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The present study describes the chemical and enantiomeric composition of a new essential oil, distilled from the dry leaves of Gynoxys buxifolia (Kunth) Cass. The chemical analysis was conducted by GC-MS and GC-FID, on two orthogonal capillary columns. A total of 72 compounds were detected and quantified with at least one column, corresponding to about 85% by weight of the whole oil mass. Of the 72 components, 70 were identified by comparing the respective linear retention indices and mass spectra with data from the literature, whereas the two main constituents were identified by preparative purification and NMR experiments. The quantitative analysis was carried out calculating the relative response factor of each compound according to their combustion enthalpy. The major constituents of the EO (≥3%) were: furanoeremophilane (31.3–28.3%), bakkenolide A (17.6–16.3%), caryophyllene oxide (6.0–5.8%), and (E)-β-caryophyllene (4.4%). Additionally, the hydrolate was also analyzed with respect to the dissolved organic phase. About 40.7–43.4 mg/100 mL of organic compounds was detected in solution, of which p-vinylguaiacol was the main component (25.4–29.9 mg/100 mL). Finally, the enantioselective analysis of some chiral terpenes was carried out, with a capillary column based on β-cyclodextrin chiral stationary phase. In this analysis, (1S,5S)-(−)-α-pinene, (1S,5S)-(−)-β-pinene, (S)-(+)-α-phellandrene, (S)-(+)-β-phellandrene, and (S)-(−)-terpinen-4-ol were detected as enantiomerically pure, whereas (S)-(−)-sabinene showed an enantiomeric excess of 69.2%. The essential oil described in the present study is a good source of two uncommon volatile compounds: furanoeremophilane and bakkenolide A. The former lacks bioactivity information and deserves further investigation, whereas the latter is a promising selective anticancer product.

Chemical compositions and internal transcribed spacer (ITS) sequences of five samples of Ligularia lamarum collected in Sichuan Province, China, were analyzed. Fourteen compounds, including four new eremophilanes and one new seco-eremophilane, were isolated and their structures were elucidated by spectroscopic methods. Intra-specific diversity in the chemical composition was found to be higher than previously known. The result of DNA analysis suggested that one of the samples was introgressed, although its chemical composition was typical of L. lamarum., Phytochemistry Letters, 20, pp.139-145; 2017

The composition of root chemicals was examined for samples of L. cyathiceps × L. duciformis, L. duciformis × L. yunnanensis, and L. yunnanensis. Various furanoeremophilanes were isolated from a sample of L. cyathiceps × L. duciformis and found to be very similar to those isolated from L. cyathiceps. Lupeol and docosyl ferulate were isolated from L. yunnanensis, L. duciformis, and L. duciformis × L. yunnanensis.

The chemical composition of 3 samples of Ligularia dictyoneura was studied. Nine furanoeremophilanes 1 to 9 and bakkenolide A (10) were isolated, among which compound 6 was a new furanoeremophilane-15,6-olide. These results, together with our previous results on 20 L. dictyoneura samples, show that furanoeremophilane is the major compound in the peripheries of the plant’s distribution area, while eremophilan-8-one, in the center. DNA analysis suggests that a furanoeremophilane producer in the center, an exception, is introgressed; namely, the ability to produce furanoeremophilane in the sample may have its origin in some other plant.

The composition of root chemicals was studied for 7 samples of Ligularia tongolensis collected in Yunnan and Sichuan Provinces of China. The structures of 2 new 3β-angeloyloxy-6β-acyloxyfuranoeremophilan-15-oic acids were determined. It was found that the plant harbors chemical diversity in the acyloxy groups in 3,6-bis(acyloxy)eremophilan-15-oic acids. The presence of a 3-methylpentanoate moiety at C-3 appears geographically differentiated to a degree. Consistent with this low diversity, results of DNA analysis indicated little genetic differentiation, although introgression was inferred for one of the samples.

Two new furanoeremophilanes, 1α, 6α-epoxy-9-oxo-10β-hydroxyl-furanoeremophilane (1), and 9-oxo-1α, 6β, 10β-trihydroxy-furanoeremophilane (2) were isolated from Senecio nemorensis. Their structures were elucidated by spectroscopic methods and X-ray crystallography. This is the first report of the isolation of the C1-C6 oxygen bridge of furanoeremophilane. Their cytotoxic effects on BEL7402 and NF-KB cell lines were tested.

Root chemicals and DNA sequences were analyzed for Ligularia virgaurea collected in the northern Sichuan Province and adjacent areas of China. Thirty-eight samples were found to contain five chemotypes, two known and three new ones. From samples of the new chemotypes, 13 new compounds were isolated, including 3 sesquiterpene dimers and some rearranged eremophilanes. The DNA sequences suggested that the chemotype differentiation had a genetic origin. (C) 2012 Elsevier Ltd. All rights reserved.

Chemical and genetic study of Ligularia anoleuca and L. veitchiana, which belong to section Ligularia, series Speciosae, was carried out. From L. anoleuca samples, collected in Yunnan and Sichuan Provinces of China, a new compound, furanoeremophil-1(10)-en-6 alpha-ol, was isolated together with known 6 beta-{[2-(hydroxymethyl)prop-2-enoyl]oxy}furanoeremophil-1(10)-ene and 1 beta,10 beta-epoxy-6 beta-{[2-(hydroxymethyl)prop-2-enoyl]oxy}furanoeremophilane. From L. veitchiana samples, collected in Yunnan Province, euparin, 2-isopropenyl-5,6-dimethoxybenzofuran, and 6-hydroxy-3 beta-methoxytrementone were isolated. DNA Sequencing of the internal transcribed spacers of the ribosomal RNA gene showed that the two species are not particularly close despite morphological similarities, in agreement with the chemical results.

The chemical composition of the root extract and neutral base sequences of L. hodgsonii samples collected in Japan and China were examined. From the Japanese and the Chinese samples, 6 beta-(angeloyloxy)furanoeremophilan-15-oic acid (2) and 3 beta-acetoxy-6 beta-[(2-methyl butanoyl)oxy]furaneremophilan-10 beta-ol (3) were isolated as the major component, respectively. The sequence of the internal transcribed spacers (ITSs) of the ribosomal RNA gene was different in the Japanese and the Chinese samples. In contrast to the significant genetic difference, chemical diversity was limited to the positions of O-functionalities on the furanoeremophilane skeleton, supporting our hypothesis that the production of furanocremophilanes is ecologically advantageous

Twenty-six eremophilane-type sesquiterpenoids, including six new compounds, were isolated from the title species. One of the new compounds, kanaitzensol, suggested the presence of an enzyme for the conversion of eremophil-7(11)-en-8-one derivative to furanoeremophilanes. The plant was collected at 15 locations in Yunnan Province of China and found to be diverse with respect to its sesquiterpenoid composition. DNA sequencing also revealed a large intraspecific diversity of the plant. (c) 2008 Elsevier Ltd. All rights reserved.

Diels–Alder reaction of furanoeremophilan-6β-ol (petasalbin) and its synthetic analogue, 4-hydroxy-4,5,6,7-tetrahydrobenzofuran, was studied using N-ethyl- and N-phenylmaleimides as the dienophiles...

Ligularia hodgsonii was found to be diverse in China. Furanoeremophilanes were isolated from samples collected in Yunnan Province, while such compounds were absent from samples from Sichuan, Gansu, and Chongqing. DNA sequencing showed that the Yunnan samples were also genetically distinct. γ-Humulene and a new bisabolane sesquiterpene were isolated.

Three Ligularia species (L. tongolensis, L. cymbulifera, and L. atroviolacea) were examined with respect to the chemical composition and nucleotide sequence. Furanoeremophilanes were found to be produced in the root of all samples of the three species collected in northwest Yunnan and southwest Sichuan. Eight furanoeremophilanes were identified, two of which were new. Most of the identified furanoeremophilanes were oxygenated at 3, 6, and 15-positions. The nucleotide sequence of the atpB-rbcL intergenic region was found to be essentially the same in the three species. These similarities imply that the three Ligularia species, all belonging to the section Corymbosae, are close to one another. The intra-specific diversity in the two widely distributed species in the Hengduan Mountains area, L. tongolensis and L. cymbulifera, were in contrast. Four out of 19 L. tongolensis samples contained a strongly Ehrlich-positive compound besides a number of positive compounds, and five variants of the atpB-rbcL sequence were found in these samples. In contrast, no variation was observed in 13 L. cymbulifera samples with respect to the furanoeremophilane composition or the atpB-rbcL sequence. The lack of diversity in L. cymbulifera probably resulted from the uniformity of its habitat.

Two new naturally occurring sesquiterpenes (1 and 3) along with a known sesquiterpene (2) were isolated from Vitex negundo L. stem. 13C NMR data of 2 are also reported in the present study as it was not reported. Structures of compounds were elucidated by NMR spectroscopy and their stereochemistries were established by X-ray diffraction.

The chemical composition of a sample of the title species collected in Pianma, Lushui County, Yunnan Province of China, was examined. Two 3,6,10-oxygenated and two 3,6-oxygenated furanoeremophilanes were isolated. Structures of two new compounds were elucidated. The 3,6-oxygenated furanoeremophilanes were not detected in a sample of the same species previously collected in Laojunshan, Jianchuan County, Yunnan, indicating chemical diversity in the species.

From the roots of Ligularia cymbulifera collected in Yunnan Province, China, two new eremophilane-type sesquiterpenoids (1 and 2) together with ten known compounds (3–12) were obtained through the precise chemical component elucidation. The structure determination was mainly carried out with 1D and 2D NMR data.

Ligularol (1), a furanoeremophilane, was isolated together with eremophil-1(10)-en-11-ol (2) from one of eight collected samples of Ligularia nelumbifolia and L. kongkalingensis, a closely related species. It is proposed that the ability to produce the furanoeremophilane has been acquired through hybridization.

The aerial parts of Senecio flavus contain besides known eremophilane derivatives, four new furanoeremophilanes oxidized at C-3 and a new eremophilenone lactam. The rhizomes of the plant also contain the same ketoeremophilenes found in the aerial parts and a new epoxyeremophilanolide. The structure of these compounds has been established by spectroscopic methods.

The sesquiterpenoid composition in the root and the DNA sequences of evolutionarily neutral regions were studied in Ligularia anoleuca and Ligularia fischeri (Asteraceae) collected in the Sichuan Province of China. LC-MS analysis showed that L anoleuca populations from different localities had different chemical compositions. However, the isolated compounds were similar to each other, indicating that the differences in chemical composition were not large. The DNA analysis suggested that the two species were indistinguishable. Seventeen furanoeremophilanes and an eremophilane acetal were isolated. (C) 2014 Elsevier Ltd. All rights reserved.

The chemical and genetic diversity of Ligularia species in the Hengduan Mountains area of China is reviewed. A hypothesis that the production of furanoeremophilanes is ecologically advantageous is proposed.

Senecio species have been used in folk medicine for treatment of wounds, as antiemetic, antiinflammatory and their crude extract or dry powder as crop protection agents. The toxicity exhibited to livestock by these plants has been attributed to their content in pyrrolizidine alkaloids and furanoeremophilane type sesquiterpenes. Sesquiterpenoids with eremophilane, cacalol, bisabolane, silphinene, caryophillane, humulane, germacrane and benzofurane skeletons have been isolated from this genus. Here we focus on bioactive sesquiterpenoids with plant defensive properties isolated from Senecio., This work has been partially supported by a MICINN (CTQ2009-14629-C01) grant and A.G. Portero by a JAE-CSIC predoctoral fellowship.

The aerial parts of Senecio flavus contain besides known eremophilane derivatives, four new furanoeremophilanes oxidized at C-3 and a new eremophilenone lactam. The rhizomes of the plant also contain the same ketoeremophilenes found in the aerial parts and a new epoxyeremophilanolide. The structure of these compounds has been established by spectroscopic methods.

Investigation of the aerial parts and roots of Ecuadorian Senecio canescens afforded in addition to known furanoeremophilanes the first natural furanoeremophilane hydroperoxide and two new cacalohastine derivatives, one of which is a dimer. The volatile fraction was analysed by GC and GC-mass spectrometry.

A chemical study of Psacalium sinuatum afforded the furanoeremophilane decompostine, the modified eremophilanes: cacalol, cacalol acetate, dehydrocacalol, maturinin, cacalohastin, dehydrocacalohastin, adenostin B, cacalone-epi-cacalone mixture, dimaturin, adenostylide, radulifolin F, and epi-radulifolin F, in addition to hyperin, sucrose and a mixture of sitosterol-stigmasterol. Extracts and isolated compounds were tested for anti-inflammmatory activity. The hexanic extract of root showed a dose dependent activity (IC50 0.20 mg/ear).

Pairs of the skeletal isomers of eremophilane-type lactones were synthesized from furanofukinol via photosensitized oxygenation, followed by lactone cleavage and reformation. Their stereochemistry has been clarified so as to be consistent with a classification method outlined in our earlier papers.

Using established procedures, volatile components of cooked scorzonera were analysed for the first time. A total of 114 components ( ca 74% of the isolate) was positively identified, and a further 43 components ( ca 24%) were partially characterized. Eight aliphatic acids and 32 aliphatic hydrocarbons represented the two most abundant chemical classes, comprising 30.6 and 26.9% respectively of the isolate. The single most abundant component was hexadecanoic acid at 22.1%. Of greater relevance are the 40 sesquiterpenoids at a combined level of 20.3%, which included some furanoeremophilane derivatives.

A new furanoeremophilane, 1alpha-chloro-6beta-isobutyroxy-9-oxo-10beta-hydroxy-furanoeremophilane (1) was isolated from the root of Ligularia atroviolacea and identified mainly on the basis of detailed spectral analyses including X-ray. Moreover, five known furanoeremophilanes,1alpha-hydroxy-6beta-isobutyroxy-9-oxo-10beta-H-furanoeremophilane (2), 1alpha-hydroxy-6beta-isobutyroxy-9-oxo-10alpha-H-furanoeremophilane (3), 1alpha,10beta-dihydroxy-6beta-angeloyloxy-9-oxo-furanoeremophilane (4), furanoeremophil-3-en-15,6alpha-olide (5) and furanoeremophil-15beta,6alpha-olide (6) were isolated from the same source.

In an attempt to explore the biogenetic relationship of furanoeremophilane derivatives and eremophilan-8 alpha, 12-olides, produced in Ligularia and their structure-activity relationship, we studied the photosensitized oxidation of furanoeremophilane - type sesquiterpenes. Under the condition of several solvents solution Irradiation with a 200 W incandescent lamp of furanoeremophilan-14 beta,6 alpha-olide isolated from Ligularia vellerea, in various solutions with methylene blue, rose bengal, toluidine blue and safranine T gave several products. The products were isolated by chromatographic procedure and their structures were elucidated as eremophilan-14 beta,6 alpha,8 alpha,12-diolide derivatives by NMR, IR and MS methods. A reaction mechanism has been proposed.

[reaction: see text] 13-Hydroxy-14-nordehydrocacalohastine (2) and 13-acetoxy-14-nordehydrocacalohastine (3), two novel modified furanoeremophilane-type sesquiterpenes isolated from Trichilia cuneata, showed inhibitory activities for membrane lipid peroxidation in mitochondria and microsomes. The first, highly convergent total syntheses of new compounds 2 and 3 have also been achieved via a palladium-mediated three-component coupling reaction between 2-iodotoluene (7), 1-penten-4-yn-3-ol (8), and diethyl ethoxymethylenemalonate (9).

6-Ethoxyfuranoeremophilane and its synthetic analogue, 4-ethoxy-4,5,6,7-tetrahydrobenzofuran, reacted with p-dimethylaminobenzaldehyde (Ehrlich's reagent) under acidic conditions in a 2:1 ratio to afford condensation products in 34% and 78% yields, respectively, 6-Hydroxyfuranoeremophilane and 4-hydroxy-4,5,6,7-tetrahydrobenzofuran afforded the same products as in the case of ethoxy derivatives, respectively. The intermediate 1:1 adduct was not obtained from 6-ethoxyfuranoeremophilane, but obtained from the synthetic analogue in low yield. It was deduced that the colored compound in Ehrlich's test is the cationic species of the intermediate 1:1 adduct, and that the concentration of the colored intermediate in the reaction mixture is very low.

A new modified furanoeremophilane type sesquiterpene, (+)-14-methoxy-1,2-dehydrocacalol methyl ether (2), isolated from Trichilia cuneata exhibited inhibitory activity for mitochondrial lipid perox...

The naturally occurring furanoeremophilane 6[small beta]-hydroxyeuryopsin was synthesized by a novel route which involved Stille coupling of a 2-furylstannane with a cyclohexylmethyl bromide, followed by intramolecular formylation of the furan to complete the tricyclic nucleus of the sesquiterpenoid.

Together with seven known sesquiterpenes, a new guaiane, a new furanoeremophilane, and a new eudesmane were isolated from the roots of Ligularia veitchiana. Their structures were elucidated by spectroscopic methods. The bioactivities of three known guaiane sesquiterpenes were determined.

A new modified furanoeremophilane type sesquiterpene, (+)-14-methoxy-1,2-dehydrocacalol methyl ether (2), isolated from Trichilia cuneata exhibited inhibitory activity for mitochondrial lipid perox...

The recent findings of antihyperglycemic and antimicrobial activities for a modified furanoeremophilane sesquiterpene cacalol (1) prompted us to achieve the first total synthesis of five cacalol fa...

From the roots of Ligularia oligonema and an unidentified sample of Ligularia collected in Yunnan Province of China, two new sesquiterpenoids, 3 beta-acetoxy-6 beta-(2-methylbutyryloxy)furanoereinophilan-10 beta-ol and 3 beta-acetoxy-6 beta-isobutyryloxyfuranoeremophilan-10 beta-ol, were isolated. DNA sequencing showed that the unidentified sample was likely to be L. oligonema. In addition, the DNA data suggested that the chemical evolution among L. oligonema and related Ligularia species is rather complex.

Three new eremophilanes (1-3) and a new oplopane (4) were isolated from Pittocaulon bombycophole. Additionally, three known sesquiterpenes (5-7) and the alkaloid 7-angeloylplatynecine (8) were isolated. The structures of the new compounds were elucidated by spectroscopic methods.

Reaction of 4,5,6,7-tetrahydrobenzofuran derivatives, model compounds of furanoeremophilanes, with p-dimethylamino-benzaldehyde (Ehrlich's reagent) under acidic conditions was studied both on TLC and in a flask. 4-Hydroxy, 4-methoxy, and 4-acetoxy derivatives showed a pink/purple color, while 7-hydroxy, 7-methoxy, and 7-acetoxy derivatives showed a dark green color. The reaction of a 4-oxo derivative was slow showing an orange color on TLC. 7-Oxo derivatives and benzofuran were negative to Ehrlich's test. It was shown that an intermediate cation corresponding to the pink color was generated from both 4- and 7-substituted derivatives except for the oxo-derivatives.

The investigation of two further Senecio species and the re-investigation of S. inaequidens afforded, in addition to known compounds, seven new furanoeremophilane derivatives. Six of these are closely related to cacalol, a sesquiterpene type which predominates in the species investigated.

Three new furanosesquiterpenes have been isolated from Ligularia japonica LESS., and their structures including absolute configurations have been determined as furanoeremophilane-6β-diol (1), 10β-hydroxyfu-ranoeremophilan-6β-yl 2′ξ-methylbutanoate (2), and 10β-hydroxy-6β-methoxyfuranoeremophilane (3).

Mass spectral fragmentations of furanoeremophilane derivatives bearing oxygen-function on B ring were investigated. It was found that mass spectra measured by direct inlet system gave characteristic retro-Diels-Alder fragmentations, while indirect introduction of the samples afforded intense peaks at m/e 159 and m/e 145 containing the furan moiety. Fragmentation patterns of other poly-functional derivatives were examined by measurements of accurate masses and metastable ions.

The investigation of two further Senecio species afforded two new furanoeremophilanes, four eremophilanolides and a new hydroxyeremophilane. The structures of two furanoeremophilane, isolated before, have been revised.

Die Untersuchung weiterer Othonna-Arten ergibt 23 neue Furanoeremophilane (2–6, 10–14, 17–23, 30, 32–34, 36 und 37), deren Strukturen durch spektroskopische Daten sowie durch einige Reaktionen geklart werden. Erneut bestatigt sich, das die Gattung Othonna durch relativ stark oxidierte Furanoeremophilane charakterisiert ist, die offenbar stets eine cis-Ringverknupfung besitzen. Naturally Occurring Terpene Derivatives, LVII. Further Furanoeremophilanes from Othonna Species The investigation of further Othonna species yields 23 new furanoeremophilanes (2–6, 10–14, 17–23, 30,32–34, 36, and 37). Their structures have been elucidated by spectroscopic data and some reactions. Once again it has been established that the genus Othonna is characterized by relatively strong oxidated furanoeremophilanes, which obviously always have cis-fused rings.

Total syntheses of (±)-furanoeremophilane (34), (±)-furanoligularane (37), (±)-9, 10-dehydrofuranoeremophilane (32), (±)-ligularone (1), (±)-3β-hydroxyfuranoeremophilane (25), and (±)-3β-furanoligularanol (31) are described. Reduction of cis-annulated 6, 9-dioxo-3-ketal (9) with NaBH4 gave ketols (10a and 11a). 11a was desketalized and subjected to selective reduction with P-I2 to give 3, 6-diketone (13), which was already converted into (±)-1. Reduction of 3, 9-dioxo-6α-ol (14), derived from 10a, with P-I2 afforded a mixture of 17-20. Both 3, 9-diketones (18 and 19) were converted into 3, 9-diol acetates (24b and 30b), respectively. The Birch reductions were effected for deacetoxylation of α'-acetoxy-α-substituted furan, e.g. (26) and the results are shown in Table I. Reductive deacetoxylation of 24b and 30b by the Birch procedure gave (±)-25 and (±)-31, respectively. (±)-Hydroxyfuranoeremophilane (6), derived from 18, was treated with POCL3-pyridine to give (±)-32. Reductive deacetoxylation of acetate (33) by the Birch procedure gave (±)-34. trans-Annulated 3, 9-diketone (19) was derived to the acetate (36b), which was converted by the Birch procedure into (±)-37.

Zusammenfassung Uberblickt man das jetzt vorliegende Material uber die Gattung Senecio , so bestatigt sich die schon eingangs erwahnte Festellung, das in Eine klare Differenzierung der Gattung Senecio von den Nachbargruppen von der Seite der Inhaltsstoffe her, ist nach wie vor problematisch. Wahrsche

Aus Vertretern der Sektion Rigidi werden neben bereits bekannten Verbindungen vier neue Benzofurane (3, 5, 6 und 10) sowie sechs neue Furanoeremophilane (13, 15, 19–21 und 23) isoliert. Aus Senecio pterophorus wird ein neuer Typ eines Pyrrolizidin-Derivats (25) isoliert. Ahnliche Verbindungen (34–37) enthalt Senecio cissampelinus. Die Konstitutionen werden durch spektroskopische Methoden sowie durch einige chemische Reaktionen geklart. Die chemotaxonomischen Aspekte werden diskutiert. Naturally Occurring Terpene Derivatives, 78 Further Constituents of South African Senecio Species From representatives of the section Rigidi besides already known compounds four new benzofurans (3, 5, 6, and 10) as well as six new furanoeremophilanes (13, 15, 19–21, and 23) are isolated. From Senecio pterophorus a new type of a pyrrolizidine derivative (25) is isolated. Senecio cissampelinus contains similar compounds (34–37). The structures are elucidated by spectroscopic methods as well as by some chemical reactions. The chemotaxonomical aspects are discussed.

Two new furanoeremophilane derivatives isolated from Farfugium japonicum Kitamura have been shown to be 3β-angeloyloxy-10β-hydroxy-9β-senecioyloxyfuranoeremophilane and 3β-angeloyloxy-10β-hdroxyfuranoeremophilane.

Die Untersuchung von Vertretern aus funf Sektionen der Gattung Othonna zeigt, das hier relativ stark oxidierte Furanoeremophilane charakteristisch sind. Die Konstitutionen von 20 neuen Vertretern (1, 2, 6, 7, 9, 11, 12, 14, 16, 18, 28, 31, 34 und 37–43) werden durch ihre Spektren sowie durch chemische Reaktionen geklart. Daneben werden einige Sequiterpene (24, 35, 36) sowie eine Nor-Verbindung (22) isoliert und ihrer Struktur geklart. Die engen chemotaxonomischen Beziehungen zu den Nachbargattungen werden diskutiert. Naturally Occuring Terpene Derivatives, XLII. New Sesquiterpenes o the Genus Othonna The investigation of representatives from five sections of the genus Othonna shows that they are characterized by the presence of relatively strongly oxidized furanoeremophilanes. The constitution of 20 new members (1, 2, 6, 7, 9, 11, 12, 14, 16, 18, 28, 31, 34 and 37–43) has been established by means of their spectra as well as by chemical reactions. Besides these some sequiterpenes (24, 35, and 36) as well as a nor-compound (22) have been isolated and their structures elucidated. The close chemotaxonomical relationships to the neighbouring genera are discussed.