Flavones and Cytotoxic Constituents from the Stem Bark of Muntingia Calabura

Two new flavones, 8‐hydroxy‐7,3′,4′,5′‐tetramethoxyflavone and 8,4′‐dihydroxy‐7,3′,5′‐trimethoxyflavone, together with thirteen known compounds have been isolated from the stem bark of Muntingia calabura. The structures of two new compounds were determined through spectral analyses. Among the isolates, 8‐hydroxy‐7,3′,4′,5′‐tetramethoxyflavone, 8,4′‐dihydroxy‐7,3′,5′‐trimethoxyflavone, and 3‐hydroxy‐1‐(3,5‐dimethoxy‐4‐hydroxyphenyl)propan‐1‐one exhibited effective cytotoxicities (ED₅₀ values = 3.56, 3.71, and 3.27 μg/mL, respectively) against the P‐388 cell line in vitro.     

Semi‐synthesis and NMR spectral assignments of flavonoid and chalcone derivatives

Previous investigations of the aerial parts of the Australian plant Eremophila microtheca and Syzygium tierneyanum resulted in the isolation of the antimicrobial flavonoid jaceosidin ( 4 ) and 2′,6′‐dihydroxy‐4′‐methoxy‐3′,5′‐dimethyl chalcone ( 7 ), respectively. In this current study, compounds 4 and 7 were derivatized by acetylation, pivaloylation, and methylation reactions. The final products, 5,7,4′‐triacetoxy jaceosidin ( 10 ), 5,7,4′‐tripivaloyloxy jaceosidin ( 11 ), 5,7,4′‐trimethoxy jaceosidin ( 12 ), 2′,6′‐diacetoxy‐4′‐methoxy‐3′,5′‐dimethyl chalcone ( 13 ), 2′‐hydroxy‐4′‐methoxy‐6′‐pivaloyloxy‐3′,5′‐dimethyl chalcone ( 14 ), and 2′‐hydroxy‐4′,6′‐dimethoxy‐3′,5′‐dimethyl chalcone ( 15 ) were all fully characterized by NMR and MS. Derivatives 10 and 13 have been previously reported but were only partially characterized. This is the first reported synthesis of 11 and 14 . The natural products and their derivatives were evaluated for their antibacterial and antifungal properties, and the natural product, jaceosidin ( 4 ) and the acetylated derivative, 5,7,4′‐triacetoxy jaceosidin ( 10 ), showed modest antibacterial activity (32–128 µg/ml) against Staphylococcus aureus strains. Copyright © 2016 John Wiley & Sons, Ltd.     

Cytotoxic Activity of Capnellene‐8β, 10α‐Diol Derivatives from a Taiwanese Soft Coral Capnella sp.

The sesquiterpene capnellene‐8β, 10α‐diol ( 1 ) was isolated from non‐polar extract of the soft coral Capnella sp. Ten acylation products of capnellene‐8β, 10α‐diol were prepared: 10α‐hydroxy‐8β‐O‐benzoylcapnellene ( 2 ), 10α‐hydroxy‐8β‐O‐p‐toluoylcapnellene ( 3 ), 10α‐hydroxy‐8β‐O‐4‐chlorobenzoyl‐capnellene ( 4 ), 10α‐hydroxy‐8β‐O‐2‐furoylcapnellene ( 5 ), 10α‐hydroxy‐8β‐O‐2‐thiophenoylcapnellene ( 6 ), 10α‐hydroxy‐8β‐O‐4‐fluorobenzoylcapnellene ( 7 ), 10α‐hydroxy‐8β‐O‐4‐propylbenzoylcapnellene ( 8 ), 10α‐hydroxy‐8β‐O‐cinnamoylcapnellene ( 9 ), 10α‐hydroxy‐8β‐O‐4‐nitrobenzoylcapnellene ( 10 ), and 10α‐hydroxy‐8β‐O‐4‐anisoylcapnellene ( 11 ). The structures of capnellene‐8β, 10α‐diol as well as its derivatives were established through standard spectroscopic analysis. The in vitro cytotoxic activities of the eleven compounds were evaluated against Hela, KB, Daoy, and WiDr human tumor cell lines.     

An Ethylenedioxy Flavonoid Carboxylic Acid from Limnophila Indica

The hexane extract of the aerial parts and roots of Limnophila indica yielded a new flavone, 3′,4′‐ethylenedioxy‐5‐hydroxy‐3‐(1‐hydroxy‐1‐methylethyl)‐6,7‐dimethyl‐5′‐methoxyflavone‐8‐carboxylic acid ( 1 ), characterized by spectral studies.     

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.     

Synthesis and properties of novel polyimides derived from 2,2′,3,3′‐benzophenonetetracarboxylic dianhydride

A new synthetic route to 2,2′,3,3′‐BTDA (where BTDA is benzophenonetetracarboxylic dianhydride), an isomer of 2,3′,3′,4′‐BTDA and 3,3′,4,4′‐BTDA, is described. Single‐crystal X‐ray diffraction analysis of 2,2′,3,3′‐BTDA has shown that this dianhydride has a bent and noncoplanar structure. The polymerizations of 2,2′,3,3′‐BTDA with 4,4′‐oxydianiline (ODA) and 4,4′‐bis(4‐aminophenoxy)benzene (TPEQ) have been investigated with a conventional two‐step process. A trend of cyclic oligomers forming in the reaction of 2,2′,3,3′‐BTDA and ODA has been found and characterized with IR, NMR, matrix‐assisted laser desorption/ionization time‐of‐flight mass spectrometry, and elemental analyses. Films based on 2,2′,3,3′‐BTDA/TPEQ can only be obtained from corresponding polyimide (PI) solutions prepared by chemical imidization because those from their polyamic acids by thermal imidization are brittle. PIs from 2,2′,3,3′‐BTDA have lower inherent viscosities and worse thermal and mechanical properties than the corresponding 2,3′,3′,4′‐BTDA‐ and 3,3′,4,4′‐BTDA‐based PIs. PIs from 2,2′,3,3′‐BTDA and 2,3′,3′,4′‐BTDA are amorphous, whereas those from 3,3′,4,4′‐BTDA have some crystallinity, according to wide‐angle X‐ray diffraction. Furthermore, PIs from 2,2′,3,3′‐BTDA have better solubility, higher glass‐transition temperatures, and higher melt viscosity than those from 2,3′,3′,4′‐BTDA and 3,3′,4,4′‐BTDA. Model compounds have been prepared to explain the order of the glass‐transition temperatures found in the isomeric PI series. The isomer effects on the PI properties are discussed. © 2004 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 42: 2130–2144, 2004     

Identification of Three New Flavonoids from the Peels of Citrus unshiu

Three new flavonoids, 5,6,7,8,3′,4′‐hexamethoxyhomoflavone ( 1 ), 5,6,7,8,4′‐pentamethoxyhomoflavone ( 2 ) and 3,6,7,8,2′,5′‐hexamethoxyflavone ( 3 ) were isolated from the peels of mature fruits of Citrus unshiu Marcow (Rutaceae), together with the three known compounds 6,7,8,4′‐tetramethoxyflavone (=6,7,8‐trimethoxy‐2‐(4‐methoxyphenyl)‐4H‐1‐benzopyran‐4‐one), 3,5,7,8,2′,5′‐hexamethoxyflavone (=2‐(2,5‐dimethoxyphenyl)‐3,5,7,8‐tetramethoxy‐4H‐1‐benzopyran‐4‐one), and scopoletin (=7‐hydroxy‐6‐methoxy‐2H‐1‐benzopyran‐2‐one) of which the former two have never been isolated from natural resources, although they have been reported as synthetic compounds. The structures of 1 – 3 were elucidated on the basis of spectroscopic evidence, including 1D‐ and 2D‐NMR analysis.     

Flavone Glycosides from Strobilanthes Formosanus

Two new flavone glycosides, 3′‐hydroxy‐5,7‐dimethoxyflavone 4′‐O‐β‐D‐apiofuranoside ( 1 ), and 5,7‐dimethoxyflavone 4′‐O‐[β‐D‐apiofuranosyl(1→5)‐ β‐D‐glucopyranoside] ( 2 ) along with four known compounds, 4′‐hydroxy‐5,7‐dimethoxyflavone ( 3 ), 2,6‐dimethoxy‐1,4‐benzoquinone ( 4 ), lupeol ( 5 ) and betulin ( 6 ) were isolated from the stem and roots of Strobilanthes formosanus. Their structures were elucidated on the basis of their spectroscopic evidence.     

Synthesis and micropatterning properties of a novel base‐soluble,positive‐working,photosensitive polyimide having an o‐nitrobenzyl ether group

A novel positive‐working, photosensitive polyimide, poly[1,4‐phenyleneoxy‐1,4‐phenylene‐2,2′‐di(2‐nitrobenzyloxy)benzophenone‐3,3′,4,4′‐tetracarboxdiimide] (OPI‐Nb), developable with an aqueous base was prepared by the o‐nitrobenzylation of a polyimide, poly(1,4‐phenyleneoxy‐1,4‐phenylene‐2,2′‐dihydroxybenzophenone‐3,3′,4,4′‐tetracarboxdiimide) (OPI), derived from 2,2′‐dihydroxy‐3,3′,4,4′‐benzophenonetetracarboxylic dianhydride (DHBA) and 4,4′‐oxydianiline, and it micropatterning properties were investigated. The o‐nitrobenzylation of OPI to OPI‐Nb was conducted with o‐nitrobenzyl bromide in N‐methyl‐2‐pyrrolidinone containing Et₃N. The DHBA monomer was synthesized by exhaustive KMnO₄ oxidation of bis(2‐dimethoxy‐3,4‐dimethylphenyl)methane obtained by etherification of bis(2‐hydroxy‐3,4‐dimethylphenyl)methane with iodomethane, followed by deprotection of the methoxy groups and cyclodehydration of the obtained 2,2′‐dihydroxy‐3,3′4,4′‐benzophenonetetracarboxylic acid. The intermediate bis(2‐hydroxy‐3,4‐dimethylphenyl)methane was prepared by the condensation of 2,3‐dimethylphenol with paraformaldehyde. The degree of o‐nitrobenzylation was determined to be over 94 mol % from ¹H NMR absorption of benzylic CH₂ protons. The aromatic OPI was perfectly soluble in a dilute aqueous NaOH solution and tetramethylammonium hydroxide (TMAH), whereas OPI‐Nb was not even swellable in them. In the micropatterning process, OPI‐Nb showed a line‐width resolution of 0.4‐μm and a sensitivity of 5.4 J/cm² when its thin films were irradiated with 365‐nm light and developed with a 2.38% aqueous TMAH solution at room temperature for 90 s. The thickness loss of OPI‐Nb films measured after postbaking at 350 °C was in the 8–9% range. © 2007 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 45: 776–788, 2007     

Effect of Metal Ions on the Structures of Coordination Polymers Based on Biphenyl‐2,2′,4,4′‐Tetracarboxylate

Two new coordination polymers, {[Cd₂(btc)(2,2′‐bpy)₂] · H₂O}_n ( 1 ) and [Zn₂(btc)(2,2′‐bpy)(H₂O)]_n ( 2 ) (H₄btc = biphenyl‐2,2′,4,4′‐tetracarboxylic acid, 2,2′‐bpy = 2,2′‐bipyridine), were synthesized hydrothermally under similar conditions and characterized by elemental analysis, IR spectra, TGA, and single‐crystal X‐ray diffraction analysis. In complexes 1 and 2 , the (btc)^4– ligand acts as connectors to link metal ions to give a 2D bilayer network of 1 and a 3D metal‐organic framework of 2 , respectively. The differences in the structures are induced by diverging coordination modes of the (btc)^4– ligand, which can be attributed to the difference metal ions in sizes. The results indicate that metal ions have significant effects on the formation and structures of the final complexes. Additionally, the fluorescent properties of the two complexes were also studied in the solid state at room temperature.     

Masking of Lewis acidity trends in the solid‐state structures of trichlorido‐ and tribromido(2,2′:6′,2′′‐terpyridine‐κ3N,N′,N′′)gallium(III)

The molecular structures of trichlorido(2,2′:6′,2′′‐terpyridine‐κ³N,N′,N′′)gallium(III), [GaCl₃(C₁₅H₁₁N₃)], and tribromido(2,2′:6′,2′′‐terpyridine‐κ³N,N′,N′′)gallium(III), [GaBr₃(C₁₅H₁₁N₃)], are isostructural, with the Ga^III atom displaying an octahedral geometry. It is shown that the Ga—N distances in the two complexes are the same within experimental error, in contrast to expected bond lengthening in the bromide complex due to the lower Lewis acidity of GaBr₃. Thus, masking of the Lewis acidity trends in the solid state is observed not only for complexes of group 13 metal halides with monodentate ligands but for complexes with the polydentate 2,2′:6′,2′′‐terpyridine donor as well.     

Synthesis and properties of new aromatic poly‐(ether benzoxazole)s from 2,2′‐bis(4‐amino‐3‐hydroxyphenoxy)biphenyl and aromatic dicarboxylic acid chlorides

A new bis(o‐aminophenol) with a crank and twisted noncoplanar structure and ether linkages, 2,2′‐bis(4‐amino‐3‐hydroxyphenoxy)biphenyl, was synthesized by the reaction of 2‐benzyloxy‐4‐fluoronitrobenzene with biphenyl‐2,2′‐diol, followed by reduction. Biphenyl‐2,2′‐diyl‐containing aromatic poly(ether benzoxazole)s with inherent viscosities of 0.52–1.01 dL/g were obtained by a conventional two‐step procedure involving the polycondensation of the bis(o‐aminophenol) monomer with various aromatic dicarboxylic acid chlorides, yielding precursor poly(ether o‐hydroxyamide)s, and subsequent thermal cyclodehydration. These new aromatic poly(ether benzoxazole)s were soluble in methanesulfonic acid, and some of them dissolved in m‐cresol. The aromatic poly(ether benzoxazole)s had glass‐transition temperatures of 190–251 °C and were stable up to 380 °C in nitrogen, with 10% weight losses being recorded above 520 °C. © 2002 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 40: 2656–2662, 2002     

Two Zinc(II) Coordination Polymers Based on Terphenyl‐2,2′,4,4′‐tetracarboxylate and Dipyridyl Ligands: Syntheses,Crystal Structures,and Luminescent Properties

Two coordination polymers, {[Zn₂(L)(bpy)] · 2H₂O}_n ( 1 ) and [Zn₂(L)(bpe)]_n ( 2 ) [H₄L = terphenyl‐2,2′,4,4′‐tetracarboxylic acid, bpy = 4,4′‐bipyridine, and bpe = 1,2‐bis(4‐pyridyl)ethane], were hydrothermally synthesized under similar conditions and characterized by elemental analysis, IR spectroscopy, TGA, and single‐crystal X‐ray diffraction analysis. Compound 1 has a 3D framework containing Zn–O–C–O–Zn 1D chains. Compound 2 exhibits a 3D framework, which features tubular channels. The channels are occupied by bpe molecules. The differences in the structures demonstrate that the auxiliary dipyridyl‐containing ligand has a significant effect on the construction of the final framework. Additionally, the fluorescent properties of the two compounds were also studied in the solid state at room temperature.     

New organo‐soluble aromatic polyimides based on 3,3′,5,5′‐tetrabromo‐2,2‐bis[4‐(3,4‐dicarboxyphenoxy)phenyl]propane dianhydride and aromatic diamines

New aromatic tetracarboxylic dianhydride, having isopropylidene and bromo‐substituted arylene ether structure 3,3′,5,5′‐tetrabromo‐2,2‐bis[4‐(3,4‐dicarboxyphenoxy)phenyl]propane dianhydride, was synthesized by the reaction of 4‐nitrophthalonitrile with 3,3′,5,5′‐tetrabromobisphenol A, followed by alkaline hydrolysis of the intermediate bis(ether dinitrile) and subsequent dehydration of the resulting bis(ether diacid). The novel aromatic polyetherimides having inherent viscosities up to 1.04 dL g⁻¹ were obtained by either a one‐step or a conventional two‐step polymerization process starting from the bis(ether anhydride) and various aromatic diamines. All the polyimides showed typical amorphous diffraction patterns. Most of the polyimides were readily soluble in common organic solvents such as N,N‐dimethylacetamide (DMAc), N‐methyl‐2‐pyrrolidone (NMP), pyridine, and even in less polar solvents like chloroform and tetrahydrofuran (THF). These aromatic polyimides had glass transition temperatures in the range of 256–303°C, depending on the nature of the diamine moiety. Thermogravimetric analysis (TGA) showed that all polymers were stable, with 10% weight loss recorded above 470°C in nitrogen. © 1999 John Wiley & Sons, Inc. J Polym Sci A: Polym Chem 37: 1673–1680, 1999     

New Lignans from the Roots of Taiwania cryptomerioides Hayata

The five new lignans designated 3′,4′‐de‐O‐methylenehinokinin ( 1 ), taiwaninolide ( 2 ), 8′‐hydroxysavinin ( 3 ), isoguamarol ( 4 ), and 4′‐O‐methylsalicifolin ( 5 ), as well as the new 4‐(3,4‐dimethoxybenzyl)dihydro‐3‐(4‐hydroxybenzyl)furan‐2(3H)‐one ( 6 ) were isolated from the roots of Taiwania cryptomerioides, besides the three known compounds hinokinin ( 8 ), savinin ( 9 ), and 3,4‐de‐O‐methylenehinokinin ( 7 ). The structures of the new constituents were elucidated through chemical and spectral studies. A compound previously isolated from the heartwood of Chamaecyparis obtusa var. formosana was assigned structure 1 ; however, this structure has now been revised to be 3,4‐de‐O‐methylenehinokinin ( 7 ).     

A three‐dimensional CdII coordination polymer constructed from 1,1′‐biphenyl‐2,2′,5,5′‐tetracarboxylate and 1,4‐bis(1H‐imidazol‐1‐yl)benzene ligands

The title coordination polymer, poly[[aqua(μ₅‐1,1′‐biphenyl‐2,2′,5,5′‐tetracarboxylato)bis[μ₂‐1,4‐bis(1H‐imidazol‐1‐yl)benzene]dicadmium(II)] dihydrate], {[Cd₂(C₁₆H₆O₈)(C₁₂H₁₀N₄)₂(H₂O)]·2H₂O}_n, was crystallized from a mixture of 1,1′‐biphenyl‐2,2′,5,5′‐tetracarboxylic acid (H₄bpta), 1,4‐bis(1H‐imidazol‐1‐yl)benzene (1,4‐bib) and cadmium nitrate in water–dimethylformamide. The crystal structure consists of two crystallographically independent Cd^II cations, with one of the Cd^II cations possessing a slightly distorted pentagonal bipyramidal geometry. The second Cd^II centre is coordinated by carboxylate O atoms and imidazole N atoms from two separate 1,4‐bib ligands, displaying a distorted octahedral CdN₂O₄ geometry. The completely deprotonated bpta⁴⁻ ligand, exhibiting a new coordination mode, bridges five Cd^II cations to form one‐dimensional chains viaμ₃‐η¹:η²:η¹:η² and μ₂‐η¹:η¹:η⁰:η⁰ modes, and these are further linked by 1,4‐bib ligands to form a three‐dimensional framework with a (4².6⁴)(4.6²)(4³.6⁵.7²) topology. The structure of the coordination polymer is reinforced by intermolecular hydrogen bonding between carboxylate O atoms, aqua ligands and crystallization water molecules. The solid‐state photoluminescence properties were investigated and the complex might be a candidate for a thermally stable and solvent‐resistant blue fluorescent material.     

Synthesis of 1-O-R-5-deoxy-β-D-ribofuranosides with (CH3)2As and (CH3)2AsO as substituents at the 5-position and a methyl or 2′,3′-dihydroxypropyl group as the aglycone in the 1-position

Six arsenic-containing β-D -ribofuranosides, including the naturally occurring (2′R)-dimethyl[1-O-(2′,3′-dihydroxypropyl)-5-deoxy-β-D -ribofuranos-5-yl]arsine oxide, were prepared in multi-step reactions from D -ribose and tetramethyldiarsine. The synthetic procedure uses the early substitution of the hydroxy group with bromine at C5, subsequent attachment of a chiral three-carbon aglycone at C1, and final delivery of arsenic at C5. The synthesis provides a viable route for the preparation of multigram quantities of the natural product.     

Axially Dissymmetric Chiral (R)‐N,W‐Bis(2‐hydroxy‐3,5‐ditert‐butyl‐arylmethyl)‐1, 1′‐binaphthalene‐2,2′‐diamine as Chiral Ligands in the Reaction of Diethylzinc to Aldehydes†

Chiral ligand (A)‐N,N′‐Bis(2‐hydroxy‐3,5‐di‐tert‐butyl‐arylmethyl)‐1,1′‐binaphthalene‐2,2′‐diamine derived from the reduction of Schiff base (R)‐2,2′‐bis (3,5‐di‐tert‐butyl‐2‐hydroxybenzylideneamino)‐1, 1′‐binaphthyl with LiAlH₄, is fairly effective in the asymmetric addition reaction of diethylzinc to aldehydes by which good yields (46%‐94%) of the corresponding sec‐alcohols can be obtained in moderate ee (51%‐79%) with R configuration for a variety of aldehydes.     

One‐dimensional CuII coordination polymers containing C2h‐symmetric 1,1′:4′,1′′‐terphenyl‐3,3′‐dicarboxylate linkers

Two new one‐dimensional Cu^II coordination polymers (CPs) containing the C_2h‐symmetric terphenyl‐based dicarboxylate linker 1,1′:4′,1′′‐terphenyl‐3,3′‐dicarboxylate (3,3′‐TPDC), namely catena‐poly[[bis(dimethylamine‐κN)copper(II)]‐μ‐1,1′:4′,1′′‐terphenyl‐3,3′‐dicarboxylato‐κ⁴O,O′:O′′:O′′′] monohydrate], {[Cu(C₂₀H₁₂O₄)(C₂H₇N)₂]·H₂O}_n, (I), and catena‐poly[[aquabis(dimethylamine‐κN)copper(II)]‐μ‐1,1′:4′,1′′‐terphenyl‐3,3′‐dicarboxylato‐κ²O³:O^3′] monohydrate], {[Cu(C₂₀H₁₂O₄)(C₂H₇N)₂(H₂O)]·H₂O}_n, (II), were both obtained from two different methods of preparation: one reaction was performed in the presence of 1,4‐diazabicyclo[2.2.2]octane (DABCO) as a potential pillar ligand and the other was carried out in the absence of the DABCO pillar. Both reactions afforded crystals of different colours, i.e. violet plates for (I) and blue needles for (II), both of which were analysed by X‐ray crystallography. The 3,3′‐TPDC bridging ligands coordinate the Cu^II ions in asymmetric chelating modes in (I) and in monodenate binding modes in (II), forming one‐dimensional chains in each case. Both coordination polymers contain two coordinated dimethylamine ligands in mutually trans positions, and there is an additional aqua ligand in (II). The solvent water molecules are involved in hydrogen bonds between the one‐dimensional coordination polymer chains, forming a two‐dimensional network in (I) and a three‐dimensional network in (II).     

Five Aromatics Bearing a 4‐O‐Methylglucose Unit from Cordyceps cicadae

Five new aromatics bearing a 4‐O‐methylglucose unit, namely 3‐methoxy‐1,4‐hydroquinone 1‐(4′‐O‐methyl‐β‐glucopyranoside) (=4‐hydroxy‐3‐methoxyphenyl 4‐O‐methyl‐β‐glucopyranoside; 1 ), 3‐methoxy‐1,4‐hydroquinone 4‐(4′‐O‐methyl‐β‐glucopyranoside) (=4‐hydroxy‐2‐methoxyphenyl 4‐O‐methyl‐β‐glucopyranoside; 2 ), vanillic acid 4‐(4′‐O‐methyl‐β‐glucopyranoside) (=3‐methoxy‐4‐[(O‐methyl‐β‐glucopyranosyl)oxy]benzoic acid; 3 ), 5‐methoxycinnamic acid 3‐O‐(4′‐O‐methyl‐β‐glucopyranoside) (=(2E)‐3‐{3‐methoxy‐5‐[(4‐O‐methyl‐β‐glucopyranosyl)oxy]phenyl}prop‐2‐enoic acid; 4 ), and naphthalene‐1,8‐diol 1,8‐bis(4′‐O‐methyl‐β‐glucopyranoside) (=naphthalene‐1,8‐diyl bis(4‐O‐methyl‐β‐glucopyranoside; 5 ), were isolated from the cultivated Cordyceps cicadae mycelia, together with thirteen known compounds. Their structures were determined by spectroscopic methods. The absolute configurations of the sugar units were not determined.