A presentation by John Emmanuel, department of Pharmacognosy, Faculty of pharmacy of the University of Lagos...on psoralenepsoralene.pptx

Psoralen (also called Psoralene) is the parent compound in a family of naturally occurring organic compounds known as the linear furanocoumarins.
Psoralen occurs naturally in the seeds of Psoralea corylifolia, as well as in the common fig, celery, parsley, West Indian satinwood, and in all citrus fruits

1. PRESENTATION Psoralen BY JOHN EMMANUEL August 2024 DEPARTMENT OF PHARMACOGNOSY, FACULTY OF PHARMACY, UNIVERSITY OF LAGOS JULY 2024 ON

2. OUTLINES Psoralen => The Meaning Botanical Sources of Psoralen Chemical Structure of Psoralene Biosynthesis of Psoralen Extraction of Psolalen Isolation of Psoralen Properties of Psoralen Uses of Psoralen

3. PSORALEN Psoralen  (also called  Psoralene ) is the parent compound in a family of naturally occurring organic compounds known as the linear   furanocoumarins . Psoralen occurs naturally in the seeds of  Psoralea corylifolia , as well as in the common fig,   celery, parsley, West Indian satinwood , and in all  citrus fruits .

4. PSORALEN 8 - methoxsalen and 5 - methoxsalen are furocoumarins referred to collectively as psoralens that have photosensitizing activity and are used orally and topically in conjunction with ultraviolet irradiation for the therapy of psoriasis and vitiligo . 5 -methoxsalen 8 -methoxsalen

5. PSORALEN Psoralen , a natural occurring compound, has rich history of use in traditional medicine and modern therapies. Traditional medicine Skin disease, infection and Cancer Phytochemotherapy PUVA

6. BOTANICAL SOURCES OF PSORALEN Figwort ( Scrophularia nodosa ):This plant, belonging to the Scrophulariaceae family, is a traditional medicinal herb that has been used for various ailments. It contains psoralen , along with other furanocoumarins . Scrophularia nodosa Petroselinum crispum Parsley ( Petroselinum crispum ): This common culinary herb, part of the Apiaceae family, is another source of psoralen . It's important to note that the concentration of psoralen in parsley is generally lower than in other sources.

7. Botanical Sources of PSORALEN CONT’D Ammi majus ( Bishop's weed ): This annual herb, also in the Apiaceae family, is a significant source of psoralen and is often used in traditional medicine. Ammi majus Psoralea corylifolia Ruta graveolens Psoralea corylifolia ( Babchi ): This plant, belonging to the Fabaceae family, is native to India and is a rich source of psoralen . It has been used in traditional Indian medicine for centuries. Ruta graveolens ( Rue ): A member of the Rutaceae family.

8. CHEMICAL STRUCTURE OF PSORALENE Psoralen  (also called  psoralene ) is the parent compound in a family of naturally occurring organic compounds known as the linear   furanocoumarins . It is structurally related to  coumarin  by the addition of a fused  furan  ring, and may be considered as a derivative of  umbelliferone . IUPAC name: 7 H -Furo[3,2- g ][ 1]benzopyran-7-one Properties Chemical formula : C 11 H 6 O 3 Molar mass : 186.16 g/ mol Melting point : 158 to 161 °C (316 to 322 °F; 431 to 434 K)

9. BIOSYNTHESIS OF PSORALEN ∆ ↓↑ Psoralen

10. EXTRACTION OF PSOLALEN

11. ISOLATION OF PSORALEN 120 g of 120∼200 mesh chromatographic neutral alumina to be taking. 2 g of  Psoralea corylifolia   L . coumarin crystals to be dissolve in a small amount of hot methanol, mix with 6 g of alumina, and dry it in the air at room temperature. After dry column chromatography with 15 drops of acetone per 50 ml of benzene/petroleum ether ( 40:10 ) as the eluent, the sample is to be observe under UV light. T wo fluorescence bands were separately selected for extraction under reflux with methanol, after solvent is reduce to a small volume, the remaining is to be crystallize, and filter to give crystals I and II

12. PROPERTIES OF PSORALEN Anti-inflammatory : Psoralen has anti-inflammatory properties, potentially due to its interaction with immune cells. Anti-proliferative : It can inhibit cell growth and proliferation Photoactive: Psoralen absorbs ultraviolet (UV) light, becoming chemically reactive. DNA-binding: It binds to DNA, forming a complex that can be crosslinked by UV light. Proliferative inhibition

13. USES OF PSORALEN PUVA therapy : Oral or topical Psoralen (P) is used in combination with ultraviolet A radiation ( UVA ) light to treat psoriasis , vitiligo , and other skin conditions . The process revert pathologically altered patterns of keratinocyte differentiation and the number of proliferating epidermal cells Photochemotherapy : It is used in photochemotherapy revert cell proliferation rates to normal in psoriasis. They also stimulate metanogenesis to treat certain types of lymphoma. Photoconjugation of psoralen to DNA with subsequent suppression of mitosis, DNA synthesis and cell proliferation. UVA PUVA

14. USES OF PSORALEN CONT’D Agriculture : Psoralen is used in agriculture to control weeds and pests . A technology of psoralen and insecticide , applied in the agricultural field, can solve the problem of no psoralen fungicide or insecticide , and achieve the effects of favorable environmental protection , broad antibacteria l spectrum and remarkable effect.

15. Uses of Psoralen Cont’d Research: Psoralen is used in research to study DNA damage and repair mechanisms. For instance, Psoralen plus UVA light (PUVA) is commonly used to treat psoriasis, a common skin disorder associated with rapid proliferation of cells. PUVA exerts its antiproliferative activity through formation of DNA monoadducts and interstrand cross-links (ICLs). Schematic representation of the psoralen cross-linking procedure and advantages for studies on DNA replication intermediates and nucleosome dynamics. For sake of clarity, linker and nucleosomal DNA are not drawn to scale in the graphical representation

16. Some Selected References   Dewick , P.M. (2009). Medicinal Natural Products: A Biosynthetic Approach (3rd ed.). Wiley. pp. 164–5. ISBN  978-0-471-49641-0 Honghui L.,   Lihai Z.,Daohong L.,   Peifu T., &   Feixiang S. “Isolation and purification of psoralen and isopsoralen and their efficacy and safety in the treatment of osteosarcoma in nude rats” Afr Health Sci   v.14(3); 2014 Sep  Menter , A., & D'Amico, A. (2018). Psoralen and ultraviolet A (PUVA) therapy for psoriasis. Dermatologic Therapy, 31(1), e12785. Wolf, R., & Gershwin, M. E. (2019). Psoralen and ultraviolet A (PUVA) therapy for vitiligo. Journal of the American Academy of Dermatology, 80(6), 1487-1495.

17. T H A N K Y O U F O R L I S T E N I N G ! ! !