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

Keiko Ogawa; Seikou Nakamura; Kohei Hosokawa; Hanako Ishimaru; Natsuki Saito; Kaori Ryu; Masahiro Fujimuro; Souichi Nakashima; Hisashi Matsuda

doi:10.1007/s11418-017-1166-6

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

J Nat Med. 2018 Mar;72(2):439-447. doi: 10.1007/s11418-017-1166-6. Epub 2017 Dec 29.

Authors

Keiko Ogawa¹, Seikou Nakamura¹, Kohei Hosokawa¹, Hanako Ishimaru¹, Natsuki Saito¹, Kaori Ryu¹, Masahiro Fujimuro¹, Souichi Nakashima¹, Hisashi Matsuda²

Affiliations

¹ Department of Pharmacognosy, Kyoto Pharmaceutical University, Misasagi, Yamashina-ku, Kyoto, 607-8412, Japan.
² Department of Pharmacognosy, Kyoto Pharmaceutical University, Misasagi, Yamashina-ku, Kyoto, 607-8412, Japan. matsuda@mb.kyoto-phu.ac.jp.

PMID: 29288328
DOI: 10.1007/s11418-017-1166-6

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.

Keywords: Antiviral activity; Diterpene; HSV-1; Nigella damascena; Ranunculaceae.

MeSH terms

Antiviral Agents / pharmacology
Antiviral Agents / therapeutic use*
Diterpenes / chemistry*
Herpesvirus 1, Human / drug effects*
Nigella damascena / chemistry*
Seeds / chemistry*

Substances

Antiviral Agents
Diterpenes