Free accessResearch articleFirst published online 2018-2
Oleanane-type Triterpenes with Highly-Substituted Oxygen Functional Groups from the Flower Buds of Camellia sinensis and Their Inhibitory Effects against NO Production and HSV-1
Acylated oleanane-type triterpenes named chakasapogenins I (1), II (2), and III (3) were isolated from the hydrolysis product of the extract obtained from the flower buds of Camellia sinensis. The chemical structures of new triterpenes were elucidated on the basis of chemical and physicochemical evidence. chakasapogenin III (3) inhibited nitric oxide (NO) production in lipopolysaccharide- (LPS) activated RAW264.7 macrophages. In addition, R1-barrigenol (7) showed antiviral effect at 10μM against herpes simplex virus type-1 (HSV-1).
YokosukaA, OkabeG, TatsunoS, MimakiY. (2016) Stryphnosides G-P, 10 new triterpene glycosides from the pericarps of Stryphnodendron fissuratum. Carbohydrate Research, 434, 18–26.
4.
MatsudaH, NakamuraS, MorikawaT, MuraokaO, YoshikawaM. (2016) New biofunctional effects of the flower buds of Camellia sinensis and its bioactive acylated oleanane-type triterpene oligoglycosides. Journal of Natural Medicines, 70, 689–701.
5.
SilvaFSG, OliveiraPJDuarteMF. (2016) Oleanolic, Ursolic, and Betulinic Acids as Food Supplements or Pharmaceutical Agents for Type 2 Diabetes: Promise or Illusion?Journal of Agricultural and Food Chemistry, 64, 2991–3008.
6.
YoshiokaI, NishimuraT, MatsudaA, KitagawaI. (1970) Saponin and sapogenol. I. Seeds sapogenols of Thea sinensis. L. (1). Barringtogenol C (=theasapogenol B). Chemical & Pharmaceutical Bulletin, 18, 1610–1620.
7.
YoshiokaI, HinoK, MatsudaA, KitagawaI. (1972) Saponin and sapogenol. VI. Sapogenol constituents of leaves of Pittosporum tobira. Chemical & Pharmaceutical Bulletin, 20, 1499–1506.
8.
NakamuraS, LiuJ, NakashimaS, OgawaK, UedaT, OnishiE, KurookaK, MoriwakiY, RyuK, XuB, MatsumotoT, OhtaT, FukayaM, YoshikawaM, MatsudaH. (2016) Structure of a coumaric acid analogue with a monoterpene moiety from the flowers of Osmanthus fragrans var. aurantiacus and evaluation of cinnamic acid analogues as Nitric Oxide production and degranulation inhibitors. Natural Product Communications, 11, 1123–1128.
9.
LiuJ, NakamuraS, XuB, MatsumotoT, OhtaT, FujimotoK, OgawaK, FukayaM, MiyakeS, YoshikawaM, MatsudaH. (2015) Chemical structures of constituents from the flowers of Osmanthus fragrans var. aurantiacus. Journal of Natural Medicines, 69, 135–141.
10.
NakamuraS, IwamiJ, MatsudaH, WakayamaH, PongpiriyadachaY, YoshikawaM. (2009) Structures of new phenylbutanoids and nitric oxide production inhibitors from the rhizomes of Zingiber cassumunar. Chemical and Pharmaceutical Bulletin, 57, 1267–1272.
11.
HegazyM E F.MatsudaH.NakamuraS.YabeM.MatsumotoT.YoshikawaM. (2012) Sesquiterpenes from an Egyptian herbal medicine, Pulicaria undulata, with inhibitory effects on nitric oxide production in RAW264.7 macrophage cells. Chemical and Pharmaceutical Bulletin. 60, 363–370.
12.
PiretJ, BoivinG. (2011) Resistance of herpes simplex viruses to nucleoside analogues: mechanisms, prevelance, and management. Antimicrobial Agents and Chemotherapy, 55, 459–472.
13.
JiangYC, FengH, LinYC, GuoXR (2016) New strategies against drug resistance to herpes simplex virus. International Journal of Oral Science, 8, 1–6.
14.
IkedaT, YokomizoK, OkawaM, TsuchihashiR, KinjoJ, NoharaT, UyedaM. (2005) Anti-herpes virus type 1 activity of oleanane-type triterpenoids. Biological and Pharmaceutical Bulletin, 28, 1779- 1781.
15.
OgawaK, NakamuraS, HosokawaK, IshimaruH, SaitoN, RyuK, FujimuroM, NakashimaS, MatsudaH. (2018) New diterpenes from Nigella damascena seeds and their antiviral activities against herpes simplex virus type-1. Journal of Natural Medicines, 72, in press [DOI: 10.1007/s11418-017-1166-6].
16.
MastudaH, MorikawaT, UedaK, ManagiH, YoshikawaM. (2002) Structural requirements of flavonoids for inhibition of antigen-induced degranulation, TNF-α and IL-4 production from RBL-2H3 cells. Bioorganic & Medicinal Chemistry, 10, 3123–3128.
17.
NakazawaT, OhmaeT, FujimuroM, ItoM, NishinagaT, IyodaM. (2012) Synthesis, molecular structures, and antiviral activities of 1- and 2-(2’- deoxy-D-ribofuranosyl)cyclohepta[5368-5374.