A New Pregnane and a New Diphenylmethane from the Root Barks of Periploca sepium

A new polyoxygenated pregnane genin and a new diphenylmethane, along with five known pregnane derivatives, were isolated from the root barks of Periploca sepium. The structures of the new compounds were elucidated as (3β,14β)‐3,14‐dihydroxy‐21‐methoxypregn‐5‐en‐20‐one ( 1 ) and 2‐hydroxy‐5‐(2‐hydroxy‐4‐methoxybenzyl)‐4‐methoxybenzaldehyde ( 2 ) on the basis of spectroscopic methods, especially 2D‐NMR and MS analyses. The known compounds were identified by comparing their physical and spectroscopic data with those reported in the literature.     

Cytotoxic Diterpenoids from the Stem Bark of Annona squamosa L.

Three new ent‐kaurane diterpenoids, (4α)‐19‐nor‐ent‐kaurane‐4,16,17‐triol ( 1 ), (4α,16α)‐17‐(acetyloxy)‐19‐nor‐ent‐kaurane‐4,16‐diol ( 2 ), and 17‐hydroxy‐ent‐kaur‐15‐en‐19‐al ( 3 ), together with 11 known compounds, were isolated from the stem bark of Annona squamosa L. The structures of 1 – 3 were identified by analysis of their spectroscopic data. All compounds were evaluated for cytotoxic activity against human lung cancer (95‐D) and ovarian cancer (A2780) cell lines, and compounds 3, 5, 7, 11 – 14 exhibited promising antiproliferative activities with IC₅₀ values ranging from 0.38 to 34.66 μM .     

A new Sequiterpenoid from Eupatorium adenophorum Spreng

A new sequiterpenoid compound 8aα-hydroxy-1-isopropyl-4,7-dimethyl-1,2,3,4,6,8a-hexahydro-naphthalene-2,6-dione(1),together with seven known compounds anti-HH-dimer-coumarin(2),(-)-5-exo-hydroxy-bomeol(3),O-hydroxyl cinnamic acid(4),9β-hydroxy-ageraphorone(5),10Hα-9-oxo-ageraphorone(6),10Hβ-9-oxo-ageraphorone(7)and 9-oxo-10,11-dehydroageraphorone 8,was isolated from the leaves of Eupatorium adenopho-rum Spreng.The structures were elucidated by IR,~1H and ~(13)C NMR,EIMS,HMBC and single-crystal X-ray spec-tral data.     

Diterpenoids from Isodon Eriocalyx

Two new diterpenoids, Maoecrystal U and epi‐maoecrystal P , together with nine known diterpenoids and eight other known compounds were isolated from Isodon eriocalyx ( ). The structures of two new diterpenoids were elucidated as 6β‐acetoxy‐15β‐hydroxy‐3α,20‐epoxy‐ent‐kaur‐16‐ene‐1,7‐dione and 16(S)‐methoxymethy‐6β,7β‐dihydroxy‐7α,20‐epoxy‐ent‐kaur‐2,3‐ethenylene‐1,15‐dione on the basis of spectroscopic evidence, especially by 2D NMR techniques.     

Two New Cytotoxic Naphthoquinones from Didymocarpus hedyotideus

A new naphthoquinone, 6‐hydroxy‐α‐dunnione ( 1 ) and a new binaphthoquinone, methyl 1,1′,4,4′‐tetrahydro‐3‐hydroxy‐1,1′,4,4′‐tetraoxo[2,2′‐binaphthalene]‐3′‐carboxylate ( 2 ), along with ten known compounds, including naphthoquinones, anthraquinones, and phenylethanoid glucosides, were isolated from the roots of Didymocarpus hedyotideus Chun . Their structures were identified by spectroscopic analyses, particularly 1D‐ and 2D‐NMR spectroscopy. The cytotoxic activities of the two new naphthoquinones were also evaluated.     

Three Terpenoids and a Tocopherol‐Related Compound from Ricinus communis

Four new compounds named (3E,7Z,11E)‐19‐hydroxycasba‐3,7,11‐trien‐5‐one ( 1 ), 6α‐hydroxy‐10β‐methoxy‐7α,8α‐epoxy‐5‐oxocasbane‐20,10‐olide ( 2 ), 15α‐hydroxylup‐20(29)‐en‐3‐one ( 3 ), and (2R,4aR, 8aR)‐3,4,4a,8a‐tetrahydro‐4a‐hydroxy‐2,6,7,8a‐tetramethyl‐2‐(4,8,12‐trimethyltridecyl)‐2H‐chromene‐5,8‐dione ( 4 ) were isolated from the MeOH extracts of the aerial parts of Ricinus communis L. by chromatographic methods. Their structures were elucidated by extensive spectroscopic experiments.     

Diversity of Sesquiterpenoids from Carpesium cernuum

Two new sesquiterpene lactones, 6β‐hydroxy‐8α‐ethoxyeremophil‐7(11)‐en‐12,8β‐olide ( 1 ) and 4β,10β‐dihydroxy‐1αH,5αH,11αH‐guaian‐12,8β‐olide ( 2 ), together with 22 known sesquiterpenoids with various structural types, were isolated from Carpesium cernuum (Compositae). Their structures and configurations were elucidated by extensive 1D‐ and 2D‐NMR spectroscopic analysis in combination with MS experiments, and comparison with literature data of related compounds.     

Flavone Glycosides from Strobilanthes Formosanus

Two new flavone glycosides, 3′‐hydroxy‐5,7‐dimethoxyflavone 4′‐O‐β‐D‐apiofuranoside ( 1 ), and 5,7‐dimethoxyflavone 4′‐O‐[β‐D‐apiofuranosyl(1→5)‐ β‐D‐glucopyranoside] ( 2 ) along with four known compounds, 4′‐hydroxy‐5,7‐dimethoxyflavone ( 3 ), 2,6‐dimethoxy‐1,4‐benzoquinone ( 4 ), lupeol ( 5 ) and betulin ( 6 ) were isolated from the stem and roots of Strobilanthes formosanus. Their structures were elucidated on the basis of their spectroscopic evidence.     

Two New Diterpenoids and Other Constituents from Isodon japonicus

Two new ent‐kaurene diterpenoids, 15α,20‐dihydroxy‐6,7‐seco‐entkaur‐16‐ene‐7,1α(6,11α)‐diolide ( 1 ), 6β‐butyroxy‐3β‐hydroxy‐6,7‐seco‐6,20‐epoxy‐7,1α‐olide‐entkaur‐16‐en‐15‐one ( 2 ), together with 25 known compounds, 3 – 27 , were isolated from the leaves of Isodon japonicus. Their structures were established by spectroscopic methods, including 2D‐NMR techniques.     

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.     

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.     

Eudesmanolides and Guaianolides from Carpesium triste

A new eudesmanolide, 1‐oxo‐11αH‐eudesma‐2,4(14)‐dien‐12,8β‐olide ( 1 ), and four new guaianolides, 9β,10β‐epoxy‐4α‐hydroxy‐1βH,11αH‐guaian‐12,8α‐olide ( 2 ), 9β,10β‐epoxy‐4α‐hydroxy‐1βH,11βH‐guaian‐12,8α‐olide ( 3 ), 4α,9α‐dihydroxy‐1βH,11αH‐guai‐10(14)‐en‐12,8α‐olide ( 4 ), and 4α,9α‐dihydroxy‐1βH,11βH‐guai‐10(14)‐en‐12,8α‐olide ( 5 ), together with one known eudesmanolide and two known germacranolides, were isolated from the whole plants of Carpesium triste. Their structures and relative configurations were elucidated on the basis of spectroscopic methods, including 2D‐NMR techniques.     

New Prenylated Flavones from the Roots of Ficus Beecheyana

Two new prenylated flavanones, ficubee A and ficubee B, respectively, as 7,8‐(2,2‐dimethylpyrano)‐6‐prenyl‐5,3′,4′‐trihydroxyflavone and 6,7‐(2,2‐dimethylpyrano)‐8‐prenyl‐5,3′,4′‐trihydroxyflavone were isolated from the roots of Ficus beecheyana together with twelve known compounds: β‐sitosterol, 5‐stigmasten‐3β,7α‐diol, 5‐stigmasten‐3β,7β‐diol, 3β‐hydroxystigmast‐5‐en‐7‐one, 4‐hydroxybenzaldehyde, 4‐hydroxy‐3‐methoxybenzaldehyde, 1‐(4‐hydroxyphenyl)‐ethanone, 4‐hydroxy‐3‐methoxybenzoic acid, 4‐hydroxy‐cinnamic acid, seseline, xanthyletin, and psoralene. The structures of these secondary metabolites were determined by spectroscopic means and in comparison with published data.     

Two New Sesquiterpene Polyol Esters from Celastrus angulatus

Two novel sesquiterpene polyol esters with a dihydro‐β‐agarofuran (=(3R,5aS,9R,9aS)‐octahydro‐2,2,5a,9‐tetramethyl‐2H‐3,9a‐methano‐1‐benzoxepin) skeleton, (1α,2α,4β,8α,9α)‐1,2,8,12‐tetrakis(acetyloxy)‐9‐(furoyloxy)‐4‐hydroxydihydro‐β‐agarofuran ( 1 ) and (1α,2α,6β,8α,9α)‐1,2,6,8,12‐pentakis(acetyloxy)‐9‐(benzoyloxy)dihydro‐β‐agarofuran ( 2 ), and the three known compounds (1α,2α,4β,6β,8α,9β)‐1,2,6‐tris(acetyloxy)‐9‐(benzoyloxy)‐4‐hydroxy‐8,12‐bis(isobutyryloxy)dihydro‐β‐agarofuran ( 3 ), (1α, 2α,4β,6β,8α,9β)‐1,2,6,8‐tetrakis(acetyloxy)‐9‐(furoyloxy)‐4‐hydroxy‐12‐isobutyryloxy)dihydro‐β‐agarofuran ( 4 ), and (1α,2α,4β,6β,8α,9β)‐1,2,6‐tris(acetyloxy)‐9‐(benzoyloxy)‐4‐hydroxy‐8‐(isobutyryloxy)‐12‐[(2‐methylbutanoyl)oxy]dihydro‐β‐agarofuran ( 5 ) were isolated from the root bark of Celastrus angulatus. Their chemical structures were elucidated by analyses of their MS and NMR data.     

Thrombin Inhibitory Constituents from Duranta repens

The C‐alkylated flavonoids 3,7,4′‐trihydroxy‐3′‐(4‐hydroxy‐3‐methylbutyl)‐5,6‐dimethoxyflavone ( 1 ), 3,7‐dihydroxy‐3′‐(4‐hydroxy‐3‐methylbutyl)‐5,6,4′‐trimethoxyflavone ( 2 ) and the trans‐clerodane diterpenoids 6β‐hydroxy‐15,16‐epoxy‐5β,8β,9β,10α‐cleroda‐3,13(16),14‐trien‐18‐oic acid ( 3 ) and 2β‐hydroxy‐15,16‐epoxy‐5β,8β,9β,10α‐cleroda‐3,13(16),14‐trien‐18‐oic acid ( 4 ) were isolated from Duranta repens. Their structures and the relative configuration of 3 and 4 were determined by spectroscopic methods (¹H‐ and ¹³C‐NMR, IR, and MS) and 2D‐NMR experiments. The known flavonoid 5 is also reported for the first time from this species. The compounds 1 , 3 , and 5 showed significant enzyme‐inhibitory activity against thrombin.     

Phenolic Compounds from Elsholtzia Bodinieri Van't

Seven phenolic compounds, including one new compound trans‐3,4,3′,5′‐tetrahydroxy‐4′‐methylstilbene 4‐O‐β‐D‐xylopyranosyl‐(1→6)‐β‐D‐glucopyranoside ( 1 ), together with six known compounds (+)‐hinokiol ( 2 ), 6‐hydroxy‐5,7‐dimethoxycoumarin ( 3 ), caffeic acid ( 4 ), vanillic acid ( 5 ), 4‐hydroxy‐2,6‐dimethoxyphenol‐1‐O‐β‐D‐glucopyranoside ( 6 ) and 4‐allyl‐2,6‐dimethoxyphenol‐1‐O‐β‐D‐glucopyranoside ( 7 ), were isolated from the root bark of Elsholtzia bodinieri Van't. Their structures were determined on the basis of spectroscopic and chemical evidence.     

Diarylheptanoids from the Rhizomes of Alpinia officinarum

A novel dimeric diarylheptanoid, (5R,5′R)‐7,7′‐(6,6′‐dihydroxy‐5,5′‐dimethoxy[1,1′‐biphenyl]‐3,3′‐diyl)bis[5‐methoxy‐1‐phenylheptan‐3‐one] ( 1 ), and two new diarylheptanoids, (4E,6R)‐6‐hydroxy‐7‐(4‐hydroxy‐3‐methoxyphenyl)‐1‐phenylhept‐4‐en‐3‐one ( 2 ) and (4E,6R)‐6‐hydroxy‐1,7‐diphenylhept‐4‐en‐3‐one ( 3 ), together with seven known diarylheptanoids, were isolated from the rhizomes of Alpinia officinarum. Their structures were elucidated by application of extensive spectroscopic analyses and the modified Mosher method.     

Four New Podocarpane‐Type Trinorditerpenes from Aleurites moluccana

Four new podocarpane‐type trinorditerpenenes, (5β,10α)‐12,13‐dihydroxypodocarpa‐8,11,13‐trien‐3‐one ( 1 ), (5β,10α)‐12‐hydroxy‐13‐methoxypodocarpa‐8,11,13‐trien‐3‐one ( 2 ), (5β,10α)‐13‐hydroxy‐12‐methoxypodocarpa‐8,11,13‐trien‐3‐one ( 3 ), and (3α,5β,10α)‐13‐methoxypodocarpa‐8,11,13‐triene‐3,12‐diol ( 4 ), together with four known diterpenes, 12‐hydroxy‐13‐methylpodocarpa‐8,11,13‐trien‐3‐one ( 5 ), spruceanol ( 6 ), ent‐3α‐hydroxypimara‐8(14),15‐dien‐12‐one ( 7 ), and ent‐3β,14α‐hydroxypimara‐7,9(11),15‐triene‐12‐one ( 8 ), were isolated from the twigs and leaves of Aleurites moluccana. Their structures were elucidated by means of comprehensive spectroscopic analyses, including NMR and MS. Except 8 , all compounds were evaluated for their cytotoxicity; compound 4 exhibited moderate inhibitory activity against Raji cells with an IC₅₀ value of 4.24 μg/ml.     

Godavarin K: a New Limonoid with an Oxygen Bridge between C(1) and C(29) from the Godavari Mangrove Xylocarpus moluccensis

Godavarin K ( 1 ), a new limonoid with an oxygen bridge between C(1) and C(29), was obtained from seeds of an Indian mangrove, Xylocarpus moluccensis, together with a known tetranortriterpene, 6‐de(acetyloxy)‐7‐deacetylchisocheton compound E (=(5α,7α,13α,17α)‐7‐hydroxy‐4,4,8‐trimethyl‐3‐oxocarda‐1,14‐dienolide; 2 ). The structure of godavarin K was established on the basis of spectroscopic data. In addition, the confusion of ¹H‐ and ¹³C‐NMR data for compound 2 in previous literature was clarified.     

Thioglucosides from the Seeds of Raphanus sativus L.

Three new thioglucosides, (4E)‐5‐{6‐O‐[(2E)‐3‐(4‐hydroxy‐3‐methoxyphenyl)prop‐2‐enoyl]‐β‐glucopyranosylsulfanyl}pent‐4‐enenitrile ( 1 ), (4E)‐5‐{6‐O‐[(2E)‐3‐(4‐hydroxy‐3,5‐dimethoxyphenyl)prop‐2‐enoyl]‐β‐glucopyranosylsulfanyl}pent‐4‐enenitrile ( 2 ) and its (4Z)‐isomer 3 , were isolated from the seeds of Raphanus sativus L. (radish), together with two known compounds. Their structures were determined by spectroscopic methods, including UV/VIS, 1D‐ and 2D‐NMR, FAB‐ and HR‐FAB‐MS experiments.