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.     

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.     

Three New 24‐Noroleanane Triterpenoids from Quercus aliena var. acuteserrata

Three new 24‐noroleanane triterpenoids, i.e., 2α,19α‐dihydroxy‐3‐oxo‐24‐norolean‐12‐en‐28‐oic acid ( 1 ) and 19α‐hydroxy‐3‐oxo‐24‐norolean‐12‐en‐28‐oic acid ( 2 ), and 2α,3β,19α‐trihydroxy‐24‐norolean‐12‐en‐28‐oic acid ( 3 ) were isolated from Quercus aliena var. acuteserrata, together with three known compounds, bartogenic acid ( 4 ), ilexgenin A ( 5 ), and aophitolic acid ( 6 ). Their structures were established by spectroscopic methods, especially 2D‐NMR and MS analyses.     

Two New Polyoxygenated Triterpenoids from Actinidia valvata

Two new polyoxygenated triterpenoids, (2β,3α,6α)‐2,3,6,20,23,30‐hexahydroxyurs‐12‐en‐28‐oic acid ( 1 ) and (2β,3α)‐2,3,20,23,24,30‐hexahydroxyurs‐12‐en‐28‐oic acid O‐β‐D ‐glucopyranosyl ester ( 2 ) were isolated from the roots of Actinidia valvata Dunn . Their structures were elucidated by means of extensive spectroscopic studies. Both compounds showed moderate cytotoxic activity in vitro against the BEL‐7402 and SMMC‐7721 tumor cell lines.     

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.     

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.     

Diterpenes from Xylopia langsdorffiana

The phytochemical investigation of Xylopia langsdorffiana A.St.‐Hil. & Tul . led to the isolation of eight diterpenes, i.e., of the four new compounds (5β,7β,8α,9β,10α,12α)‐atisane‐7,16‐diol 7‐acetate ( 1 ), named xylodiol 7‐acetate, (5β,8α,9β,10α,12α)‐16‐hydroxyatisan‐7‐one ( 2 ), named xylopinone, (3α,12Z)‐3‐hydroxy‐ent‐labda‐8(20),12,14‐trien‐18‐oic acid ( 3 ), named labdorffianic acid A, and 8,20‐epoxy‐13‐hydroxy‐ent‐labd‐14‐en‐18‐oic acid ( 4 ), named labdorffianic acid B, and of the four known compounds 5 – 8 , i.e., ent‐kauran‐16‐ol, ent‐kaur‐16‐en‐19‐oic acid, ent‐kaur‐16‐en‐19‐ol, and ent‐trachyloban‐18‐oic acid. The structures were established by IR, HR‐ESI‐MS, and NMR data analysis with the aid of 2D techniques.     

New Polyoxygenated Triterpenoids from Stachyurus himalaicus var. himalaicus

Two new polyoxygenated triterpenoids, stachlic acid A (= (2α,3β)‐2,3,23,29‐tetrahydroxyolean‐12‐en‐28‐oic acid; 1 ) and stachlic acid B (= (2α,3α)‐2,29‐dihydroxy‐3,23‐[(1,1‐dimethylmethylene)dioxy]olean‐12‐ene‐28‐oic acid; 2 ), were isolated from Stachyurus himalaicus var. himalaicus. Their structures were established by means of extensive spectroscopic studies and chemical evidence. The purified product 1 was found to have moderate in vitro cytotoxic activity against human Hela cells.     

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.     

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.     

Triterpenoids and Iridoid Glycosides from Gentiana dahurica

One new and six known pentacyclic triterpenoids, 1 and 4 – 9 , resp., along with two new and three known iridoid glycosides, 2 and 3 , and 10 – 12 , resp., were isolated from the roots of Gentiana dahurica (‘Qin‐Jiao’). The new structures were elucidated by means of spectroscopic and chemical methods as 1β,2α,3α,24‐tetrahydroxyursa‐12,20(30)‐dien‐28‐oic acid ( 1 ), 6′‐O‐acetylgentiopicroside ( 2 ), and 3′‐acetylgentiopicroside ( 3 ). Isolated compounds were tested for their cytotoxicity against the MCF‐7 human breast cancer cell line using the MTT assay. Among them, triterpenoids 2α,3β,24‐trihydroxyurs‐12‐en‐28‐oic acid ( 6 ) and 3β,24‐dihydroxyurs‐12‐en‐28‐oic acid ( 9 ) were found to have moderate cytotoxic effects with IC₅₀ values of 20.9 and 21.7 μg/ml, respectively. Additionally, the chemotaxonomic significance of the identified secondary metabolites is briefly discussed.     

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.).     

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.     

Triterpenoid Saponins from the Spikes of Prunella vulgaris

Three new oleanane‐skeleton triterpenoid saponins, 3β,4β,16α‐17‐carboxy‐16,24‐dihydroxy‐28‐norolean‐12‐en‐3‐yl 4‐O‐β‐D ‐xylopyranosyl‐β‐D ‐glucopyranosiduronic acid ( 1 ), (3β,4β,16α)‐17‐carboxy‐16,24‐dihydroxy‐28‐norolean‐12‐en‐3‐yl β‐D ‐glucopyranosiduronic acid methyl ester ( 2 ), and (3β,4β)‐24‐hydroxy‐16‐oxo‐28‐norolean‐12‐en‐3‐yl 4‐O‐β‐D ‐xylopyranosyl‐β‐D ‐glucopyranosiduronic acid ( 3 ), together with eight known constituents, i.e., the oleanane‐type triterpenoids 4 – 6 , and the ursane‐type triterpenoids 7 – 11 , were isolated from the spikes of Prunella vulgaris. The new structures were established by means of detailed spectroscopic analysis (IR, HR‐ESI‐MS, 1D‐ and 2D‐NMR experiments). Compounds 1 – 3 were tested for their inhibition activity against the growth of tumor cell lines; only compound 3 displayed marginal inhibition activity.     

New ent‐Pimarane Diterpenes from the Roots of Aralia dumetorum

Four new ent‐pimarane diterpenes were isolated from the EtOH extract of Aralia dumetorum, together with three known compounds involving ent‐pimar‐8(14),15‐dien‐19‐oic acid ( 5 ), ent‐pimar‐8(14),15‐dien‐19‐ol ( 6 ), and ent‐kaur‐16‐en‐19‐oic acid ( 7 ). By detailed analyses of the MS, IR, and NMR data, the structures of four new diterpenes were characterized as (5β,9β,10α,13α)‐pimara‐6,8(14),15‐trien‐18‐oic acid ( 1 ), (5β,7β,9β,10α,13α)‐7‐methoxypimara‐8(14),15‐dien‐18‐oic acid ( 2 ), (5β,9β,10α,13α,14β)‐14‐methoxypimara‐7,15‐dien‐18‐oic acid ( 3 ), and (5β,10α,13α,14α)‐14‐hydroxypimara‐7,9(11),15‐trien‐18‐oic acid ( 4 ). The cytotoxic activities of compounds 1  –  7 were assayed in vitro through MTT method.     

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 ).     

Triterpenoids from the Mangrove Plant Hibiscus tiliaceus

Three new triterpenoids with the rarely occurring nigrum skeleton, namely (20E)‐22‐hydroxynigrum‐20‐en‐3‐one ( 1 ), 21β‐hydroxynigrum‐22(29)‐en‐3‐one ( 2 ), and 21α‐hydroxynigrum‐22(29)‐en‐3‐one ( 3 ), were isolated from the mangrove plant Hibiscus tiliaceus. Additionally, five known triterpenoids including friedelin ( 4 ), 12‐oleanen‐3β‐ol ( 5 ), 3β‐hydroxy‐12‐oleanen‐28‐oic acid ( 6 ), 20(29)‐lupen‐3β,28‐diol ( 7 ), and cucurbita‐5,23‐dien‐3β,25‐diol ( 8 ) were also isolated and identified. The latter structures were elucidated by a detailed NMR and MS analyses, as well as by comparison with reported literature data.     

Two New Diterpenoids from Callicarpa pedunculata

Two new diterpenoids, pedunculatic acid A (= (4R,5α,7α)‐7‐ethoxy‐9β,13β‐dioxyabiet‐8(14)‐en‐18‐oic acid; 1 ) and pedunculatic acid B (= (4S,5α,12β)‐8β,14β‐epoxy‐12‐hydroxy‐11‐oxototaran‐19‐oic acid; 2 ), together with three known sesquiterpenoids, were isolated from the Chinese medicinal herb Callicarpa pedunculata R. Brown . Their structures were elucidated by spectroscopic analyses, including 1D‐ and 2D‐NMR, and by high‐resolution mass spectrometry.     

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.     

Chemical Constituents from Annona Glabra

A new kaurane diterpenoid, annoglabasin G (16α‐hydro‐19‐acetoxy‐ent‐kauran‐17‐al) ( 1 ), along with 27 compounds including 18 kaurane diterpenoids, 16β‐hydro‐ent‐kauran‐17‐oic acid ( 2 ), 16α‐hydro‐ent‐kauran‐17‐oic acid ( 3 ), 19‐nor‐ent‐kauran‐4α‐ol‐17‐oic acid ( 4 ), 16α‐hydro‐19‐ol‐ent‐kauran‐17‐oic acid ( 5 ), ent‐kaur‐16‐en‐19‐oic acid ( 6 ), 16α‐hydroxy‐ent‐kauran‐19‐oic acid ( 7 ), 16α,17‐dihydroxy‐ent‐kauran‐19‐oic acid ( 8 ), 16β,17‐dihydroxy‐ent‐kauran‐19‐oic acid ( 9 ), 16α‐hydro‐ent‐kauran‐17,19‐dioic acid ( 10 ), 16β‐hydroxy‐17‐acetoxy‐ent‐kauran‐19‐oic acid ( 11 ), 16β‐hydro‐17‐hydroxy‐ent‐kauran‐19‐al ( 12 ), 16α‐hydro‐17‐hydroxy‐ent‐kauran‐19‐al ( 13 ), 16β,17‐dihydroxy‐ent‐kauran‐19‐al ( 14 ), 16α‐hydro‐19‐al‐ent‐kauran‐17‐oic acid ( 15 ), 16α‐hydro‐17‐acetoxy‐ent‐kauran‐19‐al ( 16 ), 16α‐hydro‐19‐acetoxy‐ent‐kauran‐17‐oic acid ( 17 ), ent‐kaur‐15‐en‐19‐oic acid ( 18 ) and ent‐kaur‐15‐en‐17‐ol‐19‐oic acid ( 19 ); four acetogenins, annomontacin ( 20 ), annonacin ( 21 ), isoannonacinone ( 22 ) and squamocin ( 23 ); four steroids, β‐sitosterol ( 24 ), stigmasterol ( 25 ), β‐sitosteryl‐D‐glucoside ( 26 ) and stigmasteryl‐D‐glucoside ( 27 ) and one oxoaporphine, liriodenine ( 28 ), were isolated from the fresh fruits of Annona glabra. These compounds were characterized and identified by physical and spectral evidence.