Three new acylphloroglucinol glycosides, hypericumols A - C, together with fifteen known phenolic derivatives, were isolated from the total phenolic extract of Hypericum japonicum. Hypericumols A, B, and C were characterized as 4,6-dimethyl-2-methylpropanoylphloroglucinol-1-O-β-D-glucopyranoside (1), 4-methyl-2-methylpropanoylphloroglucinol-1-O-β-D-glucopyranoside (2), and (2′S)-4,6-dimethyl-2-methylbutyrylphloroglucinol-1-O-β-D-glucopyranoside (3), respectively, on the basis of spectroscopic data interpretation and chemical degradation reaction.
Editorial committee of Flora of China, the Chinese Academy of Sciences. (1990) Flora Reipublicae Popularis Sinicae. Science Press, Beijing, 47.
2.
ZhangYQ, HuangMQ, LiH, XuW, ChuKD, ZhengHY, ShaM, ChenLD. (2012) Hepatoprotective and antioxidant activity of the total flavonoids extraction from Hypericum japonicum by response surface methodology. Latin American Journal of Pharmacy, 31, 1270–1278;
3.
SamagaPV, RaiVR. (2013) Evaluation of pharmacological properties and phenolic profile of Hypericum japonicum Thunb. from Western Ghats of India. Journal of Pharmacy Research, 7, 626–632;
4.
WangXW, MaoY, FanM, DingAS, WangNL, YaoXS. (2009) Isolation, identification and activity determination on the anti-hypoxic components of Hypericum japonicum Thunb. Journal of Shenyang Pharmaceutical University, 26, 701–704.
5.
ZhengC, LiuM, LiJ. (2014) Study on anti-HBV active ingredient of Hypericum japonicum. Natural Product Research and Development, 26, 1350–1356;
6.
PanXJ, YangK, ZengJQ, WeiZY, ChenC. (2009) Experimental study on anti-hepatitis B and anti-hepatoma effect of different extracts in serum of Hypericum japonicum Thunb. in vitro. Lishizhen Medicine and Materia Medica Research, 20, 1076–1078;
7.
LiuN, HuXL, MengYR, ZhuYT, HuangBS, LinPZ. (2008) Effect of anti-influenza virus H3N2 of Hypericum japonicum in vivo. Journal of Chinese Medicinal Materials, 31, 1022–1024.
8.
ZhangSD, YinJ, LiX, ZhangJG, YueRC, DiaoYY, LiHL, WangH, ShanL, ZhangWD. (2014) Jacarehyperol A induced apoptosis in leukaemia cancer cell through inhibition the activity of Bcl-2 proteins. BMC Cancer, 14, 689–699;
9.
LiangS, SuWW, WangYG, PengW, NieYC, LiPB. (2013) Effect of quercetin 7-rhamnoside on glycochenodeoxycholic acid-induced L-02 human normal liver cell apoptosis. International Journal of Molecular Medicine, 32, 323–330.
10.
LiXF, FuZR, WeiY, YangT, OuyangYZ. (2014) Research on antibacterial activity of total flavone in Hypericum japonicum. Applied Chemical Industry, 43, 432–434;
11.
ZuoGY, AnJ, HanJ, ZhangYL, WangGC, HaoXY, BianZQ. (2012) Isojacareubin from the Chinese herb Hypericum japonicum: potent antibacterial and synergistic effects on clinical methicillin-resistant Staphylococcus aureus (MRSA). International Journal of Molecular Sciences, 13, 8210–8218;
12.
AnJ, ZuoGY, HaoXY, WangGC, LiZS. (2011) Antibacterial and synergy of a flavanonol rhamnoside with antibiotics against clinical isolates of methicillin-resistant Staphylococcus aureus (MRSA). Phytomedicine, 18, 990–993.
13.
WangN, LiPB, WangYG, PengW, WuZ, TianSY, LiangSL, ShenX, SuWW. (2008) Hepatoprotective effect of Hypericum japonicum extract and its fractions. Journal of Ethnopharmacology, 116, 1–6.
14.
LiuLS, LiuMH, HeJY. (2014) Hypericum japonicum Thunb. ex Murray: phytochemistry, pharmacology, quality control and pharmacokinetics of an important herbal medicine. Molecules, 19, 10733–10754.
15.
WangQ, MiJ, LiXP, LiuJY, BaiXL. (2013) Effects of Hypericum japonicum total flavonoids on chronic renal failure rats induced by 5/6 nephrectomy. Pharmacology and Clinics of Chinese Materia Medica, 29, 61–64;
16.
GaoQL, MeiX, YangDQ, MiJ, LiuWW, ZhaoJ, ZhangBC, GaoYX. (2014) The influence of herba Hypericum japonicum extract (MSN) on renal function and immune status of chronic renal failure model rats with five sixths kidney removal. Asia-Pacific Traditional Medicine, 10, 7–9;
17.
LiuWW, GaoYX, ZhaoJ, TangSQ, LiXP. (2014) Research on influence of correlation genes on kidney fibrosis of 5/6 nephrectomized rats CRF model by MSN. Pharmacy and Clinics of Chinese Materia Medica, 5, 28–30;
18.
ZhaoJ, LiuWW, YangDQ, MeiX, LiXP, MiJ, GaoYX. (2014) Study on interference of renal fibrosis by NSF in 5/6 nephrectomize rats. Journal of Chengdu University of TCM, 37, 35–38.
19.
LuoYG, ZhouM, YeQ, PuQ, ZhangGL. (2012) Dihydroagarofuran derivatives from the dried roots of Tripterygium wilfordii. Journal of Natural Products, 75, 98–102;
CoskunM, SakushimaA, NishibeS, HisadaS. (1982) Phloroglucinol derivatives of Dryopteris abbreviata. Chemical and Pharmaceutical Bulletin, 30, 4102–4106;
23.
ChangXL, LiW, KoikeK, WuLJ, NikaidoT. (2006) Phenolic constituents from the rhizomes of Dryopteris crassirhizoma. Chemical and Pharmaceutical Bulletin, 54, 748–750.
24.
ChengQ, SnyderJK. (1991) Two new phloroglucinol derivatives with phosphodiesterase inhibitory activity from the leaves of Eucalyptus robusta. Zeitschrift für Naturforschung B - AJournal of Chemical Sciences, 46b, 1275–1277.
25.
PeiYH, LiX, ZhuTR. (1989) An empirical correlation between optical rotation and absolute configuration of optical active α-methylbutyrylphloroglucinols and its synthesis. Acta Pharmaceutica Sinica, 24, 413–421.
26.
WangXW, MaoY, WangNL, YaoXS. (2008) A new phloroglucinol diglycoside derivative from Hypericum japonicum Thunb. Molecules, 13, 2796–2803.
27.
RoelensF, HeldringN, DhoogeW, BengtssonM, ComhaireF, GustafssonJÅ, TreuterE, De KeukeleireD. (2006) Subtle side-chain modifications of the hop phytoestrogen 8-prenylnaringenin result in distinct agonist/antagonist activity profiles for estrogen receptors a and p. Journal of Medicinal Chemistry, 49, 7357–7365;
28.
BohrG, GerhäuserC, KnauftJ, ZappJ, BeckerH. (2005) Anti-inflammatory acylphloroglucinol derivatives from hops (Humulus lupulus). Journal of Natural Products, 68, 1545–1548.
29.
MokSY, LeeS. (2013) Identification of flavonoids and flavonoid rhamnosides from Rhododendron mucronulatum for. albiflorum and their inhibitory activities against aldose reductase. Food Chemistry, 136, 969–974.
30.
FuP, LiTZ, LiuRH, ZhangW, ZhangC, ZhangWD, ChenHS. (2004) Studies on the flavonoids of Hypericum japonicum Thunb. ex Murray. Chinese Journal Natural Medicines, 2, 283–284.
31.
ZhangJ, ChuCJ, LiXJ, YaoS, YanB, RenHL, XuNY, LiangZT, ZhaoZZ. (2014) Isolation and identification of antioxidant compounds in Vaccinium bracteatum Thunb. by UHPLC-Q-TOF LC/MS and their kidney damage protection. Journal of Functional Foods, 11, 62–70.
32.
WangPP, LuoJ, YangMH, KongLY. (2013) Chemical constituents of Lobelia chinensis. Chinese Traditional and Herbal Drugs, 44, 794–797.
33.
RhoHS, AhnSM, LeeBC, KimMK, GhimerayAK, JinCW, ChoDH. (2010) Changes in flavonoid content and tyrosinase inhibitory activities in kenaf leaf extract after far-infrared treatment. Bioorganic Medicinal Chemistry Letters, 20, 7534–7536.
34.
CookRG, HaynesHF. (1960) Colouring matters of Australian plants VII. Flavonoid glycosides from Exocarpus cupressiformis Labill. Australian Journal of Chemistry, 13, 150–155;
35.
WuW, WangCZ, LiX, LiXR, XuQM, YangSL. (2011) Chemical constituents of antitumor active fraction of Lysimachia clethroides. Chinese Traditional and Herbal Drugs, 42, 38–41.
36.
IshiguroK, NagataS, FukumotoH, YamakiM, TakagiS, IsoiK. (1991) A flavanonol rhamnoside from Hypericum japonicum. Phytochemistry, 30, 3152–3153.
37.
ZhengJX, WangNL, ChenHF, YaoXS. (2007) Isolation and identification of phenolic constituents from Selaginella uncinata (Desv.) Spring. Chinese Journal of Medicinal Chemistry, 17, 302–305.
38.
QiuYK, DouDQ, PeiYP, YoushikawaM, MatsudaH, ChenYJ. (2005) Chemical constituents of Opuntia dillenii. Journal of China Pharmaceutical University, 36, 213–215.
39.
SunZH, ZhangCF, ZhangM. (2010) A new benzoic acid derivative from Eclipta prostrata. Chinese Journal of Natural Medicines, 8, 244–246.
40.
ShangXY, LiS, WangYH, WangSJ, YangYC, ShiJG. (2007) Dihydroflavonol glycosides and flavan-3-ols from Bauhinia aurea. China Journal of Chinese Materia Medica, 32, 815–818.
41.
IshiguroK, NagataS, FukumotoH, YamakiM, IsoiK, YamagataY. (1994) A 2-pyrone derivative from Hypericum japonicum. Phytochemistry, 37, 283–284.
42.
WuQL, WangSP, DuLJ, ZhangSM, YangJS, XiaoPG. (1998) Chromone glycosides and flavonoids from Hypericum japonicum. Phytochemistry, 49, 1417–1420.
43.
HsiehCL, PengCC, ChenKC, PengRY. (2013) Rutin (quercetin rutinoside) induced protein-energy malnutrition in chronic kidney disease, but quercetin acted beneficially. Journal of Agriculture and Food Chemistry, 61, 7258–7267.
44.
HuQ, NoorM, WongYF, HylandsPJ, SimmondsMSJ, XuQ, JiangD, HendryBM, XuQH. (2009) In vitro anti-fibrotic activities of herbal compounds and herbs. Nephrology Dialysis Transplantation, 24, 3033–3041;
45.
SatyanarayanaPSV, SinghD, ChopraS. (2001) Quercetin, a bioflavonoid, protects against oxidative stress-related renal dysfunction by cyclosporine in rats. Methods and Findings in Experimental and Clinical Pharmacology, 23, 175–181.
46.
RodrigoR, RiveraG. (2002) Renal damage mediated by oxidative stress: a hypothesis of protective effects of red wine. Free Radical Biology and Medicine, 33, 409–422;
47.
QinJ, TaoLJ. (2014) Progress in study on reactive oxygen species and renal fibrosis. Journal of Clinical and Pathological Research, 34, 182–189.
