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.
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References
Piret J, Boivin G (2011) Resistance of herpes simplex viruses to nucleoside analogues: mechanisms, prevelance, and management. Antimicrob Agents Chemother 55:459–472
Jiang YC, Feng H, Lin YC, Guo XR (2016) New strategies against drug resistance to herpes simplex virus. Int J Oral Sci 8:1–6
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 70:856–860
Matsuda H, Nakamura S, Yoshikawa M (2016) Degranulation inhibitors from medicinal plants in antigen-stimulated rat basophilic leukemia (RBL-2H3) cells. Chem Pharm Bull 64:96–103
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 70:689–701
Matsuda H, Nakamura S, Yoshikawa M (2014) Search for new type of PPARγ agonist-like anti-diabetic compounds from medicinal plants. Biol Pharm Bull 37:884–891
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)
Tillequin F, Leconte C, Paris M (1976) Carbures sesquiterpeniques des grains de Nigella damascena. Plant Med 30:59–61
Doepke W, Fritsch G (1970) Alkaloid content of Nigella damascena. Pharmazie 25:69–70
Toki K, Saito N, Nogami A, Tatsuzawa F, Shigihara A, Honda T (2009) Flavonoid glycosides isolated from the blue flowers of Nigella damascena. Heterocycles 78:2287–2294
Fico G, Braca A, Tome F, Morelli I (2000) Phenolic derivatives from Nigella damascena seeds. Pharm Biol 38:371–373
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 67:161–173
Harada N, Iwabuchi J, Yokota Y, Uda H (1981) A chiroptical method for determining the absolute configuration of allylic alcohols. J Am Chem Soc 103:5590–5591
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 68:5368–5374
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 28:1779–1781
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This research was supported in part by a Ministry of Education, Culture, Sports, Science and Technology (MEXT)-Supported Program for the Strategic Research Foundation at Private Universities 2015–2019.
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Ogawa, K., Nakamura, S., Hosokawa, K. et al. New diterpenes from Nigella damascena seeds and their antiviral activities against herpes simplex virus type-1. J Nat Med 72, 439–447 (2018). https://doi.org/10.1007/s11418-017-1166-6
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DOI: https://doi.org/10.1007/s11418-017-1166-6