Cytotoxic Components from the Leaves of <i>Schefflera Taiwaniana</i>

The searching for biologically active compounds produced by living organisms led to the discovery of a number of compounds with more or less complicated structure. One of the simplest molecules are monoterpenoid lactones and loliolide is the most common among them. Loliolide was found in animals (insects) and plants (flowers, shrubs, trees) both terrestrial and marine, such as algae and corals. Many years of research on plants used in traditional folk medicine of different countries have led to the conclusion that this compound has a variety of biological properties such as anti-cancer, antibacterial, antifungal and antioxidant ones. Moreover, plants containing loliolide are used in alternative medicine in treatment of diabetes and depression. It is extremely interesting that this lactone also affects the behavior of ants as well as the development of certain plants (allelopathic activity). However, sometimes there are side effects as in the case of structural analogues of loliolide contributing to extinction of tropical coral.

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“…(1) Leaves of Schefflera taiwaniana, plant from the Araliaceae family, growing in Taiwan (Kuo et al 2002) 6.0·10…”

Section: Compoundmentioning

confidence: 99%

Loliolide - the most ubiquitous lactone

et al. 2015

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“…1). Isolation of impressic acid from four species has been reported: Acanthopanax trifoliatus (Ty et al, 1984), A. koreanum (Cai et al, 2004;Kim et al, 2010a;Park et al, 2010), Schefflera impressa (Srivastava, 1992), and S. taiwaniana (Kuo et al, 2002). However, Fig.…”

Section: Introductionmentioning

confidence: 99%

Effects of impressic acid from Acanthopanax koreanum on NF-κB and PPARγ activities

et al. 2011

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Impressic acid, 3α,11α-dihydroxylup-20(29)-en-28-oic acid, is a lupane-type triterpenoid isolated from Acanthopanax koreanum, which has been used as a Korean folk medicine for rheumatism, hepatitis, diabetes, and inflammatory disorders. Recently, it was reported that impressic acid has inhibitory effects on the LPS-stimulated pro-inflammatory cytokine production in bone marrow-derived dendritic cells and on the nuclear factor of activated T-cells transcription factor activity. Thus, to investigate whether impressic acid has effects on the inhibition of nuclear factor kappa B (NF-κB) and activation of peroxisome proliferator-activated receptor gamma (PPARγ), luciferase reporter assays were used. The effects on the expression of NF-κB and PPARγ target genes were also examined by reverse transcription-polymerase chain reaction. In this study, impressic acid was found to inhibit tumor necrosis factor (TNF)-α induced NF-κB activity and to up-regulate transcriptional activity of PPARγ.

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“…Accordingly, the structure of 1 was elucidated as (S)-4-hentriacontyldihydrofuran-2-one, which was further confirmed by 13 C NMR, COSY, NOESY, HMQC, and HMBC ( Fig. 1) (14),22-tetraen-3-one (5) [9], cinnamic acid (6) [10], a mixture of palmitic acid (7) [11] and stearic acid (8) [12], octadecyl ferulate (9) [13], and 4,5,4c,5c-tetrahydroxy-1,1c-binaphthyl (10) [14] were readily identified by comparison of their spectral data (UV, IR, 1 H NMR, MS) with data from the literature. Among them, all known compounds except 10 were isolated from Annulohypoxylon species for the first time.…”

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confidence: 80%

Chemical constituents from the endophytic fungus Annulohypoxylon squamulosum

Cheng

Chen

et al. 2012

Chem Nat Compd

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Keywords: Annulohypoxylon squamulosum, Xylariaceae, secondary metabolites, J-lactone.Endophytes, commonly present in almost all plants, are important sources of natural products with pharmaceutical potential [1,2]. An endophytic fungal strain, named BCRC 34022, was collected from Fu-shan Botanical Garden, I-lan County, Taiwan, during August of 2004. This strain was determined to be Annulohypoxylon squamulosum (family Xylariaceae), based on their cultural and anamorphic data, by Ju [3]. The Xylariaceae is a large family (Xylariales, Ascomycotina) of 36 or more genera. Secondary metabolites produced by representatives from at least one-third of these genera have now been isolated and identified [4]. The secondary metabolites of the genus Annulohypoxylon have received less attention, and only one paper has been reported [4]. To further understand the chemotaxonomy of the genus Annulohypoxylon and to continue searching for novel bioactive metabolites from Xylariaceae, A. squamulosum was chosen for chemical investigation. Careful examination on the above title fungus has resulted in the isolation of one new J-lactone, named 4-hentriacontyl-dihydrofuran-2-one (1), together with nine known constituents (2-10). Compounds 2-9 were obtained for the first time from this species. The structures of these compounds were established by means of spectral experiments. We herein report the isolation and characterization of the new compound.(S)-4-Hentriacontyl-dihydrofuran-2-one (1) was obtained as a colorless powder. The absence of UV absorption showed that the structure has no conjugated chromophore. IR spectrum revealed the J-lactone absorption at 1780 cm -1 . The 1 H NMR spectra of 1 showed one n-hentriacontyl group at G 0.89 (3H, t, J = 7.2 Hz), 1.24-1.50 (58H, br.s), 1.62 (1H, m), and 1.89 (1H, m), which was assigned to H-35, H-6-34, and H-5b/H-5a, respectively. The presence of a J-butyrolactone moiety was suggested by the signals of two CH 2 groups at 1.91 (1H, m, H-3b), 2.35 (1H, m, H-3a), and 2.56 (2H, J = 9.4, 8.9 Hz, H-2) and an oxymethine signal at 4.55 (1H, m, H-4). The n-hentriacontyl group is occupied at C-4 of the J-butyrolactone ring according to the contacts of the signals at 4.55 (H-4) and 1.62, and 1.89 (H-5) in the COSY spectrum. The molecular formula of 1 was established as C 35 H 68 O 2 by ESI-and HR-ESI-MS data, and the existence of a butyrolactone ring was supported by prominent mass fragments at m/z 85 [C 4 H 4 O 2 ] + . The configuration at C-4 was determined to be 4S based on the correlation between the [D] D -20.7q and the known S-configuration for the levorotatory (5S)-3,4-dihydro-5-nonyl-2(5H)-furanone ([D] 25 D -32.2q) [5].

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Cytotoxic Components from the Leaves of Schefflera Taiwaniana

Cited by 31 publications

References 22 publications

Loliolide - the most ubiquitous lactone

Loliolide - the most ubiquitous lactone

Effects of impressic acid from Acanthopanax koreanum on NF-κB and PPARγ activities

Chemical constituents from the endophytic fungus Annulohypoxylon squamulosum

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