17-Norkauran-18-oic acid, 16-oxo-, (4α)-
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| Category | Others |
| Catalog number | BBF-05020 |
| CAS | 18671-67-5 |
| Molecular Weight | 304.42 |
| Molecular Formula | C19H28O3 |
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Description
17-Norkauran-18-oic acid, 16-oxo-, (4α)- is a substance obtained from Wemeria-Ciliolata.
Specification
| Synonyms | (4α)-16-Oxo-17-norkauran-18-oic acid |
| IUPAC Name | (4R,4aS,6aS,9R,11aR,11bS)-4,11b-dimethyl-8-oxotetradecahydro-6a,9-methanocyclohepta[a]naphthalene-4-carboxylic acid |
Properties
| Appearance | Crystals |
| Boiling Point | 456.7±38.0°C (Predicted) |
| Melting Point | 165-166°C |
| Density | 1.16±0.1 g/cm3 (Predicted) |
Reference Reading
1. Constituents of Polyalthia longifolia var. pendula
Tzong-Huei Lee, Mei-Jhen Wang, Pi-Yu Chen, Tung-Ying Wu, Wu-Che Wen, Fu-Yu Tsai, Ching-Kuo Lee J Nat Prod. 2009 Nov;72(11):1960-3. doi: 10.1021/np900207z.
Three new clerodane-type diterpenes, 6alpha,16-dihydroxycleroda-3,13-dien-15-oic acid (1), 6alpha,16-dihydroxycleroda-4(18),13-dien-15-oic acid (2), and 4alpha,18beta-epoxy-16-hydroxyclerod-13-en-15-oic acid (3), and four new protoberberine alkaloids, (-)-8-oxo-10-hydroxy-2,3,9-trimethoxyberberine (4), (-)-8-oxo-2,11-dihydroxy-3,10-dimethoxyberberine (5), (-)-8-oxo-11-hydroxy-2,3,9,10-tetramethoxyberberine (6), and (-)-8-oxo-2,10-dihydroxy-3,9,11-trimethoxyberberine (7), together with 11 known substances, were isolated from a methanol extract of the stems of Polyalthia longifolia var. pendula. The structures of 1-7 were elucidated on the basis of spectroscopic data analysis. Compounds were evaluated for their antiproliferative activities against A549 and MCF-7 cancer cells, and among the substances tested, only 16-oxo-cleroda-3,13-dien-15-oic acid (8) exhibited cytotoxicity.
2. Microbial transformation of isosteviol oxime and the inhibitory effects on NF-kappaB and AP-1 activation in LPS-stimulated macrophages
Shwu-Fen Chang, Bo-Hon Chou, Li-Ming Yang, Feng-Lin Hsu, Wen-Kuang Lin, Yi Ho, Shwu-Jiuan Lin Bioorg Med Chem. 2009 Sep 1;17(17):6348-53. doi: 10.1016/j.bmc.2009.07.029. Epub 2009 Jul 18.
Microbial transformation of isosteviol oxime (ent-16-E-hydroxyiminobeyeran-19-oic acid) (2) with Aspergillus niger BCRC 32720 and Absidia pseudocylindrospora ATCC 24169 yielded several compounds. In addition to bioconverting the d-ring to lactone and lactam moieties, 4alpha-carboxy-13alpha-hydroxy-13,16-seco-ent-19-norbeyeran-16-oic acid 13,16-lactone (7) and 4alpha-carboxy-13alpha-amino-13,16-seco-ent-19-norbeyeran-16-oic acid 13,16-lactam (10), one known compound, ent-1beta,7alpha-dihydroxy-16-oxo-beyeran-19-oic acid (6), and five new compounds, ent-7alpha-hydroxy-16-E-hydroxyiminobeyeran-19-oic acid (3), ent-1beta,7alpha-dihydroxy-16-E-hydroxyiminobeyeran-19-oic acid (4), ent-1beta-hydroxy-16-E-hydroxyiminobeyeran-19-oic acid (5), ent-8beta-cyanomethyl-13-methyl-12-podocarpen-19-oic acid (8), and ent-8beta-cyanomethyl-13-methyl-13-podocarpen-19-oic acid (9), were isolated from the microbial transformation of 2. Elucidation of the structures of these isolated compounds was primarily based on 1D and 2D NMR, and HRESIMS data, and 3-5 were further confirmed by X-ray crystallographic analyses. Additionally, the inhibitory effects of all of these compounds were evaluated on NF-kappaB and AP-1 activation in LPS-stimulated RAW 264.7 macrophages. Among the compounds tested, 5 and 10 significantly inhibited NF-kappaB activation, with 5 showing equal potency to dexamethasone; 3 and 6-9 significantly inhibited AP-1 activation, particularly 8, which showed more inhibitory activity than dexamethasone.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
