Absolute configuration of phomactatriene diterpenoids obtained by Wagner‐Meerwein rearrangement of epimeric verticillols

The epimeric diterpenes (+)‐(1S,3E,7E,11S,12S)‐verticilla‐3,7‐dien‐12‐ol ( 1 ), isolated from Bursera suntui, and (+)‐(1S,3E,7E,11S,12R)‐verticilla‐3,7‐dien‐12‐ol ( 2 ), isolated from Bursera kerberi, gave the same Wagner‐Meerwein rearrangement product (?)‐(1E,4Z,8Z,11S,12R)‐phomacta‐1,(15)4,8‐triene ( 3 ). The Et₂O:BF₃‐induced transformations evidence that verticillenes and phomactanes, both containing the bicyclo[9.3.1]pentadecane skeleton, are biogenetically related through the verticillen‐12‐yl cation ( A ⁺ ), which also is a key intermediate in the biosynthetic pathways to generate antitumor taxanes. Molecular modeling using the Monte Carlo protocol, followed by density functional theory (DFT) geometry optimization employing the hybrid functionals B3LYP and B3PW91, both with the DGDZVP basis set, secured the configuration of 3 as followed from the good agreement between the calculated and experimental vibrational circular dichroism spectra. Similar DFT calculations allowed determining the absolute configuration of (+)‐(1R,4R,5R,8S,9S,11S,12R,15R)‐1,15:4,5:8,9‐triepoxyphomactane ( 9 ), which surprisingly derives from epoxidation of the second minimum energy conformer of 3 .     

Triterpenoids and Flavonoids from the Leaves of Astragalus membranaceus and Their Inhibitory Effects on Nitric Oxide Production

Four new cycloartane triterpenes, named huangqiyegenins V and VI and huangqiyenins K and L ( 1 – 4 , resp.), together with nine known triterpenoids, 5 – 13 , and eight flavonoids, 14 – 21 , were isolated from a 70%‐EtOH extract of Astragalus membranaceus leaves. The structures of the new compounds were elucidated by detailed spectroscopic analyses, and the compounds were identified as (9β,11α,16β,20R,24S)‐11,16,25‐trihydroxy‐20,24‐epoxy‐9,19‐cyclolanostane‐3,6‐dione ( 1 ), (9β,16β,24S)‐16,24,25‐trihydroxy‐9,19‐cyclolanostane‐3,6‐dione ( 2 ), (3β,6α,9β,16β,20R,24R)‐16,25‐dihydroxy‐3‐(β‐D ‐xylopyranosyloxy)‐20,24‐epoxy‐9,19‐cyclolanostan‐6‐yl acetate ( 3 ), and (3β,6α,9β,16β,24E)‐26‐(β‐D ‐glucopyranosyloxy)‐16‐hydroxy‐3‐(β‐D ‐xylopyranosyloxy)‐9,19‐cyclolanost‐24‐en‐6‐yl acetate ( 4 ). All isolated compounds were evaluated for their inhibitory activities against LPS‐induced NO production in RAW264.7 macrophage cells. Compounds 1 – 3, 14, 15 , and 18 exhibited strong inhibition on LPS‐induced NO release by macrophages with IC₅₀ values of 14.4–27.1 μM .     

Two New Ergosterol Derivatives from the Basidiomycete Cortinarius glaucopus

Two new sterols 1 and 2 and five known ones 3 – 7 were isolated for the first time from the fruiting bodies of Cortinarius glaucopus. Their structures were established by 1‐ and 2D‐NMR spectra and HR‐FABS‐MS. The relative configuration of 1 was firmly determined by comparison of the observed ¹H–¹H couplings and NOESY correlations, with those predicted for the computed geometries of the conformers. Calculations were performed by means of DFT with the B3LYP functional at 6‐31 + G(d,p) level of theory, in CHCl₃ as the solvent. The structures of the new ergosterol derivatives, called glaucoposterol A ( 1 ) and B ( 2 ), were thus established as (3S,5R,7R,10R,13R,17R,20S,22R,23R,24R)‐5,6‐epoxy‐3,7,23‐trihydroxystrophast‐8‐en‐14‐one and (22E,3S,5S,9S,10R,13R,17R,20R,24R)‐3,5‐dihydroxyergosta‐6,8(14),22‐trien‐15‐one, respectively. Moreover, the configuration of known strophasterol C ( 3 ) was determined as (3S,5R,6S,7R,10R,13R,17R,20S,22S,24R). Glaucoposterol A ( 1 ) and strophasterol C ( 3 ) represent the second finding in nature of steroids with the rare strophastane skeleton.     

Identification and Biological Evaluation of Secondary Metabolites from the Endolichenic Fungus Aspergillus versicolor

A chemical investigation of the endolichenic fungus Aspergillus versicolor (125a), which was found in the lichen Lobaria quercizans, resulted in the isolation of four novel diphenyl ethers, named diorcinols F–H ( 1 – 3 , resp.) and 3‐methoxyviolaceol‐II ( 4 ), eight new bisabolane sesquiterpenoids, named (?)‐(R)‐cyclo‐hydroxysydonic acid ( 5 ), (?)‐(7S,8R)‐8‐hydroxysydowic acid ( 6 ), (?)‐(7R,10S)‐10‐hydroxysydowic acid ( 7 ), (?)‐(7R,10R)‐iso‐10‐hydroxysydowic acid ( 8 ), (?)‐12‐acetoxy‐1‐deoxysydonic acid ( 9 ), (?)‐12‐acetoxysydonic acid ( 10 ), (?)‐12‐hydroxysydonic acid ( 11 ), and (?)‐(R)‐11‐dehydrosydonic acid ( 12 ), two new tris(pyrogallol ethers), named sydowiols D ( 13 ) and E ( 14 ), and fifteen known compounds, 15 – 29 . All of the structures were determined by spectroscopic analyses, and a number of them were further identified through chemical transformations and electronic circular dichroism (ECD) calculations. Preliminary bioassays of these isolates for the determination of their inhibitory activities against the fungus Candida albicans, and their cytotoxicities against the human cancer cell lines PC3, A549, A2780, MDA‐MB‐231, and HEPG2 were also evaluated.     

Resolution of 1‐n‐Butyl‐3‐Methyl‐3‐Phospholene 1‐Oxide With TADDOL Derivatives and Calcium Salts of O,O'‐Dibenzoyl‐(2R,3R)‐ or O,O'‐di‐p‐Toluoyl‐(2R,3R)‐tartaric Acid

The resolution methods applying (?)‐(4R,5R)‐4,5‐bis(diphenylhydroxymethyl)‐2,2‐dimethyldioxolane (“TADDOL”), (?)‐(2R,3R)‐α,α,α',α'‐tetraphenyl‐1,4‐dioxaspiro[4.5]decan‐2,3‐dimethanol (“spiro‐TADDOL”), as well as the acidic and neutral Ca²⁺ salts of (?)‐O,O'‐dibenzoyl‐ and (?)‐O,O'‐di‐p‐toluoyl‐(2R,3R)‐tartaric acid were extended for the preparation of 1‐n‐butyl‐3‐methyl‐3‐phospholene 1‐oxide in optically active form. In one case, the intermediate diastereomeric complex could be identified by single‐crystal X‐ray analysis. The absolute P‐configuration of the enantiomers of the phospholene oxide was also determined by comparing the experimentally obtained and calculated CD spectra. Chirality 26:174–182, 2014. © 2014 Wiley Periodicals, Inc.     

Isolation of Ceramides from Tagetes patula L. Yellow Flowers and Nematicidal Activity of the Fractions and Pure Compounds against Cyst Nematode,Heterodera zeae

Investigation of yellow flower extract of Tagetes patula L. led to the identification of an aggregate of five phytoceramides. Among them, (2R)‐2‐hydroxy‐N‐[(2S,3S,4R,8E)‐1,3,4‐trihydroxyicos‐8‐en‐2‐yl]icosanamide, (2R)‐2‐hydroxy‐N‐[(2S,3S,4R,8E)‐1,3,4‐trihydroxyicos‐8‐en‐2‐yl]heneicosanamide, (2R)‐2‐hydroxy‐N‐[(2S,3S,4R,8E)‐1,3,4‐trihydroxyicos‐8‐en‐2‐yl]docosanamide, and (2R)‐2‐hydroxy‐N‐[(2S,3S,4R,8E)‐1,3,4‐trihydroxyicos‐8‐en‐2‐yl]tricosanamide were identified as new compounds and termed as tagetceramides, whereas (2R)‐2‐hydroxy‐N‐[(2S,3S,4R,8E)‐1,3,4‐trihydroxyicos‐8‐en‐2‐yl]tetracosanamide was a known ceramide. A steroid (β‐sitosterol glucoside) was also isolated from the subsequent fraction. The structures of these compounds were determined on the basis of spectroscopic analyses, as well as chemical method. Several other compounds were also identified by GC/MS analysis. The fractions and some commercial products, a ceramide HFA, β‐sitosterol, and stigmasterol were evaluated against an economically important cyst nematode, Heterodera zeae. Ceramide HFA showed 100 % mortality, whereas, β‐sitosterol and stigmasterol were 40–50 % active, at 1 % concentration after 24 h of exposure time, while β‐sitosterol glucoside revealed no activity against the nematode.     

The Chemical Constituents of Endophytic Fungus Trichoderma sp. MFF‐1

A fungal strain named MFF‐1 was isolated from the flower of Pyrethrum cinerariifolium. Based on the sequence at the internal transcribed spacer (ITS) region, this strain was identified as a Trichoderma sp. Two new compounds, including a mitorubrin derivative and its potential biogenetic precursor, together with a known compound, were isolated from the cultures of the endophytic fungus. Their structures were established by spectroscopic methods and determined to be (3S*,6R*,7R*)‐3,4,5,6,7,8‐hexahydro‐7‐hydroxy‐7‐methyl‐8‐oxo‐3‐[(E)‐prop‐1‐enyl]‐1H‐isochromen‐6‐yl 2,4‐dihydroxy‐6‐methylbenzoate ( 1 ), named deacetylisowortmin, (E)‐2‐(hydroxymethyl)‐3‐(2‐hydroxypent‐3‐enyl)phenol ( 2 ), and wortmannin ( 3 ). All compounds were assayed for antimicrobial activity. Compound 3 showed activity against Candida albicans and Bacillus cereus.     

Enantioselective synthesis and antioxidant activity of 3‐(3,4‐dihydroxyphenyl)‐glyceric acid—Basic monomeric moiety of a biologically active polyether from Symphytum asperum and S. caucasicum

The racemic and enantioselective synthesis of a novel glyceric acid derivative, namely, 2,3‐dihydroxy‐3‐(3,4‐dihydroxyphenyl)‐propionic acid as well as the antioxidant activities is described. The virtually pure enantiomers, (+)‐(2R,3S)‐2,3‐dihydroxy‐3‐(3,4‐dihydroxyphenyl)‐propionic acid and (?)‐(2S,3R)‐2,3‐dihydroxy‐3‐(3,4‐dihydroxyphenyl)‐propionic acid were synthesized for the first time via Sharpless asymmetric dihydroxylation of trans‐caffeic acid derivatives using the enantiocomplementary catalysts, (DHQD)₂‐PHAL and (DHQ)₂‐PHAL. The determination of enantiomeric purity of the novel chiral glyceric acid derivatives was performed by high‐performance liquid chromatographic techniques on the stage of their alkylated precursors. The novel glyceric acid derivatives show strong antioxidant activity against hypochlorite and N,N‐diphenyl‐N‐picryl‐hydrazyl free radical. Their antioxidant activity is about 40‐fold higher than that of the corresponding natural polyether and three‐fold higher of trans‐caffeic acid itself. Chirality, 2010. © 2010 Wiley‐Liss, Inc.     

Novel Neolignan from Penthorum chinense

A new neolignan （7＇E）-2＇,4,8-trihydroxy-3-methoxy-2,4＇-epoxy-8,5＇-neolign-7＇-en-7-one （1） was isolated from the whole plants of Penthorum chinense Pursh, along with Iupeol （2）, betulinic acid （3）, glyceryl monopalmitate （4）, β-sitosterol （5）, palmitic acid （5）, ursolic acid （7）, 2β,3β,23-trihydroxy-urs-12-ene-28-oic acid （8）, glyceryl monolaurate （9）, scopoletin （10）, （-）syringaresinol （11）, 9,9＇-O-diferuIoyl-（-）-secoisolariciresionl （12）, pinocembrin （13）, apigenin （14）, kaempferol （15）, Iuteolin （16）, β-daucosterol （17）, quercetin （18）, 1-O-（β-D-glucopyranosyl）-（2S, 2＇R, 3R,4E,8E）-2-（2＇-hydroxyhexadecanoy- lamino）-4,8-octdecadiene-1,3-diol （19）, gallic acid （20）, pinocembrin-7-O-β-D-glucoside （21）, and quercetin-3-O-β-D- glucoside （22）. The structures of these compounds were elucidated on the basis of chemical and spectral evidence.     

Four New Chromone Derivatives from Colletotrichum gloeosporioides

Four previously unreported chromones, 5‐hydroxy‐2‐(hydroxymethyl)‐8‐methoxy‐4H‐chromen‐4‐one ( 1 ), (5R,7S)‐5,7‐dihydroxy‐2‐propyl‐5,6,7,8‐tetrahydro‐4H‐chromen‐4‐one ( 2 ), (5R,7S)‐5,7‐dihydroxy‐2‐methyl‐5,6,7,8‐tetrahydro‐4H‐chromen‐4‐one ( 3 ), and (5R,7S)‐5,7‐dihydroxy‐2‐[(E)‐prop‐1‐en‐1‐yl]‐5,6,7,8‐tetrahydro‐4H‐chromen‐4‐one ( 4 ), as well as one known analogue 5‐hydroxy‐2‐methyl‐4H‐chromen‐4‐one ( 5 ) were isolated from the fermentation broth of the endophytic fungus Colletotrichum gloeosporioides derived from the mangrove Ceriops tagal. Their structures were elucidated based on extensive spectroscopic analyses. The absolute configurations of 2 – 4 were determined by comparison the experimental and calculated electronic circular dichroism (ECD) spectra. Compound 2 showed cytotoxic activity against A549 cell line with the IC₅₀ value of 0.094 mm .     

Sex pheromone components of the carpenterworm moth,Holcocerus vicarius

Extracts of the female sex pheromone gland of the carpenterworm moth, Holcocerus vicarius (Walker) (Lepidoptera: Cossidae), a pest of Ulmus pumila L. (Ulmaceae), were found to contain Z7‐tetradecenyl acetate (Z7‐14Ac), E3‐tetradecenyl acetate (E3‐14Ac), (Z3,E5)‐tetradecenyl acetate (Z3,E5‐14Ac), and Z7‐tetradecenyl alcohol (Z7‐14OH) by coupled gas chromatographic‐electroantennographic detection (GC‐EAD) and coupled gas chromatography‐mass spectrometry (GC‐MS). Field trapping studies with impregnated rubber septa indicated that Z7‐14Ac was essential for attraction of males of H. vicarius. However, the most attractive blend contained Z7‐14Ac, E3‐14Ac, Z3,E5‐14Ac, and Z7‐14OH in a 50:22:17:10 ratio. Our results demonstrated that a blend of Z7‐14Ac, E3‐14Ac, Z3,E5‐14Ac, and Z7‐14OH represented the sex pheromone of H. vicarius. The optimized four‐component lure blend may be useful for monitoring H. vicarius infestations and mating disruption.     

Biological Evaluation of Secondary Metabolites from the Root of Machilus obovatifolia

Bioassay‐guided fractionation of the root of Machilus obovatifolia led to the isolation of four new lignans, epihenricine B ( 1 ), threo‐(7′R,8′R) and threo‐(7′S,8′S)‐methylmachilusol D ( 2 and 3 ), and isofragransol A ( 4 ), along with 23 known compounds. The compounds were obtained as isomeric mixtures (i.e., 2 / 3 and 4 / 20 , resp.). The structures were elucidated by spectral analyses. Among the isolates, 1 , licarin A ( 12 ), guaiacin ( 14 ), (±)‐syringaresinol ( 21 ), and (?)‐epicatechin ( 23 ) showed ABTS (=2,2′‐azinobis(3‐ethylbenzothiazoline‐6‐sulfonic acid) cation radical‐scavenging activity, with SC₅₀ values of 11.7±0.5, 12.3±1.1, 11.0±0.1, 10.6±0.3, and 9.5±0.2 μM in 20 min, respectively. In addition, kachirachirol B ( 17 ) showed cytotoxicity against the NCI‐H460 cell line with an IC₅₀ value of 3.1 μg/ml.     

Four New Tirucallane Triterpenoids from the Fruits of Melia azedarach and Their Cytotoxic Activities

Four new tirucallane triterpenoids, (21S,23R,24R)‐21,23‐epoxy‐21,24‐dihydroxy‐25‐methoxytirucall‐7‐en‐3‐one ( 2 ), (3S,21S,23R,24S)‐21,23‐epoxy‐21,25‐dimethoxytirucall‐7‐ene‐3,24‐diol ( 8 ), (21S,23R,24R)‐21,23‐epoxy‐24‐hydroxy‐21‐methoxytirucalla‐7,25‐dien‐3‐one ( 11 ), and (21S,23R,24R)‐21,23‐epoxy‐21,24‐dihydroxytirucalla‐7,25‐dien‐3‐one ( 12 ), along with 16 known analogues, 1 , 3  –  7 , 9  –  10 , and 13  –  20 , were isolated from the fruits of Melia azedarach. Their structures were elucidated by spectroscopic methods including 1D‐ and 2D‐NMR techniques and mass spectrometry. These compounds were evaluated for their cytotoxicities against HepG2 (liver), SGC7901 (stomach), K562 (leukemia), and HL60 (leukemia) cancer cell lines. Compound 20 exhibited potent cytotoxicity against HepG2 and SGC7901 cancer cells with the IC₅₀ values of 6.9 and 6.9 μm , respectively.     

Antifungal Monoterpene Derivatives from the Plant Endophytic Fungus Pestalotiopsis foedan

A new monoterpene lactone, (1R,4R,5R,8S)‐8‐hydroxy‐4,8‐dimethyl‐2‐oxabicyclo[3.3.1]nonan‐3‐one ( 1 ), along with one related known compound, (2R)‐2‐[(1R)‐4‐methylcyclohex‐3‐en‐1‐yl]propanoic acid ( 2 ), were isolated from the liquid culture of the plant endophytic fungus Pestalotiopsis foedan obtained from the branch of Bruguiera sexangula. The structure and absolute configuration of 1 were determined on the basis of extensive analysis of NMR spectra combined with computational methods via calculation of the optical rotation (OR) and ¹³C‐NMR. Both compounds exhibited strong antifungal activities against Botrytis cinerea and Phytophthora nicotianae with MIC values of 3.1 and 6.3 μg/ml, respectively, which are comparable to those of the known antifungal drug ketoconazole. Compound 2 also showed modest antifungal activity against Candida albicans with a MIC value of 50 μg/ml.     

NOVEL STEROLS OF THE TOXIC DINOFLAGELLATE KARENIA BREVIS (DINOPHYCEAE): A DEFENSIVE FUNCTION FOR UNUSUAL MARINE STEROLS?1

The “red tide” organism Karenia brevis (Davis) Hansen & Moestrup (=Gymnodinium breve Davis) produces a mixture of brevetoxins, potent neurotoxins responsible for neurotoxic shellfish poisoning in humans and massive fish kills in the Gulf of Mexico and the southern Atlantic coast of the United States. The sterol composition of K. brevis was found to be a mixture of six novel and rare Δ⁸⁽¹⁴⁾ sterols. The two predominant sterols, (24R)‐4α‐methylergosta‐8(14), 22‐dienol and (24R)‐4α‐methyl‐27‐norergosta‐8(14), 22‐dienol, were named gymnodinosterol and brevesterol and represent potentially useful biomarkers for K. brevis. A possible function for such unusual marine sterols is proposed whereby structural modifications render the sterols non‐nutritious to marine invertebrates, reducing predation and thereby enhancing the ability of the dinoflagellates to form massive blooms.     

Phytochemical Investigation of Annulohypoxylon ilanense,an Endophytic Fungus Derived from Cinnamomum Species

Cultivation of the fungal strain Annulohypoxylon ilanense, an endophytic fungus isolated from the wood of medicinal plant Cinnamomum species, resulted in the isolation of one new furanoid derivative, ilanefuranone ( 1 ), one new pyrrole alkaloid, ilanepyrrolal ( 2 ), and one new biarylpropanoid derivative, ilanenoid ( 3 ), together with 22 known compounds, of which one α‐tetralone analog, (?)‐(4R)‐3,4‐dihydro‐4,6‐dihydroxynaphthalen‐1(2H)‐one ( 4 ) was isolated for the first time from a natural source. The structures were elucidated on the basis of physicochemical evidence, in‐depth NMR spectroscopic analysis, and high‐resolution mass spectrometry, and the antimycobacterial activities were also evaluated.     

Synthesis and nootropic activity of some 2,3-dihydro-1H-isoindol-1-one derivatives structurally related with piracetam

Three 2,3‐dihydro‐1H‐isoindol‐1‐ones structurally related with piracetam (=2‐oxopyrrolidine‐1‐acetamide) have been synthesized and tested for their nootropic effects in the passive avoidance test in mice. Compounds (RS)‐ 2 , (R,R)‐ 3 , and (R,S)‐ 3 were obtained in good yields in only two steps starting from methyl dl ‐phthaloylalanine. Compound (RS)‐ 2 exhibited nootropic activity at lower doses than piracetam, used as reference drug, but it showed lower efficacy. Whereas diastereoisomers (R,R)‐ 3 and (R,S)‐ 3 were as potent as piracetam to revert amnesia induced by scopolamine, (R,S)‐ 3 showed lower efficacy than (R,R)‐ 3 . Only (R,R)‐ 3 showed myorelaxant effect at doses of 10 and 30 mg/kg; other compounds did not exhibit any anticonvulsant, sedative, myorelaxant, or impaired motor‐coordination effect in mice. These synthesized 2,3‐dihydro‐1H‐isoindol‐1‐one derivatives constitute a new kind of nootropic compounds.     

Enantioselective LC/ESI-MS/MS analysis and pharmacokinetic and tissue distribution study of (2RS)-1-(7-methoxy-1H-indol-4-yloxy)-3-(2-(2-methoxyphenoxy)ethylamino)-propan-2-ol in rats

A sensitive and stereospecific liquid chromatography‐tandem mass spectrometry method for the quantitative determination of TWo8 enantiomers ((2RS)‐1‐(7‐methoxy‐1H‐indol‐4‐yloxy)‐3‐(2‐(2‐methoxyphenoxy)ethylamino)‐propan‐2‐ol) was developed and validated in rat serum and some tissues. Racemic TWo8 is a new chemical entity, and it has been shown to possess pharmacological activity in vivo. The assay involved the diastereomeric derivatization of racemic TWo8 with 2,3,4,6‐tetra‐O‐acetyl‐beta‐glucopyranosyl isothiocyanate. The TWo8 diastereoisomers quantification was performed on a triple quadrupole mass spectrometer employing an electrospray ionization technique. The precursor to the product ion transition for TWo8 derivatives and for the internal standard (carbamazepine) was m/z 776.4 → 387.2 and 237.4 → 194.4, respectively. The assay was validated with a linear range of 10–2000 ng/ml of racemic TWo8. The inter‐day precisions for (?)‐(S)‐TWo8 and (+)‐(R)‐TWo8 were 2.1% to 14.9% and 1.3% to 14.8%, respectively. The inter‐day accuracy for (?)‐(S)‐TWo8 and (+)‐(R)‐TWo8 was within 86% to 114% and 91% to 114%, respectively. A pilot pharmacokinetic study of this new β‐adrenolytic compound has shown that (?)‐(S)‐TWo8 is eliminated faster than its antipode. The terminal half‐lives of (?)‐(S)‐TWo8 and (+)‐(R)‐TWo8 were 3.2 and 3.9 h, respectively. The compound distribution into different organs, evaluated in tissue homogenate samples following TWo8 intravenous administration, showed an enantioselective penetration of TWo8 enantiomers in the liver (p < 0.03), in the kidney (p < 0.001), and in the lungs (p < 0.05). The developed method using liquid chromatography‐tandem mass spectrometry method with electrospray ionization could be employed for quantitative determination of compounds with similar structure. Chirality 24:591–599, 2012. © 2012 Wiley Periodicals, Inc.     

New Metabolites from Endolichenic Fungus Pleosporales sp.

Eight new metabolites were obtained from the culture of an endolichenic fungus, Pleosporales sp. Their structures were determined as three terphenyl derivatives, cucurbitarins A–C ( 1 – 3 , resp.), two structurally related compounds, cucurbitarins D and E ( 4 and 5 , resp.), two benzocoumarins, 3,10‐dihydroxy‐4,8‐dimethoxy‐6‐methylbenzocoumarin ( 6 ) and 3,8,10‐trihydroxy‐4‐methoxy‐6‐methylbenzocoumarin ( 7 ), as well as one cyclohexenone, (5R)‐5‐hydroxy‐2,3‐dimethylcyclohex‐2‐en‐1‐one ( 8 ), based on the spectroscopic data.