Sesquiterpenoid Lactones Research Articles

Six New Sesquiterpenes from Eupatorium lindleyanum

AbstractThe six new germacrane‐type sesquiterpenoid lactones 1–6 were isolated from the CHCl3 extract of Eupatorium lindleyanum DC. The structures of these compounds were determined by spectroscopic analyses, including interpretation of 1D‐ and 2D‐NMR spectra. Compounds 1–6 were tested for cytotoxicity against NB4 and K562 leukemia cell lines, showing that 2 and 5 possess potent cytotoxicity (Table 3).

Preparative Isolation and Purification of Three Sesquiterpenoid Lactones from Eupatorium lindleyanum DC. by High-Speed Counter-Current Chromatography

A high-speed counter-current chromatography (HSCCC) method was established for the preparative separation of three sesquiterpenoid lactones from Eupatorium lindleyanum DC. The two-phase solvent system composed of n-hexane–ethyl acetate–methanol–water (1:4:2:3, v/v/v/v) was selected. From 540 mg of the n-butanol fraction of Eupatorium lindleyanum DC., 10.8 mg of 3β-hydroxy-8β-[4'-hydroxy-tigloyloxy]-costunolide, 17.9 mg of eupalinolide A and 19.3 mg of eupalinolide B were obtained in a one-step HSCCC separation, with purities of 91.8%, 97.9% and 97.1%, respectively, as determined by HPLC. Their structures were further identified by ESI-MS and 1H-NMR.

Terpenoids from Chloranthus elatior

Two new eudesmane-type sesquiterpenoid lactones, named chlorelactone A (1) and chlorelactone B (2), and one new labdane-type diterpenoid, named elatiorlabdane (3), along with seven known sesquiterpenoids and one known disesquiterpenoid were isolated from the whole plants of Chloranthus elatior. Their structures and relative configurations were established on the basis of extensive spectroscopic analysis. Electronic Supplementary MaterialSupplementary material is available for this article at 10.1007/s13659-012-0039-7 and is accessible for authorized users.

Argutalactone, an unprecedented sesquiterpenoid lactone with a 6/5/7 tricyclic system from Incarvillea arguta

Argutalactone (1), a novel sesquiterpenoid lactone featuring an unprecedented 6/5/7 rigid skeleton, was isolated from the roots of Incarvillea arguta. The structure and relative configuration of 1 were established by extensive analysis of spectroscopic data. The absolute configuration of 1 was determined as 2R,5S,10R,12S based on the analysis of biogenetical transformation, comparison of the optical rotation with literature data, and comparison of the experimental circular dichroism spectrum with the calculated electronic circular dichroism spectra.

A new eudesmane sesquiterpenoid lactone from Chloranthus japonicus

Aim To study the chemical constituents of the whole plant of Chloranthus japonicus. Methods Compounds were isolated and purified by column chromatography. Their structures were elucidated on the basis of spectroscopic methods. Results Six sesquiterpenoids were obtained and their structures were identified as chlojaponilactone A ( 1), atractylenolide III ( 2), neolitacumone B ( 3), 10α-hydroxy-1-oxoeremophila-7(11), 8(9)-diene-8, 12-olide ( 4), shizukanolide C ( 5), and shizukanolide H ( 6). Conclusion Compound 1 is a new eudesmane-type sesquiterpenoid lactone, and compounds 3 and 4 have been isolated from this species for the first time.

Volvalerelactones A and B, Two New Sesquiterpenoid Lactones with an Unprecedented Skeleton from Valeriana officinalis var. latifolia

Volvalerelactones A and B (1 and 2), two new sesquiterpenoid lactones with an unprecedented 3/7/6 tricyclic ring system, were isolated from the roots of Valeriana officinalis var. latifolia. Their structures and relative configurations were elucidated by spectroscopic data and single-crystal X-ray diffraction crystallography, and the absolute configuration was assigned by computational methods. The possible biosynthetic pathways of 1 and 2 were also proposed.

New Eremophilenolides from Senecio dianthus

AbstractFrom the aerial parts of Senecio dianthus, four new eremophilenolides (1–4, resp.) and one new eremophilenolide alkaloid (5), of the relatively uncommon eremophilenoid‐type sesquiterpenoid lactones, were isolated together with three known sesquiterpenoid lactones, 10β‐hydroxyeremophil‐7(11)‐en‐12,8α‐olide (6), 8β,10β‐dihydroxyeremophil‐7(11)‐en‐12,8α‐olide (7), and 10α‐hydroxy‐1‐oxoeremophila‐7(11),8(9)‐dien‐12,8‐olide (8). On the basis of IR, MS, and NMR data, particularly 2D‐NMR analyses, the structures of the new compounds were established as: 2β‐(angeloyloxy)‐10β‐hydroxyeremophil‐7(11)‐en‐12,8α‐olide (1), 6β‐(angeloyloxy)‐10β‐hydroxyeremophil‐7(11)‐en‐12,8α‐olide (2), 2β‐(angeloyloxy)‐8β,10β‐dihydroxyeremophil‐7(11)‐en‐12,8α‐olide (3), 2β‐(angeloyloxy)‐8α‐hydroxyeremophila‐7(11),9(10)‐dien‐12,8β‐olide (4), and 8β‐amino‐10β‐hydroxyeremophil‐7(11)‐en‐12,8α‐olide (5). In addition, the relative configuration of 1 was corroborated by X‐ray diffraction analysis.

A New Cadinane Sesquiterpenoid Lactone from Lepidozia reptans

Aim To study the chemical constituents of Lepidozia reptans (L.) Dumont. Methods The chemical constituents were isolated and purified with column chromatography and their structures were elucidated on the basis of 1D and 2D NMR analysis. Results Three compounds were obtained and identified as 5α-hydroxy-9α,10α-epoxycadinan-3-en-2β,14-olide ( 1), abieslactone ( 2), and 24, 25-dihydroabieslactone ( 3). Conclusion Compound 1 is a new cadinane sesquiterpenoid lactone, and compounds 2 and 3 have been isolated from this genus for the first time.

Antiplasmodial activities of sesquiterpene lactone from Carpesium cernum

The whole plant of genus Carpesium is used in traditional medicine as an anti-pyretic, analgesic and vermifugic, including a topical application for sores and inflammation. Previous experiments on Carpesium rosulatum suggested that the antiplasmodial effect was due to the existence of ineupatorolide A. In present paper, screening of Carpesium species from South Korea showed that this plant refers to which species had promising antiplasmodial activity. Subsequently, this species was selected for bioassay-guided fractionation in order to identify the active principles. Fractionation of the ethyl acetate extract of the whole plants by chromatographic techniques yielded four characterised sesquiterpenoid lactones which exhibited antiplasmodial activity against Plasmodium falciparum. This being the first time that this has been reported from Carpesium cernum. The antiplasmodial activity of the isolated compounds was determined against the Plasmodium falciparum.

DETECTION OF SESQUITERPENE LACTONES IN TEN ARTEMISIA SPECIES POPULATION OF KHORASAN PROVINCES

Objective During the last three decades sesquiterpenoid lactones have emerged as one of the largest groups of plant products with over 3000 naturally occurring substances known. The genus Artemisia characteristically contains this biologically active type of secondary metabolites. With respect to increasing interest in the cytotoxic, antibiotic, phototoxic and antineoplastic activities of sesquiterpene lactones, identification of these compounds in Khorasanian Artemisia species, that some of them are endemic to Iran, can be worth while. Materials and Methods Ten species of Artemisia were collected from different parts of Khorasan Provinces of Iran. IR spectra recorded as KBr disks and in CH2Cl2 on a Unicam dp 110 spectrometer (UK). 1H-NMR (500 MHz) spectra were measured in CDCl3 using a Bruker DRX 500 spectrometer. Number of scans was 32 for all of the samples. The Herz-Hogenauer technique was applied for preparation of the terpenoid extracts. Results Our findings revealed that A. absinthium, A. ciniformis, A. fragrans, A. khorassanica, A. kopetdaghensis, A. santolina and A. sieberi had a high amount of sesquiterpene lactones. A little or no sesquiterpene lactone had been detected in other species. Differentiation of saturated and unsaturated sesquiterpene lactones was one of the advantages of 1H-NMR application in this method. Conclusion Many of tested Khorasanian Artemisia species contained high amounts of sesquiterpene lactones

Bisabolane‐Type Sesquiterpenoids from the Rhizomes of Glochidion coccineum

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Inhibition of mycobacterial arylamine N-acetyltransferase contributes to anti-mycobacterial activity of Warburgia salutaris

In this study, we show that extracts and a purified compound of Warburgia salutaris exhibit anti-mycobacterial activity against Mycobacterium tuberculosis H37Rv and Mycobacterium bovis BCG Pasteur. The extracts did not inhibit growth of Escherichia coli and were not toxic to cultured mammalian macrophage cells at the concentrations at which anti-mycobacterial activity was observed. The extract and pure compound inhibited pure recombinant arylamine N-acetyltransferase (NAT), an enzyme involved in mycobacterial cell wall lipid synthesis. Moreover, neither extract nor pure compound inhibited growth of a strain of M. bovis BCG in which nat has been deleted suggesting that NAT may indeed be a target within the mycobacterial cell. The purified compound is a novel drimane sesquiterpenoid lactone, 11α-hydroxycinnamosmolide. These studies show that W. salutaris is a useful source of anti-tubercular compounds for further analysis and supports the hypothesis of a link between NAT inhibition and anti-mycobacterial activity.

Bisabolane‐Type Sesquiterpenoids from the Rhizomes of Glochidion coccineum

AbstractA novel bisabolane‐type sesquiterpenoid lactone, glochicoccin A (1), and three new norbisabolane sesquiterpenoids, glochicoccins B–D (2–4), together with two known norbisabolane sesquiterpenoids, phyllaemblic acid (5) and phyllaemblic acid methyl ester (6), were isolated from the rhizomes of Glochidion coccineum. Their structures were elucidated by different spectroscopic (IR, UV, NMR) and mass‐spectrometric (MS) techniques. The structure and relative configuration of 1 was confirmed by single‐crystal X‐ray diffraction (Fig. 2). None of the compounds were found to exhibit cytotoxic or antioxidant activities.

Chemical constituents from three Inula species. Biological activities

The genus Inula consists of variable perennial herbs distributed in Asia, Europe, Africa and predominantly in the Mediterranean region (Asteraceae family, tribe Inuleae). Plants of the genus are used as traditional herbal medicines throughout the world [1]. Inula viscosa (L.) Aiton. (syn. Dittrichia viscosa (L.) Greuter) is a widespread Mediterranean plant proven to be a rich source of sesquiterpenes, lactones and flavonoids. Inula pseudolimonella (Rech. F.) and I. candida subsp. candida are both Greek endemic plants and have never been studied phytochemically before [2]. The non-polar (dichloromethane) and the polar (methanolic) extracts of all species were investigated thoroughly and afforded a new sesquiterpenoid lactone

Two New Cytotoxic Sesquiterpenoids from Eupatorium lindleyanum DC.

AbstractTwo new sesquiterpenoid lactones, namely eupalinilides K and L, were isolated from Eupatorium lindleyanum DC. Their structures were determined by spectral methods, including 1D‐ and 2D‐NMR spectra. Cytotoxic evaluation showed that eupalinilide L exhibited potent cytotoxicity against P‐388 and A‐549 tumor cell lines with IC50 values of 0.17 and 2.60 μmol/L, respectively.(Managing editor: Wei Wang).

New Picrotoxane Terpenoids from Picrodendron baccatum

AbstractFor Abstract see ChemInform Abstract in Full Text.

New picrotoxane terpenoids from Picrodendron baccatum

Two new picrotoxane norditerpenoid lactones, picrodendrins X ( 1 ) and Y ( 2 ), and four new picrotoxane sesquiterpenoid lactones, picrodendrins Z ( 3 ), α ( 4 ), β ( 5 ) and picrodendrioside A ( 6 ) were isolated from the bark and leaves of Picrodendron baccatum. Their structures were determined by spectral analysis and X-ray crystallographic analysis.

Synthesis of 5,6-dehydro-7-oxoisodrimenin from drim-8-en-7-one

The natural drimane sesquiterpenoid lactone 5,6-dehydro-7-oxoisodrimenin was synthesized from drim-8-en-7-one as well as from 7-oxoisodrimenin.

Cloning and expression of sesquiterpene synthase genes from lettuce ( Lactuca sativa L.)

Two genes encoding germacrene A synthases were cloned from lettuce seedlings producing the sesquiterpenoid lactone phytoalexin, lettucenin A.

New sesquiterpene lactones from Elephantopus mollis and their leishmanicidal activities.

The leishmanicidal compounds isolated from whole plants of Elephantopus mollis H.B.K. were identified as follows. Three new sesquiterpenoid lactones, 2,5-epoxy-2beta-hydroxy-8alpha-(2-methylpropenoyloxy)-4(15),10(14),11(13)-germacratrien-12,6alpha-olide, (4betaH)-8alpha-(2-methylpropenoyloxy)-2-oxo-1(5),10(14), 11(13)-guaiatrien-12,6alpha-olide and (4betaH)-5alpha-hydroxy-8alpha-(2-methylpropenoyloxy)-1(10),11(13)-guaiadiene-12,6alpha-olide, were isolated from Peruvian and Brazilian collections together with four known sesquiterpenoids, molephantin, elephantopin, isoelephantopin and 2-deethoxy-2beta-methoxyphantomolin. They exhibited potent in vitro leishmanicidal activities against Leishmania major. The alpha-methylene-gamma-butyrolactone moiety was found to be essential to the potent leishmanicidal effect observed.