| Plants of the genus Hypericum (family Guttiferae), such as Hypericum perforatum, Hypericum japonicum, Hypericum scabrum, and Hypericum ascyron, have been widely used as folk medicines because of their broad-spectrum antibacterial, antidepressant, and neuroprotective activities. Hypericum obtains diverse scaffolds, such as flavonoids and xanthones, and a series of polycyclic polyprenylated acylphloroglucinols (PPAPs) have been isolated from plants of the Guttiferae family, possessing various biological activities. Thus, PPAPs have attracted attention of researchers in both chemistry and pharmacology. In 2016, approximately 350 PPAPs had been identified, the majority being isolated from the genus Hypericum.Hypericum scabrum belongs to the Hypericum genus of the Guttiferae family, which is rich in PPAPs; H. scabrum exhibits anticancer activity and has been used as a promising anticancer herb in China. As part of a program to assess the chemical and biological diversity of several traditional Chinese medicines, this dissertation investigated chemical constituents of the aerial parts of Hypericum scabrum, and bioactivities of petroleum ether extracts and purified compounds on several pharmacological models with the help of pharmacological staff.The ethanol extract of air-dried aerial parts of H. scabrum was partitioned between H2O and petroleum ether. The petroleum ether layer was subjected to purification using a silica gel column and preparative TLC coupled with RP-18 silica gel HPLC; a total of 68 compounds were obtained, with several different structural types. Those compounds included sixty PPAPs, twenty-five new compounds, two triterpenes and six other kinds of compounds. Their structures were characterized as hyperscubrone A-Y (1-25) (2S,4S,6S)-2-Benzoyl-4,6-bis(3’-methylbut-2’-en-1’-yl)-3,3-dimethylcyclohexanone (26), Hyperibone J (27),7-epiclusianone a and b (28,29), 8-Hydroxyhyperforin 8,1-hemiacetal (30), hypermongone G (31), hypermongone D (32), furohyperforin isomer 1 (33), hypermongone C (34), hyperibone A (35), hyperibone B (36), hypermongone H (37), hypermongone B (38), hyperibone G (39), ochrocarpinone B (40), scrobiculatone A a and b (41,42),27-epifurohyperforin isomer 1 (43), hyperibone L-a and hyperibone L-b (44,45), hyperibone I (46), sampsoniones P a and b (47,48), sampsonione L (49),8-hydroxyhyperforin 8,1-hemiacetal (50), hypermongone E (51), hypermongone F (52), hypermongone A (53), garcinielliptone I (54), propolone C (55), hyperscabrin A (56), garcinielliptone N (57), yezo’otogirin A (58), (2R,4R,6S)-2-Benzoyl-4,6-bis(3’-methylbut-2’-en-1’-yl)-3,3-dimethylcyclohexanone) (59), hyperibone K (60),β-sitosterol (61), ursane (62), dibutyl phthalate (63),1-octadecanol (64), dioctadecyl succinte (65), ((5E,8Z,10Z)-pentadeca-5,8,10-trienoic acid) (66), ((5E,9Z,11Z,13Z)-octadeca-5,9, 11,13-tetraenoic acid) (67), eicosane (68). Parts of the products were evaluated for neuroprotective effects on the glutamate-induced toxicity in SK-N-SH cells. The result showed that compounds 2*,3*,5*,6*,7*,12*,18*,31,32,34,38-40,47, and 60 had significant neuroprotection at 10μM. Additionally, they were also bioassayed for hepatoprotective activity against paracetamol-induced HepG2 cell damage, and the hepatoprotective activity drug bicyclol was used as the positive control. Compounds 3*,4*,7*,9*,18*,28,32,35,37,38,43,47,58, and 60 exhibited moderate hepatoprotective activity at 10μM. The inhibitory activities of the aforementioned compounds were examined against three human tumor cell lines Bel7402, A-549, and HCT-8 using the MTT method. However, no compounds showed significant inhibitory activities. |
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