nach oben

Erschienen in:

29.12.2017 | Original Paper

New diterpenes from Nigella damascena seeds and their antiviral activities against herpes simplex virus type-1

verfasst von: Keiko Ogawa, Seikou Nakamura, Kohei Hosokawa, Hanako Ishimaru, Natsuki Saito, Kaori Ryu, Masahiro Fujimuro, Souichi Nakashima, Hisashi Matsuda

Erschienen in: Journal of Natural Medicines | Ausgabe 2/2018

Einloggen, um Zugang zu erhalten

Abstract

Nigella species are rich source of dolabellane diterpenes. During our study of Nigella species, new dolabellane diterpenes, damasterpenes V–VIII were isolated. The structural determination of new compounds damasterpenes V–VIII is described with consideration of their absolute configurations. The antiviral activities against herpes simplex virus type-1 of the isolated compounds and their derivatives are also evaluated. Damasterpene V (inhibition 35.0%) and 2-phenylacetyl 13-benzoyl damasterpenol (32.0%) showed significant antiviral activity at 10 μM.

Piret J, Boivin G (2011) Resistance of herpes simplex viruses to nucleoside analogues: mechanisms, prevelance, and management. Antimicrob Agents Chemother 55:459–472CrossRef

Jiang YC, Feng H, Lin YC, Guo XR (2016) New strategies against drug resistance to herpes simplex virus. Int J Oral Sci 8:1–6CrossRef

Barbosa JP, Pereira RC, Abrantes JL, dos Santos SS, Robello MA, Frugulhetti IC, Taixeira VL (2004) In vitro antiviral diterpenes from the Brazilian brown alga dictyota pfaffii. Plant Med 70:856–860CrossRef

Matsuda H, Nakamura S, Yoshikawa M (2016) Degranulation inhibitors from medicinal plants in antigen-stimulated rat basophilic leukemia (RBL-2H3) cells. Chem Pharm Bull 64:96–103CrossRef

Matsuda H, Nakamura S, Morikawa T, Muraoka O, Yoshikawa M (2016) New biofunctional effects of the flower buds of Camellia sinensis and its bioactive oleanane-type triterpene oligoglycosides. J Nat Med 70:689–701CrossRef

Matsuda H, Nakamura S, Yoshikawa M (2014) Search for new type of PPARγ agonist-like anti-diabetic compounds from medicinal plants. Biol Pharm Bull 37:884–891CrossRef

Ogawa K, Nakamura S, Asada Y, Yamashita M, Matsuda H (2017) Oxazonigelladine and dolabellane-type diterpene constituents from Nigella damascena seeds. Tetrahedron. https://doi.org/10.1016/j.tet.2017.10.061 (In press) CrossRef

Tillequin F, Leconte C, Paris M (1976) Carbures sesquiterpeniques des grains de Nigella damascena. Plant Med 30:59–61CrossRef

Doepke W, Fritsch G (1970) Alkaloid content of Nigella damascena. Pharmazie 25:69–70

10.

Toki K, Saito N, Nogami A, Tatsuzawa F, Shigihara A, Honda T (2009) Flavonoid glycosides isolated from the blue flowers of Nigella damascena. Heterocycles 78:2287–2294CrossRef

11.

Fico G, Braca A, Tome F, Morelli I (2000) Phenolic derivatives from Nigella damascena seeds. Pharm Biol 38:371–373CrossRef

12.

Schuler E, Juanico N, Teixidó J, Michelotti EL, Borrell J (2006) A diversity oriented synthesis of 2, 10-dioxo-10H-1,2,3,4,4a,5-hexahydropyridazino[3,2-b]quinazolines. Heterocycles 67:161–173CrossRef

13.

Harada N, Iwabuchi J, Yokota Y, Uda H (1981) A chiroptical method for determining the absolute configuration of allylic alcohols. J Am Chem Soc 103:5590–5591CrossRef

14.

Nakazawa T, Ohmae T, Fujimuro M, Ito M, Nishinaga T, Iyoda M (2012) Synthesis, molecular structures, and antiviral activities of 1- and 2-(2′-deoxy-D-ribofuranosyl)cyclohepta[d][1-3]triazol-6(1H)-ones and 1-(2′-deoxy-D-ribofuranosyl)cyclohepta[b]pyrrol-8(1H)-one. Tetrahedron 68:5368–5374CrossRef

15.

Ikeda T, Yokomizo K, Okawa M, Tsuchihashi R, Kinjo J, Nohara T, Uyeda M (2005) Anti-herpes virus type 1 activity of oleanane-type triterpenoids. Biol Pharm Bull 28:1779–1781CrossRef

Titel: New diterpenes from Nigella damascena seeds and their antiviral activities against herpes simplex virus type-1
verfasst von: Keiko Ogawa
Seikou Nakamura
Kohei Hosokawa
Hanako Ishimaru
Natsuki Saito
Kaori Ryu
Masahiro Fujimuro
Souichi Nakashima
Hisashi Matsuda
Publikationsdatum: 29.12.2017
Verlag: Springer Singapore
Erschienen in: Journal of Natural Medicines / Ausgabe 2/2018
Print ISSN: 1340-3443
Elektronische ISSN: 1861-0293
DOI: https://doi.org/10.1007/s11418-017-1166-6

Springer Medizin

Abstract

Bitte loggen Sie sich ein, um Zugang zu diesem Inhalt zu erhalten

Weitere Artikel der Ausgabe 2/2018

Structure–activity relationships of flavanones, flavanone glycosides, and flavones in anti-degranulation activity in rat basophilic leukemia RBL-2H3 cells

Lanostane triterpenoids from Fomitopsis officinalis and their trypanocidal activity

Correction to: Ephedra Herb extract activates/desensitizes transient receptor potential vanilloid 1 and reduces capsaicin-induced pain

Oxyresveratrol prevents murine H22 hepatocellular carcinoma growth and lymph node metastasis via inhibiting tumor angiogenesis and lymphangiogenesis

Lignosulfonic acid attenuates NF-κB activation and intestinal epithelial barrier dysfunction induced by TNF-α/IFN-γ in Caco-2 cells

Degranulation inhibitors from the arils of Myristica fragrans in antigen-stimulated rat basophilic leukemia cells