Four new polyprenylated acylphloroglucinol derivatives from Hypericum beanii.

Two new polycyclic polyprenylated acylphloroglucinols (PPAPs), hyperbeanins P-Q (1-2), and two new biosynthetic precursors, hyperbeanins R-S (3-4), were isolated from Hypericum beanii, together with three known analogs (5-7). Compound 1 was one of type A PPAPs featured with unusual bicyclo[5.3.1]hendecane core. The structures of isolates were established by NMR spectroscopic methods, experimental electronic circular dichroism (ECD) spectra and comparisons with known compounds. Compounds 5 and 6 showed obvious hepatoprotective activity at 10 µM against paracetamol-induced HepG2 cell damage.

Hypseudohenrins I - K: three new polycyclic polyprenylated acylphloroglucinol derivatives from Hypericum pseudohenryi.

Three previously unidentified polycyclic polyprenylated acylphloroglucinols (PPAPs) derivatives, hypseudohenrins I-K (1-3), along with a known analogue hyphenrone X (4), were isolated from the aerial part of Hypericum pseudohenryi. The structures of the new compounds were elucidated by NMR spectroscopy and ECD calculation. The anti-inflammatory activity of the compounds was evaluated. Compounds 1-3 showed mild anti-inflammatory activity while hyphenrone X showed prominent anti-inflammatory activity.[Formula: see text].

Two new polycyclic polyprenylated acylphloroglucinols derivatives from Hypericum acmosepalum.

Polycyclic polyprenylated acylphloroglucinols (PPAPs) were mainly obtained from the plants of Hypericum genus of Guttiferae family, and possessed intriguing chemical structures and appealing biological activities. Two new PPAPs derivatives, hyperacmosin C (1) and hyperacmosin D (2) were isolated from H. acmosepalum. Their structures were established by NMR, HREIMS, and experimental electronic circular dichroism spectra. Besides, compound 1 showed significant hepatoprotective activity at 10 µM against paracetamol-induced HepG2 cell damage and compound 2 could moderately increase the relative glucose consumption.

Hyperacmosins H-J, three new polycyclic polyprenylated acylphloroglucinol derivatives from Hypericum acmosepalum.

Three new polycyclic polyprenylated acylphloroglucinol derivatives, hyperacmosins H-J (1-3), with four known compounds (4-7), were isolated from the air-dried aerial parts of Hypericum acmosepalum. Especially, compounds 1 and 2 were identified as methylated polycyclic polyprenylated acylphloroglucinol derivatives (mPPAPs). Their structures were established by NMR, HRESIMS and experimental electronic circular dichroism (ECD) spectra. The hepatoprotective activity of seven compounds were evaluated. Compounds 1 and 5 exhibited hepatoprotective activity against paracetamol-induced HepG2 cell damage.[Formula: see text].

Prenylaromadendrane-type diterpenoids from the gum resin of Boswellia sacra flueck and their cytotoxic effects.

Two new prenylaromadendrane-type diterpenoids, and three known analogues, were isolated from the ethanol extract of the gum resin of B. sacra Flueck. The structures of the new compounds were elucidated using 1 D and 2 D NMR spectroscopic analyses, mass spectrometric data, circular dichroism spectra, and comparison with the other compounds in the literature. One diterpenoid represents the first example of an acetoxyl-substituted prenylaromadendranoid in frankincense. All compounds exhibited notable cytotoxicity against human malignant glioma (U87-MG) cell line, with inhibitory rates exceeding that of the positive control 5-fluorouracil. However, nitric oxide inhibition induced by lipopolysaccarides was not observed in primary mouse peritoneal macrophages.

Ten undescribed cembrane-type diterpenoids from the gum resin of Boswellia sacra and their biological activities.

Ten undescribed cembrane-type diterpenes boscartins AL-AU, as well as five known analogues were isolated from Boswellia sacra Flueck. The relative configurations of these boscartins were established by extensive spectroscopic analysis of NMR spectra, IR and MS. The absolute configurations of boscartin AL, boscartin AN and isoincensole oxide were unequivocally assigned by single crystal X-ray diffraction. Meanwhile, the absolute configurations of boscartin AM, boscartin AP and boscartin AQ were determined by an empirical in situ formed Rh-complex ECD method. Biological evaluations showed that four compounds exhibited obvious hepatoprotective activities against paracetamol-induced HepG2 cell damage at 10 µM. Regarding neuroprotective activity, some isolates displayed moderate to evident protective effects against glutamate-induced toxicity in primary cultured fetal rat cortical neurons or oxygen-glucose deprivation toxicity in SK-N-SH Cells at 10 µM.