Myrrhanolide D and Myrrhasin A,New Germacrane‐Type Sesquiterpenoids from the Resin of Commiphora opobalsamum

Two new germacrane‐type sesquiterpenoids bearing an epoxy ring, myrrhanolide D ( 1 ) and myrrhasin A ( 2 ), together with eight known compounds, 3 – 10 , were isolated from the resinous exudates of Commiphora opobalsamum. Their structures were elucidated based on the analyses of their spectroscopic data. The isolated compounds 1, 2, 6 , and 8 were evaluated for their cytotoxic activities against human prostate cancer DU145 and PC3 cells.     

Two New Prenylated Xanthones from the Pericarp of Garcinia mangostana (Mangosteen)

Two new prenylated xanthones (=9H‐xanthen‐9‐ones), garcimangosxanthones D ( 1 ) and E ( 2 ), together with the six known xanthones 3 – 8 , were isolated from the pericarp of Garcinia mangostana. Their structures were determined by analysis of their spectroscopic data. All of the isolated compounds were biologically evaluated for their in vitro cytotoxic activity against A549, Hep‐G2, and MCF‐7 human‐cancer cell lines and antioxidant activity. Compound 1 exhibited moderate cytotoxicity against Hep‐G2 (IC₅₀=19.2 μM ) and weak cytotoxicity against MCF‐7 (IC₅₀=62.8 μM ) cell lines, and compound 2 showed moderate cytotoxicity against A549, Hep‐G2, and MCF‐7 cell lines with IC₅₀ values of 12.5–20.0 μM (Table 2). Both compounds 1 and 2 demonstrated a weak antioxidant activity with ferric reducing antioxidant power (FRAP) values of 41±7 and 130±4 μmol/g, respectively (Table 3).     

Two New Cytotoxic Spirostane‐Steroidal Saponins from the Roots of Bletilla striata

Two new spirostane‐steroidal saponins, bletilnoside A ( 1 ) and bletilnoside B ( 2 ), together with five known compounds, 3 – 7 , were isolated from the roots of Bletilla striata (Thunb .) Reichb . F. The structures of the new compounds were determined based on their 1D‐ and 2D‐NMR spectral data. The isolated compounds 1 – 7 were tested for cytotoxicity against four human tumor cells (A549, SK‐OV‐3, SK‐MEL‐2, and HCT15) in vitro using a sulforhodamin B bioassay, and compounds 1, 2 , and 5 showed significant cytotoxicities against all tested tumor cell lines with IC₅₀ values ranging from 3.98±0.16 to 12.10±0.40 μM .     

Two New Cycloartane Triterpenoids from Kleinhovia hospita

Two new cycloartane triterpenoids, (23R)‐21,23:23,27‐diepoxycycloarta‐1,24‐diene‐3,27‐dione ( 1 ) and (3α)‐(α‐L ‐arabinopyranosyloxy)‐1α‐hydroxy‐23‐oxocycloartan‐28‐oic acid ( 2 ), together with six known pentacyclic triterpenoids, 3 – 8 , and five known C₂₉ steroids, 9 – 13 , were isolated from Kleinhovia hospita. The structures of these compounds were determined by analysis of their spectroscopic data. Moreover, the absolute configuration of 1 was confirmed by quantum‐chemical TDDFT calculation of its ECD spectrum. All compounds were evaluated for their cytotoxic activities against human colon carcinoma (HCT116) and gastric carcinoma (SGC7901) cell lines, and compounds 6, 7, 8, 11 , and 12 exhibited antiproliferative activities with IC₅₀ values ranging from 23.0 to 91.8 μM .     

Two Unusual Rearranged Flavan Derivatives from Narcissus tazetta var. chinensis

Two unusual rearranged flavan derivatives with a rare bicyclo[3.3.1]non‐3‐ene‐2,9‐dione ring, tazettone A ( 1 ) and tazettone B ( 2 ), together with five known flavans, 3 – 7 , were isolated from the bulbs of Narcissus tazetta var. chinensis Roem . The structures of two new compounds were elucidated by spectroscopic analyses, including 1D‐ and 2D‐NMR spectroscopy. All of the isolated compounds were evaluated for their cytotoxicities against four human tumor cell lines A549, HCT116, SK‐BR‐3, and HepG2. Compounds 1 and 2 were almost inactive against all tested cell lines, while compounds 3 – 7 exhibited moderate or weak cytotoxicities against the tested cell lines.     

人面果树皮中口 山 酮 化合物及其DPPH自由基的清除活性

从人面果乙酸乙酯提取物中分离出5个新的口 山 酮 化合物garcinenone A (1), B (3), C (4), D (7) and E (8)和7个已知化合物,其结构经过波谱技术,特别是2D-NMR技术来鉴定。Jacareubin (2), 1,4,6-trihydroxy-5-methoxy-7-(3-methyl-2-buteny1)xanthone (6), subeliptenone B (11) 和symphoxanthone (12)为首次从该植物中分离出来。在DPPH自由基的清除活性实验中,所有的化合物都显示抗氧化活性,其IC50的值在 6.0-23.2 mM。结果表明人面果是潜在的有前景的天然抗氧化剂。     

A novel icariin type flavonoid from Epimedium pseudowushanense

A novel icariin type flavonoid glycoside with a malonaldehydic acid intramolecular ester and two known flavonoid glycosides were isolated from Epimedium pseudowushanense. Their structures were elucidated on the basis of spectroscopic analysis and comparison of their data to the values reported in the literatures. The anti-inflammatory activities of these compounds icariin 3′′′-O-malonaldehydic acid intramolecular 1′′′′, 2′′′ ester (1), icariin (2) and epimedin C (3) were tested. The results indicated that compounds 1, 2 and 3 showed maximal inhibitory ratio of 27.91, 44.80 and 46.61%, respectively in in vitro anti-inflammatory activity on LPS-induced TNF-α secretion in RAW264.7 cells. Compounds icariin (2) and epimedin C (3) were found to inhibit the secretion of TNF-α to a comparable degree as quercetin.     

Terpenoids from the Stems of Drypetes congestiflora

Two new eremophilane‐type sesquiterpenoids, 1α‐hydroxyeremophila‐6,9,11‐trien‐8‐one ( 1 ), 4α‐hydroxyeremophila‐1,9‐diene‐3,8‐dione ( 2 ), and a new friedelane‐type triterpenoid, friedelane‐3α,16β‐diol ( 4 ), along with six known terpenoids, 3 and 5 – 9 , have been isolated from the stems of Drypetes congestiflora. Their structures and relative configurations were elucidated on the basis of detailed spectroscopic analyses and by comparison of their NMR data with those reported in the literature. All of the compounds, 1 – 9 , were isolated for the first time from this species. Compound 3 exhibited moderate cytotoxic activities against the A549 and B16F10 cell lines.     

β-Hydroxydihydrochalcone and flavonoid glycosides along with triterpene saponin and sesquiterpene from the herbs of Pimpinella rhodantha Boiss.

A new β-hydroxydihydrochalcone glycoside named ziganin (1) and a new acylated flavonol glycoside named isorhamnetin-3-O-α-L-(2″,3″-di-O-trans-coumaroyl)-rhamnopyranoside) (2), along with two known flavonoid glycosides, a β-hydroxydihydrochalcone glycoside, a hydroxybenzoic acid derivative, a trinorguaiane type sesquiterpenoid, a triterpenic saponin and a polyol were isolated from the herbs of Pimpinella rhodantha Boiss. Their structures were elucidated on the basis of spectroscopic analyses including 1D-and 2D-NMR, UV, IR, CD, ESI-MS, APCI-MS, HR-ESI-MS techniques. The isolated compounds were evaluated for their antioxidant capacity through the DPPH free-radical scavenging assay and ferrous ion-chelating power test.     

Polyprenylated Xanthones and Benzophenones from the Bark of Garcinia oblongifolia

A new polyprenylated xanthone (=9H‐xanthen‐9‐one) and a new polyprenylated benzophenone, namely oblongifolixanthone A ( 1 ) and garciniagifolone A ( 2 ), were isolated from the bark of Garcinia oblongifolia, together with five known compounds including the four xanthones 3 – 5 and 7 and a benzophenone 6 . The structures of 1 and 2 were established by detailed analysis of their spectroscopic data, especially 1D‐ and 2D‐NMR spectra and HR‐ESI‐MS data. All these compounds were assayed for their cytotoxic activities against three human tumor cell lines (HeLa, SGC7901, and HepG2). The 1,3,6,7‐tetrahydroxy‐9H‐xanthen‐9‐one ( 3 ) was inactive, and the other compounds showed weak to moderate activity.     

A new antifungal and antiprotozoal bibenzyl derivative from Gavilea lutea

A new bibenzyl derivative (4), together with two glycosylated flavonoids (1 and 2), batatasin III (3) and the phenanthrene isohircinol (5) were isolated from the aerial parts of Gavilea lutea. Their structures were elucidated on the basis of spectroscopic studies including 1D and 2D NMR, UV, IR and HRESIMS. All isolated compounds were evaluated for their antifungal activity towards Candida albicans. The new compound 4 showed inhibitory activity with a MIQ of 50 μg. In addition, compound 4 exhibited a selective activity (IC₅₀ = 2.3 μg/mL) against Leishmania donovani.     

Structural and Biological Properties of Vermistatin and Two New Vermistatin Derivatives Isolated from the Marine‐Mangrove Endophytic Fungus Guignardia sp. No. 4382

Vermistatin (=(3R)‐4,6‐dimethoxy‐3‐{4‐oxo‐6‐[(1E)‐prop‐1‐en‐1‐yl]‐4H‐pyran‐3‐yl}‐2‐benzofuran‐1(3H)‐one; 1 ) and two new vermistatin derivatives, compounds 2 and 3 , were isolated from the fungal strain Guignardia sp. No. 4382 obtained from the South‐China Sea. Their structures were elucidated by various methods, including circular dichroism (CD), 1D‐ and 2D‐NMR, and HR‐EI‐MS. The structures of 1 and 2 were unequivocally corroborated by X‐ray crystallography, and their absolute configurations were derived by CD spectroscopy based on a literature comparison. The in vitro cytotoxic and antifungal activities of 1 and 2 were tested.     

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).     

Further Diterpenes from the Seeds of Caesalpinia minax Hance

Three new cassane‐type diterpenes, neocaesalpin AF ( 1 ), neocaesalpin AG ( 2 ), and neocaesalpin AH ( 3 ), were isolated from the seeds of Caesalpinia minax Hance . Their structures were elucidated on the basis of extensive spectroscopic analyses. The partially hydrogenated lactone unit in a tetracyclic cassane diterpene in 2 is rarely encountered in the cassane diterpenes isolated from the genus Caesalpinia. All compounds were evaluated for their in vitro cytotoxic activities against HCT‐8 and MCF‐7 human cancer cell lines.     

Triterpenoids from the Roots of Camellia oleifera C.Abel and Their Cytotoxic Activities

Three new triterpenoids, 21β,22α‐diangeloyloxy‐3β,15α,16α,28‐tetrahydroxyolean‐12‐en‐23‐al ( 1 ), 21β‐angeloyloxy‐3β,15α,16α,28‐tetrahydroxy‐22α‐(2‐methylbutanoyloxy)olean‐12‐en‐23‐al ( 2 ), and 21β‐angeloyloxy‐3β,16α,28‐trihydroxy‐22α‐(2‐methylbutanoyloxy)olean‐12‐en‐23‐al ( 3 ), along with six known triterpenoids, were isolated from the roots of Camellia oleifera C.Abel . The structures of compounds 1 – 3 were elucidated on the basis of spectroscopic analyses. Moreover, all compounds isolated were evaluated for their cytotoxic activities by MTT (=3‐(4,5‐dimethylthiazol‐2‐yl)‐2,5‐diphenyl‐2H‐tetrazolium bromide) assay.     

Three new sesquiterpenes from Ainsliaea glabra

Three new sesquiterpenes: 4-acrylic-6-methyl-α-tetralone (1), ainsliaea acid A (2) and ainsliaea acid B (3), together with 8 known compounds (4-11) were isolated from the whole herb of Ainsliaea glabra and their structures were established by means of 1D and 2D NMR spectroscopy and HR-ESIMS. Compounds 1–6 were tested for the inhibition of nuclear factor kappa B (NF-κB) in the 293-NF-κB-luciferase reporter cell line induced by lipopolysaccharide (LPS), and compound 2 was further tested for the production of tumor necrosis factor-α (TNF-α), interleukin-1β (IL-1β), IL-6 and IL-10 in RAW264.7 macrophages induced by LPS. The isolated compound 2 exhibited significant anti-inflammatory activity.     

Sesquiterpenes from Rhizomes of Cyperus rotundus with Cytotoxic Activities on Human Cancer Cells in vitro

Two new sesquiterpenes, cyperusol A₃ ( 1 ) and 3β‐hydroxycyperenoic acid ( 2 ), along with three known sesquiterpenes, britanlin E ( 3 ), 1β,4α‐dihydroxyeudesm‐11‐ene ( 4 ), and 11,12‐dihydroxyeudesm‐4‐en‐3‐one ( 5 ), were isolated from the AcOEt‐soluble fraction of rhizomes of Cyperus rotundus L. The structures of 1 and 2 were elucidated by physical and spectroscopic methods (¹H‐ and ¹³C‐NMR, 2D‐NMR, and MS). All of the isolates, 1 – 5 , were evaluated for their cytotoxic activities against human ovarian cancer cells (A2780) and endometrial adenocarcinoma cells (Ishikawa) using MTT assays.     

New Triterpenoid Saponins from the Roots of Gypsophila paniculata L.

The seven new triterpenoid saponins 1 – 7 were isolated from the roots of Gypsophila paniculata L. Their structures were established by 1D ‐ and 2D‐NMR techniques, HR‐MS, and acid hydrolysis. The isolated compounds include 3,28‐O‐bidesmosides with or without a 4‐methoxycinnamoyl group (see 1 vs. 2 and 3 ), and 3‐O‐monoglucosides 4 – 7 . All isolated saponins 1 – 7 and their aglycones were evaluated for their α‐glucosidase inhibition activity. Compound 1 showed inhibitory activity against yeast α‐glucosidase with an IC₅₀ value of 100.9±3.3 μM , whereas compounds 2 – 7 were inactive.     

Two Antioxidant Alkaloids from Portulaca oleracea L.

Two alkaloids, oleraceins F and G, were isolated from Portulaca oleracea L., and their structures were determined as methyl (2S)‐6‐[(β‐D ‐glucopyranosyl)oxy]‐2,3‐dihydro‐5‐hydroxy‐1‐[(2E)‐3‐(4‐hydroxy‐3‐methoxyphenyl)prop‐2‐enoyl]‐1H‐indole‐2‐carboxylate and methyl (2S)‐6‐[(β‐D ‐glucopyranosyl)oxy]‐2,3‐dihydro‐5‐hydroxy‐1‐[(2E)‐3‐(4‐hydroxyphenyl)prop‐2‐enoyl]‐1H‐indole‐2‐carboxylate, based on their spectroscopic data. Oleraceins F and G exhibited scavenging activity against 1,1‐diphenyl‐2‐picrylhydrazyl (DPPH) radical, with EC₅₀ values of 21.00 and 37.69 μM , respectively.     

Two New Flavonoids from Retama raetam

Two new furanoflavonoids, retamasins A and B ( 1 and 2 , resp.), along with five known flavonoids, 3 – 7 , were isolated from the aerial parts of Retama raetam. Their structures were determined on the basis of extensive spectroscopic (IR, MS, and 1D‐ and 2D‐NMR) analyses and by comparison with the literature data. This is the first report of the isolation of new furanoflavonoids 1 and 2 from Retama genus, while compounds 3, 5 , and 6 were found for the first time from R. raetam. Antioxidant and anti‐inflammatory activities of the isolated compounds were also evaluated. Compounds 2, 3 , and 5 – 7 exhibited potent inhibitions of iNOS activity with IC₅₀ values of 2.9, 5.0, 3.1, 1.2, and 4.8 μg/ml, respectively. All compounds inhibited NF‐κB except 1 and 5 . Compound 6 was most active in inhibiting iNOS and NF‐κB activity, as well as in decreasing oxidative stress.