Two New Phenolic Compounds from Artemisia iwayomogi

Two new phenolic compounds, (Z)‐5′‐hydroxyjasmone 5′‐O‐{6″‐O‐[(E)‐caffeoyl]‐β‐D ‐glucopyranoside} ( 1 ) and quercetin‐7‐O‐β‐D ‐glucuronide methyl ester ( 2 ), along with ten known phenolic compounds, 3 – 12 , were isolated from the aerial parts of Artemisia iwayomogi. Their structures were elucidated by spectroscopic methods, including 1D‐ and 2D‐NMR, and HR‐ESI‐TOF‐MS techniques. The inhibitory effects of compounds 1 – 12 on the LPS‐stimulated production of IL‐12 p40, IL‐6, and TNF‐α in bone marrow‐derived dendritic cells were evaluated.     

Three New Phenolic Compounds from Nepeta Prattii

Three new phenolic compounds, 2‐(glycer‐2‐yl)‐5‐(2‐hydroxyethyl)phenyl‐O‐β‐D‐glucopyranoside, 2‐(glycer‐2‐yl)‐5‐(2‐hydroxyethyl)phenyl‐O‐β‐D‐galactopyranoside and ethyl 3‐(3,4‐dihydroxyphenyl)lactate were isolated from Nepeta prattii. Their structures were elucidated by spectral methods.     

A New Triterpene and Phenolic Compounds from the Roots of Pteroxygonum giraldii

A chemical investigation of the roots of Pteroxygonum giraldii led to the isolation of a new arborane‐type triterpene, pteroxygonumnol A ( 1 ), a new myricetin glycoside, myricetin 3‐O‐β‐D ‐galactopyranoside 3′‐O‐β‐D ‐xylopyranoside ( 2 ), and a group of phenolic lipids, 3 – 6 , along with four known phenolic compounds, (?)‐epigallocatechin, (?)‐epigallocatechin gallate, gallic acid, and 2‐(4‐hydroxyphenyl)acetic acid. Their structures were elucidated on the basis of extensive spectroscopic analyses.     

Four New Phenolic Compounds from Curculigo crassifolia (Hypoxidaceae)

Four new phenolic compounds, named crassifogenin A ( 1 ), crassifogenin B ( 2 ), crassifoside A ( 3 ), and crassifoside B ( 4 ), were isolated from the EtOH extract of the rhizomes of Curculigo crassifolia, and based on the chemical transformation and modern spectroscopic experiments, including 2D‐NMR techniques (HMQC, HMBC, COSY, HMQC‐TOCSY, and NOE), their structures were elucidated as 2,5‐bis(3,4‐dihydroxyphenyl)furan‐3‐carbaldehyde ( 1 ), (3,4‐dihydroxyphenyl)(3,6,7‐trihydroxynaphthalen‐1‐yl)methanone ( 2 ), (3,4‐dihydroxyphenyl)[3‐(β‐D ‐glucopyranosyloxy)‐6,7‐dihydroxynaphthalen‐1‐yl]methanone ( 3 ), and 1,2‐O‐{2‐(3,4‐dihydroxyphenyl)‐1‐[3‐(3,4‐dihydroxyphenyl)prop‐2‐ynyl]ethane‐1,2‐diyl}‐β‐D ‐glucopyranose ( 4 ).     

Three New Phthalides from Gnaphalium adnatum

Three new phthalides, gnaphalides A–C ( 1 – 3 , resp.), together with three known phthalides, were isolated from the aerial part of Gnaphalium adnatum. The structures of the new compounds were elucidated as 6‐(1,1‐dimethylprop‐2‐en‐1‐yl)‐5,7‐dihydroxy‐2‐benzofuran‐1(3H)‐one ( 1 ), 5‐hydroxy‐7‐[(2‐hydroxy‐3‐methylbut‐3‐en‐1‐yl)oxy]‐2‐benzofuran‐1(3H)‐one ( 2 ), and 1,3‐dihydro‐7‐[(3‐methylbut‐2‐en‐1‐yl)oxy]‐1‐oxo‐2‐benzofuran‐5‐yl β‐D ‐glucopyranoside ( 3 ) on the basis of spectral analyses. The structure of 1 was also confirmed by X‐ray crystallographic analysis. The three known phthalides, identified as 5,7‐dihydroxyisobenzofuran‐1(3H)‐one ( 4 ), anaphatol ( 5 ), and 7‐O‐(β‐glucopyranosyl)‐5‐hydroxyisobenzofuran‐1(3H)‐one ( 6 ), were isolated from the genus Gnaphalium for the first time.     

Phenolic Compounds from Viburnum cylindricum

Three novel quinic acid esters, i.e., neochlorogenic acid methyl ester ( 1 ), cryptochlorogenic acid methyl ester ( 2 ), and chlorogenic acid methyl ester ( 3 ), were isolated from Viburnum cylindricum. Their structures were determined by spectroscopic analysis.     

Phenolic Compounds from Artemisia namanganica

Chemistry of Natural Compounds -     

Phenolic Compounds from Carthamus tinctorius

The contents of quercetin, luteolin, apigenin, isorhamnetin, umbelliferone, and daphnoretin in common safflower and of acacetin in the flowers were determined based on the physical and chemical properties of the isolated substances.     

Two New Phenolic Compounds from the Rhizomes of Gastrodia elata Blume

Phytochemical investigation of the rhizomes of Gastrodia elata Blume (Orchidaceae) led to the isolation and identification of twelve compounds, including two new phenolic compounds, 4‐hydroxybenzyl vanillyl ether (=4‐{[(4‐hydroxyphenyl)methoxy]methyl}‐2‐methoxyphenol; 1 ) and 4‐{{4‐[4‐(methoxymethyl)phenoxy]benzyl}oxy}benzyl methyl ether (=1‐[4‐(methoxymethyl)phenoxy]‐4‐{[4‐(methoxymethyl)phenoxy]methyl}benzene; 2 ). The structures of 1 and 2 were elucidated by spectroscopic data analysis including 1D‐ and 2D‐NMR experiments.     

Bioactive Phenolic Compounds from Peperomia obtusifolia

Peperomia obtusifolia (L.) A. Dietr., native to Middle America, is an ornamental plant also traditionally used for its mild antimicrobial properties. Chemical investigation on the leaves of P. obtusifolia resulted in the isolation of two previously undescribed compounds, named peperomic ester (1) and peperoside (2), together with five known compounds, viz. N-[2-(3,4-dihydroxyphenyl)ethyl]-3,4-dihydroxybenzamide (3), becatamide (4), peperobtusin A (5), peperomin B (6), and arabinothalictoside (7). The structures of these compounds were elucidated by 1D and 2D NMR techniques and HREIMS analyses. Compounds 1–7 were evaluated for their anthelmintic (against Caenorhabditis elegans), antifungal (against Botrytis cinerea, Septoria tritici and Phytophthora infestans), antibacterial (against Bacillus subtilis and Aliivibrio fischeri), and antiproliferative (against PC-3 and HT-29 human cancer cell lines) activities. The known peperobtusin A (5) was the most active compound against the PC-3 cancer cell line with IC₅₀ values of 25.6 µM and 36.0 µM in MTT and CV assays, respectively. This compound also induced 90% inhibition of bacterial growth of the Gram-positive B. subtilis at a concentration of 100 µM. In addition, compound 3 showed anti-oomycotic activity against P. infestans with an inhibition value of 56% by using a concentration of 125 µM. However, no anthelmintic activity was observed.     

Phenolic Compounds from Formosan Euphorbia tirucalli

Fourteen polyphenolic compounds were isolated from the 60% aqueous acetone extract of Formosan Euphorbia tirucalli L. (Euphorbiaceae). Two compounds, 5‐desgalloylstarchyurin and 3,3′,4‐tri‐O‐methyl‐4′‐O‐rutinosyl ellagic acid, were deduced by concerted application of 1D and 2D NMR methods, and reassigned their NMR data.     

Phenolic Compounds from Elsholtzia Bodinieri Van't

Seven phenolic compounds, including one new compound trans‐3,4,3′,5′‐tetrahydroxy‐4′‐methylstilbene 4‐O‐β‐D‐xylopyranosyl‐(1→6)‐β‐D‐glucopyranoside ( 1 ), together with six known compounds (+)‐hinokiol ( 2 ), 6‐hydroxy‐5,7‐dimethoxycoumarin ( 3 ), caffeic acid ( 4 ), vanillic acid ( 5 ), 4‐hydroxy‐2,6‐dimethoxyphenol‐1‐O‐β‐D‐glucopyranoside ( 6 ) and 4‐allyl‐2,6‐dimethoxyphenol‐1‐O‐β‐D‐glucopyranoside ( 7 ), were isolated from the root bark of Elsholtzia bodinieri Van't. Their structures were determined on the basis of spectroscopic and chemical evidence.     

Oldhamioside, A New Phenolic Glucoside from Daphniphyllum oldhamii

Further phytochemical investigation of the ethyl acetate extract of the stem of Daphniphyllum oldhamii afforded a new phenolic glucoside, named oldhamioside 1, together with eleven known compounds, koaburaside 2, betulin, 28-hydroxyl-3-1upenone, pineresinol,syringaresinol, 4-O-methyl- cedrusin, narigenin, eriodictyol, apigenin, loureirin C, and asperuloside. The structures of new and known compounds were characterized by detailed spectroscopic analysis and comparison of their spectral data with reported values.