Hongoquercin A
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| Category | Antibiotics |
| Catalog number | BBF-00973 |
| CAS | |
| Molecular Weight | 372.50 |
| Molecular Formula | C23H32O4 |
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Description
Hongoquercin A is a sesquiterpene antibiotic produced by an unidentified fungus. It has moderate anti-Gram-positive bacteria activity with a MIC of 4-8 μg/mL.
Specification
| IUPAC Name | (4aS,6aR,12aR,12bS)-11-hydroxy-4,4,6a,9,12b-pentamethyl-1,2,3,4a,5,6,12,12a-octahydrobenzo[a]xanthene-10-carboxylic acid |
| Canonical SMILES | CC1=CC2=C(CC3C4(CCCC(C4CCC3(O2)C)(C)C)C)C(=C1C(=O)O)O |
| InChI | InChI=1S/C23H32O4/c1-13-11-15-14(19(24)18(13)20(25)26)12-17-22(4)9-6-8-21(2,3)16(22)7-10-23(17,5)27-15/h11,16-17,24H,6-10,12H2,1-5H3,(H,25,26)/t16-,17+,22-,23+/m0/s1 |
| InChI Key | NGQPPHRBPAZXBM-VQDLLJBESA-N |
Properties
| Appearance | White Powder |
| Antibiotic Activity Spectrum | Gram-positive bacteria |
| Boiling Point | 490.8±45.0 °C at 760 mmHg |
| Melting Point | 145-148°C |
| Density | 1.1±0.1 g/cm3 |
Reference Reading
1. Application of cyclohexane-1,3-diones for six-membered oxygen-containing heterocycles synthesis
Dharminder Sharma, Manish Kumar, Pralay Das Bioorg Chem. 2021 Feb;107:104559. doi: 10.1016/j.bioorg.2020.104559. Epub 2020 Dec 15.
Cyclohexan-1,3-dione derivatives are versatile scaffolds for the synthesis of a variety of value-added organic molecules including heterocycles and natural products. Six-membered oxygen heterocycles prepared from cyclohexan-1,3-diones are of much importance as they are intermediate for the synthesis of a number of natural products and several other valuable bioactive molecules which shows anti-viral, anti-bacterial, analgesic, antimalarial, anti-inflammatory, anti-allergic, anti-tumor and anti-cancer activities. These advantages have inspired us to write a detailed survey on the newly developed methods which are very essential in the construction of six-membered oxygen heterocycles. Further, the versatility in the chemistry of cyclohexan-1,3-dione and its derivatives is due to the presence of highly active methylene moiety and its active di-carbonyl groups. Recently, reactions of cyclohexane-1,3-dione and its derivatives with other substrates for instance aldehydes, malononitriles, NMSM, chalcones, isatin etc. have been established for the construction of a variety of six-membered oxygen heterocycles. The studies reported in this review article involved the synthesis of six-membered oxygen-containing heterocycles which includes 4H-chromen-5(6H)-one, 2H-xanthen-1(9H)-one, 2H-xanthen-1,8(5H,9H)-dione, 6H-chromen-2,5-dione derivatives and natural products having six-membered oxygen heterocycles from cyclohexane-1,3-dione and its derivatives as one of the substrate.
2. Biomimetic Syntheses of Analogs of Hongoquercin A and B by Late-Stage Derivatization
Thomas Mies, Andrew J P White, Philip J Parsons, Anthony G M Barrett J Org Chem. 2021 Jan 15;86(2):1802-1817. doi: 10.1021/acs.joc.0c02638. Epub 2020 Dec 28.
The hongoquercins are tetracyclic meroterpenoid natural products with the trans-transoid decalin-dihydrobenzopyran ring system, which display a range of different bioactivities. In this study, the syntheses of a range of hongoquercins using gold-catalyzed enyne cyclization reactions and further derivatization are described. The parent enyne resorcylate precursors were synthesized biomimetically from the corresponding dioxinone keto ester via regioselective acylation, Tsuji-Trost allylic decarboxylative rearrangement, and aromatization. The dioxinone keto ester 12 was prepared in 6 steps from geraniol using allylic functionalization and alkyne synthesis.
3. Daurichromenic Acid from the Chinese Traditional Medicinal Plant Rhododendron dauricum Inhibits Sphingomyelin Synthase and Aβ Aggregation
Hadya Virupaksha Deepak, Mahadeva M M Swamy, Yuta Murai, Yoshiko Suga, Masaki Anetai, Takuro Yo, Masahiro Kuragano, Koji Uwai, Kiyotaka Tokuraku, Kenji Monde Molecules. 2020 Sep 7;25(18):4077. doi: 10.3390/molecules25184077.
Species of the genus Rhododendron have been used in traditional Chinese medicine, with the medicinal herb "Manshanfong" used as an expectorant and for the treatment of acute bronchitis. Daurichromenic acid (DCA), a constituent of Rhododendron dauricum, is a meroterpenoid with antibacterial, anti-HIV, and anti-inflammatory activities. However, the mechanisms underlying these pharmacologic activities are poorly understood. To develop new drugs based on DCA, more information is required regarding its interactions with biomolecules. The present study showed that DCA inhibits the activity of the enzyme sphingomyelin synthase, with an IC50 of 4 µM. The structure-activity relationships between DCA and sphingomyelin synthase were evaluated using derivatives and cyclized hongoquercin A. In addition, DCA was found to inhibit amyloid β aggregation. These results may help in the design of effective drugs based on DCA.
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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 ╳
