cis-4-Hydroxymellein
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| Category | Others |
| Catalog number | BBF-05479 |
| CAS | 60132-20-9 |
| Molecular Weight | 194.18 |
| Molecular Formula | C10H10O4 |
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Description
It is produced by the strain of Aspergillus ochraceus and Lasiodiplodia theobromae.
Specification
| Synonyms | (3S-cis)-4-hydroxymellein; (3S,4S)-4,8-dihydroxy-3-methylisochroman-1-one; cis-3S,4S-4-Hydroxymellein; 4-Hydroxymellein, (3S-cis-(+))-; 3,4-Dihydro-4beta,8-dihydroxy-3beta-methyl-1H-2-benzopyran-1-one; 1H-2-Benzopyran-1-one, 3,4-dihydro-4,8-dihydroxy-3-methyl-, (3S,4S)-; 1H-2-Benzopyran-1-one, 3,4-dihydro-4,8-dihydroxy-3-methyl-, (3S-cis)- |
| IUPAC Name | (3S,4S)-4,8-dihydroxy-3-methyl-3,4-dihydroisochromen-1-one |
| Canonical SMILES | CC1C(C2=C(C(=CC=C2)O)C(=O)O1)O |
| InChI | InChI=1S/C10H10O4/c1-5-9(12)6-3-2-4-7(11)8(6)10(13)14-5/h2-5,9,11-12H,1H3/t5-,9+/m0/s1 |
| InChI Key | STSOHAOGZMLWFR-SSDLBLMSSA-N |
Properties
| Appearance | Prisms |
| Boiling Point | 427.2±45.0°C at 760 mmHg |
| Melting Point | 112-117°C |
| Density | 1.4±0.1 g/cm3 |
| Solubility | Soluble in Methanol |
Reference Reading
1. Isolation of anticancer and anti-trypanosome secondary metabolites from the endophytic fungus Aspergillus flocculus via bioactivity guided isolation and MS based metabolomics
Ahmed F Tawfike, Muhammad Romli, Carol Clements, Gráinne Abbott, Louise Young, Marc Schumacher, Marc Diederich, Mohamed Farag, RuAngelie Edrada-Ebel J Chromatogr B Analyt Technol Biomed Life Sci. 2019 Feb 1;1106-1107:71-83. doi: 10.1016/j.jchromb.2018.12.032. Epub 2019 Jan 6.
This study aims to identify bioactive anticancer and anti-trypanosome secondary metabolites from the fermentation culture of Aspergillus flocculus endophyte assisted by modern metabolomics technologies. The endophyte was isolated from the stem of the medicinal plant Markhamia platycalyx and identified using phylogenetics. Principle component analysis was employed to screen for the optimum growth endophyte culturing conditions and revealing that the 30-days rice culture (RC-30d) provided the highest levels of the bioactive agents. To pinpoint for active chemicals in endophyte crude extracts and successive fractions, a new application of molecular interaction network is implemented to correlate the chemical and biological profiles of the anti-trypanosome active fractions to highlight the metabolites mediating for bioactivity prior to purification trials. Multivariate data analysis (MVDA), with the aid of dereplication studies, efficiently annotated the putatively active anticancer molecules. The small-scale RC-30d fungal culture was purified using high-throughput chromatographic techniques to yield compound 1, a novel polyketide molecule though inactive. Whereas, active fractions revealed from the bioactivity guided fractionation of medium scale RC-30d culture were further purified to yield 7 metabolites, 5 of which namely cis-4-hydroxymellein, 5-hydroxymellein, diorcinol, botryoisocoumarin A and mellein, inhibited the growth of chronic myelogenous leukemia cell line K562 at 30 μM. 3-Hydroxymellein and diorcinol exhibited a respective inhibition of 56% and 97% to the sleeping sickness causing parasite Trypanosoma brucei brucei. More interestingly, the anti-trypanosomal activity of A. flocculus extract appeared to be mediated by the synergistic effect of the active steroidal compounds i.e. ergosterol peroxide, ergosterol and campesterol. The isolated structures were elucidated by using 1D, 2D NMR and HR-ESIMS.
2. [Chemical constituents from Cinnamomum cassia]
Shan He, Yong Jiang, Peng-fei Tu Zhongguo Zhong Yao Za Zhi. 2015 Sep;40(18):3598-602.
Various column chromatography, such as silica gel, Sephadex LH-20, ODS, and semi-preparative HPLC was used to isolate and purify the chemical constituents from Cinnamomum cassia. The structures were determined on the basis of NMR and MS spectral data analysis, together with the comparison with literature data. Fifteen compounds were isolated from the 85% aqueous ethanol extract of C. cassia, and their structures were identified as (2R, 3R)-5,7,3',4'-tetramethoxyflavan-3-ol( 1), (2R, 3R)-5,7-dimethoxy-3',4'-methylenedioxyflavan-3-ol (2), coumarin (3), cinnamic acid (4), (E)-2-hydroxy-phenylpropionic acid cinnamoyl ester (5), 3, 3', 4, 4'-tetrahydroxy biphenyl (6), methylstictic acid (7), epi-boscialin (8), (1R,2S,3S,4S)-2,3-epoxy-1, 4-dihydroxy-5-methyl-5-cyelohexene (9), 4,5-dihydroxy-3-methyl cyclohex-2-enone (10), cis-4-hydroxymellein (11), and 2-hydroxy-4-methoxyl-cinnamaldehyde (12). Compounds 5-11 were obtained from this genus plants for the first time.
3. Colletotrilactam A-D, novel lactams from Colletotrichum gloeosporioides GT-7, a fungal endophyte of Uncaria rhynchophylla
Bo Wei, Zhong-Duo Yang, Xiao-Wei Chen, Shuang-Yan Zhou, Hai-Tao Yu, Jing-Yun Sun, Xiao-Jun Yao, Yong-Gang Wang, Hong-Yan Xue Fitoterapia. 2016 Sep;113:158-63. doi: 10.1016/j.fitote.2016.08.005. Epub 2016 Aug 9.
Four novel lactams, colletotrilactam A-D (1-4), along with six known compounds (5-10) were isolated from the culture broth of Colletotrichum gloeosporioides GT-7, a fungal endophyte of Uncaria rhynchophylla. The structures of these compounds were elucidated by comprehensive NMR spectroscopy. Isolates were tested for monoamine oxidase (MAO) inhibitory activity and compound 9 showed potent MAO inhibitory activity with IC50 value of 8.93±0.34μg/mL, when the IC50 value of iproniazid as a standard was 1.80±0.5μg/mL.
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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 ╳
