Trimethylsilyl chloride

Fifteen willow hybrids (Tables S1 and S2) were harvested and supplied
from Carbons Finland Oy, VTT Technical Research Center of Finland
Ltd., and Lantmännen Lantbruk. The bark was manually peeled
and cut into 2 cm pieces and stored at −20 °C for further
use. The barks were ground into 1 mm particle size and dried at 40
°C in an oven. Acetone, arabinose, N,O-bistrifluoroacetamide (BSTFA), (+)-catechin, DMSO-d₆, fructose, galactose, glucose, heneicosylic
acid (C21 acid), mannose, picein, pyridine-d5, raffinose,
rhamnose, salicin, trimethylsilyl chloride (TMCS), xylitol, and xylose
were supplied from Sigma-Aldrich, Finland. Betulinol (99.5% purity)
was supplied by Åbo Akademi University. Triandrin was purified
by chromatography (Figure S1) based on
its size and hydrophobicity differences among all bioactive molecules
from willow hybrid Karin bark extract.^{15 (link)} The purity (ca. 90%) of triandrin was assessed from its nuclear
magnetic resonance (NMR) spectra (Figures S2–S4).^{16 (link)} The exact match between the willow
hybrid and their associated experiment is summarized in Table S1.

Anhydrous dimethyl acetamide (DMAc, 99%), anhydrous pyridine (Py), dimethyl amino pyridine (DMAp), trimethylsilylchloride (TMSC, >98%), N, N dimethyl formamide (DMF), 3-methoxycarbonyl-phenylboronic acid and tetrahydrofuran (THF, 99%) were purchased from Sigma Aldrich (Sigma Aldrich, St. Louis, MO, USA) and used as received. NaOH (sodium hydroxide), sulfuric acid (H₂SO₄), Tetrakis(triphenylphosphine) palladium (0) (Pd(PPh₃)₄), potassium carbonate (K₂CO₃), hydrochloric acid and thionyl chloride (SOCl₂) were obtained from Scharlau (Scharlab, Barcelona, Spain). The diacid 5′-tert-butyl-m-terphenyl-3,3″-dicarboxylic acid (tBTmDA) was synthesized following the procedure previously reported [27 (link)].
o-Hydroxydiamine 2,2-bis(3-amino-4-hydroxy phenyl)-hexafluoropropane (APAF) was purchased from Apollo Scientific (Apollo Scientific, Stockport, Cheshire, UK) and purified through sublimation at 220–225 °C before use. 4,4′-(hexafluoroisopropylidene) dianiline (6FpDA, Apollo Scientific, Stockport, Cheshire, UK) purified through sublimation at 220 °C and 5′-terbutil-m-terphenyl-3,3″-dichloride (tBTmCl) were employed as monomers to create the polyamide without o-hydroxy groups (PA). The synthesis of the corresponding HPA was carried out as described elsewhere [28 (link)].
The dichloride monomer (tBTmCl) was prepared from the corresponding diacid, as described below.

Dithiothreitol (DTT), nitroblue tetrazolium (NBT), H₂O₂, titanium dioxide, dichloromethane, pyridine, N,O-bis(trimethylsilyl) trifluoroacetamide, trimethylsilyl chloride, sodium azide, thiobarbituric acid (TBA), methionine, catalase, peroxidase, cholesterol, maltose, octadecane, phenol, palmitic acid, sorbitol, ammonia and potassium phosphate buffer were purchased from Sigma-Aldrich (Saint Louis, MO, USA). Tetracosane and 4-aminoantipyrine were purchased from Fluka (Bucharest, Romania). Sulfuric acid was purchased from Fisher Chemical (New Hampshire, EUA). TrichloroAcetic acid (TCA) was purchased from BIOCHEM Chemopharma (Cosne-Cours-sur-Loire, France). Guaiacol and polyvinylpyrrolidone (PVP) were purchased from Acrós Organics. Triton-X and ascorbic acid were purchased from Panreac. Acetic acid, ethylenediaminetetraAcetic acid (EDTA) and phenylmethylsulfonyl fluoride (PMSF) were purchased from VWR (Pennsylvania, EUA). Riboflavin, n-hexane p.a., methanol p.a., sodium carbonate (Na₂CO₃), dimethyl sulfoxide (DMSO), potassium sulfate and quercetin were purchased from Merck (Darmstadt, Germany). Luteolin and oleuropein were purchased from Extrasynthese (Genay, France).