Sesquiterpene lactones from Saussurea alata

Two new guaianolides, namely, 3beta,8alpha-dihydroxy-13-methoxyl-4(14),10(15)-dien-(1alphaH,5alphaH,6beta H,11betaH)-12,6-olide (1) and 3beta,8alpha-dihydroxy-13-methoxyl-4(14),10(15)-dien-(1alphaH,5alphaH,6beta H,11alphaH)-12,6-olide (2), together with six known guaianolides, 8-hydroxyzaluzanin C, austricin, chlorojanerin, cynaropicrin, chlorohyssopifolin E and chlorohyssopifolin A were isolated from the aerial parts of Saussurea alata. The structures were established mainly based on spectral analysis, especially 2D NMR techniques.     

Sesquiterpenoid alkaloid from Acroptilon repens

One new sesquiterpenoid alkaloid, namely 3 beta,8 alpha-dihydroxy-13-pyrrolidine-4(15),10(14)-(1 alpha H,5 alpha H,6 beta H,11 beta H)-guaiadien-12,6-olide (1), together with two known guaiane-type sesquiternoids (2-3) was isolated from the aerial part of Acroptilon repens. The structure of 1 was established by spectroscopic methods, especially 2D NMR (HMQC, HMBC, and NOESY). Cytotoxic activity against tumor cell line was assessed for compounds 2-3, and found to show potent cytotoxic activities against tumor cell line P-388.     

A cytotoxic and apoptosis-inducing sesquiterpenoid isolated from the aerial parts of Artemisia princeps PAMPANINI (Sajabalssuk)

Repeated silica gel and octadecyl silica gel (ODS) column chromatography of the aerial parts of Artemisia princeps PAMPANINI (Sajabalssuk) led to the isolation of a new sesquiterpenoid, 3-((S)-2-methylbutyryloxy)-costu-1(10),4(5)-dien-12,6 alpha-olide (2), along with two previously reported sesquiterpenoids: 8 alpha-angeloyloxy-3beta,4 beta-epoxy-6 beta H,7 alpha H,8 beta H-guaia-1(10),11(13)-dien-12,6 alpha-olide (1, carlaolide B) and 3beta,4 beta-epoxy-8 alpha-isobutyryloxy-6 beta H,7 alpha H,8 beta H-guaia-1(10),11(13)-dien-12,6 alpha-olide (3, carlaolide A). The structure of compound 2 was elucidated by spectroscopic data analysis, including one dimensional (1D) and two dimensional (2D) nuclear magnetic resonance (NMR) experiments. Of the isolates, compound 2 exhibited potent cytotoxicity against human cervix adenocarcinoma cells and induced apoptosis.     

Complete 1H and 13C NMR assignments of sesquiterpene glucosides from Ixeris sonchifolia

Four sesquiterpene glucosides were isolated from Ixeris sonchifolia Hance. The structure of a new compound (1) was assigned as 9beta-monohydroxy-2,12-dioxo-guaia-3,11(13)-dien-1alpha,5alpha,6beta,7alpha,9beta,10alphaH-12,6-olide-9-O-beta-D- glucopyranoside (ixerinoside). In addition, unambiguous and complete assignments of (1)H NMR chemical shifts for crepidiaside A (2), ixerin Z (3), and 11,13alpha-dihydroixerin Z (4) are presented. The assignments were achieved by two-dimensional NMR (gCOSY, gHSQC, gHMBC, NOESY) and one-dimensional nuclear Overhauser effect (NOE) experiments.     

Sesquiterpene lactones from Crepis cameroonica (Asteraceae)

In addition to one known compound, 3beta,8alpha-dihydroxyguaian-4(15),10(14),11(13)-trien-6,12 olide (8-desacylcynaropicrin) (3), two new sesquiterpene lactones have been isolated from the aerial parts of Crepis cameroonica. By means of spectroscopic analysis, the structures and relative configurations of the new compounds were established as 3beta,9beta-dihydroxyguaian-4(15),10(14),11(13)-trien-6,12 olide (1) and 8alpha-hydroxy-4alpha(13),11beta(15)-tetrahydrozaluzanin C (2). The in vitro antimicrobial spectrum of pure compounds and crude extracts are also reported.     

Complete assignments of 1H and 13C NMR spectral data for three sesquiterpenoids from Inula helenium

The complete assignments of all the (1)H and (13)C NMR signals of three sesquiterpene lactones, 4-oxo-5(6),11-eudesmadiene-8,12-olide (1), 4-oxo-11-eudesmaene-8,12-olide (2) and (1(10)E)-5beta-Hydroxygermacra-1(10),4(15),11-trien-8, 12-olide (3), were carried out by various 2D NMR experiments. Compounds 1-3 were isolated from the roots of Inula helenium for the first time. Among them, 1 was identified as a new nor-sesquiterpene lactone, and 2 was isolated from a natural source for the first time. The (13)C-NMR data of compound 3 was also reported for the first time.     

Two New Diterpenoids from Hedychium forrestii

Two new labdane diterpenes isolated from the rhizomes of Hedychium forrestii were determined by spectroscopic evidence to be labda-8(17), 11, 13-trien-7β-hydroxyl- 15(16)-olide (1,hedyforrestin B) and labda-8(17), 11, 13-trien-7β,16-dihydroxyl-16(15)-olide (2, hedyforrestinC).     

Terpenoids of Crepis tectorum. Molecular and crystal structure of the sesquiterpene lactone 8-epideacylcynaropicrin

Sesquiterpene lactones of the guaianolide type — isolipidiol (I) and 8-epideacylcynaropicrin (II) — have been isolated from narrow-leaf hawk's-beard,Crepis tectorum L. On the basis of the results of an x-ray experiment the structure of (1R, 3S, 5R, 6R, 7R, 8R)-3,8-dihydroxy-cis,trans-guaia-4(15),10(14),-11(13)-trien-6,12-olide is proposed for (II).     

Labdane diterpenes from the rhizomes of Hedychium coronarium

A new labdane diterpenoid, (E)-labda-8(17),12-dien-15,16-olide (1) together with eight known compounds, coronarin D (2), coronarin D methyl ether (3), coronarin D ethyl ether (4), isocoronarin D (5), coronarin B (6), labda-8(17),11,13-trien-15,16-olide (7), (E)-labda-8(17),12-diene-15,16-dial (8) and 16-hydroxylabda-8(17),11,13-trien-15,16-olide (9), are isolated from the rhizomes of Hedychium coronarium. Compounds 2-4, 5 and 9 are isolated as mixtures of C-15, C-14 and C-16 epimers, respectively. Their structures are determined on the basis of their spectroscopic data. The epimeric mixtures of 2 and 3 have not been reported before. Some of them were evaluated for their cytotoxicity.     

Labdane-type diterpenoids from the rhizomes of Hedychium coronarium inhibit lipopolysaccharide-stimulated production of pro-inflammatory cytokines in bone marrow-derived dendritic cells

The rhizomes of Hedychium coronarium have been used for the treatment of inflammation, skin diseases, headache, and sharp pain due to rheumatism in traditional medicine. From this plant, two new labdanes, 15-methoxylabda-8(17),11E,13-trien-16,15-olide (1) and 16-methoxylabda-8(17),11E,13-trien-15,16-olide (3), named hedycoronens A and B, as well as four known, labda-8(17),11,13-trien-16,15-olide (2), 16-hydroxylabda-8(17),11,13-trien-15,16-olide (4), coronarin A (5), and corronarin E (6) were isolated. Their chemical structures were elucidated by mass, 1D- and 2D-nuclear magnetic resonance (NMR) spectroscopy. They were evaluated for inhibitory effects on the lipopolysaccharide (LPS)-stimulated production of pro-inflammatory cytokines in bone marrow-derived dendritic cells. Among of them, compounds 1-3 were potent inhibitors of LPS-stimulated interleukin-6 (IL-6) and IL-12 p40, with IC(50) ranging from 4.1±0.2 to 9.1±0.3?μM. Compounds 1 and 3 showed moderate inhibitory activity on the tumor necrosis factor-α (TNF-α) production with IC(50) values of 46.0±1.3 and 12.7±0.3?μM. The remains of compounds showed inactivity. These results warrant further studies concerning the potential anti-inflammatory benefits of labdane-diterpenes from H. coronarium.     

Two New Sesquiterpenes from Eupatorium lindleyanum

Various germacrane sesquiterpenes have been isolated from many species of the Eupatorium.In recent years these compounds have been increasing interest due to their insecticidal,cytotoxic,antitumor-promoting and insect-antifeedant activities1.In our present study,we have investigated the chemical constituents of Eupatorium lindleyanum DC.,which is a geo-authentic medicine of Jiangsu province.It is used as a antipyretic drug.Two novel germacrane sesquiterpenes(Figure1)were found by us from th…     

Further cytotoxic sesquiterpene lactones from Elephantopus mollis KUNTH

Three new sesquiterpene lactones, (4betaH)-5alpha-hydroxy-8alpha-(2-methylbut-2-enoyloxy)-2-oxo-1(10),11(13)-guaiadien-12,6alpha-olide (1), (4betaH)-8alpha-(2-methylbut-2-enoyloxy)-2-oxo-1(5),10(14),11(13)-guaiatrien-12,6alpha-olide (2) and 2,5-epoxy-2beta-hydroxy-4alpha-methoxy-8alpha-(2-methylbut-2-enoyloxy)-4(15),10(14),11(13)-germacratrien-12,6alpha-olide (3), have been isolated from roots and stems of Elephantopus mollis together with two known sesquiterpene lactones (4, 5). The identification of the isolates was accomplished by spectroscopic methods. Compounds (1-5) exhibited significant cytotoxic activities against mouse neuroblastoma B104 cells.     

A new pyrrolidine derivative and steroids from an algicolous Gibberella zeae strain

A new pyrrolidine derivative, 3-hydroxy-5-(hydroxymethyl)-4-(4'-hydroxyphenoxy)pyrrolidin-2-one (1), and eight known steroids, (22E,24R)-7beta,8beta-epoxy-3beta,5alpha,9alpha-trihydroxyergosta-22-en-6-one (2, a reassigned structure of (22E,24R)-5alpha,6alpha-epoxy-3beta,8beta,14alpha-trihydroxyergosta-22-en-7-one), (22E,24R)-3beta,5alpha,9alpha-trihydroxyergosta-7,22-dien-6-one (3), (22E,24R)-3beta,5alpha-dihydroxyergosta-7,22-dien-6-one (4), (22E,24R)-ergosta-7,22-dien-3beta/,5alpha,6beta-triol (5), (22E,24R)-ergosta-5,22-dien-3beta-ol (6), (22E,24R)-5alpha,8alpha-epidioxyergosta-6,22-dien-3beta-ol (7), (22E,24R)-5alpha,8alpha-epidioxyergosta-6,9(11),22-trien-3beta-ol (8), and (22E,24R)-1(10 --> 6)-abeo-ergosta-5,7,9,22-tetraen-3alpha-ol (9), were isolated from the cultures of Gibberella zeae, an endophytic fungus isolated from the marine green alga Codium fragile. Their structures and relative stereochemistry were elucidated by 1D, 2D NMR and mass spectroscopic techniques. Compound 1 showed cytotoxicity against A-549 and BEL-7402 cell lines.     

Five new diterpenoids from the bark of Taiwania cryptomerioides

Five new diterpenoids, 11-hydroxyabieta-8,11,13-trien-7-one (1), 11,12,14-trihydroxyabieta-8,11,13-trien-7-one (2), 6beta,7alpha-diacetoxyroyleanone (3), 7beta-hydroxymanoyl oxide (4), and 9alpha-hydroxyisopimara-8(14),15-dien-7-one (5) were obtained from the bark of Taiwania cryptomerioides. The structures of the new compounds 1-5 were elucidated on the basis of spectral analysis and chemical evidence.     

1H and 13C assignments of three new drimenes from Iresine diffusa Humb. & Bonpl. ex Willd

The structure elucidation and (1)H and (13)C assignments of iresin (1) and three new drimenes, 3beta,14-dihydroxy-Delta(7, 8)-drimen-11,12-acetonide (2), 3beta,7beta,14-trihidroxy-Delta(8, 9)-drimen-11,12-olide (3) and 3beta,7alpha,14-trihydroxy-Delta(8, 9)-drimen-11,12-olide (4), isolated from the aerial parts of the medicinal plant Iresine diffusa Humb. & Bonpl. ex Willd. are reported.     

Two new guaianolides from Amberboa ramosa

Two new sesquiterpene lactones named amberbins A (1) and B (2), have been isolated from the ethyl acetate soluble fraction of Amberboa ramosa, together with jaseocidine (3), crysoeriol (4) and 3beta,8alpha-dihydroxy-11alpha-methyl-1alphaH,5alphaH,6betaH, 7alphaH,11betaH-guai-10(14), 4(15)-dien-6,12-olide (5). The structures of the isolated compounds have been elucidated on the basis of their spectroscopic data.     

Cytotoxic diterpenoids from Vietnamese medicinal plant Croton tonkinensis GAGNEP

Six new ent-kaurane-type diterpenoids were isolated from the leaves of the endemic Vietnamese medicinal plant Croton tonkinensis GAGNEP. (Euphorbiaceae) together with three known ent-11alpha-acetoxy-7beta,14alpha-dihydroxykaur-16-en-15-one (1), ent-kaur-16-en-15-one 18-oic acid (5) and ent-18-hydroxykaur-16-ene (7). Their structures were determined by spectroscopic analyses to be ent-7beta-acetoxy-11alpha-hydroxykaur-16-en-15-one (2), ent-18-acetoxy-11alpha-hydroxykaur-16-en-15-one (3), ent-11alpha-acetoxykaur-16-en-18-oic acid (4), ent-15alpha,18-dihydroxykaur-16-ene (6), ent-11alpha,18-diacetoxy-7beta-hydroxykaur-16-en-15-one (8), and ent-(16S)-1alpha,14alpha-diacetoxy-7beta-hydroxy-17-methoxykauran-15-one (14). ent-Kaurane-type diterpenoids from Croton tonkinensis 2-4, 6, and 9-13, were tested for toxicity in the brine shrimp lethality assay. Compounds 9, 10, and 12 demonstrated significant activity, compounds 2, 3, 6, and 11 showed weak activity, and compounds 4 and 13 were inactive.     

Cytotoxicity of labdane-type diterpenoids from Hedychium forrestii

Two new labdane-type diterpenoids, hedyforrestin D (1) and 15-ethoxy-hedyforrestin D (2), and three known compounds, yunnancoronarin A (4), B (3) and C (5) were isolated from the rhizomes of Hedychium forrestii. The structure of the new diterpenoids was established as 6beta,15xi-dihydroxylabda-8(17),11,13-trien-15,16-olide (1), and 6beta-hydroxy-15xi-ethoxylabda-8(17),11,13-trien-15,16-olide (2) on the basis of spectroscopic analyses. In addition, the isolated compounds were evaluated for their cytotoxicity against the lung adenocarcinoma cells A549 and leukemia cells K562 through 3-[4,5-dimethylthiazol-2-yl]-2,5-diphenyltetrazolium bromide (MTT) assays. Of these, compounds 3 and 4 exhibited the most activity with IC(50) values of 0.92 and 2.20 microM, respectively, whereas 5 was inactive against A549 cells and 1 was inactive against both cell lines up to a concentration of 300.81 microM. This shows that both the hydroxy substitution and orientation of unsaturated lactone group in the five-membered ring of C-13 to C-16 seem to play an important role in the anti-tumor activities of human lung adenocarcinoma and leukemia.     

Novel Sesquiterpenoids from Siegesbeckia orientalis

Five new sesquiterpenoids, namely, 8β‐(angeloyloxy)‐4β,6α,15‐trihydroxy‐14‐oxoguaia‐9,11(13)‐dien‐12‐oic acid 12,6‐lactone ( 1 ), 4β,6α,15‐trihydroxy‐8β‐(isobutyryloxy)‐14‐oxoguaia‐9,11(13)‐dien‐12‐oic acid 12,6‐lactone ( 2 ), 11,12,13‐trinorguai‐6‐ene‐4β,10β‐diol ( 3 ), (1(10)E,4E,8Z)‐8‐(angeloyloxy)‐6α,15‐dihydroxy‐14‐oxogermacra‐(1(10),4,8,11(13)‐tetraen‐12‐oic acid 12,6‐lactone ( 9 ), and (1(10)E,4β)‐8β‐(angeloyloxy)‐6α,14,15‐trihydroxygermacra‐1(10),11(13)‐dien‐12‐oic acid 12,6‐lactone ( 11 ), and three new artifacts, (1(10)E,4Z)‐8β‐(angeloyloxy)‐9α‐ethoxy‐6α,15‐dihydroxy‐14‐oxogermacra‐1(10),4,11(13)‐trien‐12‐oic acid 12,6‐lactone ( 6 ), (1(10)E,4Z)‐8β‐(angeloyloxy)‐9α,13‐diethoxy‐6α,15‐dihydroxy‐14‐oxogermacra‐1(10),4‐dien‐12‐oic acid 12,6‐lactone ( 7 ), and (1(10)E,4Z)‐8β‐(angeloyloxy)‐9α‐ethoxy‐6α,15‐dihydroxy‐13‐methoxy‐14‐oxogermacra‐1(10),4‐dien‐12‐oic acid 12,6‐lactone ( 8 ), together with the three known sesquiterpenoids 4, 5 , and 10 , were isolated from the aerial parts of Siegesbeckia orientalis L. Their structures were established by spectral methods, especially 1D‐ and 2D‐NMR spectral methods.     

Terpenoids of Crepis tectorum. Molecular and crystal structure of the sesquiterpene lactone 8-epideacylcynaropicrin

Sesquiterpene lactones of the guaianolide type — isolipidiol (I) and 8-epideacylcynaropicrin (II) — have been isolated from narrow-leaf hawk's-beard,Crepis tectorum L. On the basis of the results of an x-ray experiment the structure of (1R, 3S, 5R, 6R, 7R, 8R)-3,8-dihydroxy-cis,trans-guaia-4(15),10(14),-11(13)-trien-6,12-olide is proposed for (II).Institute of Organic Synthesis and Coal Chemistry, Kazakh Academy of Sciences, Karaganda. A. N. Nesmeynaov Institute of Organometallic Compounds, Russian Academy of Sciences, Moscow. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 638–642, September–October, 1991.