3α,11α-Dihydroxylup-20(29)-ene-23,28-dioic acid from Schefflera octophylla

Lischewski, M.; Ty,; Schmidt, Jürgen; Preiß, A.; Phiet, H.V.; Adam, G.

doi:10.1016/s0031-9422(00)83471-8

Cited by 36 publications

(30 citation statements)

References 6 publications

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“…The bark, leaves and roots are the parts used medicinally, and can easily be collected all year round. Chemical studies of S. heptaphylla indicated that triterpenoids and saponins are the major constituents of the plant (Adam et al, 1982;Lischewski et al, 1984;Schmidt et al, 1984;Kitajima and Tanaka, 1989;Kitajima et al, 1990;Sung et al, 1991a, b, c;Sung and Adam, 1991;Sung and Adam, 1992;Maeda et al, 1994). The specific components isolated from S. heptaphylla are sulfated triterpenoids and their glycosides (Kitajima et al, 1990;Sung and Adam, 1991).…”

Section: Introductionmentioning

confidence: 99%

Antiviral triterpenoids from the medicinal plant Schefflera heptaphylla

Jiang

Ooi

et al. 2007

Phytotherapy Research

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Schefflera heptaphylla (L.) Frodin is a principal ingredient of an herbal tea formulation widely used for the treatment of common cold in southern China. An extract of the long leafstalk of the compound leaf of S. heptaphylla exhibited the most potent antiviral activity against respiratory syncytial virus (RSV). Further antiviral-guided fractionation and isolation of the leafstalk extract of S. heptaphylla led to obtain two highly active pure triterpenoids, namely 3alpha-hydroxylup-20(29)-ene-23,28-dioic acid and 3-epi-betulinic acid 3-O-sulfate, together with an inactive saponin, 3alpha-hydroxylup-20(29)-ene-23,28-dioic acid 28-O-alpha-l-rhamnopyranosyl-(1-->4)-O-beta-d-glucopyranosyl-(1-->6)-beta-d-glucopyranoside. An antiviral assay using a cytopathic effect (CPE) reduction method showed that the two triterpenoids possessed broader antiviral activity against respiratory syncytial virus (RSV) with a similar 50% inhibition concentration (IC(50)) value of 6.25 microg/mL, influenza A (H1N1) virus with IC(50) values of 25 and 31.3 microg/mL, Coxsackie B3 (Cox B3) virus with IC(50) values of 12.5 and 20 microg/mL and herpes simplex virus type 1 (HSV-1) with IC(50) values of 18.8 and 25 microg/mL, respectively, whereas the saponin did not have antiviral activity against these four viruses at a concentration of 100 microg/mL.

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Section: Introductionmentioning

confidence: 99%

Antiviral triterpenoids from the medicinal plant Schefflera heptaphylla

Jiang

Ooi

et al. 2007

Phytotherapy Research

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“…Only four spe cies of Schefflera (Araliaceae) are in dig enous to Tai wan. The chem i cal stud ies of S. octophylla [1][2][3][4][5][6][7] and S. arboricola [8][9] have been de scribed, and these con tain steroids, ste roid glycosides, sesquiterpenes, diterpenes, triterpenes, triterpene glycosides, and sug ars. The spe cial com ponents of S. octophylla are 3 -and 3 -betulinic acid sul fate.…”

Section: Introductionmentioning

confidence: 99%

“…int.) 472 (M + , 3), 454(21), 421(9), 300(20), 285(21), 237 (40), 234 (98), 201 (57), 175 (88), 135 (100);1 H NMR (CDCl 3 ): 0.82, 0.91, 0.91, 0.98, 1.03, 1.67 (each 3H, s), 1.60 (1H, t, J = 10.8 Hz, H-18), 2.98 (1H, ddd, J = 10.8, 10.8, 5.2 Hz, H-19), 4.60 and 4.74 (each 1H, br s); 13 C NMR (pyridine-d 5 ): 14.7 (q, C-27), 16.3 (q, C-26), 17.3 (q, C-25), 18.0 (t, C-6), 19.4 (q, C-30), 22.3 (q, C-24), 25.6 (t, C-2), 28.7 (q, C-23), 29.4 (t, C-21), 30.5 (t, C-15), 32.1 (t, C-16), 35.1 (t, C-1, 7), 36.9 (t, C-12), 37.3 (d, C-13), 37.8 (s, C-10, 22), 39.1 (s, C-4), 42.3 (s, C-8), 42.6 (s, C-14), 46.7 (d, C-18), 48.7 (d, C-5), 48.9 (d, C-19), 55.6 (d, C-9), 56.3 (s, C-17), 70.5 (d, C-11), 75.9 (d, C-3), 110.2 (d, C-29), 149.8 (t, C-20), 181.5 (s, C-28). 3 -Hydroxyolean-12,28-dioic dimethyl es ter (10b) Amor phous; IR (KBr) max : 3505, 3050, 1730, 1667 cm -1 ; EIMS (70 eV) m/z (rel.…”

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confidence: 99%

Cytotoxic Components from the Leaves of Schefflera Taiwaniana

Kuo

Chan

2002

J Chinese Chemical Soc

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The isolation and identification of eighteen components from the leaves of Schefflera taiwaniana are presented. Their structures were determined on the basis of spectral data as well as direct comparison with authentic samples. These compounds include two polyacetylenes, one carotenoid‐like, three sesquiterpenes, one diterpene, four triterpenes, two tocopherols, and five alkyl 4‐hydroxycinnamate mixtures. Among these, 4‐hydroxy‐trans‐cinnamic acid docosyl ester and 4‐hydroxy‐cis‐cinnamic acid tetracosyl ester are new compounds. Some of these components exhibit cytotoxic activity.

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“…By comparison of their NMR data to those reported in the literature, the structures of these compounds were identified as impressic acid (3) (Kuo et al 2002), 3a,11a-dihydroxy-lup-20(29)-en-23-al-28-oic acid (4) (Chang et al 1999), 3a-hydroxy-lup-20(29)-en-23,28-dioic acid (5) (Chang et al 1998), 3a,11a-dihydroxy-lup-20(29)-en-23,28-dioic acid (6) (Lischewski et al 1984), 3a-hydroxylup-20(29)-en-30-ol-23,28-dioic acid (7) (Wanas et al 2010), ent-kaur-15-en-17-al-19-oic acid (8) (Harrigan et al 1994), 17-hydroxy-16a-ent-kauran-19-oic acid (9) (Duan et al 1999), 16a-hydroxy-ent-kauran-19-oic acid (10) (Duan et al 1999), 13-epi-ent-manoyloxide-19-oic acid (11) (Zdero et al 1992), ent-kaur-16-en-19-al (12) (Catalano et al 1993), ent-kaur-16-en-19-oic acid (13) (Catalano et al 1993), 18-nor-ent-kaur-16-ene-4b-ol (14) (Jung et al 2009) and ent-19-hydroxy-13-epi-manoyl oxide (15) (Fraga et al 1989) (Fig. 1), respectively.…”

Section: Structural Elucidation Of the Isolated Compoundsmentioning

confidence: 99%

Terpenoid composition and the anticancer activity of Acanthopanax trifoliatus

Zheng

Chen

et al. 2015

Arch. Pharm. Res.

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The petroleum ether and ethyl acetate fractions of extract from an edible and medicinal plant Acanthopanax trifoliatus were found to show significant inhibitory effects against SF-268, MCF-7, HepG2 and NCI-H460 cancer cells. Two new ursane-type triterpenoids, acantrifoic acid C (1) and acantrifoic acid D (2), along with five known triterpenoids (3-7) and eight known diterpenoids (8-15) were obtained from these two fractions. To the best of our knowledge, this is the first report concerning the isolation of compounds (5-12, 14, 15) from A. trifoliatus. Among all the isolated compounds, 3, 5 and 8 from the ethyl acetate fraction showed the strongest inhibitory effects against cancer cells, while 12 and 13 from the petroleum ether fraction showed moderate activities. These terpenoid compounds may be responsible for the anticancer activities of A. trifoliatus. Our study provides the first evidence that terpenoids from A. trifoliatus exert anticancer activities and indicates that A. trifoliatus may be a useful edible plant for further development of anticancer health supplement.

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3α,11α-Dihydroxylup-20(29)-ene-23,28-dioic acid from Schefflera octophylla

Cited by 36 publications

References 6 publications

Antiviral triterpenoids from the medicinal plant Schefflera heptaphylla

Antiviral triterpenoids from the medicinal plant Schefflera heptaphylla

Cytotoxic Components from the Leaves of Schefflera Taiwaniana

Terpenoid composition and the anticancer activity of Acanthopanax trifoliatus

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