Pinoresinol monomethyl ether

Chemical Compounds and Antioxidant Activity of Forsythia suspensa Leaves Black Tea.[Pubmed:42197240]

Molecules. 2026 May 16;31(10):1687.

Forsythia suspensa leaves black tea (FSLBT) is a fermented herbal tea traditionally consumed in Northern China, yet its bioactive constituents and antioxidant basis remain insufficiently understood. In this study, a phytochemical investigation of FSLBT led to the isolation and structural identification of nine compounds, including five lignans and four pentacyclic triterpenic acids, whose structures were elucidated by (1)H-NMR, (13)C-NMR, and HRESIMS spectral analysis. Notably, epipinoresinol and Pinoresinol monomethyl ether were isolated from Forsythia suspensa leaves (FSL) for the first time. Among the isolated lignans, phillygenin, epipinoresinol, Pinoresinol monomethyl ether, and pinoresinol were further evaluated for antioxidant activity using DPPH*, ABTS*+, and FRAP assays. The four lignans exhibited concentration-dependent antioxidant activities, with IC(50) (half maximal inhibitory concentration) values ranging from 20.32 to 46.40 mug/mL for DPPH* scavenging and 37.29 to 72.71 mug/mL for ABTS*+ scavenging, while FRAP EC(50) (half maximal effective concentration) values ranged from 1.53 to 1.90 mg/mL. Quantitative HPLC analysis showed that the contents of phillygenin, epipinoresinol, Pinoresinol monomethyl ether, and pinoresinol in FSLBT were 3.48 +/- 1.12 wt%, 0.39 +/- 0.21 wt%, 0.26 +/- 0.20 wt%, and 0.18 +/- 0.07 wt%, respectively. These results indicate that FSLBT is enriched in lignan aglycones, particularly phillygenin, and that these major lignans possess measurable chemical antioxidant activities, providing a phytochemical basis for further investigation of the functional properties of this fermented herbal tea.

In vitro and in silico studies of SARS-CoV-2 main protease M(pro) inhibitors isolated from Helichrysum bracteatum.[Pubmed:35799933]

RSC Adv. 2022 Jun 22;12(29):18412-18424.

Discovering SARS-CoV-2 inhibitors from natural sources is still a target that has captured the interest of many researchers. In this study, the compounds (1-18) present in the methanolic extract of Helichrysum bracteatum were isolated, identified, and their in vitro inhibitory activities against SARS-CoV-2 main protease (M(pro)) was evaluated using fluorescence resonance energy transfer assay (FRET-based assay). Based on 1D and 2D spectroscopic techniques, compounds (1-18) were identified as 24-beta-ethyl-cholesta-5(6),22(23),25(26)-triene-3-ol (1), alpha-amyrin (2), linoleic acid (3), 24-beta-ethyl-cholesta-5(6),22(23),25(26)-triene-3-O-beta-d-glucoside (4), 1,3-propanediol-2-amino-1-(3',4'-methylenedioxyphenyl) (5), (-)-(7R,8R,8'R)-acuminatolide (6), (+)-piperitol (7), 5,7,4'-trihydroxy-8,3'-dimethoxy flavanone (8), 5,7,4'-trihydroxy-6-methoxy flavanone (9), 4',5-dihydroxy-3',7,8-trimethoxyflavone (10), 5,7-dihydroxy-3',4',5',8-tetramethoxy flavone (11), 1,3-propanediol-2-amino-1-(4'-hydroxy-3'-methoxyphenyl) (12), 3',5',5,7-tetrahydroxy-6-methoxyflavanone (13), simplexoside (piperitol-O-beta-d-glucoside) (14), Pinoresinol monomethyl ether-beta-d-glucoside (15), orientin (16), luteolin-3'-O-beta-d-glucoside (17), and 3,5-dicaffeoylquinic acid (18). Compounds 6, 12, and 14 showed comparable inhibitory activities against SARS-CoV-2 M(pro) with IC(50) values of 0.917 +/- 0.05, 0.476 +/- 0.02, and 0.610 +/- 0.03 muM, respectively, compared with the control lopinavir with an IC(50) value of 0.225 +/- 0.01 muM. The other tested compounds showed considerable inhibitory activities. The molecular docking study for the tested compounds was carried out to correlate their binding modes and affinities for the SARS-CoV-2 M(pro) enzyme with the in vitro results. Analyzing the results of the in vitro assay together with the obtained in silico results led to the conclusion that phenylpropanoids, lignans, and flavonoids could be considered suitable drug leads for developing anti-COVID-19 therapeutics. Moreover, the phenylpropanoid skeleton oxygenated at C3, C4 of the phenyl moiety and at C1, C3 of the propane parts constitute an essential core of the SARS-CoV-2 M(pro) inhibitors, and thus could be proposed as a scaffold for the design of new anti-COVID-19 drugs.

Chemical constituents from Amentotaxus yunnanensis and Torreyayunnanensis.[Pubmed:12880325]

J Nat Prod. 2003 Jul;66(7):1002-5.

In a chemical study of taxonomically related Taxaceae plants of Yunnan Province, China, seven compounds, including a new amentoflavone biflavonoid, 2,3-dihydro-7,7' '-dimethoxyamentoflavone (1), were isolated from Amentotaxus yunnanensis, and 12 isolates were obtained from Torreya yunnanensis. From the latter plant, a new abietane diterpene, torreyayunnin (7), is reported for the first time. The known isolates from A. yunnanensis have been identified as sequoiaflavone (3), sotetsuflavone (4), 7,7' '-dimethoxyamentoflavone (5), lutein, beta-sitosterol, and sequoyitol. Amentoflavone (2), sotetsuflavone (4), sciadopitysin (6), 12-hydroxydehydroabietinol, meridinol, balanophonin, (+)-Pinoresinol monomethyl ether, (+)-Pinoresinol monomethyl ether glucoside, erythro-1-(4-hydroxy-3-methoxyphenyl)-2-[4-[2-formyl-(E)-vinyl]-2- methoxyphenoxy]propane-1,3-diol, threo-1-(4-hydroxy-3-methoxyphenyl)-2- [4-[2-formyl-(E)-vinyl]-2-methoxyphenoxy] propane-1,3-diol, and (E)-2-butenedioic acid were identified as known isolates from T. yunnanensis. The presence of the amentoflavone biflavonoids (1, 3-5) in A. yunnanensis supports its placement in the Taxaceae. The occurrence of the biflavonoid sotetsuflavone (4) in both A. yunnanensis and T. yunnanensis suggests that these two genera are closely related. The identification and structural elucidation of these isolates were based on spectral data analysis including 1D and 2D NMR.

New biflavanones and bioactive compounds from Stellera chamaejasme L.[Pubmed:12580104]

Yao Xue Xue Bao. 2001 Sep;36(9):669-71.

AIM: To study the chemical constituents of the root of Stellera chamaejasme L. METHODS: Various column chromatographies on silica gel and RP-18 were employed for isolation and purification. Structures of compounds were elucidated by spectral analysis. RESULTS: Eight lignans and three biflavonoids possessing a C-3/C-3" linkage were isolated. They are ruixianglangdusu A (1) and B (2), 4',4'",5,5",7,7"-hexahydroxy-3,3"-biflavone (3), (+)-kusunokinin (4), lirioresinol-B (5), magnolenin C (6), (-)-Pinoresinol monomethyl ether (7), (-)-pinoresinol (8), (+)-matairesinol (9), isohinokinin (10) and (-)-eudesmin (11). CONCLUSION: Compounds 1 and 2 are new biflavanones, 1 is enantiomeric to known chamaejasmenin C, 4, 6, 8, 9, 10 and 11 were isolated from this plant for the first time, and 7 was isolated from natural resources for the first time. In vitro bioassays showed that 3 and 8 exhibited antibacterial activity, and 1, 2, 9 and 11 exhibited immunomodulatory activity.

Short and stereoselective total synthesis of furano lignans (+/-)-dihydrosesamin, (+/-)-lariciresinol dimethyl ether, (+/-)-acuminatin methyl ether, (+/-)-sanshodiol methyl ether, (+/-)-lariciresinol, (+/-)-acuminatin, and (+/-)-lariciresinol monomethyl ether and furofuran lignans (+/-)-sesamin, (+/-)-eudesmin, (+/-)-piperitol methyl ether, (+/-)-pinoresinol, (+/-)-piperitol, and (+/-)-pinoresinol monomethyl ether by radical cyclization of epoxides using a transition-metal radical source.[Pubmed:12003531]

J Org Chem. 2002 May 17;67(10):3242-8.

Intramolecular radical cyclization of suitably substituted epoxy ethers 4a-g using bis(cyclopentadienyl)titanium(III) chloride as the radical source resulted in trisubstituted tetrahydrofurano lignans and 2,6-diaryl-3,7-dioxabicyclo[3.3.0]octane lignans depending on the reaction conditions. The titanium(III) species was prepared in situ from commercially available titanocene dichloride and activated zinc dust in THF. Upon radical cyclization followed by acidic workup, epoxy olefinic ethers 4a-g afforded furano lignans dihydrosesamin 1a, lariciresinol dimethyl ether 1b, acuminatin methyl ether 1e, and sanshodiol methyl ether 1g directly and lariciresinol 1h, acuminatin 1i, and lariciresinol monomethyl ether 1j after removal of the benzyl protecting group by controlled hydrogenolysis of the corresponding cyclized products. The furofuran lignans sesamin 2a, eudesmin 2b, and piperitol methyl ether 2e were also prepared directly by using the same precursors 4a-f on radical cyclization followed by treatment with iodine and pinoresinol 2h, piperitol 2i, and Pinoresinol monomethyl ether 2j after controlled hydrogenolysis of the benzyl protecting group of the corresponding cyclized products. Two naturally occurring acyclic lignans, secoisolariciresinol 5h and secoisolariciresinol dimethyl ether 5b, have also been prepared by exhaustive hydrogenolysis of 2h and 2b, respectively.

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