Brine Shrimp Lethality Test Active Constituents and New Highly Oxygenated Seco-prezizaane-Type Sesquiterpenes from Illicium merrillianum.

Huang, Jianmei; Nakade, Kousuke; Kondo, Mamiko; Yang, Chunshu

doi:10.1248/cpb.50.133

Cited by 25 publications

(15 citation statements)

References 16 publications

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“…Finally, this assay has been successfully used to biomonitor the isolation of cytotoxic and antineoplasic (Siqueira, 2001) compounds from plant extracts as well as to evaluate some constituents of plants as pharmaceutical products (Huang, Nakade, Kondo, Yang, & Fukuyama, 2002) because this shrimp is highly sensitive to a wide variety of chemical substances and plant extracts (Melchor, Carballo, & Hernández, 2005).…”

Section: Brine Shrimp Lethality Test (Bst) With a Salina Lmentioning

confidence: 99%

Characterisation and preliminary bioactivity determination of Berberis boliviana Lechler fruit anthocyanins

Jiménez

Flores

et al. 2011

Food Chemistry

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Section: Brine Shrimp Lethality Test (Bst) With a Salina Lmentioning

confidence: 99%

Characterisation and preliminary bioactivity determination of Berberis boliviana Lechler fruit anthocyanins

Jiménez

Flores

et al. 2011

Food Chemistry

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“…The known compounds, (2S)-5,7,3Ј,4Ј-tetrahydroxyfla- 3) 5,7-dihydroxychromone (14), 10) 5-hydroxychromone-7-O-glucoside (15), 10) methyl-3-O-feruloylquinate (16), 11) 4-O-cinnamoylquinic acid (17), 3) oleanolic acid (18), 3) betulinic acid (19), 12) b-amyrin acetate (20), 3) lupeol (21), 13) b-sitostenone (22), 14) stigmasterol (23)ϩb-sitosterol (24) mixtures, 15) 15) cinnamic acid (27), 16) coumaric acid (28), 15) ferulic acid (29), 15) caffeic acid (30), 15) 4-hydroxybenzaldehyde (31), 3) 4-hydroxybenzoic acid (32), 3) vanillin (33), 3) vanillic acid (34), 17) protocatechuic acid (35), 3) syringaldehyde (36), 17) acetovanillone (37), 18) 2,6-dimethoxy-p-benzoquinone (38), 19) 2-deoxyepi-inositol (39), 3) thymine (40) 20) and uracil (41) 21) were also isolated and identified by comparison of their spectral data with corresponding literature values.…”

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confidence: 99%

The Inhibition of Superoxide Anion Generation in Human Neutrophils by Viscum coloratum

et al. 2006

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In clinical use, Taxillus genus plants could be placed by Viscum genus plants. But, they belong to different genera of Loranthaceae. The genus of Viscum, the plants of Loranthaceae family, are photosynthetic shrubby, hemiparasites on the tree branches. Viscum coloratum has commonly been used for Chinese medicine as a curative for a number of ailments such as hemorrhage, pleurisy, gout, heart disease, epilepsy, arthritis and hypertension.1,2) In our research, we found oleanolic acid showed significantly anti-inflammatory activitiy in V. articulatum.3) Oleanolic acid concentration-dependently inhibited superoxide anion generation by human neutrophils in response to fMLP (formyl-L-methionyl-Lleucyl-L-phenylalanine), but not to PMA (phorbol myristate acetate). It suggested that the inhibitory effect of oleanolic acid was through protein kinase C-independent pathway.In a previous screening for the inhibitory activities on superoxide anion generation in fMLP-stimulated human neutrophils by Viscum and Taxillus medicinal plants, V. coloratum also exhibited the strong inhibition. From V. coloratum, two new and thirty-nine known compounds were isolated and characterized. This paper deals with the structural determination of two new compounds, viscolin (4Ј,4Љ-dihydroxy-2Ј,3Ј,6Ј,3Љ-tetramethoxy-1,3-diphenylpropane) (1) and (2S)-7,4Ј-dihydroxy-5,3Ј-dimethoxyflavanone (2) by spectral analysis. The inhibitory activities of crude extract and pure compounds on neutrophils stimulated by fMLP/CB were also tested. Results and DiscussionThe crude extract and partitioned layers were examined for their anti-inflammatory effect using neutrophils. The chloroform soluble layer revealed significantly anti-inflammatory activities and the butanol soluble layer demonstrated slight functions in the results (Table 1). The resultant chloroform and butanol fractions were repeatedly subjected to silica gel and reverse phase column chromatographies and yielded two new compounds, viscolin (1) and (2S)-7,4Ј-dihydroxy-5,3Ј-dimethoxyflavanone (2).Viscolin (1) was a pale yellow needles, and its chemical formula, C 19 H 24 O 6 , was gained by HR-EI-MS (high resolution electron impact mass). UV spectrum of viscolin (1) revealed the maximum absorption at 282 and 229 (sh) nm and the absorption band at 3393 cm Ϫ1 showed hydroxyl group in its IR spectrum.In the 1 H-NMR spectrum (Table 2) of viscolin (1), four methoxyl signals appeared at d 3.88, 3.85, 3.82 and 3.74, respectively. In the aromatic region, an ABX splitting pattern and one singlet signals showed at d 6.83, 6.72, 6.70 and 6.31 indicated a tri-substituted and a penta-substituted phenyl moieties in 1. In addition, there were three mutual coupled methylene signals showed at d 2.62, 2.60 and 1.79 confirmed One new 1,3-diphenylpropane, viscolin (1), and one new flavanone, (2S)-7,4-dihydroxy-5,3-dimethoxyflavanone (2), together with thirty-nine known compounds, which included eleven known flavanones, two chromones, fourteen benzenoids, one inositol, two pyrimidines, four triterpenoids and five steroids...

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“…We utilized BST as a primary bioassay for screening plant extracts and natural products [9,10] because BST has been shown to have a positive correlation to cytotoxicity and/or pesticidal activity [20]. All the isolated compounds were assessed by BST.…”

Section: Npc Natural Product Communicationsmentioning

confidence: 99%

“…The few chemical studies of this plant that have been reported in the literature [1] revealed the presence of steroidal sapogenins, and some Smilax species have been reported to contain steroidal compounds, flavonoids, and phenolic compounds [2][3][4][5][6][7][8]. As part of our research into biologically active natural products, we screened the MeOH extract of the twigs of S. longifolia, a Brazilian medicinal plant, by using the brine shrimp (Artemia salina) lethality test (BST) [9][10][11], and found its extract to be BST active (LD 50 = 100 ppm). Phytochemical studies on the MeOH extract of this plant resulted in the isolation of three new bibenzyls 1-3, together with previously known bibenzyls 4-6 [12][13][14][15], the diarylpropanoid 7, three diarylheptanoids 8-10, and two steroidal sapogenins, diosgenin and pennogenin [12].…”

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Three New Bibenzyls from the Twigs of Smilax longifolia

Imura

Harada

Kubo

2017

Natural Product Communications

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Three new bibenzyl compounds, 1-3, were isolated along with the previously known bibenzyls 4-6, one diarylpropanoid 7, and three diarylheptanoids 8-10 from the twigs of Smilax longifolia. The structures of the new compounds were elucidated by analyzing their spectroscopic data and comparing them with those of known compounds. Diarylheptanoid 9 exhibited potent lethality in the brine shrimp lethality test (BST). Smilax longifoliaRich. (smilacaceae), widely distributed in Brazil and French Guiana, is commonly called "Cipo-em", and its roots have been used in folk medicine for the treatment of syphilis, nephritis, and rheumatism and for lowering cholesterol [1]. The few chemical studies of this plant that have been reported in the literature [1] revealed the presence of steroidal sapogenins, and some Smilax species have been reported to contain steroidal compounds, flavonoids, and phenolic compounds [2][3][4][5][6][7][8]. As part of our research into biologically active natural products, we screened the MeOH extract of the twigs of S. longifolia, a Brazilian medicinal plant, by using the brine shrimp (Artemia salina) lethality test (BST) [9][10][11], and found its extract to be BST active (LD 50 = 100 ppm). Phytochemical studies on the MeOH extract of this plant resulted in the isolation of three new bibenzyls 1-3, together with previously known bibenzyls 4-6 [12][13][14][15], the diarylpropanoid 7, three diarylheptanoids 8-10, and two steroidal sapogenins, diosgenin and pennogenin [12]. In this paper, we report the isolation and structure elucidation of new compounds 1-3 and the BST activity of the isolated compounds.Compound 1 was obtained as a colorless oil, and its molecular formula was established to be C 17 H 20 O 4 by high-resolution electron ionization MS (HR-EI-MS), which showed a peak at m/z 288 [M] + . The IR spectrum showed absorption bands at 3414 cm -1 from a hydroxy group and at 1596 and 1469 cm -1 from a phenyl ring. The 1 H and 13 C NMR spectra (Table 1) of 1 revealed the presence of three methoxy groups at  H 3.76 (6H, s) and  C 55.3 and  H 3.79 (3H, s) and C 55.7, a 2,6-disubstituted phenyl ring at  H 6.42 (dd, J = 8.1, 0.7 Hz), 6.49 (dd, J = 8.1, 0.7 Hz) and 7.03 (t, J = 8.1 Hz), a 3,5-disubstituted phenyl ring at  H 6.32 (d, J = 2.2 Hz) and 6.37 (2H, d, J = 2.2 Hz), and two benzylic methylenes at  H 2.76 (2H, t, J = 9.0 Hz) and  C 25.4 and  H 2.92 (2H, t, J = 9.0 Hz) and  C 35.7.

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Brine Shrimp Lethality Test Active Constituents and New Highly Oxygenated Seco-prezizaane-Type Sesquiterpenes from Illicium merrillianum.

Cited by 25 publications

References 16 publications

Characterisation and preliminary bioactivity determination of Berberis boliviana Lechler fruit anthocyanins

Characterisation and preliminary bioactivity determination of Berberis boliviana Lechler fruit anthocyanins

The Inhibition of Superoxide Anion Generation in Human Neutrophils by Viscum coloratum

Three New Bibenzyls from the Twigs of Smilax longifolia

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