Three New Diterpenoids from Isodon nervosus

Three new ent‐kaurane diterpenoids, rabdonervosins D–F ( 1 – 3 ), were isolated from the leaves and stems of Isodon nervosus. Their structures were elucidated on the basis of spectroscopic methods including 1D‐ and 2D‐NMR analyses. Compounds 1 – 3 were evaluated for their cytotoxicity against HepG2, CNE2, PC‐9/ZD, HeLa, MCF‐7, and HCT116 cell lines. No compounds exhibited potent cytotoxicity.     

Splendidins A – C,Three New Clerodane Diterpenoids from Salvia splendens

Three new clerodane diterpenoids, splendidins A–C ( 1 – 3 , resp.), were isolated from Salvia splendens, together with six known ones. Their structures were elucidated by extensive spectroscopic analysis. Splendidin C ( 3 ) was the first diterpenoid glucoside reported from this plant. These compounds were evaluated for their cytotoxic activity; however, none of them were cytotoxic.     

Four New Briarane Diterpenoids from the Gorgonian Coral Junceella fragilis

Chemical investigation of the gorgonian coral Junceella fragilis, collected by scuba diving in Taiwan, resulted in the isolation of four new briarane‐type diterpenoids, frajunolides A–D ( 1 – 4 ), along with three known briaranes. Their structures were elucidated on the basis of spectroscopic studies, especially 1‐ and 2D‐NMR as well as HR‐MS experiments. The inhibitory effect of all isolated metabolites towards superoxide‐anion generation and elastase release by human neutrophils in response to formylmethionyl‐leucyl‐phenylalanine/dihydrocytochalasin B (FMLP/CB) was 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.     

New Cytotoxic Myrsinane‐Type Diterpenes from Euphorbia prolifera

Four new myrsinol diterpenes, proliferins A–D ( 1 – 4 , resp.) were isolated from the EtOH extracts of the roots of Euphorbia prolifera, along with four known compounds, euphorprolitherin B ( 5 ), euphorprolitherin D ( 6 ), SPr5 ( 7 ), and 14‐desoxo‐3‐O‐propionyl‐5,15‐di‐O‐acetyl‐7‐O‐nicotinoylmyrsinol‐14β‐acetate ( 8 ). Their structures were established on the basis of spectroscopic methods, including HR‐ESI‐MS, and 1D‐ and 2D‐NMR techniques. The cytotoxicity of compounds 1, 3 , and 4 against cancer cells was evaluated, with compound 1 being active against A2780 cancer cells.     

Three New Phenylpropanoids from Inula nervosa Wall.

Three new phenylpropanoid compounds, named nervolans A–C ( 1 – 3 , resp.), together with two other known phenylpropanoids, coniferyl diangelate and sinapyl diangelate, were isolated from the aerial parts of Inula nervosa Wall . (Asteraceae), a traditional Chinese medicinal plant. The structures of 1 – 3 were elucidated by detailed spectroscopic analyses, including HR‐ESI‐MS data and 2D‐NMR spectroscopy. Compounds 1 – 5 exhibited mild inhibitory effects against NO production in LPS‐stimulated RAW264.7 cells.     

Eight New Diterpenoids from the Roots of Euphorbia nematocypha

From the dried roots of Euphorbia nematocypha, eight new diterpenoids, with ent‐atisane (i.e., 1 – 5 ) and isopimarane (i.e., 6 – 8 ) type skeletons, together with five known compounds, were isolated. The structures of these new compounds were elucidated by spectroscopic data. Compounds 1 – 8 were evaluated for their cytotoxicity against a small panel of human cancer cell lines.     

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.     

Three New Glycosides from the Stems of Miliusa balansae

Three new glycosides with the same saccharides, namely miliusoside A ( 1 ), miliusoside B ( 2 ), and miliusoside C ( 3 ), together with five known compounds were isolated from the stems of Miliusa balansae. Their structures were elucidated on the basis of detailed spectroscopic analysis and by comparison with the spectra of related model compounds. There was a rarely encountered α‐D ‐apiose moiety occurring in all new compounds.     

Three New Triterpene Saponins from Hemsleya chinensis

Three new triterpenoid saponins, xuedanglycosides A–C ( 1 – 3 , resp.), along with six known ones, were isolated from the rhizomes of Hemsleya chinensis. By detailed analysis of the NMR spectra, by chemical methods, and by comparison with spectral data of known compounds, the structures of new compounds were determined to be 16α,23α‐epoxy‐2β,3α,20β‐trihydroxy‐10α,23α‐cucurbita‐5,24‐dien‐11‐on‐2‐yl β‐D ‐glucopyranoside ( 1 ), 2β,3α,16α,20β‐tetrahydroxycucurbita‐5,25‐diene‐11,22‐dion‐2‐yl β‐D ‐glucopyranoside ( 2 ), and oleanolic acid 28‐O‐β‐xylopyranosyl‐(1→6)‐O‐β‐glucopyranoside ( 3 ). In addition, hemslecin A 2‐O‐β‐D ‐glucopyranoside ( 6 ), hemsamabilinin B ( 7 ), and hemslonin A ( 9 ) were obtained for the first time from this plant.     

Three New Triterpenes from Xylarialean sp. A45, an Endophytic Fungus from Annona squamosa L.

From the fermentation extract of Xylarialean sp. A45, an endophytic fungus of Annona squamosa L., three new triterpenes, namely xylariacins A–C ( 1 – 3 , resp.) were obtained. Their structures were determined by spectroscopic analyses, including 1D‐ and 2D‐NMR experiments and HR‐ESI‐Q‐TOF mass spectrometry. The in vitro cytotoxic activities of compounds 1 – 3 were tested against human tumor cell line HepG2, and these compounds showed modest cytotoxic activity.     

Three New Sesquiterpene Pyridine Alkaloids from Euonymus fortunei

Three new macrocyclic β‐dihydroagarofuran‐type sesquiterpene pyridine alkaloids, fortuneines A ( 1 ), B ( 2 ), and C ( 3 ), together with the four known alkaloids wilfornine E ( 4 ), aquifoliunine E‐I ( 5 ), euoverrine B ( 6 ), and euojaponine I ( 7 ), were isolated from the aerial parts of Euonymus fortunei. Their structures were elucidated by spectroscopic methods, including HR‐ESI‐MS, ¹H‐ and ¹³C‐NMR, DEPT, ¹H,¹H‐COSY, HSQC, HMBC, and ROESY. This is the first isolation of the above sesquiterpene pyridine alkaloids from this plant, except for compound 6 .     

Three New Monoterpene Glucosides from Lamium amplexicaule

Three new monoterpene glucosides, lamiuamplexosides A–C ( 1 – 3 ), along with thirteen known glucosides, were isolated from the whole plant of Lamium amplexicaule L. The structures of 1 – 3 were elucidated on the basis of spectroscopic, chemical, and physicochemical evidence.     

Three New Hasubanan Alkaloids from Stephania hernandifolia (Willd.) Walp.

Three new hasubanan alkaloids, hernsubanines A–C ( 1 – 3 , resp.), were isolated from the whole plants of Stephania hernandifolia. Their structures were elucidated on the basis of physical and spectroscopic data. In in vitro tests for cytotoxic activity against two human cancer cell lines, A 549 and K 562, compound 1 did not exhibit any cytotoxicity.     

Three New Dimeric Orcinol Glucosides from Curculigo orchioides

Three new phenolic glucosides named orcinosides A, B, and C ( 1, 2 , and 3 , resp.) were isolated in low yields (4.0×10⁻⁶, 11.5×10⁻⁶, 4.5×10⁻⁶%, resp.) from the rhizomes of Curculigo orchioides. Their structures were elucidated by comprehensive spectroscopic analyses including FAB‐MS, HR‐ESI‐MS, IR, and 1D‐ and 2D‐NMR (HSQC, HMBC) data. Compounds 1 – 3 contained two orcinol‐glucoside moieties linked through a CH₂ group.     

Three New C19‐Diterpenoid Alkaloids from Aconitum transsectum

Three new C₁₉‐diterpenoid alkaloids, named aconitramines A ( 1 ), B ( 2 ), and C ( 3 ), were isolated from Aconitum transsectum. By UV, IR, 1D‐ and 2D‐NMR, and MS analyses, their structures were elucidated as 18‐methoxyvilmoraconitine, 18‐demethoxydolichotine A, and 18‐demethoxydolichotine B. Compound 1 is the second known C₁₉‐diterpenoid alkaloid with a three‐membered ring formed by C(8), C(9), and C(10).     

Three New Clerodane Diterpenoids from the Bulbils of Dioscorea bulbifera L. var. sativa

From the bulbils of Dioscorea bulbifera L. var. sativa, three new clerodane diterpenoids, bafoudiosbulbin C (=methyl (2β,8α,12S)‐17‐oxo‐2,19 : 8,19 : 12,17 : 15,16‐tetraepoxycleroda‐3,13(16), 14‐triene‐18‐carboxylate; 1 ), bafoudiosbulbin D (=methyl (2β,6β,12R)‐17,19‐dioxo‐2,19 : 6,17 : 8,12 : 15,16‐tetraepoxycleroda‐13(16),14‐diene‐18‐carboxylate; 2 ), and bafoudiosbulbin E (=methyl (2β,3α,4α,6β,12R)‐17,19‐dioxo‐2,19 : 3,4 : 6,17 : 8,12 : 15,16‐pentaepoxycleroda‐13(16),14‐diene‐18‐carboxylate; 3 ) were isolated, together with the known compounds bafoudiosbulbins A and B, 3‐O‐β‐D ‐glucopyranosyl‐β‐sitosterol, and 6′‐stearoyl‐3‐O‐β‐D ‐glucopyranosyl‐β‐sitosterol. Their structures were established by high‐field NMR techniques (¹H,¹H‐COSY, ¹³C‐DEPT, HSQC, HMBC, and NOESY), MS analyses, as well as by comparison of their spectral data with those of related compounds.     

Three New Medicagenic Acid Saponins from Polygala micrantha Guill. & Perr.

Three new medicagenic acid saponins, micranthosides A–C ( 1 – 3 ), were isolated from the roots of Polygala micrantha Guill . & Perr ., along with six known presenegenin saponins. Their structures were elucidated on the basis of extensive 1D‐ and 2D‐NMR experiments (¹H, ¹³C, DEPT, COSY, TOCSY, NOESY, HSQC, and HMBC) and mass spectrometry as 3‐O‐β‐D ‐glucopyranosylmedicagenic acid 28‐[O‐β‐D ‐galactopyranosyl‐(1→4)‐O‐β‐D ‐xylopyranosyl‐(1→4)‐O‐α‐L ‐rhamnopyranosyl‐(1→2)‐β‐D ‐fucopyranosyl] ester ( 1 ), 3‐O‐β‐D ‐glucopyranosylmedicagenic acid 28‐[O‐6‐O‐acetyl‐β‐D ‐galactopyranosyl‐(1→4)‐O‐β‐D ‐xylopyranosyl‐(1→4)‐O‐α‐L ‐rhamnopyranosyl‐(1→2)‐β‐D ‐fucopyranosyl] ester ( 2 ), and 3‐O‐{O‐β‐D ‐glucopyranosyl‐(1→3)‐O‐[β‐D ‐glucopyranosyl‐(1→6)]‐β‐D ‐glucopyranosyl}medicagenic acid 28‐{O‐β‐D ‐apiofuranosyl‐(1→3)‐O‐β‐D ‐xylopyranosyl‐(1→4)‐O‐[β‐D ‐apiofuranosyl‐(1→3)]‐O‐α‐L ‐rhamnopyranosyl‐(1→2)‐β‐D ‐fucopyranosyl} ester ( 3 ). Compounds 1 – 3 were evaluated against HCT 116 and HT‐29 human colon cancer cells, but they did not show any cytotoxicity.     

Three New Alkaloids from the Traditional Chinese Medicine ChanSu

Three new alkaloids, named bufoserotonins A–C ( 1 – 3 ), were isolated from the traditional Chinese medicine ChanSu. Their structures were elucidated on the basis of spectroscopic analysis, especially of 2D‐NMR data.