Longipedlactones A-I, nine novel triterpene dilactones possessing a unique skeleton from Kadsura longipedunculata

Nine novel triterpene dilactones with an unprecedented rearranged pentacyclic skeleton, longipedlactones A-I (1-9), have been isolated from the leaves and stems of Kadsura longipedunculata Finet et Gagnep (Schisandraceae). Their structures were determined on the basis of comprehensive spectroscopic analysis and single-crystal X-ray structure determination. A biogenetic pathway for longipedlactone A (1) was also proposed. Compounds 1-3, 6, and 8 showed significant cytotoxicity against A549, with HT-29 and K562 cell lines having IC₅₀ values of 0.84-11.38 μM in vitro.     

Silvaglenamin—a novel dimeric triterpene alkaloid from Aglaia silvestris

An unusual dimeric triterpene structure with two dammarane units linked with an enaminic -NH- group was isolated from the root extract of Aglaia silvestris. The structure was elucidated by 1D and 2D NMR analysis and ESI mass spectrometry.     

Multidione, a novel diterpenoid from Jatropha multifida

A novel diterpenoid, multidione, has been isolated from the stems of Jatropha multifida and its structure has been settled from 1D and 2D NMR spectra. The compound possesses a phenolic moiety and a long side chain, structurally similar to the B ring of other lathyrane-diterpenoids in seco-form.The compound has possibly been derived biogenetically from a related lathyrane-diterpenoid.     

New pentacyclic triterpene saponins with strong anti-leishmanial activity from the leaves of Maesa balansae

Six new triterpene saponins bearing an oxygen bridge between C-13 and C-28 and with pronounced anti-leishmanial activity were isolated from the methanolic extract of leaves of the Vietnamese medicinal plant Maesa balansae. The structure was established on the basis of detailed NMR (COSY, NOESY, HMQC, HMBC, TOCSY and DEPT) and FAB-MS studies along with chemical degradation. All saponins identified contained the same pentaglycosidic side chain, but a different esterification pattern on the triterpenoid part. Biological evaluation of the individual compounds against visceral leishmaniasis (Leishmania infantum amastigotes) revealed a much better activity in vitro compared to the reference compound Pentostam^®, which is currently used as first-line treatment for leishmaniasis.     

Cannabioxepane, a novel tetracyclic cannabinoid from hemp, Cannabis sativa L.

Apart from large amounts of cannabidiol, the known stilbenoids 1-4 and the oxylipins 7 and 8, a fibre cultivar of Cannabis sativa derived from the historical Carmagnola variety gave the novel spiranic stilbenoid isocannabispiradienone (5) and the biphenyl-type cannabinoid cannabioxepane (CBX, 6), a tetracyclic compound characterized by an unprecedented C-5/C-8′ oxygen bridge and devoid of cannabinoid activity. Structures were established by analysis of MS and NMR data, and the biogenetic derivation of the new compounds is discussed.     

Aminocadambines A and B, two novel indole alkaloids from Neolamarckia cadamba

Two novel monoterpenoid indole alkaloids, aminocadambines A (1) and B (2), characterized by tetrahydrofuran and 1,2,3,4-tetrahydropyridine rings, were isolated from the leaves of Neolamarckia cadamba. Their structures were elucidated on the basis of spectroscopic and computational methods. The absolute configuration of 1 was established by CD analysis. A plausible biosynthetic pathway for 1 and 2 is proposed.     

New tri- and tetracyclic diterpenes from Euphorbia villosa

Three new tetracyclic diterpenes were isolated from the chloroform-soluble extract of Euphorbia villosa, together with one new and one known lathyrane diterpene. The structures were elucidated by means of various spectroscopic methods, including HREI-MS, HRFAB-MS, UV, and 1D and 2D NMR techniques. Spectral analyses revealed that two of the tetracyclic compounds contain the rare 5-6-6-4 fused ring system, while the third has a 5-6-7-3 fused diterpene core. Such diterpene skeletons have previously been found only in euphoractines A-E isolated from Euphorbia micractina. As a new structural feature, the diterpene framework described here has a C-2 epimer configuration. The new lathyrane diterpene is a diester of a hitherto unknown polyfunctional parent alcohol.     

New premyrsinane-type diterpene polyesters from Euphorbia falcata

Four new premyrsinane-type diterpenes (1-4) were isolated from the methanol extract of the whole, undried plant of Euphorbia falcata. Their structures were determined by a combination of 1D and 2D NMR (COSY, HMBC, HSQC and NOESY) techniques and mass spectral data as di-, tetra-, penta- and hexaesters of diterpene polyols, esterified with acetic, benzoic, propanoic, isobutanoic and n-hexanoic acids. One of the compounds contains a rare hemiacetal moiety. This type of diterpenes was previously detected only in four Euphorbia species (Euphorbia aleppica, Euphorbia decipiens, Euphorbia macroclada and Euphorbia pithyusa subsp. cupani).     

Isolation and structure determination of new 4,12-dideoxyphorbol esters from Euphorbia pannonica Host.

Phytochemical study of the aerial parts of Euphorbia pannonica led to the isolation of two new tigliane diterpenes, 4,12-dideoxy(4β)phorbol-20-benzoate-13-isobutyrate (1) and 4,12-dideoxy(4β)phorbol-20-benzoate-13-isovalerianate (2). The structures and relative stereochemistry were elucidated on the basis of extensive spectroscopic analyses, including 1D and 2D NMR experiments (¹H NMR, JMOD, COSY, NOESY, HSQC and HMBC).     

Unusual octalactones from Corynespora cassiicola, an endophyte of Laguncularia racemosa

Chemical investigation of the EtOAc extract of the mangrove-derived endophyte Corynespora cassiicola, isolated from Laguncularia racemosa (Combretaceae), afforded five new secondary metabolites, named coryoctalactones A–E (1–5). The structures of the new compounds were determined on the basis of 1D- and 2D-NMR spectroscopy as well as high-resolution mass spectrometry. The absolute configuration of the side chain in 1–3 and 5 were tentatively deduced based on biogenetic consideration in comparison with xestodecalactones, previously isolated from C. cassiicola. All isolated compounds were evaluated for their antimicrobial, cytotoxic, and antitrypanosomal activities.     

Psoracorylifols A-E, five novel compounds with activity against Helicobacter pylori from seeds of Psoralea corylifolia

Five novel compounds, psoracorylifols A-E (1-5) with important activity against Helicobacter pylori have been isolated from a well-known traditional Chinese medicine (TCM), the seeds of Psoralea corylifolia. The structures of compounds 1-5, including their absolute configurations, were established on the basis of spectral methods and biogenetic reason. The structure of 1 was confirmed by a single-crystal X-ray diffraction. Psoracorylifols D and E (4 and 5) represent an unprecedented carbon skeleton. The biogenetic origin of psoracorylifols A-E (1-5) was also postulated.     

Four new colchicinoids, gloriosamines A-D, from Gloriosa rothschildiana

Four new colchicinoids, gloriosamines A-D, were isolated from the aerial parts of Gloriosa rothschildiana. The structure of gloriosamine A, including the absolute configuration, was determined by chemical conversion from colchicine.     

New oxindole and indole alkaloids from Gelsemium rankinii

Six new humantenine-type (1-6) and two new gelsemine-type (7, 8) oxindole alkaloids and one new indole alkaloid (9) were isolated from the leaves and branches of Gelsemium rankinii. The structures of the new alkaloids were determined by spectroscopic analyses. Among them, 6-hydroxyhumantenine (5) is the first example of a Gelsemium alkaloid with an oxygen function at C-6 position, and is a plausible biogenetic precursor of gelsemine-type alkaloids.     

Xylomexicanins E-H,new limonoids from Xylocarpus granatum

Four novel tetranortriterpenoids, xylomexicanins E–H (1–4), were isolated from the seeds of the Chinese mangrove, Xylocarpus granatum. Among them, xylomexicanin E (1) represents the first example of limonoid with azaspiro skeleton between B (pyrrolidine) and C rings, whose biosynthetic pathways were proposed. The structures were elucidated on the basis of one- and two-dimensional NMR (including ¹H, ¹³C NMR, DEPT, ¹H–¹H COSY, HSQC, HMBC, and NOESY) and confirmed by high-resolution mass spectrometry. Compound 2, the second example of a limonoid with a C-9–C-30 linkage, showed moderate activity against the A549 and RERF cell line with IC₅₀ value of 18.83 and 15.83 μM,     

Two novel tetracycles,cassibiphenols A and B from the flowers of Cassia siamea

Chemical investigation of the flowers of Cassia siamea (Leguminosae), resulted in the isolation of two novel tetracycles connecting 5-(2-hydroxypropyl)benzene-1,3-diol, cassibiphenols A (1) and B (2). The structures were elucidated by analysis of the 1D, 2D NMR, and HRMS spectra. Synthesis of a tetracyclic core of 1 and 2 led to determine the absolute configuration of 1 and C-12 of 2.     

Novel grayanane diterpenoids from Rhododendron principis

Six new grayanane diterpenoids, principinols A–F (1–6), were isolated from Rhododendron principis. Compounds 1 and 2 possess unprecedented 6,10-epoxy and 5α-OH moieties, and 1 and 3 are the first two examples of 9α-H in grayanoids. Their structures were determined by extensive spectroscopic analysis, and the absolute configurations of 1–4 were assigned by single-crystal X-ray crystallography. Compounds 4 and 5 inhibit PTP1B phosphatase activity in vitro. A preliminary structure–activity relationship discussion is presented.     

New humantenine-type indole alkaloids with iridoid unit from Gelsemium species

Two new oxindole alkaloids, rankiniridine (1) and humanteniridine (2), having a nitrogen-carbon linkage between a humantenine-type monoterpenoid indole alkaloid and a monoterpene unit with an iridoid skeleton, were isolated from Gelsemium rankinii and Gelsemium elegans, respectively.     

Four new ginkgolic acids from Ginkgo biloba

Four new compounds, 2-hydroxy-6-(12′-hydroxyheptadec-13′(E)-en-1-yl)benzoic acid (1), 2-hydroxy-6-(13′-hydroxyheptadec-11′(E)-en-1-yl)benzoic acid (2), 2-hydroxy-6-(10′-hydroxypentadec-11′(E)-en-1-yl)benzoic acid (3), and 2-hydroxy-6-(11′-hydroxypentadec-9′(E)-en-1-yl)benzoic acid (4) were isolated from the leaves of Ginkgo biloba and the structures of new ginkgolic acids were deduced on the basis of spectroscopic methods and chemical means. Compounds 1 and 2, and 3 and 4 examined as an inseparable mixture of hydroxyl and double bond positional isomers, were ultimately defined by total synthesis. Compounds 1–4 showed moderate lipid droplets accumulation inhibitory activity on mouse pre-adipocyte cell line, MC3T3-G2/PA6.     

Laetiporic acid, a new polyene pigment from the wood-rotting basidiomycete Laetiporus sulphureus (Polyporales, Fungi)

A new pigment, laetiporic acid, has been isolated from fruit-bodies of the wood-rotting fungus Laetiporus sulphureus (sulfur shelf). Structure elucidation by application of extensive 2D NMR techniques permitted its identification as a polyene of non-isoprenoid origin. Laetiporic acid, which represents the main pigment in L. sulphureus basidiocarps, bears an unprecedented decaene skeleton as part of its chromophore and, interestingly, contains double bonds with a stable cis configuration.     

Platypodiol a novel clerodane diterpene from Baccharis platypoda

There is an urgent need for effective leishmanicidal drugs to replace or supplement those in current use. Our group has been bioprospecting many Brazilian plants looking for potential new ‘hits’ to combat leishmaniasis. We found that Baccharis platypoda was one of the Asteraceae species that displayed leishmanicidal activity. We now describe the isolation of the new clerodane diterpene (1), named platypodiol after its ethanolic leaf extract. Its structure was determined by detailed NMR and ESI-TOF/MS/MS experiments. Considering the few publications about this species, this result has increased the phytochemical knowledge about B. platypoda.