New Polyphenols and Triterpene from the Pseudobulbs of Pleione Formosana

Three new polyphenolic compounds including a dihydrophenanthrene, pleioanthrenin ( 1 ), two bibenzyls, pleiobibenzynin A ( 2 ) and B ( 3 ), and a new cycloartane triterpenoid, (24R)‐cyclomargenyl p‐coumarate ( 4 ), together with eight known compounds, were isolated from the pseudobulbs of Pleione formosana. The structures of the new compounds were elucidated by extensively spectroscopic analysis.     

Constituents from the Roots of Semiaquilegia adoxoides

In present literature search, some cyano-containing compounds, which are very rare in plants, from the traditional anticancer herb Tiankuizi were reported. To find more cyano-containing compounds in the important plant Semiaquilegia adoxoides （DC） Makino （Chinese name Tiankuizi）, the isolation of the chemical constituents was investigated for advancing the research. Two new compounds, a new alkaloid, 1,2,3,4-tetrahydro-6-hydroxy-1[（3,4-dihydroxyphenyl）methyl]-7-methoxy-2,2-dimethyl-isoquinolinium, named Semiaquilegine A （1）, and a new ester, 3-（4＇-hydroxyphenyl）-2-propenoic acid （4＂-carboxyl）-phenyl ester （2）, and four cyano-containing compounds, （Z）-6a-（β-D-glucosyloxy）-4a,5a-dihydroxy-2-cyclohexene-△^1,a-acetonitrile （3）, （L0-6α-（β-D-glucosyloxy）-4α-hydroxy-2-cyclohexene-△^1,α-acetonitrile （4）, lithospermoside （5）, ehretioside B （6）, as well as eleven known compounds, were isolated from the roots of Semiaquilegia adoxoides. The structures of new compounds 1 and 2 were elucidated mainly by 1D/2D-NMR techniques. Very unusual cyano-containing compounds 3 and 4 were first isolated from Ranunculaceae family. Hitherto, there were six cyano-containing compounds found in the herb.     

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 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 Terpenoids from Pinus yunnanensis

A new abietatrienoid, 15‐methoxydidehydroabietic acid ( 1 ), a new ring B‐seco abietatrienoid, 10‐hydroxy‐9,10‐secoabieta‐8,11,13‐trien‐18‐oic acid ( 2 ), and a new tetracyclic triterpenoid, pinusyunnanol ( 3 ), together with five known compounds, were obtained from the twigs and needles of Pinus yunnanensis. The structures of the new compounds were elucidated by means of extensive spectroscopic analyses.     

Three New Pregnane Alkaloids from Pachysandra terminalis

Three new pregnane alkaloids, pachystermine C ( 1 ), pachysanamine A ( 2 ), and pachysanamine B ( 3 ), together with four known ones, pachystermine B ( 4 ), pachysamine A ( 5 ), (20S)‐20‐(dimethylamino)‐16α‐hydroxy‐3β‐(3′α‐isopropyl)lactam‐5α‐pregnan‐4‐one ( 6 ), and E‐salignone ( 7 ), were isolated from Pachysandra terminalis. The chemical structures of the new alkaloids were elucidated by spectroscopic methods. All the compounds were evaluated for their inhibitory activities against HL‐60, SMMC‐7721, A‐549, MCF‐7, and SW480 cell lines, some of the compounds showed stronger cytotoxicity for the test cell lines, especially compounds 2 , 3 , and 7 .     

Four New Lanostane Triterpenoids from Euphorbia humifusa

Four new lanostane triterpenoids, namely (3β)‐3‐hydroxy‐24‐methylenelanost‐8‐ene‐7,11‐dione ( 1 ), (3β)‐3‐hydroxylanosta‐8,24‐diene‐7,11‐dione ( 2 ), (3β,7α)‐3,7‐dihydroxylanosta‐8,24‐dien‐11‐one ( 3 ), and (3β,11β)‐3,11‐dihydroxylanosta‐8,24‐dien‐7‐one ( 4 ) were isolated from Euphorbia humifusa, together with 2 known compounds. The structures of these new compounds were elucidated on the basis of extensive spectroscopic analysis and comparison with the related known compounds.     

Two New Iridoids from the Stem of Catalpa ovata

Two new iridoids, 6‐O‐[(E)‐feruloyl]jioglutin D ( 1 ) and 6‐O‐(4‐hydroxybenzoyl)jioglutin D ( 2 ), and six known compounds, minecoside ( 3 ), specioside ( 4 ), picroside II ( 5 ), picroside III ( 6 ), 4‐hydroxybenzoic acid ( 7 ), and martynoside ( 8 ), were isolated from the stem of Catalpa ovata. The structures of the new compounds were established on the basis of spectroscopic techniques, including 1D‐ and 2D‐NMR.     

Rotundifolides A and B,Two New Enol‐Derived Butenolactones from the Bark of Litsea rotundifolia var. oblongifolia

Two new enol‐derived butenolactones, rotundifolides A ( 1 ) and B ( 2 ), along with four known related compounds, lincomolide C ( 3 ), lincomolide A ( 4 ), marliolide ( 5 ), and litsenolide A₁ ( 6 ), were isolated from the bark of Litsea rotundifolia var. oblongifolia. The structures of the new metabolites were characterized by spectroscopic methods and comparison with known compounds.     

Four New Compounds from Sinacalia tangutica

Four new compounds, 9α‐hydroxy‐1β‐methoxycaryolanol ( 1 ), stigmast‐5‐ene‐7α,22α‐diol‐3β‐tetradecanoate ( 2 ), 7‐O‐(6′‐acetoxy‐β‐D ‐glucopyranosyl)coumarin ( 3 ), and 8‐O‐(6′‐acetoxy‐β‐D ‐glucopyranosyl)‐7‐hydroxycoumarin ( 4 ), together with ten known compounds, were isolated from the aerial parts of Sinacalia tangutica. The structures of the new compounds were established by means of extensive spectroscopic analyses (1D‐ and 2D‐NMR, EI‐MS, HR‐ESI‐MS, as well as IR and UV) and by comparison of their spectroscopic data with those of structurally related compounds reported in the literature.     

Constituents from Rubia Ustulata Diels and R. Yunnanensis Diels and Their Antiplatelet Aggregation Activity

A new anthraquinone glycoside, rubiayannone‐A ( 1 ), and a new coumarin, rubilatin‐A ( 2 ), together with twenty‐two known compounds were isolated and characterized from the roots of Rubia ustulata. A new anthraquinone, 2‐carbomethoxyanthraquinone ( 3 ), and rubiayannone‐A, 2‐formylanthraquinone were obtained from the roots of R. yunnanensis. The structures of those compounds were elucidated by spectroscopic methods. The antiplatelet aggregation activity of the isolated compounds 1, 4～6 were also discussed.     

Labdane Diterpenes and Flavonoids from Leonurus japonicus

Chemical investigation of the aerial part of Leonurus japonicus led to the isolation and characterization of a new labdane‐type diterpene, named 3α‐acetoxy‐15‐O‐methylleopersin C ( 3 ), and a new acylated rutin derivative, named 2′′′‐syringylrutin ( 9 ), along with seven known compounds, including a labdane‐type diterpene and six flavonoids. The structures of the new compounds were established by spectroscopic methods.     

Two New Tetracyclic Triterpenoids and Other Constituents from Aster Ageratoides var. Oophyllus

Two new tetracyclic triterpenoids shiona‐19(E),21‐dien‐3β‐ol ( 1 ), and shiona‐22(29)‐en‐3β,21‐diol ( 2 ), together with four known compounds shiona‐21‐en‐3β‐ol ( 3 ), friedelinol ( 4 ), β‐sitosterol ( 5 ), and (24R)‐stigmast‐7,22(E)‐dien‐3a‐ol ( 6 ) were isolated from Aster ageratoides var. oophyllus. The structures of two new compounds were established on the basis of IR, MS, ¹H, ¹³C and 2D NMR spectroscopic methods.     

Structure elucidation of new fusarielins from Fusarium sp. and their antimicrobial activity

Three new fusarielins, 3‐epi‐fusarielin H ( 1 ), 3‐O‐methyl‐fusarielin H ( 2 ), and 3‐O‐methyl‐epi‐fusarielin H ( 3 ), were isolated from the fungus Fusarium sp. together with the known analogues, fusarielins F ( 4 ) and G ( 5 ). The structures of these compounds were elucidated by analysis of their ESI‐HRTOFMS, 1D and 2D NMR spectroscopic data. The new compounds exhibited weak antibacterial effect against Staphylococcus aureus.     

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 Caged Prenylxanthones from Garcinia bracteata

Three new caged prenylxanthones (xanthone=9H‐xanthen‐9‐one), named neobractatin ( 1 ), 3‐O‐methylneobractatin ( 2 ), and 3‐O‐methylbractatin ( 3 ), along with eight known compounds, were isolated from the twig of Garcinia bracteata. The structures of the new compounds were elucidated on the basis of 1D‐ and 2D‐NMR experiments, including HMBC, HSQC, ¹H,¹H‐COSY, and ROESY, as well as HR‐MS analysis.     

New Acyclic 12‐Hydroxygeranylgeraniol‐Derived Diterpenoids from the Seeds of Carpesium triste

Five new acyclic 12‐hydroxygeranylgeraniol‐derived diterpenoids, i.e., 1 – 5 , were isolated from the seeds of Carpesium triste. The structures including the absolute configurations of the new compounds were elucidated by spectroscopic methods. All the compounds, except for 2 , were evaluated for their in vitro cytotoxic activity against cultured SMMC‐7721 (human hepatoma), HL‐60 (human promyelocytic leukemia), and L02 (human hepatocyte) cells.     

Bioactive Components from the Mycelium of Antrodia Salmonea

Three new compounds, 2,4‐dimethoxy‐6‐methylbenzene‐1,3‐diol ( 1 ), salmoquinone ( 2 ), and 3‐(4‐hydroxyphenyl)‐4‐isobutyl‐1H‐pyrrole‐2,5‐dione ( 3 ), together with six known compounds, 2‐methoxy‐6‐methyl‐p‐benzoquinone ( 4 ), 2,3‐dimethoxy‐5‐methyl‐p‐benzoquinone ( 5 ), 2‐hydroxy‐5‐methoxy‐3‐methyl‐p‐benzoquinone ( 6 ), eburcoic acid ( 7 ), fomefficinic acid C ( 8 ), and a pyrroledione ( 9 ), were isolated from the mycelium of Antrodia salmonea. The structures of these compounds were elucidated by spectrometric analyses including IR, NMR, and MS. Among these compounds, 4 and 5 exhibited cytotoxicity against KB, HepG2, and H2058 cell lines.     

New Glycosides from Cistanche salsa

Six new glycosides, salsasides A–F ( 1 – 6 , resp.), were isolated from the stems of Cistanche salsa, together with seven known glycosidic compounds. Their structures were elucidated by means of ester hydrolysis and chemical derivatization, in‐depth NMR spectroscopic and mass spectrometric analyses, and by comparison with literature data of related compounds. The new glycosides are based on β‐D ‐glucose (Glc) and α‐L ‐rhamnose (Rha), carrying acetyl (Ac), benzyl (Bn), phenethyl, coumaroyl (Cou), and caffeoyl (Caf) substituents.     

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.