Triterpenoid saponins from Eryngium yuccifolium ‘Kershaw Blue’

Phytochemical investigation on the root of Eryngium yuccifolium ‘Kershaw Blue’ resulted in the isolation and identification of two new polyhydroxyoleanene saponins, named eryngioside M and eryngioside N, together with 15 known triterpenoid saponins eryngiosides A-L, 21β-angeloyloxy-3β-[β-d-glucopyranosyl-(1 → 2)]-[β-d-xylopyranosyl-(1 → 3)]-β-d-glucuronopyranosyloxyolean-12-ene-15α,16α,22α,28-tetrol, saniculasaponin III, and saniculasaponin II. Their structures were established by extensive spectroscopic and chemical analyses. Eryngioside M and saniculasaponin II showed week cytotoxicity against human non-small cell lung tumor cells (A549) with GI₅₀ values of 37.5 ± 1.59 μM and 35.5 ± 1.11 μM, respectively.     

Bioguided Fractionation and Isolation of an Antiplasmodial Saponin from the Roots of Nauclea xanthoxylon (A.Chev.) Aubrév. (Rubiaceae)

The root extract of Nauclea xanthoxylon (A.Chev.) Aubrév. displayed significant 50 % inhibition concentration (IC₅₀s) of 0.57 and 1.26 μg/mL against chloroquine resistant and sensitive Plasmodium falciparum (Pf) Dd2 and 3D7 strains, respectively. Bio-guided fractionation led to an ethyl acetate fraction with IC₅₀s of 2.68 and 1.85 μg/mL and subsequently, to the new quinovic acid saponin named xanthoxyloside ( 1 ) with IC₅₀s of 0.33 and 1.30 μM, respectively against the tested strains. Further compounds obtained from ethyl acetate and hexane fractions were the known clethric acid ( 2 ), ursolic acid ( 3 ), quafrinoic acid ( 4 ), quinovic acid ( 5 ), quinovic acid 3-O-β-D-fucopyranoside ( 6 ), oleanolic acid ( 7 ), oleanolic acid 3-acetate ( 8 ), friedelin ( 9 ), β-sitosterol ( 10a ), stigmasterol ( 10b ) and stigmasterol 3-O-β-D-glucopyranoside ( 11 ). Their structures were characterised with the aid of comprehensive spectroscopic methods (1 and 2D NMR, Mass). Bio-assays were performed using nucleic acid gel stain (SYBR green I)-based fluorescence assay with chloroquine as reference. Extracts and compounds exhibited good selectivity indices (SIs) of >10. Significant antiplasmodial activities measured for the crude extract, the ethyl acetate fraction and xanthoxyloside ( 1 ) from that fraction can justify the use of the root of N. xanthoxylon in ethnomedicine to treat malaria.     

Two New Triterpenoid Saponins from Akebia quinata （Thunb.） Decne.

Two new triterpenoid saponins, hederagenin 3-O-α-L-arabinopyranosyl-（1→〉2）-α-L-arabinopyranoside named akeboside La （compound 1）, oleanolic acid 3-O-α-L-arabinopyranosyl-（1→〉2）-β-D-glucopyranoside named akeboside Lb （compound 2）, along with five known saponins, oleanolic acid 3-O-α-L-rhamnopyranosyl-（1→〉2）-α-L- arabinopyranoside （compound 3）, hederagenin 3-O-α-L-rhamnopyranosyl-（1→〉2）-α-L-arabinopyranoside （compound 4）, oleanolic acid 3-O-β-D-xylopyranosyl-（1→〉3）-α-L-rhamnopyranosyl-（1→〉2）-α-L-arabinopyranoside （compound 5）, 3-O-α-L-rhamnopyranosyl-（1→〉2）-α-L-arabinopyranosyl oleanolic acid 28-O-α-L-rhamnopyranosyl-（1→〉4）-α-D- glucopyranosyl-（1→〉6）-β-D-glucopyranoside （compound 6）, 3-O-α-L-rhamnopyranosyl-（1→〉2）-α-L-arabinopyranosyl hederagenin 28-α-L-rhamnopyranosyl-（1→〉4）-β-D-glucopyranosyl-（1→〉6）-β-D-glucopyranoside （compound 7） were isolated from the n-butanol part of the 80% ethanol extracts of the dried stems of Akebia quinata （Thunb.） Decne. Compound 5 was isolated from plants of genus Akebia for the first time. The structures were elucidated on the basis of physicochemical properties and spectral data.     

Triterpenoid Saponins from Pulsatilla cernua （Thunb.） Bercht. et Opiz.

To investigate saponins from the roots of Pulsatilla cernua （Thunb.） Bercht. et Opiz., two new compounds together with five known trlterpenold saponins were isolated. The structures of the two new trlterpenoid saponins, named cernuasides A and B, were elucidated as 3-O-[β-D-xylopyranosyl（1-）2）]-[α-L-rhamnopyranosyl（1-）4）]-α-L- arablnopyranosyl hederagenin 28-O-β-D-glucopyranosyl ester （compound 1） and 3-O-[α-L-arabinopyranosyl（1→）3）]- [α-L-rhamnopyranosyl （1→）2）]-α-L-arabinopyranosyl hederagenin 28-O-β-D-glucopyranosyl ester （compound 2） by 1D, 2D-NMR techniques, ESIMS analysis, as well as chemical methods.     

Starfish saponins—XI. Isolation and partial characterization of the saponins from the starfish Marthasterias glacialis

• 1.1. The saponin mixture isolated from Marthasterias glacialis was resolved through a series of chromatographic steps into four principal individual components, named marthasteroside A₁, A₂, B and C.
• 2.2. The isolated sulphate steroidal glycosides were characterized by ¹H-NMR, ¹³C-NMR, Fast Atom Bombardment mass spectrometry and GLC analysis of the sugars after acid hydrolysis.
• 3.3. Marthasteroside A₁ and A₂ contained the aglycone thornastrol A and six sugar units. The second group of compounds, marthasteroside B and C, contained five sugar units; the aglycone of marthasteroside B was identified as marthasterone, while that of marthasteroside C was identified as dihydromarthasterone. In all compounds the sulphate group is attached at C-3 of the steroid.

     

Coumarins from the stems and leaves of Clausena dunniana H. Lév

Phytochemical study on the stems and leaves of Clausena dunniana H. Lév. led to the isolation and identification of 14 coumarins (1–14). Their chemical structures were determined on the basis of MS, NMR, and further supported by comparison with those reported in the literature. This is the first report that compounds 1–2, 4, 8, and 12–14 are present in the genus Clausena, and all of these compounds were isolated from C. dunniana for the first time. The chemotaxonomic significance of these isolated compounds was discussed.     

Erythrophyllopsis perlaticosta M.J.Cano & J.A.Jiménez (Pottiaceae) a new species from the Peruvian Andes

Introduction. Over the last years we have been engaged in studies of the South American Pottiaceae. Among the bryophyte specimens collected by us in central and northern Peru, some samples of a puzzling Pottiaceae were found. In this paper, we present our arguments for recognising these plants as a new species and its inclusion in Erythrophyllopsis Broth.

Key Results. It differs most saliently from other species of Erythrophyllopsis by the combination of its oblong-ovate to ovate-lanceolate leaves, with usually fragile apex, leaf margins papillose-crenulate from apex to lower third, sometimes erose or crenate, lamina unistratose, occasionally bistratose in patches, costa broad, usually ending below the apex, without dorsal stereids near the apex where they are replaced by cells similar to those of the lamina, and short and straight peristome teeth.

Conclusions. A new moss species, Erythrophyllopsis perlaticosta M.J.Cano & J.A.Jiménez, is described and illustrated from the Andean highlands in central and northern Peru. A revised identification key for the species of Erythrophyllopsis is also provided. This species grows in crevices or fissures of calcareous rocks or banks between 3050 and 4700?m. The principal distinctive characters that separate it from the nearest species of Erythrophyllopsis and related genera such as Bryoerythrophyllum P.C.Chen and Mironia R.H.Zander are discussed.     

Chemical constituents from Dendropanax morbiferus H. Lév. Stems and leaves and their chemotaxonomic significance

The phytochemical investigation of Dendropanax morbiferus H. Lév. Led to the isolation of 28 known compounds: 4 alkaloids (1–4), 1 pyranoglucoside (5), 1 benzoic acid and 5 benzoic acid derivatives (6–11), 10 phenylpropanoids (12–21), 4 flavone glucoside derivatives (22–25), 1 neolignan (26) and 2 sesquiterpenes (27–28). The structures of these compounds were identified using spectroscopic methods; their nuclear magnetic resonance spectra were compared with those previously reported. This is the first report on compounds 2–4, 10, and 12 isolated from D. morbiferus. Compounds 5 and 26 from the genus Dendropanax and 1, 6–9, 11, 13, 14–25, 27 and 28 from the family Araliaceae were isolated for the first time. Additionally, to the best of our knowledge, this is the first comprehensive chemical investigation of D. morbiferus stems and leaf compounds. Chemotaxonomic relationship between D. morbiferus and other Dendropanax species is also discussed.     

Didymodon vulcanicus J.A.Jiménez,Hedd. & Frank Müll. (Pottiaceae), a new species from tropical Africa

Didymodon vulcanicus J.A.Jiménez, Hedd. & Frank Müll. is described and illustrated as a new species from volcanic regions of tropical Africa. The species is distinguished morphologically by its lanceolate or more rarely ovate-lanceolate leaves that are strongly incurved distally when dry, acute apices, upper and middle laminal cells arranged in longitudinal rows with a low dorsal papilla over the transverse walls which reaches the two immediate cells, basal cells not or hardly differentiated from the medial cells, and the presence of gemmae in the leaf axils. Drawings and light microscope photographs of the main characters are given, and possible confusion with other closely related taxa is discussed.     

Didymodon caboverdeanus J.A.Jiménez & M.J.Cano (Pottiaceae,Musci), a new species from the Cape Verde archipelago

A new moss species, Didymodon caboverdeanus J.A.Jiménez & M.J.Cano, from the Cape Verde archipelago is described and illustrated. It differs most saliently from other species of Didymodon Hedw. by the combination of the lanceolate leaves with obtuse and often cucullate leaf apices, recurved margins, the yellowish colour in KOH, costa ending below the apex, laminal cells with low papillae over the transverse walls, which reach the two adjacent cells, the presence of gemmae in the leaf axils, and a short and straight peristome.     

Starfish saponins—IV. Sapogenins from the starfish Astropecten aurantiacus and Marthasterias glacialis

• 1.1. The major aglycones produced by acid hydrolysis of the saponins from the starfish Astropecten aurantiacus are identified as 3β,6α-dihydroxy-5α-pregn-9(11)-en-20-one (1), (17 E)- and (17 Z)-3β,6α-dihydroxy-5α-cholesta-9(11),17(20)-dien-23-one (9 and 10), (17 E)- and (17 Z)-3β,6α-dihydroxy-5α-cholesta-9(11), 17(20),24-trien-23-one (11 and 12), (20 E)-3β,6α-dihydroxy-5α-cholesta-9(11),20(22)-dien-23-one (4), and 17β-methyl-3β,6α-dihydroxy-18-nor-5α-cholesta-9(11),13-dien-23-one (13).
• 2.2. A re-examination of the sapogenins from the starfish Marthasterias galcialis, in addition to the previously isolated 1, 3β,6α-dihydroxy-5α-cholesta-9(11)-en-23-one (2, dihydromarthasterone), 3β,6αdihydroxy-5α-cholesta-9(11),24-dien-23-one (3, marthasterone) and 3β,6α-dihydroxy-5α-chol-9(11)-en-23-one (14), has shown the presence of minor amounts of 9, 10, 4 and 13.
• 3.3. A [¹³C]NMR study of the major sapogenins, 9 and 10, from A. aurantiacus, and 1, 2 and 14 from M. glacialis is also reported.

     

Ptychomitrium subcrispatum Thér. & P.de la Varde,an east southern African species excluded from the Cape Verde bryoflora

Abstract

Pictolejeunea levis, a new species of Lejeuneaceae found in N.E. Cuba, is described and illustrated. The species stands out within Pictolejeunea on account of its smooth leaf cells and the presence of ocelli on dorsal and ventral epidermal cells of the stem. Differences between this and the other four known species in the genus are discussed.     

Solving the identity of the large Plagiomnium (Musci) from Madeira (Portugal): P. undulatum var. madeirense T. Kop. & C. Sérgio

A new variety of Plagiomnium undulatum (Hedw.) T. Kop. var. madeirense T. Kop. & C. Sérgio is described from Madeira Island. The plants present an aquatic ecology and are characterised by broadly and longly decurrent leaves and by large size of laminal cells. This taxon is illustrated and the specimens studied are mapped.     

Cheilolejeunea oncophylla (Ångstr.) Orolle & Reiner comb. nov. (Lejeuneaceae), from the Neotropics

Abstract

Cheilolejeunea oncophylla (Ångstr.) Grolle & Reiner comb. nov. (basionym: Lejeunea oncophylla Ångstr.) is described and illustrated. Trachylejeunea dominicensis Steph. and Harpalejeunea verrucosa Herzog are shown to be synon):'ms.     

Nebulosides A–B,novel triterpene saponins from under-ground parts of Gypsophila arrostii Guss. var. nebulosa

A bioassay-guided phytochemical analysis of the triterpene saponins from under ground parts of Gypsophila arrostii var. nebulosa allowed the isolation of two triterpene saponins; nebuloside A, B based on gypsogenin and quillaic acid aglycone. Two new oleanane type triterpenoid saponins (nebuloside A, B) and three known saponins (1–3) were isolated from the root bark of Gypsophila arrostii var. nebulosa. The structures of the two new compounds were elucidated as 3-O-β-d-galactopyranosyl-(1→2)-[β-d-xylopyranosyl-(1→3)]-β-d-glucuronopyranosyl quillaic acid 28-O-β-d-glucopyranosyl-(1→3)-[β-d-xylopyranosyl-(1→3)-β-d-xylopyranosyl-(1→4)]-α-l-rhamnopyranosyl-(1→2)-β-d-fucopyranosyl ester (nebuloside A) and 3-O-β-d-xylopyranosyl-(1→3)-[β-d-galactopyranosyl(1→3)-β-d-galactopyranosyl-(1→2)]-β-d-glucuronopyranosyl gypsogenin 28-O-β-d-glucopyranosyl-(1→3)-[β-d-xylopyranosyl-(1→3)-β-d-xylopyranosyl-(1→4)]-α-l-rhamnopyranosyl-(1→2)-β-d-fucopyranosyl ester (nebuloside B), on the basis of extensive spectral analysis and chemical evidence. Nebuloside A and B showed toxicity enhancing properties on saporin a type-I RIP without causing toxicity by themselves at 15 μg/mL.