New Cytochalasins from the Marine‐Derived Fungus Xylaria sp. SCSIO 156

Two new cytochalasins, 18‐deoxycytochalasin Q ( 1 ) and 21‐O‐deacetylcytochalasin Q ( 2 ), together with four known analogues, cytochalasin Q ( 3 ), 19,20‐epoxycytochalasin Q ( 4 ), 21‐O‐deacetyl‐19,20‐epoxycytochalasin Q ( 5 ), and cytochalasin D ( 6 ), were isolated from the fungus Xylaria sp. SCSIO156 originated from the South China Sea marine sediment. The structures of 1 and 2 were elucidated by MS and 1D‐ and 2D‐NMR data analyses, and comparison with known compounds. The known compounds 3 – 6 were identified by comparison of their MS and NMR data with those reported in the literature. In the in vitro antitumor assay, compounds 2 – 6 showed mild cytotoxicity against three tumor cell lines (MCF‐7, SF‐268, and NCI‐H460).     

A New Hydrolyzable Tannin from Balanophora harlandii with Radical‐Scavenging Activity

One new hydrolyzable tannin, 1‐O‐[(E)‐p‐coumaroyl]‐3‐O‐galloyl‐β‐D ‐glucopyranose ( 1 ), was isolated from the rhizome of Balanophora harlandii, together with 18 known phenolic compounds. Their structures were determined by detailed spectroscopic analysis. Of the known compounds, 3‐O‐caffeoyl‐D ‐glucopyranose ( 6 ) was obtained as a natural product for the first time, and compounds 2 – 6 and 8 – 19 were identified for the first time from this plant. The radical‐scavenging activity of the isolated compounds was tested by a DPPH assay.     

Xylocosides A – G,Phenolic Glucosides from the Stems of Xylosma controversum

Seven new phenolic glucosides, xylocosides A–G ( 1 – 7 ), together with 18 known compounds were isolated from the stems of Xylosma controversum Clos . In compounds 3 – 6 , the glucose residue is esterified at C(6) by 2‐hydroxycyclopentanecarboxylic acid. These new structures were established by spectroscopic‐data interpretation and chemical methods.     

Chemical Constituents from the Roots of Patrinia Rupestris

Phytochemical investigation of the roots of Patrinia rupestris afforded a new triterpenoid patrirupin A ( 1 ) and a new iridoid patrirupin B ( 2 ), as well as three known triterpenoids: 3‐oxo‐olean‐12‐en‐28‐oic acid ( 3 ), ursolic acid ( 4 ), α‐amyrin ( 5 ), three known iridoids: isovaltratum ( 6 ), 11‐ethoxyviburtinal ( 7 ), homobaldrinal ( 8 ), five known steroids: ergosterol ( 9 ), ergost‐6,22‐diene‐3β,5α,8α‐triol ( 10 ), 6‐hydroxenone ( 11 ), β‐sitosterol ( 12 ), daucosterol ( 13 ), and two known flavones: 1‐hydroxy‐5‐methoxy xanthen‐9‐one ( 14 ), 3′,4′,5,7‐tetrahydroxyflavanone ( 15 ). The new compounds were characterized by means of spectroscopic methods including UV, IR, 1D, 2D NMR and HRESIMS, and the known ones were established on the basis of comparing their NMR data with those of the corresponding compounds in the literature.     

Eupatozansins A – C,Sesquiterpene Lactones from Eupatorium chinense var. tozanense

Phytochemical investigation of Eupatorium chinense var. tozanense has resulted in the isolation of three new germacranolides, designated as eupatozansins A–C ( 1 – 3 ), along with five known compounds, (5S,6R,7R,8R)‐8‐angeloyloxy‐2‐oxoguaia‐1(10),3,11(13)‐trien‐12,6‐olide ( 4 ), costunolide ( 5 ), leptocarpin ( 6 ), 2α‐hydroxyeupatolide 8‐O‐angelate ( 7 ), and quercetin ( 8 ). The structures of the new compounds were identified by 1D and 2D NMR experiments, as well as high‐resolution mass spectrometry. The in vitro cytotoxic activities of compounds 1 – 8 were evaluated.     

Three New ent‐Labdane Diterpenoids from the Wood of Excoecaria agallocha Linn.

An extensive study of metabolites present in Excoecaria agallocha Linn . led to the isolation of three new ent‐labdane‐type diterpenoids, named agallochaexcoerins A–C ( 1 – 3 ), besides three known compounds. The skeleton present in compound 1 is rather unusual, containing of a seven‐membered lactone. The structures were elucidated on the basis of spectroscopic studies and comparison with known related compounds. The isolated compounds 1 – 6 were not active against Raw 264.7 (macrophage‐like), K 562 (leukemia), and COLO 205 (colon) human carcinoma cell lines.     

Pregnane‐Type Steroidal Alkaloids of Sarcococca saligna: a New Class of Cholinesterase Inhibitors

Phytochemical investigation of Sarcococca saligna by extensive bioassay‐guided fractionation resulted in the isolation of the pregnane‐type steroidal alkaloids 1 – 15 , i.e. of the five new compounds 1 – 5 and the ten known alkaloids 6 – 15 . The structures of the new alkaloids salignenamide C ( 1 ), salignenamide D ( 2 ), 2β‐hydroxyepipachysamine D ( 3 ), salignenamide E ( 4 ), and salignenamide F ( 5 ) were elucidated with the help of modern spectroscopic techniques, while the known alkaloids axillarine C ( 6 ), axillarine F ( 7 ), sarcorine ( 8 ), N³‐demethylsaracodine ( 9 ), saligcinnamide ( 10 ), salignenamide A ( 11 ), vaganine A ( 12 ), axillaridine A ( 13 ), sarsalignone ( 14 ), and sarsalignenone ( 15 ) were identified by comparing their spectral data with those reported earlier. Inhibition of electric‐eel acetylcholinesterase (EC 3.1.1.7) and horse‐serum butyrylcholinesterase (EC 3.1.1.8) by alkaloids 1 – 15 were investigated. These new cholinesterase inhibitors may act as potential leads in the discovery of clinically useful inhibitors for nervous‐system disorders, particularly by reducing memory deficiency in Alzheimer's disease patients by potentiating and effecting the cholinergic transmission process. These compounds were found to inhibit both enzymes in a concentration‐dependent fashion with the IC₅₀ values ranging from 5.21–227.92 μM against acetylcholinesterase and 2.18–38.36 μM against butyrylcholinesterase.     

New Patchoulol‐Type Sesquiterpenoids from Pogostemon cablin

Four new patchoulol derivatives, 8α,9α‐dihydroxypatchoulol ( 1 ), 3α,8α‐dihydroxypatchoulol ( 2 ), 6α‐hydroxypatchoulol ( 3 ), and 2β,12‐dihydroxypatchoulol ( 4 ), were isolated from the aerial part of Pogostemon cablin (Labiatae), together with nine known compounds, sesquiterpenoids 5 – 8 and flavonoids 9 – 13 . Their structures were elucidated by detailed spectroscopic analysis, using 1D‐ and 2D‐NMR techniques.     

New α‐Tetralone Galloylglucosides from the Fresh Pericarps of Juglans sigillata

Three new α‐tetralone galloylglucosides, 1 – 3 , were isolated from the fresh pericarps of Juglans sigillata (Juglandaceae), together with six known compounds. The structures of the new compounds were determined as 1,2,3,4‐tetrahydro‐7‐hydroxy‐4‐oxonaphthalen‐1‐yl 6‐O‐[(3,4,5‐trihydroxyphenyl)carbonyl]‐β‐D ‐glucopyranoside ( 1 ), (1S)‐1,2,3,4‐tetrahydro‐8‐hydroxy‐4‐oxonaphthalen‐1‐yl 6‐O‐[(3,4,5‐trihydroxyphenyl)carbonyl]‐β‐D ‐glucopyranoside ( 2 ), and 1,2,3,4‐tetrahydro‐7,8‐dihydroxy‐4‐oxonaphthalen‐1‐yl 6‐O‐[(3,4,5‐trihydroxyphenyl)carbonyl]‐β‐D ‐glucopyranoside ( 3 ), respectively, on the basis of detailed spectroscopic analyses, and acidic and enzymatic hydrolysis. The antimicrobial activities of the isolated compounds 2, 4 , and 7 – 9 were evaluated.     

Additional Minor Phytoecdysteroids of Serratula wolffii

Three new and one known ecdysteroids were identified in the MeOH extract of the roots of Serratula wolffii. The new compounds isolated were (11α)‐11‐hydroxyshidasterone ( 1 ), (2β,3α,5β,14β,22R)‐2,3,20,22,25‐pentahydroxycholest‐7‐en‐6‐one ( 2 ), and (2β,3α,5β,22R)‐2,3,20,22,25‐pentahydroxycholest‐7‐en‐6‐one ( 3 ), together with the known ponasterone A ( 4 ). This latter compound was now better characterized than earlier. The structures of compounds 1 – 4 were established by extensive spectroscopic techniques, including one‐ and two‐dimensional NMR methods.     

Chisiamols A-F,Triterpenoids from Chisocheton siamensis

Six new apotirucallane‐type triterpenoids, chisiamols A – F ( 1 – 6 ), along with two known compounds, were isolated from the twigs of Chisocheton siamensis. The structures of compounds 1 – 6 were established on the basis of spectroscopic and chemical methods.     

Four New Diterpenoids from Ballota limbata

Six diterpenoids ( 1 – 6 ) belonging to the clerodane and tetracyclic diterpene types were isolated from the CHCl₃ extract of Ballota limbata. The structures of the new compounds 1 and 4 – 6 (named ballatenolide A and limbatenolides A–C, resp.) were established by their spectral data, and their relative configuration was determined by 2D NMR. Compounds 2 and 3 were identified as known clerodanes. Compound 1 had a unique feature, i.e., an α,β‐unsaturated γ‐lactone moiety at C(4)/C(6), whereas limbatenolides A–C ( 4 – 6 ) belonged to the rare class of tetracyclic diterpenoids, which are known to occur only in the genus Ballota. All of the isolated compounds showed inhibitory potential in a cholinesterase‐inhibition assay.     

Three New Phenyl Ether Derivatives from Aspergillus carneus HQ889708

Three new phenyl ether derivatives, 3‐hydroxy‐5‐(3‐hydroxy‐5‐methylphenoxy)benzoic acid ( 1 ), 3,4‐dihydroxy‐5‐(3‐hydroxy‐5‐methylphenoxy)benzoic acid ( 2 ), 3‐[3‐hydroxy‐5‐(hydroxymethyl)phenoxy]‐5‐methylphenol ( 3 ), and three known compounds 4 – 6 were obtained from the fermentation broth of Aspergillus carneus HQ889708, which was isolated from sea water from South China Sea. The structures of compounds 1 – 3 were established on the basis of spectroscopic methods including ESI‐MS and NMR. Compounds 4 – 6 were reported before as synthesized products, herein, they are reported from nature for the first time.     

Itosides A – I,New Phenolic Glycosides from Itoa orientalis

Eight new benzoylated gentisyl alcohol (=2‐(hydroxymethyl)benzene‐1,4‐diol) glucosides, itosides A–H ( 1 – 8 ), together with the new pyrocatechol (=benzene‐1,2‐diol) glycoside itoside I ( 9 ) were isolated from the bark and twigs of Itoa orientalis (Flacourtiaceae). In itosides B–D ( 2 – 4 ), the gentisyl alcohol moiety was esterified by 1‐hydroxy‐6‐oxocyclohex‐2‐ene‐1‐carboxylic acid, while itosides E–H ( 5 – 8 ) contained instead an additional 2‐hydroxybenzoic acid moiety. The compounds were accompanied by the known derivatives 4‐hydroxytremulacin ( 10 ), poliothyrsoside ( 11 ), poliothyrsin ( 12 ), homaloside D ( 13 ), tremulacin, and pyrocatechol β‐D ‐glucopyranoside. The structures of the new compounds were elucidated by spectral and chemical methods.     

Steroidal Alkaloids from the Roots and Rhizomes of Vertrum nigrum L.

Two new steroidal alkaloids, neoverapatuline ( 1 ) and (1β,3α,5β)‐1,3‐dihydroxyjervanin‐12‐en‐11‐one ( 2 ), together with the four known compounds, veratramine ( 3 ), rubijervine ( 4 ), veratrosine ( 5 ), and veratroylzygadenine ( 6 ), were isolated from the roots and rhizomes of Veratrum nigrum L. Their structures were established through combined analyses of physicochemical properties and spectroscopic evidence. All compounds 1 – 6 were tested for their cytotoxicities in vitro against the human glioma cell line SF188.     

Phenolic Compounds from Scorzonera tomentosa L.

From the subaerial parts of S. tomentosa L. (Asteraceae), two new dihydroisocoumarins, compounds 1 and 2 , a new phthalide, 3 , and a new stilbene derivative, 4 , were isolated, together with four known compounds, (±)‐hydrangenol ( 5 ), (?)‐hydrangenol 4′‐O‐β‐glucoside ( 6 ), (±)‐hydramacrophyllol A ( 7 ), and (±)‐hydramacrophyllol B ( 8 ). All secondary metabolites were identified on the basis of physicochemical, spectroscopic, and mass‐spectrometric data. The known compounds 5 – 8 were isolated for the first time from this species.     

Three New Indole‐Containing Diketopiperazine Alkaloids from a Deep‐Ocean Sediment Derived Fungus Penicillium griseofulvum

Three new indole‐containing diketopiperazine alkaloids, named variecolorins M–O ( 1 – 3 ), together with the eight known analogues 4 – 11 , were isolated from a deep‐ocean sediment‐derived fungus, Penicillium griseofulvum. Their structures were determined by analysis of the spectroscopic data. The 2,2‐diphenyl‐1‐picrylhydrazinyl (DPPH) radical‐scavenging activities and the cell‐proliferation inhibitory activities of the three new compounds 1 – 3 were investigated.     

A New Isofuranonaphthalenone and Benzopyrans from the Endophytic Fungus Nodulisporium sp. A4 from Aquilaria sinensis

A new isofuranonaphthalenone, (7R*,8S*)‐3,6,7,8‐tetrahydro‐4,7,8‐trihydroxynaphtho[2,3‐c]furan‐5(1H)‐one ( 1 ), and a new benzopyran, (2R*,4R*)‐3,4‐dihydro‐4‐methoxy‐2‐methyl‐2H‐1‐benzopyran‐5‐ol ( 2 ), together with four known related analogs, 3 – 6 , were isolated from the culture of Nodulisporium sp. A4, an endophytic fungus from the stem of Aquilaria sinensis (Lour.) Gilg . The structures of the isolated compounds were determined by extensive analysis of their spectroscopic data as well as by comparison with literature reports. The isolated compounds 1 – 6 were evaluated for their cytotoxic activities against the NCI‐H460 and SF‐268 tumor cell lines.     

Five New β‐Carboline‐Type Alkaloids from Stellaria dichotoma var. lanceolata

Five new β‐carboline‐type alkaloids, dichotomines F–J ( 1 – 5 , resp.), along with nine known compounds, dichotomides I, III, V, and VII ( 6 – 9 , resp.), stellarines A and C ( 10 – 11 , resp.), dichotomine B ( 12 ), glucodichotomine B ( 13 ), and 1‐acetyl‐3‐carboxy‐β‐carboline ( 14 ), were isolated from the roots of Chinese medicinal plant Stellaria dichotoma L. var. lanceolata. Their structures were determined by chemical and spectroscopic means. Compounds 12 and 13 exhibited moderate cytotoxicity.     

Pyrrolizidine Alkaloids and Bisabolane Sesquiterpenes from the Roots of Ligularia cymbulifera

The new pyrrolizidine alkaloid glycoside 1 , and the three new highly oxygenated bisabolane sesquiterpenes 4 – 6 , together with the two known pyrrolizidine alkaloids 2 and 3 , were isolated from the roots of Ligularia cymbulifera (W. W. Smith ) Hand .‐Mazz . Their structures were established on the basis of spectroscopic analysis, especially 1D‐ and 2D‐NMR data. The cytotoxic activities of compounds 1, 2 , and 4 – 6 were evaluated against hepatoma (BEL‐7402), human leukemia (HL‐60), human ovarian carcinoma (HO‐8910), and nasopharyngeal carcinoma (KB) cell lines (Tables 1–3). Compound 6 s howed weak cell‐growth inhibition of BEL‐7402 cell.