Chemical Constituents from the Stems of Daphne holosericea (Diels) Hamaya

Abstract

Two new compounds, one flavanol dimer dapholosericol A (1) and one tigliane diterpene dapholosericin A (2), together with ten known ones, were isolated from the AcOEt extract of Daphne holosericea (Diels) Hamaya. Their structures were elucidated by their spectroscopic data analysis. Compounds 1 and 2 showed moderate activities against acetylcholinesterase with inhibition ratio of 36% and 29% at a concentration of 100 μmol/l, respectively.

LC-MS Identification, Isolation, and Structural Elucidation of Anti-HIV Tigliane Diterpenoids from Wikstroemia lamatsoensis

“…Further LC-MS-guided fractionation and separation of the EtOAc fraction using ODS and silica gel column chromatography (CC) as well as preparative HPLC led to the isolation of eight tigliane-type diterpenoids ( 1 – 8 ), which were detected in the above LC-MS analysis (Figure ). Six known compounds were identified as wikstrocin A ( 3 ), wikstrocin B ( 4 ), dapholosericin A ( 5 ), , stelleracin E ( 6 ), stelleracin C ( 7 ), and 12- O -benzoylphorbol 13-octanoate ( 8 ) based on detailed spectroscopic analysis and literature data comparison (Figure ). Notably, the known tiglianes 3 – 8 occur infrequently in the plant kingdom, with 3 and 4 obtained from Wikstroemia scytophylla , 5 from Daphne holosericea and W .…”

“…Notably, the known tiglianes 3 – 8 occur infrequently in the plant kingdom, with 3 and 4 obtained from Wikstroemia scytophylla , 5 from Daphne holosericea and W . scytophylla , , and 6 – 8 from Stellera chamaejasme . The two previously unreported tiglianes were named as wikstrocin D ( 1 ) and wikstrocin E ( 2 ), and their structures were elucidated as described below.…”

Extracts of Different Polarity of Daphne laureola L. as Valuable Source of Antioxidant and Neuroprotective Compounds

“…Instead, few studies in the literature have evaluated the potential neuroprotective activity of Daphne species [17,18]. Dapholosericol A and dapholosericin A isolated from the stems of D. holosericea exhibited moderate inhibitory effects with percentage inhibition of 36 and 29%, respectively, at the concentration of 100 µmol/L [17]. The methanol extract of D. mucronata showed a weak AChE inhibitory activity (8.2% at 300 µg/mL) [18].…”

Anti-HIV Tigliane Diterpenoids from Wikstroemia scytophylla

“…The known tigliane diterpenoids were identified as dapholosericin A ( 4 ), stelleracin E ( 5 ), and stelleracin C ( 6 ) based on detailed spectroscopic analysis and literature data comparison. Compound 4 was previously reported only from Daphne holosericea , while 5 and 6 were found in Stellera chamaejasme . Compounds 4 – 6 were isolated from the Wikstroemia genus for the first time.…”

“…The IR absorption revealed the presence of hydroxy (3399 cm –1 ) and α,β-unsaturated ketone (1716 cm –1 ) functionalities. A comparison of the NMR data of compounds 3 and 4 indicated that the compounds likely had the same tigliane skeleton but different acyl moieties . The presence of two aliphatic ester moieties in 3 were suggested by observation of two ester carbonyl carbon resonances at δ C 173.5 (C-1′) and 176.4 (C-1″), two terminal methyl triplets at δ H 0.88 (H-6′) and 0.87 (H-8″), as well as a series of aliphatic methylene multiplets at δ H 1.27–2.32.…”