Tinosporide

Last updated
Tinosporide
Tinosporide.svg
Names
IUPAC name
(2S,4aR,6aR,7S,7aS,8aS,9S,9aS,9bS)-2-(3-Furanyl)dodecahydro-7-hydroxy-6a,9b-dimethyl-9,7-(epoxymethano)-4H-oxireno[6,7]naphtho[2,1-c]pyran-4,11-dione
Other names
2,3-Epoxycolumbin; Jateorin; 5-(furan-3-yl)-12-hydroxy-3,11-dimethyl-6,14,16-trioxapentacyclo[10.3.2.02,11.03,8.013,15]heptadecane-7,17-dione
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
  • InChI=1S/C20H22O7/c1-18-7-11(9-4-6-24-8-9)25-16(21)10(18)3-5-19(2)14(18)12-13-15(26-13)20(19,23)17(22)27-12/h4,6,8,10-15,23H,3,5,7H2,1-2H3
    Key: TXOMRNMZLZXJQP-UHFFFAOYSA-N
  • [H][C@@]12CC[C@]3(C)[C@@]([H])([C@@H]4OC(=O)[C@@]3(O)[C@H]3O[C@@H]43)[C@]1(C)C[C@H](OC2=O)C1=COC=C1
Properties
C20H22O7
Molar mass 374.389 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Tinosporide is a chemical compound classified as a diterpenoid and a furanolactone. It was first isolated from the plant Tinospora cordifolia , from which it derives its name. [1] [2] It has since been found in other plants of the genus Tinospora , such as Tinospora glabra . [3] [4] [5]

Because Tinospora cordifolia has been used in traditional herbal medicine, there has been research directed at exploring the potential pharmacology of tinosporide and related compounds. [6]

Other diterpenoid furanolactones with a similar structure include columbin, palmarin, and chasmanthin.

  1. ↑ Swaminathan, K.; Sinha, U. C.; Bhatt, R. K.; Sabata, B. K.; Tavale, S. S. (1989). "Structure of tinosporide, a diterpenoid furanolactone from Tinospora cordifolia Miers". Acta Crystallographica Section C. 45 (1): 134–136. Bibcode:1989AcCrC..45..134S. doi:10.1107/s0108270188009953. PMID   2610955.
  2. ↑ Sharma, Priyanka; Dwivedee, Bharat P.; Bisht, Dheeraj; Dash, Ashutosh K.; Kumar, Deepak (2019). "The chemical constituents and diverse pharmacological importance of Tinospora cordifolia". Heliyon. 5 (9): e02437. Bibcode:2019Heliy...502437S. doi: 10.1016/j.heliyon.2019.e02437 . PMC   6827274 . PMID   31701036.
  3. ↑ "Isolation and Characterisation of clerodane diterpenoids from the traditional medicinal plant -Tinospora glabra (Burm. f.) Merrill".
  4. ↑ Girme, Aboli; Saste, Ganesh; Singh, Ruchi; Mirgal, Amit; Ingavale, Rajnita; Balasubramaniam, Arun Kumar; Ghoshal, Sautik; Ghule, Chetana; Patel, Saurabh; Verma, Mahendra Kumar; Maurya, Rakesh; Hingorani, Lal (2022). "Quantitative and rapid quality assessment methods for the multi-class bioactive constituents of Tinospora cordifolia using high-performance liquid and thin layer chromatography analysis with tandem mass spectrometry characterization" . Separation Science Plus. 5 (8): 378–392. doi:10.1002/sscp.202200048. S2CID   249304214.
  5. ↑ Adib, Mohiminul; Islam, Rashedul; Ahsan, Monira; Rahman, Arifur; Hossain, Mahmud; Rahman, Md Mustafizur; Alshehri, Sultan M.; Kazi, Mohsin; Mazid, Md Abdul (2021). "Cholinesterase inhibitory activity of tinosporide and 8-hydroxytinosporide isolated from Tinospora cordifolia: In vitro and in silico studies targeting management of Alzheimer's disease". Saudi Journal of Biological Sciences. 28 (7): 3893–3900. doi:10.1016/j.sjbs.2021.03.063. PMC   8241625 . PMID   34220245.
  6. ↑ Pathak, Ashish K.; Jain, Dharam C.; Sharma, Ram P. (1995). "Chemistry and Biological Activities of the Genera Tinospora". International Journal of Pharmacognosy. 33 (4): 277–287. doi:10.3109/13880209509065379.


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