Cholinesterase‐Inhibiting New Steroidal Alkaloids from Sarcococca hookeriana of Nepalese Origin

Bioassay‐guided phytochemical investigation of Sarcococca hookeriana has resulted in the isolation and structure elucidation of five new pregnane‐type steroidal alkaloids: (?)‐hookerianamide A (=(2β,3β,4β,20S)‐20‐(dimethylamino)‐3‐[(3‐methylbut‐2‐enoyl)amino]‐5α‐pregn‐16‐ene‐2,4‐diol; 1 ), (+)‐hookerianamide B (=(2α,3β,4β,20S)‐4‐acetoxy‐20‐(dimethylamino)‐3‐[(3‐methylbut‐2‐enoyl)amino]‐5α‐pregnan‐2‐ol; 2 ), (?)‐hookerianamide C (=(2β,3β,20S)‐2‐acetoxy‐20‐(dimethylamino)‐3‐[(3‐methylbut‐2‐enoyl)amino]‐5α‐pregnane; 3 ), (?)‐hookerianamine A (=(3β,20S)‐20‐(dimethylamino)‐3‐(methylamino)‐5α‐pregn‐14‐ene; 4 ), and (+)‐phulchowkiamide A (=(3β,20S)‐20‐(methylamino)‐3‐[(2‐methylbut‐2‐enoyl)amino]‐5α‐pregn‐2‐en‐4‐one; 5 ). These compounds, as well as the two chemically derived acetyl derivatives 6 and 7 , displayed cholinesterase inhibition in a concentration‐dependent manner.     

Three New Neolignans and One New Phenylpropanoid from the Leaves and Stems of Toona ciliata var. pubescens

Three new neolignans, (7S,8S,7′E)‐4,9‐dihydroxy‐3,7,3′,9′‐tetramethoxy‐8,4′‐oxyneolign‐7′‐ene ( 1 ), (7R,8S,7′E)‐4, 9‐dihydroxy‐3,7,3′,9′‐tetramethoxy‐8,4′‐oxyneolign‐7′‐ene ( 2 ), (7S,8S,7′E)‐5, 9‐dihydroxy‐3,7,3′,5′,9′‐pentamethoxy‐8,4′‐oxyneolign‐7′‐ene ( 3 ), and one new phenylpropanoid, threo‐5‐hydroxy‐3,7‐dimethoxyphenylpropane‐8,9‐diol ( 4 ), were isolated from the leaves and stems of Toona ciliata var. pubescens. Their structures were determined on the basis of spectroscopic analysis, especially 2D‐NMR, HR‐ESI‐MS, and CD data. The antiproliferative activities of these compounds against four tumor cell lines (A549, Colo 205, QGY‐7703, and LOVO) were also evaluated by MTT (=(3‐(4,5‐dimethylthiazol‐2‐yl)‐2,5‐diphenyl‐2H‐tetrazolium bromide) method.     

Neoclerodane Diterpenes from Amoora stellato‐squamosa

From the twigs of Amoora stellato‐squamosa, five new neoclerodane diterpenes have been isolated and characterized, methyl (13E)‐2‐oxoneocleroda‐3,13‐dien‐15‐oate (=methyl (2E)‐3‐methyl‐5‐[(1S,2R,4aR,8aR)‐1,2,3,4,4a,7,8,8a‐octahydro‐1,2,4a,5‐tetramethyl‐7‐oxo‐naphthalen‐1‐yl]pent‐2‐enoate; 1 ), (13E)‐2‐oxoneocleroda‐3,13‐dien‐15‐ol (=(4aR,7R,8S,8aR)‐1,2,4a,5,6,7,8,8a‐octahydro‐8‐[(E)‐5‐hydroxy‐3‐methylpent‐3‐enyl]‐4,4a,7,8‐tetramethylnaphthalen‐2(1H)‐one; 2 ), (3α,4β,13E)‐neoclerod‐13‐ene‐3,4,15‐triol (=(1R,2R,4aR, 5S,6R,8aR)‐decahydro‐5‐[(E)‐5‐hydroxy‐3‐methylpent‐3‐enyl]‐1,5,6,8a‐tetramethylnaphthalene‐1,2‐diol; 3 ), (3α,4β,13E)‐4‐ethoxyneoclerod‐13‐ene‐3,15‐diol (=(1R,2R,4aR,5S,6R,8aR)‐1‐ethoxydecahydro‐5‐[(E)‐5‐hydroxy‐3‐methylpent‐3‐enyl]‐1,5,6,8a‐tetramethylnaphthalen‐2‐ol; 4 ), and (3α,4β,14RS)‐neoclerod‐13(16)‐ ene‐3,4,14,15‐tetrol (=(1R,2R,4aR,5S,6R,8aR)‐decahydro‐5‐[3‐(1,2‐dihydroxyethyl)but‐3‐enyl]‐1,5,6,8a‐tetramethylnaphthalene‐1,2‐diol; 5 ), together with two known compounds, (13E)‐neocleroda‐3,13‐diene‐15,18‐diol ( 6 ) and (13S)‐2‐oxoneocleroda‐3,14‐dien‐13‐ol ( 7 ).     

Isolation of a New Carotenoid and Two New Carotenoid Glycosides from Curtobacterium flaccumfaciens pvar poinsettiae

An efficient method for the extraction of the carotenoids from Curtobacterium flaccumfaciens pvar poinsettiae was developed. The glucosides of C.p. 450 (=(all‐E,2R,2′R)‐2‐[4‐(β‐D ‐glucopyranosyloxy)‐3‐methylbut‐2‐enyl]‐2′‐(4‐hydroxy‐3‐methylbut‐2‐enyl)‐β, β‐carotene; 4 ) and of C.p. 473 (=(all‐E,2R,2′S)‐2‐[4‐(β‐D ‐glucopyranosyloxy)‐3‐methylbut‐2‐enyl]‐2′‐(3‐methylbut‐2‐enyl)‐3′,4′‐didehydro‐1′,2′‐dihydro‐β,ψ‐caroten‐1′‐ol; 5 ) were isolated for the first time. In addition, the hitherto unknown 3′,4′‐dihydro derivative of C.p. 450, called C.p. 460 (=(all‐E,2R,2′R)‐2‐(4‐hydroxy‐3‐methylbut‐2‐enyl)‐2′‐(3‐methylbut‐2‐enyl)‐1′,2′‐dihydro‐β,ψ‐caroten‐1′‐ol; 6 ), was identified. The structures were established by UV/VIS, CD, ¹H‐ and ¹³C‐NMR, and mass spectra.     

Scyphiphorins A and B,Two New Iridoid Glycosides from the Stem Bark of a Chinese Mangrove Scyphiphora hydrophyllacea

Two new iridoid glycosides, named scyphiphorins A ( 1 ) and B ( 2 ), together with four known compounds, geniposidic acid (=(1S,4aS,7aS)‐1‐(β‐D ‐glucopyranosyloxy)‐1,4a,5,7a‐tetrahydro‐7‐(hydroxymethyl)cyclopenta[c]pyran‐4‐carboxylic acid; 3 ), 4‐(4‐hydroxy‐3‐methoxybenzyl)butan‐2‐one, oleanolic acid (=(3β)‐3‐hydroxyolean‐12‐en‐28‐oic acid), and stigmasterol β‐D ‐glucoside (=(3β,22E)‐stigmasta‐5,22‐dien‐3‐yl β‐D ‐glucopyranoside), were isolated for the first time from the stem bark of a Chinese mangrove, Scyphiphora hydrophyllacea Gaertn . f. The structures of compounds 1 and 2 were determined as 10‐O‐benzoylgeniposidic acid and 10‐O‐[(2E,6R)‐8‐hydroxy‐2,6‐dimethyl‐1‐oxooct‐2‐en‐1‐yl]geniposidic acid, respectively, on the basis of spectroscopic data and chemical methods, including 2D NMR techniques.     

Cyclopeptide and Terpenoids from Tripterygium wilfordii Hook. f.

The EtOH extract of dried root bark of Tripterygium wilfordii Hook. f. (Celastraceae) afforded a novel macrolactone cyclopeptide named triptotin L (=cyclo[L ‐alanyl‐L ‐alanyl‐3‐(4,4,9‐trimethyldecyl‐3‐hydroxypropanoylglycyl‐L ‐valyl‐L ‐leucyl; 1 ), the new triterpene 2β,6α,22β‐trihydroxy‐24,29‐dinor‐D:A‐friedoolean‐4‐ene‐3,21‐dione named 6α‐hydroxytriptocalline A (=(2β,6α,8α,9β,10α,13α,14β,20β,22β)‐2,6,22‐trihydroxy‐9,13‐dimethyl‐24,25,26,30‐tetranorolean‐4‐ene‐3,21‐dione; 2 ), the new diterpenoid 11,16‐dihydroxy‐14‐methoxy‐18(4→3) abeo‐abieta‐3,8,11,13‐tetraene‐18‐oic acid named 16‐hydroxytriptobenzene H (=(4aS,10aS)‐3,4,4a,9,10,10a‐hexahydro‐5‐hydroxy‐7‐(2‐hydroxy‐1‐methylethyl)‐8‐methoxy‐1,4a‐dimethylphenanthrene‐2‐carboxylic acid; 3 ), and the abietane diterpenoid alkaloid named triptotin J (=(7aS,11aS,11bS)‐7,7a,8,9,10,11,11a,11b‐octahydro‐11b‐hydroxy‐α,α,8,8,11a‐pentamethyl‐6H‐naphth[1,2‐d]azepine‐4‐methanol; 4 ). Their structures were established on the basis of spectroscopic studies.     

Hydrolytic Reaction of Plant Extracts to Generate Molecular Diversity: New Dammarane Glycosides from the Mild Acid Hydrolysate of Root Saponins of Panax notoginseng

Molecular diversity was generated by hydrolyzing the crude root saponins of Panax notoginseng (Burk .) F. H. Chen under mild acidic condition (AcOH/EtOH 1 : 1). From the acid hydrolysate, five new dammarane glycosides, named notoginsenoside T₁ (=(3β,6α,12β,20E,23RS)‐24,25‐epoxy‐6‐[(β‐D ‐glucopyranosyl)oxy]‐dammar‐20(22)‐ene‐3,12,23‐triol; 1 ), notoginsenoside T₂ (=(3β,6α,12β,20E,23RS)‐24,25‐epoxy‐6‐[(β‐D ‐glucopyranosyl)oxy]‐23‐methoxydammar‐20(22)‐ene‐3,12‐diol; 2 ), notoginsenoside T₃ (=(3β,6α,12β,20S)‐6‐[(β‐D ‐glucopyranosyl)oxy]‐20‐ethoxydammar‐24‐ene‐3,12‐diol; 3 ), notoginsenoside T₄ (=(3β,6α,12β,20S,22E,24RS)‐6‐[(β‐D ‐glucopyranosyl)oxy]dammar‐22‐ene‐3,12,20,24,25‐pentol; 4 ), and notoginsenoside T₅ (=(3β,6α,12β, 24E)‐6‐[(β‐D ‐xylopyranosyl‐(1→2)‐β‐D ‐glucopyranosyl)oxy]dammara‐20(21),24‐diene‐3,12‐diol; 5 ), were isolated, together with 15 known dammarane glycosides, and their structures were elucidated on the basis of spectroscopic evidence. Among the known compounds, ginsenosides Rg₃ and Rh₁ were isolated as major constituents, in addition to ginsenosides Rg₅, Rh₄, and a mixture of (20R)‐ and (20S)‐25‐hydroxyginsenoside Rh₁, all of which were obtained from P. notoginseng for the first time.     

A New Cardenolide and Two New Pregnane Glycosides from the Root Barks of Periploca sepium

A new cardenolide and two new pregnane glycosides, periplogenin 3‐[O‐β‐glucopyranosyl‐(1→4)‐β‐sarmentopyranoside] ( 1 ), (3β,20S)‐pregn‐5‐ene‐3,17,20‐triol 20‐[O‐β‐glucopyranosyl‐(1→6)‐O‐glucopyranosyl‐(1→4)‐β‐canaropyranoside] ( 2 ), and (3β,14β,17α)‐3,14,17‐trihydroxy‐21‐methoxypregn‐5‐en‐20‐one 3‐[O‐β‐oleandropyranosyl‐(1→4)‐O‐β‐cymaropyranosyl‐(1→4)‐β‐cymaropyranoside] ( 3 ), were isolated from the root barks of Periploca sepium Bge , together with seven related known compounds, periplogenin, xysmalogenin, (3β,20S)‐pregn‐5‐ene‐3,17,20‐triol, (3β,14β,17α)‐3,14,17‐trihydroxy‐21‐methoxypregn‐5‐en‐20‐one, (3β,20S)‐pregn‐5‐ene‐3,20‐diol 3‐β‐glucopyranoside 20‐β‐glucopyranoside, (3β,20S)‐pregn‐5‐ene‐3,20‐diol 3‐[O‐2‐O‐acetyl‐β‐digitalopyranosyl‐(1→4)‐β‐cymaropyranoside] 20‐[O‐β‐glucopyranosyl‐(1→6)‐O‐β‐glucopyranosyl‐(1→2)‐β‐digitalopyranoside], and (3β,20S)‐ pregn‐5‐ene‐3,20‐diol 20‐[O‐β‐glucopyranosyl‐(1→6)‐β‐glucopyranoside]. Their structures were elucidated on the basis of spectroscopic analyses.     

Two New Ceramides from the Marine Sponge Ircinia fasciculata

A new 4‐sulfated ceramide, ircisulfamide (=N‐[(1S*,2S*,3R*)‐2‐hydroxy‐1‐(hydroxymethyl)‐3‐(sulfooxy)heptadecyl]hexadecanamide; 1 ), and a new glycosphingolipid, ircicerebroside (=(2R*)‐N‐{(1S*,2R*,3E,7E)‐1‐[(β‐D ‐glucopyranosyloxy)methyl]‐2‐hydroxy‐8‐methylheptadeca‐3,7‐dienyl}‐2‐hydroxyeicosanamide; 2 ), were isolated from the aqueous EtOH extract of the marine sponge Ircinia fasciculata (Pallas ). The structures of the new compounds were elucidated on the basis of spectroscopic analysis and by means of chemical methods.     

Photooxygenation of Pregnanes

The course of the singlet‐oxygen reaction with pregn‐17(20)‐enes and pregn‐5,17(20)‐dienes was studied to compare the reactivity of the two alkene moieties present in some steroid families. Thus, from commercially available (3β,5α)‐hydroxy‐androstan‐17‐one and (3β)‐3‐hydroxyandrost‐5‐en‐17‐one, the following 3‐{[(tert‐butyl)dimethylsilyl]oxy}‐substituted, 17(20)‐unsaturated pregnanes were prepared (see Fig. 1): (3β,5α)‐21‐norpregn‐17(20)‐ene 1 ; (3β,5α,17Z)‐pregn‐17(20)‐ene 2 , (3β,5α,16α,17E)‐pregn‐17(20)‐en‐16‐ol 3 , (16β,5α,17E)‐pregn‐17(20)‐en‐16‐ol 4 , (3β,5α,16β,17E)‐pregn‐17(20)‐en‐16‐ol acetate 5 , (3β,16α)‐21‐norpregna‐5,17(20)‐dien‐16‐ol 6 , (3β,16α,17E)‐pregna‐5,17(20)‐dien‐16‐ol 7 , (3β,17Z)‐pregna‐5,17(20)‐diene 8 , (3β,17E)‐pregna‐5,17(20)‐dien‐21‐ol 9 and (3β,17E)‐5,17(20)‐dien‐21‐ol acetate 10 . The oxygenated products (see Fig. 2) obtained from 1 – 10 and ¹O₂, generated by irradiation of Rose Bengal in ³O₂‐saturated pyridine solution, were characterized by ¹H‐, ¹³C‐NMR, and MS (EI, FAB, HR‐EI, ESI‐ and UV‐MALDI‐TOF) data. Major products were those formed by the ene reaction involving as intermediates the corresponding hydroperoxides and the cyclic tautomers of the allylic hydroperoxides, i.e., the corresponding oxiranium oxide‐like intermediate (Scheme 5).     

Chemical Constituents from Craibiodendron yunnanense

A new triterpene, (3β,12β)‐taraxast‐20(30)‐ene‐3,12‐diol (=(3β,12β,18α,19α)‐urs‐20(30)‐ene‐3,12‐diol; 1 ), together with the known compounds ursolic acid, α‐amyrin, β‐amyrin, (2α,3β)‐2,3‐dihydroxyursa‐5,12‐dien‐28‐oic acid, (2α,3β)‐2,3,23‐trihydroxyurs‐12‐en‐28‐oic acid, (2S,3S,4R,8Z)‐1‐O‐(β‐D ‐glucopyranosyl)‐2‐{[(2R)‐2‐hydroxydocosanoyl]amino}octadec‐8‐ene‐1,3,4‐triol, and (2S,3S,4R,8Z)‐1‐O‐(β‐D ‐glucopyranosyl)‐2‐[(palmitoyl)amino]octadec‐8‐ene‐1,3,4‐triol, and quercetin 3‐(β‐D ‐glucopyranoside) were isolated from the leaves of Craibiodendron yunnanense. Their structures were established on the basis of spectral evidence. The last four compounds were identified for the first time in this plant.     

Isomerization of (all‐E)‐Cucurbitaxanthin A

Cucurbitaxanthin A (=(all‐E,3S,5R,6R,3′R)‐3,6‐epoxy‐5,6‐dihydro‐β,β‐carotene‐5,3′‐diol; 1 ) was submitted to thermal isomerization and to I₂‐catalysed photoisomerization. The structure of the main reaction products (9Z)‐ ( 2 ), (9′Z)‐ ( 3 ), (13Z)‐ ( 4 ), and (13′Z)‐cucurbitaxanthin A ( 5 ) was determined by their UV/VIS, CD, ¹H‐NMR, and mass spectra.     

Muurolane‐type sesquiterpenes from marine sponge Dysidea cinerea

Seven new muurolane‐type sesquiterpenes, (4R,5R)‐muurol‐1(6),10(14)‐diene‐4,5‐diol (1), (4R,5R)‐muurol‐1(6)‐ene‐4,5‐diol (2), (4R,5R,10R)‐10‐methoxymuurol‐1(6)‐ene‐4,5‐diol (3), (4S)‐4‐hydroxy‐1,10‐seco‐muurol‐5‐ene‐1,10‐dione (4), (4R)‐4‐hydroxy‐1,10‐seco‐muurol‐5‐ene‐1,10‐dione (5), (6S,10S)‐6,10‐dihydroxy‐7,8‐seco‐2,8‐cyclo‐muurol‐4(5),7(11)‐diene‐12‐oic acid (6), and (6R,10S)‐6,10‐dihydroxy‐7,8‐seco‐2,8‐cyclo‐muurol‐4(5),7(11)‐diene‐12‐oic acid (7) were isolated from the marine sponge Dysidea cinerea. Their structures were determined by the combination of spectroscopic and chemical methods, including 1D‐NMR, 2D‐NMR, and CD spectra as well as by comparing the NMR data with those reported in the literature. Copyright © 2013 John Wiley & Sons, Ltd.     

Asymmetric Syntheses of the Macrocyclic Spermine Alkaloids (−)‐(S)‐Protoverbine, (−)‐(S)‐Buchnerine,and Their Naturally Occurring Congenial Alkaloids

Asymmetric syntheses of the following 17‐membered macrocyclic spermine alkaloids are presented: (−)‐(S)‐protoverbine (=(8S)‐8‐phenyl‐1,5,9,13‐tetraazacycloheptadecane‐6‐one; 1 ), (+)‐(S)‐protomethine (=(2S)‐2‐phenyl‐1,5,9,14‐tetraazabicyclo[12.3.1]octadecan‐4‐one; 2 ), (−)‐(S)‐buchnerine (=(8S)‐8‐(4‐methoxyphenyl)‐1,5,9,13‐tetraazacycloheptadecane‐6‐one; 8 ), (+)‐(S)‐verbamethine (=(+)‐(2S)‐9‐[(E)‐phenylprop‐2‐enoyl]‐2‐phenyl‐1,5,9,14‐tetraazabicyclo[12.3.1]octadecan‐4‐one; 4 ), (−)‐(S)‐verbacine (=(−)‐(8S)‐1‐[(E)‐phenylprop‐2‐enoyl]‐8‐phenyl‐1,5,9,13‐tetraazacycloheptadecan‐6‐one; 3 ), (−)‐(S)‐verbasikrine (=(−)‐(8S)‐1‐[(E)‐3‐(4‐methoxyphenyl)prop‐2‐enoyl]‐8‐phenyl‐1,5,9,13‐tetraazacycloheptadecan‐6‐one; 26 ), (−)‐(S)‐isoverbasikrine (=(−)‐(8S)‐1‐[(Z)‐3‐(4‐methoxyphenyl)prop‐2‐enoyl]‐8‐phenyl‐1,5,9,13‐tetraazacycloheptadecan‐6‐one; 25 ), (+)‐(S)‐verbamekrine (=(+)‐(2S)‐9‐[(E)‐3‐(4‐methoxyphenyl)prop‐2‐enoyl]‐2‐phenyl‐1,5,9,14‐tetraazabicyclo[12.3.1]octadecan‐4‐one; 23 ), and (+)‐(S)‐isoverbamekrine (=(+)‐(2S)‐9‐[(Z)‐3‐(4‐methoxyphenyl)prop‐2‐enoyl]‐2‐phenyl‐1,5,9,14‐tetraazabicyclo[12.3.1]octadecan‐4‐one; 24 ). Effective methods for ¹H‐NMR determination of the enantiomeric purity in which (S)‐2‐hydroxy‐2‐phenylacetic acid and (S)‐2‐acetoxy‐2‐phenylacetic acid are used as shift reagents for 1, 8 , and related macrocyclic alkaloids are described.     

Five New Sesquiterpenoids from Parasenecio petasitoides

From the whole plants of Parasenecio petasitoides, five new sesquiterpenoids were isolated, (E,E)‐3α,9β‐dihydroxy‐6βH,11βH‐13‐norgermacra‐1(10),4‐dien‐11,6‐carbolactone ( 2 ), (E,E)‐2α,9β‐dihydroxy‐6βH,11βH‐13‐norgermacra‐1(10),4‐dien‐11,6‐carbolactone ( 3 ), (E,E)‐2α,9β‐dihydroxy‐6βH,11αH‐13‐norgermacra‐1(10),4‐dien‐11,6‐carbolactone ( 4 ), (E)‐15‐hydroxy‐2‐oxo‐6βH,11αH‐13‐norguaia‐3‐ene‐11,6‐carbolactone ( 7 ), and (E)‐11β,15‐dihydroxy‐2‐oxo‐6βH‐13‐norguaia‐3‐ene‐11,6‐carbolactone ( 8 ), together with three known compounds, deacetyl herbolide A ( 1 ), jacquilenin ( 5 ), and (E)‐15‐hydroxy‐2‐oxo‐6βH,11βH‐13‐norguaia‐3‐ene‐11,6‐carbolactone ( 6 ). The structures of these natural products were elucidated spectroscopically, especially by 1D‐ and 2D‐NMR techniques, in combination with high‐resolution mass spectroscopy.     

Cucurbitane Triterpenoids from the Fruit Pulp of Momordica charantia and Their Cytotoxic Activity

Two new cucurbitane‐type triterpenes, 25‐methoxycucurbita‐5,23(E)‐diene‐3β,19‐diol ( 1 ) and 7β‐ethoxy‐3β‐hydroxy‐25‐methoxycucurbita‐5,23(E)‐dien‐19‐al ( 2 ), together with three known cucurbitane‐type triterpenes, 3β,7β,25‐trihydroxycucurbita‐5,23(E)‐dien‐19‐al ( 3 ), (23E)‐3β‐hydroxy‐7β,25‐dimethoxycucurbita‐5,23‐dien‐19‐al ( 4 ), and 3β‐hydroxy‐25‐methoxycucurbita‐6,23(E)‐dien‐19,5β‐olide ( 5 ), were isolated from the fruit pulp of Momordica charantia. The structures of two new compounds were elucidated on the basis of 1D and 2D NMR, MS, IR, optical rotation. Among these isolates, compounds 1 , 2 , and 5 showed slight cytotoxic activity against the SK‐Hep 1 cell line with IC₅₀ values of 33.1, 24.3, and 38.7 μM, respectively.     

Efficient Synthesis of (3E)‐3‐[Amino(aryl)methylidene]chromane‐2,4‐diones (=(3E)‐3‐[Amino(aryl)methylene]‐2H‐1‐benzopyran‐2,4(3H)‐diones) via a Three‐Component Reaction

The Michael‐type addition of a 4‐hydroxycoumarin (=4‐hydroxy‐2H‐1‐benzopyran‐2‐one) 1 to a β‐nitrostyrene (=(2‐nitroethenyl)benzene) 2 in the presence of AcONH₄ leads to substituted (3E)‐3‐[amino(aryl)methylidene]chroman‐2,4‐diones (=(3E)‐3‐[amino(aryl)methylene]‐2H‐1‐benzopyran‐2,4(3H)‐diones) 4 (Table 1). High yields, short reaction time, and easy workup are advantages of this novel one‐pot three‐component reaction.     

New Dammarane‐Type Saponins from the Roots of Panax notoginseng

Three new dammarane‐type triterpenoid saponins, 1 – 3 , were isolated and identified as (20S)‐20‐O‐[β‐D ‐xylopyranosyl‐(1→6)‐β‐D ‐glucopyranosyl‐(1→6)‐β‐D ‐glucopyranosyl]dammar‐24‐ene‐3β,6α,12β, 20‐tetrol ( 1 ), (20S)‐6‐O‐[(E)‐but‐2‐enoyl‐(1→6)‐β‐D ‐glucopyranosyl]dammar‐24‐ene‐3β,6α,12β,20‐tetrol ( 2 ), and (20S)‐6‐O‐[β‐D ‐xylopyranosyl‐(1→2)‐β‐D ‐xylopyranosyl]dammar‐24‐ene‐3β,6α,12β,20‐tetrol ( 3 ) from the roots of Panax notoginseng (Burkill ) F.H.Chen (Araliaceae). Their structures were elucidated on the basis of spectroscopic analyses, including 1D‐ and 2D‐NMR techniques and HR‐ESI‐MS, as well as by acidic hydrolysis.     

Two New Triterpene and a New Nortriterpene Glycosides from Phlomis viscosa

The isolation and structure elucidation of two new oleanane‐type triterpene glycosides, 29‐(β‐D ‐glucopyranosyloxy)‐2α,3β,23‐trihydroxyolean‐12‐en‐28‐oic acid (=(2α,3β,4α,29α)‐29‐(β‐D ‐glucopyranosyloxy)‐2,3,23‐trihydroxyolean‐12‐en‐28‐oic acid; 1 ) and its C(20)‐epimer, 30‐(β‐D ‐glucopyranosyloxy)‐2α,3β,23‐trihydroxyolean‐12‐en‐28‐oic acid (=(2α,3β,4α,29β)‐29‐β‐D ‐glucopyranosyloxy)‐2,3,23‐trihydroxyolean‐12‐en‐28‐oic acid; 2 ), and a novel nortriterpene glycoside, (17S)‐2α,18β,23‐trihydroxy‐3,19‐dioxo‐19(18→17)‐ abeo‐28‐norolean‐12‐en‐25‐oic acid β‐D ‐glucopyranosyl ester (=(1R,2S,4aS,4bR,6aR,7R,9R,10aS,10bS)‐3,4,4a,4b,5,6,6a,7,8,9,10,10a,10b,11‐tetradecahydro‐1‐hydroxy‐7‐(hydroxymethyl)‐3′,4′,4a,4b,7‐pentamethyl‐2′,8‐ dioxospiro[chrysene‐2(1H),1′‐cyclopentane]‐10a‐carboxylic acid β‐D ‐glucopyranosyl ester; 3 ) from Phlomis viscosa (Lamiaceae) are reported. The structures of the compounds were asigned by means of spectroscopic (IR, 1D‐ and 2D‐NMR, and LC‐ESI‐MS) and chemical (acetylation) methods.     

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.