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Pawhuskin A

Pawhuskin A
Skeletal formula
Ball-and-stick model of pawhuskin A
Names
Preferred IUPAC name
4-[(E)-2-{2-[(2E)-3,7-Dimethylocta-2,6-dien-1-yl]-3,5-dihydroxyphenyl}ethen-1-yl]-3-(3-methylbut-2-en-1-yl)benzene-1,2-diol
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
  • InChI=1S/C29H36O4/c1-19(2)7-6-8-21(5)10-15-25-23(17-24(30)18-28(25)32)12-11-22-13-16-27(31)29(33)26(22)14-9-20(3)4/h7,9-13,16-18,30-33H,6,8,14-15H2,1-5H3/b12-11+,21-10+
    Key: LZRXMBPDNILKDO-ZVBRSKEYSA-N
  • InChI=1/C29H36O4/c1-19(2)7-6-8-21(5)10-15-25-23(17-24(30)18-28(25)32)12-11-22-13-16-27(31)29(33)26(22)14-9-20(3)4/h7,9-13,16-18,30-33H,6,8,14-15H2,1-5H3/b12-11+,21-10+
    Key: LZRXMBPDNILKDO-ZVBRSKEYBQ
  • CC(=CCC/C(=C/CC1=C(C=C(C=C1O)O)/C=C/C2=C(C(=C(C=C2)O)O)CC=C(C)C)/C)C
Properties
C29H36O4
Molar mass 448.603 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Pawhuskin A is a naturally occurring prenylated stilbene isolated from Dalea purpurea which acts as a competitive silent antagonist of the κ-, μ-, and δ-opioid receptors (Ke = 203 nM, 570 nM, and 2900 nM, respectively).[2][3][4] The compound was named after Pawhuska, Oklahoma, a place near where the samples of Dalea purpurea that led to its discovery were taken from.[4] Other isolates of the plant with affinity for opioid receptors include Pawhuskin B and Pawhuskin C, though these compounds produce comparatively weak opioid receptor displacement (4.2–11.4 μM) relative to Pawhuskin A.[2][3] Dalea purpurea was used in traditional Native American medicine to treat various ailments, and pawhuskin A and related isolates may be some of the constituents of the plant which underlay this use.[3]

See also

References

  1. ^ "KNApSAcK Metabolite Information - C00039935". www.knapsackfamily.com.
  2. ^ a b Belofsky G, French AN, Wallace DR, Dodson SL (January 2004). "New geranyl stilbenes from Dalea purpurea with in vitro opioid receptor affinity". J. Nat. Prod. 67 (1): 26–30. doi:10.1021/np030258d. PMID 14738380.
  3. ^ a b c Neighbors JD, Buller MJ, Boss KD, Wiemer DF (November 2008). "A concise synthesis of pawhuskin A". J. Nat. Prod. 71 (11): 1949–52. doi:10.1021/np800351c. PMC 6679901. PMID 18922035.
  4. ^ a b Hartung AM, Beutler JA, Navarro HA, Wiemer DF, Neighbors JD (February 2014). "Stilbenes as κ-selective, non-nitrogenous opioid receptor antagonists". J. Nat. Prod. 77 (2): 311–9. doi:10.1021/np4009046. PMC 3993902. PMID 24456556.


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