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.     

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.     

Triterpenoids from Eucalyptus camaldulensis Dehnh. Tissue Cultures

A chemical study on tissue cultures from leaves and flowers of E. camaldulensis Dehnh . afforded the new natural product (2α,3β)‐2,3,23‐trihydroxy‐13,28‐epoxyurs‐11‐en‐28‐one (dryobalanolide) together with the known pentacyclic triterpenoids: betulinic acid, oleanolic acid, ursolic acid, (2α,3β)‐2,3,23‐trihydroxyolean‐12‐en‐28‐oic acid (arjunolic acid), (2α,3β)‐2,3,23‐trihydroxyurs‐12‐en‐28‐oic acid (asiatic acid), (2α)‐2‐hydroxyursolic acid, (2α)‐2‐hydroxyoleanolic acid (maslinic acid), as well as β‐sitosterol. The extracts and the isolated compounds were evaluated against eleven human pathogenic microorganisms, exhibiting a very interesting antibacterial spectrum of activities.     

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.).     

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.     

New Cytotoxic Triterpenoids from the Aerial Parts of Euphorbia sieboldiana

Phytochemical investigation of the EtOH extract of Euphorbia sieboldiana led to the isolation of four new oleanane‐type triterpenoids, (1β,2α,3β,19β)‐1,2,3,19‐tetrahydroxyolean‐12‐en‐28‐oic acid, (1β,3β,19β)‐1,3,19‐trihydroxyolean‐12‐en‐28‐oic acid, (1β,2α,3β,16β,19β)‐1,2,3,16,19‐pentahydroxyolean‐12‐en‐28‐oic acid, and (1β,2α,3β,19β,23)‐1,2,3,19,23‐pentahydroxyolean‐12‐en‐28‐oic acid, along with 16 known compounds. Their structures were established by extensive 1D‐ and 2D‐NMR, as well as other spectral analyses. Biological evaluation of the four new triterpenoids revealed potent cytotoxic activities against HeLa and Hep‐G2 cells.     

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.)     

Chemical Constituents from the Roots of Schnabelia tetradonta

The new rearranged‐abietane diterpene 1 , the four new triterpenoids 2 – 5 , and the new aminoethylphenyl oligoglycoside 6 , besides 19 known compounds, were isolated from the roots of Schnabelia tetradonta, a Chinese endemic herb. The structures of the new compounds were elucidated on the basis of spectroscopic evidence as 12,17‐epoxy‐11,14,16‐trihydroxy‐17(15→16)‐abeo‐abieta‐8,11,13,15‐tetraen‐7‐one ( 1 ), 21β‐(β‐D ‐glucopyranosyloxy)‐2α,3α‐dihydroxyolean‐12‐en‐28‐oic acid ( 2 ), 2β,3β,16β‐trihydroxy‐15‐oxo‐28‐norolean‐12‐en‐23‐oic acid ( 3 ), 3β‐[(4‐O‐acetyl‐β‐D ‐glucopyranuronosyl)oxy]‐2β,16β‐dihydroxy‐28‐norolean‐15‐oxo‐12‐en‐23‐oic acid ( 4 ), 3β‐[(4‐O‐acetyl‐6‐O‐methyl‐β‐D ‐glucopyranuronosyl)oxy]‐2β,16β‐dihydroxy‐15‐oxo‐28‐norolean‐12‐en‐23‐oic acid ( 5 ), and 4‐[2‐(acetylamino)ethyl]phenyl O‐6‐O‐[(Z)‐p‐methoxycinnamoyl]‐β‐D ‐glucopyranosyl‐(1→2)]‐O‐[β‐D ‐glucopyranosyl‐(1→3)]‐4‐O‐acetyl‐α‐L ‐rhamnopyranoside ( 6 ), respectively.     

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 Triterpenoid Glycosides from Centella asiatica

Four new triterpenoid glycosides named asiaticoside C ( 1 ), D ( 2 ), E ( 3 ), and F ( 4 ) were isolated from the BuOH fraction of the EtOH extract of whole plants of Centella asiatica, together with three known compounds, asiaticoside ( 5 ), madecassoside ( 6 ), and scheffuroside B ( 7 ). Based on FAB‐MS, IR, ¹H‐ and ¹³C‐NMR, and 2D‐NMR data (HMQC, HMBC, COSY), the structures of the new compounds were determined as (2α,3β,4α)‐23‐(acetyloxy)‐2,3‐dihydroxyurs‐12‐en‐28‐oic acid O‐α‐L ‐rhamnopyranosyl‐(1→4)‐O‐β‐D ‐glucopyranosyl‐(1→6)‐β‐D ‐glucopyranosyl ester ( 1 ), (2α,3β)‐2,3‐dihydroxyurs‐12‐en‐28‐oic acid O‐α‐L ‐rhamnopyranosyl‐(1→4)‐O‐β‐D ‐glucopyranosyl‐(1→6)‐β‐D ‐glucopyranosyl ester ( 2 ), asiatic acid 6‐O‐β‐D ‐glycopyranosyl‐β‐D ‐glucopyranosyl ester ( 3 ), (3β,4α)‐3,23‐dihydroxyurs‐12‐en‐28‐oic acid O‐α‐L ‐rhamnopyranosyl‐(1→4)‐O‐β‐D ‐glucopyranosyl‐(1→6)‐β‐D ‐glucopyranosyl ester ( 4 ).     

Two New Triterpenoid Glycosides from the Roots of Rosa cymosa Tratt.

Two new triterpenoid glycosides, 3α,19α,23α‐trihydroxy‐2‐oxo‐12‐ursen‐28‐O‐β‐d ‐glucopyranoside ( 1 ) and 3α,19α,23α‐trihydroxy‐2‐oxoolean‐12‐en‐28‐O‐β‐d ‐glucopyranoside ( 2 ) as well as three known compounds, 2α,3α,19α‐trihydroxyolean‐12‐en‐28‐O‐β‐d ‐glucopyranoside ( 3 ), 2α,3α,19α,23‐tetrahydroxy‐12‐ursen‐28‐O‐β‐d ‐glucopyranoside ( 4 ), and 2α,3β,19α,23‐tetrahydroxyurs‐12‐en‐28‐oic acid ( 5 ) were isolated from 75% EtOH extract of Rosa cymosa. Their structures were elucidated by extensive spectroscopic methods. All the isolated compounds displayed moderate inhibitory activity against LPS‐induced NO production in macrophages.     

Chemical Constituents from Myrsine africana L.

Three new compounds, myrsinoside A (=2,4‐dihydroxy‐6‐methylphenyl β‐D ‐(6′‐galloyl)glucopyranoside; 1 ), myrsinoside B (2,4‐dihydroxy‐6‐methylphenyl β‐D ‐glucopyranoside; 2 ), and (3β,16α,20α)‐3,16,28‐trihydroxyolean‐12‐en‐29‐oic acid 3‐{O‐β‐D ‐glucopyranosyl‐(1→2)‐O‐[β‐D ‐glucopyranosyl‐(1→4)]‐α‐L ‐arabinopyranoside} ( 3 ), along with four known compounds, were isolated from the stems of Myrsine africana L. The structures of these new compounds were elucidated on the basis of spectroscopic analysis, including 1D‐ and 2D‐NMR and ESI‐MS techniques, and chemical methods.     

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.     

Two Novel Triterpenoids from Portulaca oleracea L.

Two novel triterpenoids, (2α,3α)‐3‐{[4‐O‐(β‐D ‐glucopyranosyl)‐β‐D ‐xylopyranosyl]oxy}‐2,23‐dihydroxy‐30‐methoxy‐30‐oxoolean‐12‐en‐28‐oic acid ( 1 ) and (2α,3α)‐2,23,30‐trihydroxy‐3‐[(β‐D ‐xylopyranosyl)oxy]olean‐12‐en‐28‐oic acid ( 2 ) were isolated from Portulaca oleracea L., and they both showed weak cytotoxic activity assayed with the MTT method.     

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).     

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.     

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 ).     

New saponins from Sechium mexicanum

The chemical study of Sechium mexicanum roots led to the isolation of the two new saponins {3‐O‐β‐D ‐glucopyranosyl (1 → 3)‐β‐D ‐glucopyranosyl‐2β,3β,16α,23‐tetrahydroxyolean‐12‐en‐28‐oic acid 28‐O‐α‐L ‐rhamnopyranosyl‐(1 → 3)‐β‐D ‐xylopyranosyl‐(1 → 4)‐α‐L ‐rhamnopyranosyl‐(1 → 2)‐α‐L ‐arabinopyranoside} (1) and {3‐O‐β‐D ‐glucopyranosyl (1 → 3)‐β‐D ‐glucopyranosyl‐2β,3β,16α,23‐tetrahydroxyolean‐12‐en‐28‐oic acid 28‐O‐α‐L ‐rhamnopyranosyl‐(1 → 3)‐β‐D ‐xylopyranosyl‐(1 → 4)‐[β‐D ‐apiosyl‐(1 → 3)]‐α‐L ‐rhamnopyranosyl‐(1 → 2)‐α‐L ‐arabinopyranoside} (2), together with the known compounds {3‐O‐β‐D ‐glucopyranosyl‐(1 → 3)‐β‐D ‐glucopyranosyl‐2β,3β,6β,16α,23‐pentahydroxyolean‐12‐en‐28‐oic acid 28‐O‐α‐L ‐rhamnopyranosyl‐(1 → 3)‐β‐D ‐xylopyranosyl‐(1 → 4)‐α‐L ‐rhamnopyranosyl‐(1 → 2)‐α‐L ‐arabinopyranoside} (3), tacacosides A₁ (4) and B₃ (5). The structures of saponins 1 and 2 were elucidated using a combination of ¹H and ¹³C 1D‐NMR, COSY, TOCSY, gHMBC and gHSQC 2D‐NMR, and FABMS of the natural compounds and their peracetylated derivates, as well as by chemical degradation. Compounds 1–3 are the first examples of saponins containing polygalacic and 16‐hydroxyprotobasic acids found in the genus Sechium, while 4 and 5, which had been characterized partially by NMR, are now characterized in detail. Copyright © 2009 John Wiley & Sons, Ltd.     

Three New Triterpene Saponins from Gynostemma pentaphyllum

Three new dammarane‐type triterpene saponins, 1 – 3 , together with three known compounds, 4 – 6 , were isolated from the aerial parts of Gynostemma pentaphyllum (Thunb.) Makino . By means of chemical and spectroscopic methods, their structures were established as (20S)‐3β,20,21‐trihydroxydammara‐23,25‐diene 3‐O‐[α‐L ‐rhamnopyranosyl‐(1→2)] [β‐D ‐xylopyranosyl‐(1→3)]‐β‐D ‐glucopyranosyl‐21‐O‐β‐D ‐glucopyranoside ( 1 ), (20R,23R)‐3β,20‐dihydroxy‐19‐oxodammar‐24‐en‐21‐oic acid 21,23‐lactone 3‐O‐[α‐L ‐rhamnopyranosyl‐(1→2)] [β‐D ‐xylopyranosyl‐(1→3)]‐α‐L ‐arabinopyranoside ( 2 ), and (21S,23S)‐3β,20ξ,21,26‐tetrahydroxy‐19‐oxo‐21,23‐epoxydammar‐24‐ene 3‐O‐[α‐L ‐rhamnopyranosyl‐(1→2)] [β‐D ‐xylopyranosyl‐(1→3)]‐α‐L ‐arabinopyranoside ( 3 ).     

Sulfated Triterpenes from Lemon Balm

The hydroalcoholic (EtOH/H₂O) extract of matured leaf margins of lemon balm (Melissa officinalis L.) afforded a new 3,23‐disulfate of 2α,3β‐23,29‐tetrahydroxyolean‐12‐en‐28‐oic acid 28‐O‐β‐D ‐glucopyranoside ( 1 ) and a new 23‐monosulfate of 2α,23‐dihydroxyurs‐12‐en‐28‐oic acid 3‐O‐β‐D ‐glucopyranoside ( 2 ), along with six known compounds, i.e., 23‐monosulfate of 2α,3β,19α,23‐tetrahydroxyurs‐12‐ene‐28‐oic acid 28‐O‐β‐D ‐glucopyranoside ( 3 ), 3,5,6‐trihydroxydehydro‐α‐ionol 9‐O‐β‐D ‐glucopyranoside ( 4 ), quadranoside III ( 5 ), rosmarinic acid ( 6 ), caffeic acid ( 7 ), and luteolin ( 8 ). All the isolated compounds were evaluated for their antioxidant, antimicrobial, antimalarial, and cytotoxic activities. Only rosmarinic acid exhibited substantial antioxidant and antimicrobial activities, whereas sulfated terpenes showed considerably lower or no antimicrobial activity.