New Steroidal Glycosides from Balanites aegyptiaca

Five new steroidal glycosides were isolated from the roots of Balanites aegyptiaca, a widely used African medicinal plant. On the basis of spectroscopic and chemical evidence, their structures were determined as (3β,12α,14β,16β)‐12‐hydroxycholest‐5‐ene‐3,16‐diyl bis(β‐D ‐glucopyranoside) ( 1 ), (3β,20S,22R,25R)‐ and (3β,20S,22R,25S)‐26‐(β‐D ‐glucopyranosyloxy)‐22‐methoxyfurost‐5‐en‐3‐yl β‐D ‐xylopyranosyl‐(1→3)‐β‐D ‐glucopyranosyl‐(1→4)[α‐L ‐rhamnopyranosyl‐(1→2)]‐β‐D ‐glucopyranoside ( 2 and 3 , resp.), and (3β,20S,22R,25R)‐ and (3β,20S,22R,25S)‐spirost‐5‐en‐3‐yl β‐D ‐xylopyranosyl‐(1→3)‐β‐D ‐glucopyranosyl‐(1→4)[α‐L ‐rhamnopyranosyl‐(1→2)]‐β‐D ‐glucopyranoside ( 4 and 5 , resp.)     

Artabotryols A – E,New Lanostane Triterpenes from the Seeds of Artabotrys odoratissimus

Six new lanostane triterpenes, artabotryols A, B, C1, C2, D, and E ( 1, 2, 3a, 3b, 4 , and 5 , resp.) have been isolated from the seeds of Artabotrys odoratissimus (Annonaceae). Their structures have been established as (3α,22S,25R)‐3‐hydroxy‐22,26‐epoxylanost‐8‐en‐26‐one ( 1 ), (3α,22S,25R)‐22,26‐epoxylanost‐8‐ene‐3,26‐diol ( 2 ), (3α,22S,25R,26R)‐26‐methoxy‐22,26‐epoxylanost‐8‐en‐3‐ol ( 3a ), (3α,22S,25R, 26S)‐26‐methoxy‐22,26‐epoxylanost‐8‐en‐3‐ol ( 3b ), (3α,22S,25R)‐3,22‐dihydroxylanost‐8‐en‐26‐oic acid ( 4 ) and (3α,7α,11α,22S,25R)‐3,7,11‐trihydroxy‐22,26‐epoxylanost‐8‐en‐26‐one ( 5 ) by spectroscopic studies and chemical correlations.     

Novel Antileukemic Sterol Glycosides from Ajuga salicifolia

Two novel and three new sterol glycosides were isolated from the MeOH extract of the aerial parts of Ajuga salicifolia (L.) Schreber . The structures of the compounds were elucidated as (3R,16S,17S,20R,22S,23S, 24S,25S)‐16,23 : 16,27 : 22,25‐triepoxy‐3‐(β‐D ‐glucopyranosyloxy)coprostigmast‐7‐en‐17‐ol ( 1 ), (3R,16S,17S, 20R,22S,23S,24S,25S)‐16,23 : 16,27 : 22,25‐triepoxy‐3‐{[β‐D ‐glucopyranosyl‐(1→2)‐β‐D ‐glucopyranosyl]oxy}coprostigmast‐7‐en‐17‐ol ( 2 ), (3R,16S,17R,20S,22R,24S,25S)‐22,25‐epoxy‐3,27‐bis(β‐D ‐glucopyranosyloxy)coprostigmast‐7‐en‐16‐ol ( 3 ), (3R,16S,17R,20S,22R,24S,25S)‐22,25‐epoxy‐3‐{[β‐D ‐glucopyranosyl‐(1→2)‐β‐D ‐glucopyranosyl]oxy}‐27‐(β‐D ‐glucopyranosyloxy)coprostigmast‐7‐en‐16‐ol ( 4 ), and (3R,16R,17S,20R,22S,23S, 24S,25S)‐22,25‐epoxy‐3‐(β‐D ‐glucopyranosyloxy)coprostigmast‐7‐ene‐16,17,23,27‐tetrol 27‐acetate ( 5 ) by means of 1D and 2D NMR spectroscopy and HR‐MALDI mass spectrometry. The novel compounds, which consist of three additional ring systems at the coprostigmastane skeleton, were named ajugasalicioside A ( 1 ) and B ( 2 ), and the new compounds C ( 3 ), D ( 4 ) and E ( 5 ). In our cytotoxicity assays (HeLa cells, Jurkat T cells, and peripheral mononuclear blood cells), ajugasaliciosides A–D specifically inhibited the viability and growth of Jurkat T‐leukemia cells at concentrations below 10 μM . Ajugasalicioside A ( 1 ; (IC₅₀=6 μM ) and C ( 3 ; IC₅₀=3 μM ) were the most active compounds. Ajugasalicioside A ( 1 ) induced cell‐cell contact, inhibited Jurkat T cell proliferation, and up‐regulated mRNA levels of the cell‐cycle regulator cyclin D1, which might be an indication for cell differentiation. Furthermore, 1 down‐regulated the mRNA levels of the NF‐κB subunit p65 in a concentration‐dependent manner. These effects were not found for ajugasalicioside B ( 2 ), which has an additional glucose unit, and the onset of cytotoxicity of 2 (IC₅₀=10 μM ) was delayed by 24 h.     

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.     

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.     

Three New Alkaloids from the Leaves of Uncaria rhynchophylla

Three new alkaloids, 2′‐O‐β‐D ‐glucopyranosyl‐11‐hydroxyvincoside lactam ( 1 ), 22‐O‐demethyl‐22‐O‐β‐D ‐glucopyranosylisocorynoxeine ( 2 ), and (4S)‐corynoxeine N‐oxide ( 3 ) were isolated from the leaves of Uncaria rhynchophylla, together with four known tetracyclic oxindole or indole alkaloids, isocorynoxeine N‐oxide ( 4 ), rhynchophylline N‐oxide ( 5 ), isorhynchophylline N‐oxide ( 6 ), and dihydrocorynantheine ( 7 ), and an indole alkaloid glycoside, strictosidine ( 8 ). The structures of 1 – 3 were elucidated by spectroscopic methods including UV, IR, ESI‐TOF‐MS, 1D‐ and 2D‐NMR, as well as CD experiments. The activity assay showed that 8 (IC₅₀=8.3 μM ) exhibited potent inhibitory activity on lipopolysaccharide(LPS)‐induced nitrogen monoxide (NO) release in N9 microglia cells. However, only weak inhibitory activities were observed for 1 – 7 (IC₅₀>100 μM for 1 – 6 or >30 μM for 7 ).     

New Steroidal Saponins from the Leaves of Yucca elephantipes

Two new spirostanol saponins, namely elephanosides G and H ( 1 and 2 , resp.) were isolated from the leaves of Yucca elephantipes (Agavaceae), together with the two known furostanol saponins 3 and 4 and the six known flavonoid O‐ and C‐glycosides 5 – 10 . The new structures were elucidated as (3β,25S)‐spirost‐5‐en‐3‐yl O‐β‐D ‐glucopyranosyl‐(1→3)‐O‐β‐D ‐glucopyranosyl‐(1→4)‐β‐D ‐galactopyranoside ( 1 ) and (3β,5β,25R)‐3‐[(2‐O‐β‐D ‐glucopyranosyl‐β‐D ‐galactopyranosyl)oxy]spirostan‐12‐one ( 2 ) on the basis of detailed spectroscopic analysis and acidic hydrolysis.     

Ceramides Isolated from Helianthus annuus L.

Three new compounds (2R)‐2‐hydroxy‐N‐[(2S,3S,4R,10E)‐1,3,4‐trihydroxyicos‐10‐en‐2‐yl]docosanamide ( 1 ), (2R,3R)‐2,3‐dihydroxy‐N‐[(2S,3S,4R,10E)‐1,3,4‐trihydroxyicos‐10‐en‐2‐yl]docosanamide ( 2 ), N‐(2‐phenylethyl)tetracosanamide ( 3 ), together with a known ceramide, (2R)‐N‐[(2S,3S,4R,8E)‐1‐(β‐D ‐Glucopyranosyloxy)‐3,4‐dihydroxyoctadec‐8‐en‐2‐yl]‐2‐hydroxyhexadecanamide ( 4 ), were isolated from acetone extract of flower disc of Helianthus annuus L. The structures were identified on the basis of chemical and spectroscopic methods.     

New Furostanol Glycosides from the Roots of Digitalis ciliata Trautv.

Three new furostanol glycosides, named ciliatasides A, B, and C ( 1 – 3 , resp.), have been isolated from the roots of Digitalis ciliata, along with two known furostanol glycosides. The structures of the new compounds were identified as (2α,3β,5α,14β,25R)‐26‐(β‐D ‐glucopyranosyloxy)‐2‐hydroxyfurost‐20(22)‐en‐3‐yl β‐D ‐glucopyranosyl‐(1→2)‐[β‐D ‐glucopyranosyl‐(1→3)]‐β‐D ‐galactopyranoside ( 1 ), (2α,3β,5α,14β,22R)‐26‐(β‐D ‐glucopyranosyloxy)‐2‐hydroxy‐22‐methoxyfurost‐25(27)‐en‐3‐yl β‐D ‐galactopyranosyl‐(1→2)‐[β‐D ‐xylopyranosyl‐(1→3)]‐β‐D ‐glucopyranosyl‐(1→4)‐β‐D ‐galactopyranoside ( 2 ), and (2α,3β,5α,14β,22R,25R)‐26‐(β‐D ‐glucopyranosyloxy)‐2,22‐dihydroxyfurostan‐3‐yl β‐D ‐glucopyranosyl‐(1→2)‐[β‐D ‐glucopyranosyl‐(1→3)]‐β‐D ‐galactopyranoside ( 3 ).     

New Cholinesterase‐Inhibiting Steroidal Alkaloids from Sarcococca saligna

Seven new steroidal alkaloids, 2‐hydroxysalignarine‐E (=(2′E,20S)‐20‐(dimethylamino)‐2β‐hydroxy‐3β‐(tigloylamino)pregn‐4‐ene; 1 ), 5,6‐dihydrosarconidine (=(20S)‐20‐(dimethylamino)‐3β‐(methylamino)‐5α‐pregn‐16‐ene; 2 ), salignamine (=(20S)‐20‐(methylamino)‐3β‐methoxypregna‐5,16‐diene; 3 ), 2‐hydroxysalignamine (=(20S)‐20‐(dimethylamino)‐2β‐hydroxy‐3β‐methoxypregna‐5,16‐diene; 4 ), salignarine‐F (=(2′E, 20S)‐20‐(dimethylamino)‐4β‐hydroxy‐3β‐(tigloylamino)pregn‐5‐ene; 5 ), salonine‐C (=(2′E,20S)‐20‐(dimethylamino)‐3β‐(tigloylamino)pregna‐4,14‐diene; 6 ), and N‐[formyl(methyl)amino]salonine‐B (=(20S)‐20‐[formyl(methyl)amino]‐3β‐methoxypregna‐5,16‐diene; 7 ) have been isolated from the MeOH extract of Sarcococca saligna, along with the six known alkaloids dictyophlebine ( 8 ), epipachysamine‐D ( 9 ), saracosine ( 10 ), iso‐N‐formylchonemorphine ( 11 ), sarcodinine ( 12 ), and alkaloid‐C ( 13 ). The structures of 1 – 7 were deduced from spectral data. Compounds 1 – 13 demonstrated significant activity against acetyl‐ and butyrylcholinesterase.     

Two New Cerebrosides from the Aerial Parts of Tithonia diversifolia

Two new cerebrosides, (2R)‐N‐{(1S,2S,3R,8E)‐1‐[(β‐D ‐glucopyranosyloxy)methyl]‐2,3‐dihydroxyheptadec‐8‐en‐1‐yl}‐2‐hydroxyhexadecanamide ( 1 ) and (2R)‐N‐{(1S,2R,8E)‐1‐[(β‐D ‐glucopyranosyloxy)methyl]‐2‐hydroxyheptadec‐8‐en‐1‐yl}‐2‐hydroxyhexadecanamide ( 2 ), were isolated from the aerial parts of Tithonia diversifolia (Hemsl .) A. Gray. Their structures were determined on the basis of spectroscopic analysis (IR, HR‐ESI‐MS, and 1D‐, and 2D‐NMR).     

Two New Spirostanol Saponins from Reineckia carnea

Two new spirostanol saponins, (1β,3β,5β,25S)‐spirostan‐1,3‐diol 1‐(β‐D ‐xylopyranoside) ( 1 ) and (1β,3β,5β,25S)‐spirostan‐1,3‐diol 1‐[α‐L ‐rhamnopyranosyl‐(1→2)‐β‐D ‐fucopyranoside] ( 2 ), along with two known compounds, (1β,3β,5β,25S)‐spirostan‐1,3‐diol 1‐[α‐L ‐rhamnopyranosyl‐(1→2)‐β‐D ‐xylopyranoside] ( 3 ) and (1β,3β,4β,5β,25S)‐spirostan‐1,3,4,5‐tetrol 5‐(β‐D ‐glucopyranoside) ( 4 ) were isolated from the whole plant of Reineckia carnea. The structures of the new steroids were determined by detailed analysis of their 1D‐ and 2D‐NMR spectra and chemical methods, and by comparison with spectral data of known compounds. Compounds 3 and 4 were isolated from the genus Reineckia for the first time.     

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.     

Two New Steroidal Saponins from the Processed Polygonatum kingianum

Two new spirostanol saponins, kingianoside I ( 1 ) and kingianoside K ( 2 ), corresponding to (3β,23S,25R)‐23‐hydroxy‐12‐oxospirost‐5‐en‐3‐yl 4‐O‐β‐D ‐glucopyranosyl‐β‐D ‐galactopyranoside ( 1 ) and (3β,25R)‐7‐oxospirost‐5‐en‐3‐yl α‐L ‐arabinofuranosyl‐(1→4)‐[6‐deoxy‐α‐L ‐mannopyranosyl‐(1→2)]‐β‐D ‐glucopyranoside ( 2 ), along with 13 known compounds, daucosterol, (25R)‐kingianoside G, (25RS)‐kingianoside A, pratioside D₁, (25RS)‐pratioside D₁, (25S)‐kingianoside C, kingianoside C, ginsenoside Rb₁, saponins Tb and Pb, dioscin, gracillin, and saponin Pa, were isolated from the processed rhizomes of Polygonatum kingianum. The structures of the new compounds were elucidated by detailed spectroscopic analyses, including 1D‐ and 2D‐NMR techniques, and chemical methods. Compound 2 contains a novel unusual spirostanol saponin aglycone. Ginsenoside Rb₁ and saponin Tb were isolated for the first time from the genus Polygonatum. The 13 known compounds were detected for the first time in the processed Polygonatum kingianum.     

Three New Triterpene Saponins from Bolbostemma paniculatum

Two novel noroleanane saponins, tubeimoside A ( 1 ) and tubeimoside B ( 2 ), and a new dammarane triterpene saponin, tubeimoside C ( 3 ), together with two known compounds, 4 and 5 , were isolated from the bulbs of Bolbostemma paniculatum (Maxim .) Franquet . Compound 4 was found in this genus for the first time. Based on spectroscopic methods, including IR, NMR (DEPT, COSY, HMQC, HMBC, and TOCSY), and MS experiments, and chemical reactions, the structures of the new compounds were elucidated as 3β‐[β‐D ‐glucopyranosyl‐(1→2)‐β‐D ‐glucopyranosyloxy]‐2β,23‐dihydroxy‐28‐norolean‐12‐en‐16‐one ( 1 ), 3β‐[β‐D ‐glucopyranosyl‐(1→2)‐β‐D ‐glucopyranosyloxy]‐2β,23‐dihydroxy‐28‐norolean‐12‐en‐22‐one ( 2 ), (3β,7β)‐7,18,20‐trihydroxydammar‐24‐en‐3‐yl 2‐O‐α‐L ‐arabinopyranosyl‐β‐D ‐glucopyranoside ( 3 ).     

Four New Cycloartane (=9,19‐Cyclolanostane) Saponins from the Aerial Parts of Thalictrum fortunei

The four new cycloartane (=9,19‐cyclolanostane) glycosides 1 – 4 were isolated from the aerial parts of Thalictrum fortunei (Ranunculaceae). The structures of these new glycosides were elucidated as (3β,16β,24S)‐cycloartane‐3,16,24,25,30‐pentol 3,25‐di‐β‐D ‐glucopyranoside ( 1 ), (3β,16β,24S)‐24‐(acetyloxy)cycloartane‐3,16,25,30‐tetrol 3,25‐di‐β‐D ‐glucopyranoside ( 2 ), (3β,16β,24S)‐24‐(acetyloxy)‐3‐(β‐D ‐glucopyranosyloxy)cycloartane‐16,25,30‐triol 25‐[β‐D ‐glucopyranosyl‐(1→6)‐β‐D ‐glucopyranoside] ( 3 ), and (3β,16β,24S)‐24‐(acetyloxy)‐3‐(β‐D ‐glucopyranosyloxy)cycloartane‐16,25,30‐triol 25‐[β‐D ‐glucopyranosyl‐(1→4)‐β‐D ‐glucopyranoside] ( 4 ). The structure elucidations were accomplished by 1D ‐ and 2D‐NMR methods, HR‐ESI‐MS, and hydrolysis.     

Total Synthesis of a Natural Cerebroside from Euphorbiaceae

The regioselective total synthesis of the natural cerebroside (2R,15Z)‐N‐{(1S,2S,3R,4R,5Z)‐1‐[(β‐D ‐glucopyranosyloxy)methyl]‐2,3,4‐trihydroxyheptadec‐5‐en‐1‐yl}‐2‐hydroxytetracos‐15‐enamide ( 2 ), originally isolated from Euphorbiaceae, is reported in full detail.     

Foetidissimosides C–F,Novel Glycosides from the Roots of Cucurbita foetidissima

Two novel echinocystic acid (=(3β,16α)‐3,16‐dihydroxyolean‐12‐en‐28‐oic acid) glycosides, foetidissimosides C ( 1 ), and D ( 2 ), along with new cucurbitane glycosides, i.e., foetidissimosides E/F ( 3 / 4 ) as an 1 : 1 mixture of the (24R)/(24S) epimers, were obtained from the roots of Cucurbita foetidissima. Their structures were elucidated by means of a combination of homo‐ and heteronuclear 2D‐NMR techniques (COSY, TOCSY, NOESY, ROESY, HSQC, and HMBC), and by FAB‐MS. The new compounds were characterized as (3β,16α)‐28‐{[O‐β‐D ‐glucopyranosyl‐(1→3)‐O‐β‐D ‐xylopyranosyl‐(1→4)‐O‐6‐deoxy‐α‐L ‐mannopyranosyl‐(1→2)‐α‐L ‐arabinopyranosyl]oxy}‐16‐hydroxy‐28‐oxoolean ‐12‐en‐3‐yl β‐D ‐glucopyranosiduronic acid ( 1 ), (3β,16α)‐16‐hydroxy‐28‐oxo‐28‐{{O‐β‐D ‐xylopyranosyl‐(1→3)‐O‐[β‐D ‐xylopyranosyl‐(1→4)]‐O‐6‐deoxy‐α‐L ‐mannopyranosyl‐(1→2)‐α‐L ‐arabinopyranosyl}oxy}olean‐12‐en‐3‐yl β‐D ‐glucopyranosiduronic acid ( 2 ), and (3β,9β,10α,11α,24R)‐ and (3β,9β,10α,11α,24S)‐25‐(β‐D ‐glucopyranosyloxy)‐9‐methyl‐19‐norlanost‐5‐en‐3‐yl 2‐O‐β‐D ‐glucopyranosyl‐β‐D ‐glucopyranoside ( 3 and 4 , resp.).     

Two New Disulfated Triterpenoids from Zygophyllum fabago

From the aerial parts of Zygophyllum fabago, two new monosodium salts of sulfated derivatives of ursolic acid, along with two known quinovic acid glycosides were isolated. The structures of the new compounds were determined as (3β,4α)‐3,23,30‐trihydroxyurs‐20‐en‐28‐al 3,23‐di(sulfate) sodium salt (1 : 1) ( 1 ) and of (3β,4α)‐3,23,28‐trihydroxyurs‐20‐en‐30‐yl β‐D ‐glucopyranoside 3,23‐di(sulfate) sodium salt (1 : 1) ( 2 ) with the molecular formula C₃₀H₄₇NaO₁₀S₂ and C₃₆H₅₉NaO₁₅S₂, respectively. The structures of the known compounds were 3‐O‐(2‐O‐sulfo‐β‐D ‐quinovopyranosyl)quinovic acid 28‐β‐D ‐glucopyranosyl ester ( 3 ) and 3‐O‐(β‐D ‐glucopyranosyl)quinovic acid 28‐β‐D ‐glucopyranosyl ester ( 4 ) (quinovic acid=(3β)‐3‐hydroxyurs‐12‐ene‐27,28‐dioic acid). The structures of all these compounds were determined by using 1D‐ and 2D‐NMR spectroscopic techniques.     

Terpenoids from Two Dicranopteris Species

Two new compounds, (6S,13S)‐6‐{[β‐D ‐glucopyranosyl‐(1→4)‐α‐L ‐rhamnopyranosyl]oxy}cleroda‐3,14‐dien‐13‐ol ( 1 ) and kadsuric acid 3‐methyl ester ( 2 ), together with nine known compounds, (6S,13E)‐6‐{[β‐D ‐glucopyranosyl‐(1→4)‐α‐L ‐rhamnopyranosyl]oxy}cleroda‐3,13‐dien‐15‐ol ( 3 ), (6S,13S)‐6‐[6‐O‐acetyl‐β‐D ‐glucopyranosyl‐(1→4)‐α‐L ‐rhamnopyranosyl]oxy}‐13‐{[α‐L ‐rhamnopyranosyl‐(1→4)‐β‐D ‐fucopyranosyl]oxy}cleroda‐3,14‐diene ( 4 ), (6S,13S)‐6‐{[6‐O‐β‐D ‐glucopyranosyl‐(1→4)‐α‐L ‐rhamnopyranosyl]oxy}‐13‐{[α‐L ‐rhamnopyranosyl‐(1→4)‐β‐D ‐fucopyranosyl]oxy}cleroda‐3,14‐diene ( 5 ), 15‐hydroxydehydroabietic acid ( 6 ), 15‐hydroxylabd‐8(17)‐en‐19‐oic acid ( 7 ), junicedric acid ( 8 ), (4β)‐kaur‐16‐en‐18‐oic acid ( 9 ), (4β)‐16‐hydroxykauran‐18‐oic acid ( 10 ), and (4β,16β)‐16‐hydroxykauran‐18‐oic acid ( 11 ) were isolated from the fronds of Dicranopteris linearis or D. ampla. Their structures were established by extensive 1D‐ and 2D‐NMR spectroscopy. Compounds 1 and 3 – 8 showed no anti‐HIV activities.