem., 2001, 9, in press.
4. The molecular composition of the compound given with the chemical formula was determined by high-resolution EI-MS or FAB-MS.
5. 3), 1.94 (2H, m, 1 and 2α-H), 2.15 (2H, m, 3β and 4-H), 2.18, 2.66 (1H each, both d, J=15.2 Hz, 6β and 6α-H), 3.38 (1H, br s, 8-OH), 5.78 (1H, br s, 9-H).
6. 13C COSY), distortionless enhancement by polarization transfer (DEPT), and heteronuculear multiple bond connectivity (HMBC) experiments. Furthermore, 3-6 were also assigned with aid of correlation via long-range coupling (COLOC) experiment.
7. H. Hikino, Y. Sakurai, S. Numabe, and T. Takemoto, Chem. Pharm. Bull., 1968, 16, 39.
8. 2), 2.34 (1H, m, 2β-H), 2.34 (1H, d like, J=ca. 14 Hz, 6β-H), 2.43 (1H, d, J=14.3 Hz, 6α-H), 4.08(1H, br s, 8-OH).
9. All new compounds (2a, 2b, 5a) were chracterized by physicochemical properties and full characteristics will be presented in a full paper.
10. 2).
11. +, 5), 107 (100).
12. 2), 2.33 (1H, ddd, J=3.9, 11.3, 14.9 Hz, 2β-H), 2.75 (1H, br d, J=ca. 12 Hz 5-H), 2.86 (1H, dd, J=11.9, 12.5 Hz, 6α-H), 3.01 (1H, br d, J=ca. 13 Hz, 6β-H), 4.84 (1H, s, 9-H).
13. 3), 1.79 (1H, m, 2α-H), 1.97 (1H, m, 3α-H), 1.98 (1H, m, 2β-H), 2.08 (1H, m, 3β-H), 2.43 (1H, dd, J=12.8, 12.8 Hz, 6β-H), 2.61 (1H, ddd, J=3.7, 3.7, 12.8 Hz, 5-H), 2.80, 2.86 (2H, ABq, J=15.5 Hz, 9β and 9α-H), 2.82 (1H, dd, J=3.7, 12.8 Hz, 6α-H), 3.35 (1H, ddd, J=3.7, 7.6, 7.6 Hz, 1-H).
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