Ramulosin
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| Category | Antibiotics |
| Catalog number | BBF-02175 |
| CAS | 29914-01-0 |
| Molecular Weight | 182.22 |
| Molecular Formula | C10H14O3 |
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Description
It is produced by the strain of Pestalotia ramulosa NRRL 2826. Ramulosin has an antifungal effect and inhibits the germination of fungal meristems.
Specification
| Synonyms | Ramulosine; NSC-112906; Ramulosin, (+)-; (3S,4AR)-8-hydroxy-3-methyl-3,4,4A,5,6, 7-hexahydro-1h-isochromen-1-one |
| IUPAC Name | (3R,4aS)-8-hydroxy-3-methyl-3,4,4a,5,6,7-hexahydroisochromen-1-one |
| Canonical SMILES | CC1CC2CCCC(=C2C(=O)O1)O |
| InChI | InChI=1S/C10H14O3/c1-6-5-7-3-2-4-8(11)9(7)10(12)13-6/h6-7,11H,2-5H2,1H3/t6-,7+/m1/s1 |
| InChI Key | XQHOYOKXFNTNQZ-RQJHMYQMSA-N |
Properties
| Appearance | Achromatic Flake Crystal |
| Antibiotic Activity Spectrum | fungi |
| Boiling Point | 309.2°C at 760 mmHg |
| Melting Point | 120-121°C |
| Density | 1.2 g/cm3 |
Reference Reading
1. New Polyenes from the Marine-Derived Fungus Talaromyces cyanescens with Anti-Neuroinflammatory and Cytotoxic Activities
Hee Jae Shin, Cao Van Anh, Duk-Yeon Cho, Dong-Kug Choi, Jong Soon Kang, Phan Thi Hoai Trinh, Byeoung-Kyu Choi, Hwa-Sun Lee Molecules. 2021 Feb 5;26(4):836. doi: 10.3390/molecules26040836.
Three new polyene compounds, talacyanols A-C (1-3), along with two known compounds, ramulosin (4) and eurothiocin A (5), were isolated from the marine fungus Talaromyces cyanescens derived from a seaweed Caulerpa sp. Structures of 1-5 were established by one-dimensional and two-dimensional (1D/2D) NMR, HR-ESIMS, and the modified Mosher's methods, as well as comparison with previously reported literature data. All the compounds (1-5) were tested for their in vitro cytotoxic and anti-neuroinflammatory activities. Among them, 1 showed moderate cytotoxic activity against a panel of cancer cell lines (HCT-15, NUGC-3, NCI-H23, ACHN, PC-3, and MDA-MB-231) with GI50 values ranging from 44.4 to 91.6 μM, whereas compounds 2 and 5 exhibited anti-neuroinflammatory effect without cytotoxicity against all the tested cell lines.
2. Terphenyl derivatives and drimane - Phathalide/isoindolinones from Hypoxylon fendleri BCC32408
Chakapong Intaraudom, Nantiya Bunbamrung, Aibrohim Dramae, Nattawut Boonyuen, Palangpon Kongsaeree, Kitlada Srichomthong, Sumalee Supothina, Pattama Pittayakhajonwut Phytochemistry. 2017 Jul;139:8-17. doi: 10.1016/j.phytochem.2017.03.008. Epub 2017 Apr 3.
The genus Hypoxylon, a member of the family Xylariaceae, has been known to produce significant secondary metabolites in terms of chemical diversity. Moreover, the compounds isolated can also be used as chemotaxonomic characters for differentiation among the two sections, which are sect. Annulata and sect. Hypoxylon. In our continuing chemical screening programme for novel compounds, the crude extracts of H. fendleri BCC32408 gave significant chemical profiles in HPLC analyses. Thus, the chemical investigation of these crude extracts was then carried out. The investigation led to the isolation of ten previously undescribed compounds including three terphenylquinones (fendleryls A - C), one terphenyl (fendleryl D), and six novel drimane - phthalide-type lactone/isoindolinones derivatives (fendlerinines A - F) along with seven known compounds (2-O-methylatromentin, rickenyl E, atromentin, rickenyls C - D, (+)-ramulosin, and O-hydroxyphenyl acetic acid). The chemical structures were determined on the basis of spectroscopic analyses, including 1D, 2D NMR and high-resolution mass spectrometry, as well as chemical transformations. In addition, these isolated compounds were assessed for antimicrobial activity including antimalarial (against Plasmodium falciparum, K-1 strain), antifungal (against Candida albicans), antibacterial (against Bacillus cereus) activities. Cytotoxicity against both cancerous (KB, MCF-7, NCI-H187) and non-cancerous (Vero) cells of these compounds were also evaluated.
3. Acid-catalysed intramolecular addition of β-ketoesters to 1,3-dienes
Marie Vayer, Weizhen Fang, Régis Guillot, Sophie Bezzenine-Lafollée, Christophe Bour, Vincent Gandon Org Biomol Chem. 2017 Jan 18;15(3):584-588. doi: 10.1039/c6ob02122k.
1,3-Dienyl β-keto esters are cyclised into bicyclolactones using the Bi(OTf)3/TfOH catalytic system. This reaction represents a rare case of simultaneous C-C and C-O bond formation at positions 1 and 3 of a 1,3-diene. Application to the synthesis of ramulosin is presented.
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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 ╳
