A seco-guaianolide and other sesquiterpene lactones from Postia bombycina

Rustaiyan, Abdolhossein; Zare, Khadijeh; Biniyaz, T.; Fazlalizadeh, G.

doi:10.1016/0031-9422(89)80291-2

Cited by 24 publications

(16 citation statements)

References 3 publications

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“…In the 1 H-NMR data (Table 1) . The 13 C-NMR and DEPT spectra of compound 2 exhibited 15 carbon signals, which was similar to the known compound postiaseco-guaianolide [11,12], except for the differences in the numbers and chemical shifts of double bonds. Detailed analysis of 2D NMR data, the terminal double bond (-11, -13) in postiaseco-guaianolide was substituted by a methyl in compound 2 on the basis of the HMBC correlation of δ H 1.30 to δ C 178.1.…”

Section: Structure Elucidation Of Compoundsmentioning

confidence: 58%

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Three New Sesquiterpenoids and One New Sesquiterpenoid Derivative from Chinese Eaglewood

et al. 2016

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Abstract:Three new sesquiterpenoids (1-3) and one new sesquiterpenoid derivative (4), along with three known sesquiterpenoids (5-7), were isolated from the 95% ethanolic extract of Chinese eaglewood [Aquilaria sinensis (Lour.) Gilg]. The structures of these compounds were elucidated through extensive analysis of spectroscopic data including IR, NMR, HRESIMS, and X-ray diffraction experiments. In addition, the above new compounds were detected for their bioactivities against LPS-induced NO production in RAW 264.7 cells. Among them, compound 2 exhibited obvious anti-inflammatory activity with an IC 50 value of 8.1 µM.

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Section: Structure Elucidation Of Compoundsmentioning

confidence: 58%

“…Its molecular formula was assigned as C 12 3 -12). The 13 C-NMR and DEPT spectra ( Table 2) exhibited 12 carbon signals including two methyls, five methylenes, three methines, and two quaternary carbons (one carbonyl and an oxygenated carbons).…”

Section: Structure Elucidation Of Compoundsmentioning

confidence: 99%

Three New Sesquiterpenoids and One New Sesquiterpenoid Derivative from Chinese Eaglewood

et al. 2016

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“…Thus, for example elemanes derive from eudesmanes by bond cleavage between pos. 2 and 3, but there also exist references for other seco-sesquiterpenes, which originate for example from eudesmanes [ 20 , 21 , 22 ], cadinanes [ 23 ], germacranes [ 23 ] or guaianes [ 24 , 25 , 26 ]. Thus, compounds 1 und 2 could derive from eudesmanes like 8 by cleavage of the C-C bond between pos.…”

Section: Resultsmentioning

confidence: 99%

Sesquiterpenes from Myrrh and Their ICAM-1 Inhibitory Activity In Vitro

et al. 2020

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By using various chromatographic steps (silica flash, CPC, preparative HPLC), 16 sesquiterpenes could be isolated from an ethanolic extract of myrrh resin. Their chemical structures were elucidated by 1D and 2D NMR spectroscopy and HRESIMS. Among them, six previously unknown compounds (1–6) and another four metabolites previously not described for the genus Commiphora (7, 10, 12, 13) could be identified. Sesquiterpenes 1 and 2 are novel 9,10-seco-eudesmanes and exhibited an unprecedented sesquiterpene carbon skeleton, which is described here for the first time. New compound 3 is an 9,10 seco-guaian and the only peroxide isolated from myrrh so far. Compounds 1, 2, 4, 7–9, 11, 13–16 were tested in an ICAM-1 in vitro assay. Compound 7, as well as the reference compound furanoeudesma-1,3-diene, acted as moderate inhibitors of this adhesion molecule ICAM-1 (IC50: 44.8 and 46.3 μM, respectively). These results give new hints on the activity of sesquiterpenes with regard to ICAM-1 inhibition and possible modes of action of myrrh in anti-inflammatory processes.

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“…The HMBC correlation between HÀC(2) and C(1') established the linkage of the ester group with the backbone. Based on the ROESY interactions of HÀC(14)/HÀC(1), HÀC(14)/HÀC(2), HÀC(8)/HÀC(1), HÀC(8)/HÀC(7), HÀC(15)/H b ÀC(3), and H a ÀC(3)/HÀC(2), we concluded that HÀC(1), HÀC(2), HÀC(7), HÀC (8), and Me (14) were all a-configured, whereas Me(15) was in b-orientation. The observed NOE for HÀC(7) upon irradiation of HÀC (8) indicated that these two H-atoms were on the same side of the ring.…”

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confidence: 75%

“…Thus, the structure of compound 2 was deduced as 4-hydroxyguaia-9,11(13)-dien-12,8b-olide. Compound 2 is a new stereoisomer of the known compound 4-hydroxy-1bH-guaia-9,11(13)-dien-12,8a-olide [14]. The three known sesquiterpenes were identified as 2b-(isobutyryloxy)florilenalin (3) [16], pulchellin-2a-O-tiglate (4) [17], and florilenalin-2a-O-tiglate (5) [16] by comparison of their spectroscopic data with literature values.…”

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confidence: 99%

Two New Antibacterial Sesquiterpenoids from Centipeda minima

Bao

Dong

et al. 2007

Chemistry & Biodiversity

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Two new guaiane-type sesquiterpene lactones, compounds 1 and 2, along with three known guaianolide- or pseudoguaianolides, were isolated from Centipeda minima (whole plant). Their structures were identified by spectroscopic and mass-spectrometric analyses. The configuration at C5 of the guaiane framework of 1 was rationalized by quantum-mechanical calculations (Table 2). All compounds were found to be active against eight different microbial pathogens (Table 3), with MIC values in the range of 6.25-100 microg/ml.

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A seco-guaianolide and other sesquiterpene lactones from Postia bombycina

Cited by 24 publications

References 3 publications

Three New Sesquiterpenoids and One New Sesquiterpenoid Derivative from Chinese Eaglewood

Three New Sesquiterpenoids and One New Sesquiterpenoid Derivative from Chinese Eaglewood

Sesquiterpenes from Myrrh and Their ICAM-1 Inhibitory Activity In Vitro

Two New Antibacterial Sesquiterpenoids from Centipeda minima

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