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Pogostone

Pogostone
Names
Preferred IUPAC name
4-hydroxy-6-methyl-3-(4-methylpentanoyl)pyran-2-one
Other names
Dhelwangin
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
UNII
  • InChI=1S/C12H16O4/c1-7(2)4-5-9(13)11-10(14)6-8(3)16-12(11)15/h6-7,14H,4-5H2,1-3H3
    Key: AJFJTORMMHWKFW-UHFFFAOYSA-N
  • CC1=CC(=C(C(=O)O1)C(=O)CCC(C)C)O
Properties
C12H16O4
Molar mass 224.256 g·mol−1
Appearance Colorless needles
Melting point 32–33 °C (90–91 °F; 305–306 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Pogostone or dhelwangin is a naturally occurring organic compound with the formula C12H16O4. Classified as a secondary metabolite, primarily found in patchouli, a member of the mint family Lamiaceae.[1] This plant has historically been used in traditional Chinese medicine to treat ailments such as the common cold, nausea, diarrhea, headache, and fever,[2] and is also applied for its antifungal properties.[3] Pogostone was first identified in 1969 as the major antimicrobial constituent of Pogostemonis Herba, the dried aerial parts of patchouli used in herbal preparations.[4]

Structure and properties

Pogostone has the molecular formula C12H16O4.[1][5] Pogostone (PO) was obtained as needle-like colorless crystals.[5] Its melting point was reported as 32–33 °C.[5] It features a 2H-pyranone core and was first structurally characterized by X-ray crystallography, which also revealed the presence of intramolecular hydrogen bonding.[5]

Due to its low natural abundance in the plant, synthetic methods for pogostone production have been developed.[1] One synthetic route involves the condensation of dehydroacetic acid (DHA) with aldehydes in dry tetrahydrofuran (THF) under nitrogen at low temperature (0–5 °C), followed by hydrogenation, chromatography, and crystallization.[1][5] The reaction proceeds via deprotonation, Michael addition reaction, tautomerization, and further deprotonation steps.[5] Two diastereomeric dimers of pogostone, with (8S,9R) and (8S,9S) configurations, have also been synthesized and structurally confirmed by nuclear magnetic resonance and X-ray diffraction.[5]

Applications

The development of synthetic routes for pogostone and its analogues facilitates their potential application as novel antifungal agents, particularly in the treatment of azole-resistant Candida albicans infections.[1] Its anti-inflammatory activity also supports further exploration as a therapeutic agent for conditions such as septic shock.[6] However, its inhibitory effects on major cytochrome P450 enzymes warrant caution and further study regarding possible drug–drug interactions.[7]

References

  1. ^ a b c d e Yi, Yu-Yang; He, Jing-Jin; Su, Jun-Quan; Kong, Song-Zhi; Su, Ji-Yan; Li, Yu-Cui; huang, Si-Han; Li, Chu-Wen; Lai, Xiao-Ping; Su, Zi-Ren (2013-01-01). "Synthesis and antimicrobial evaluation of pogostone and its analogues". Fitoterapia. 84: 135–139. doi:10.1016/j.fitote.2012.11.005. ISSN 0367-326X. PMID 23160088.
  2. ^ Pharmacopoeia of the People's Republic of China. Vol. 3, vol. 1, Chinese Pharmacopoeia Commission ([9. ed.], English version 2010 ed.), Beijing: China Medical Science Press, 2010, pp. 42–373, ISBN 978-7-5067-5005-9{{citation}}: CS1 maint: others (link)
  3. ^ Miyazawa, Mitsuo; Okuno, Yoshiharu; Nakamura, Sei-ichi; Kosaka, Hiroshi (2000-03-01). "Antimutagenic Activity of Flavonoids from Pogostemon cablin". Journal of Agricultural and Food Chemistry. 48 (3): 642–647. Bibcode:2000JAFC...48..642M. doi:10.1021/jf990160y. ISSN 0021-8561. PMID 10725128.
  4. ^ Klein, E; Rojahn, W (1969-06-01). "[Isolation, structure and synthesis of dhelwangin]". Tetrahedron Letters (27): 2279–2280. doi:10.1016/s0040-4039(01)88141-7. ISSN 0040-4039. PMID 5796586.
  5. ^ a b c d e f g Zhao, Xiaoning; Li, Chuwen; Cao, Yongkai; Yi, Yuyang; Shi, Shujiang; Feng, Xuexuan; Su, Ziren; Zeng, Huifang (2014-01-24). "Structural elucidation of Pogostone and its dimers-two novel diastereomers combined with X-ray diffraction and spectroscopy". Journal of Molecular Structure. 1058: 189–196. Bibcode:2014JMoSt1058..189Z. doi:10.1016/j.molstruc.2013.10.054. ISSN 0022-2860.
  6. ^ Li, Yu-Cui; Xian, Yan-Fang; Su, Zi-Ren; Ip, Siu-Po; Xie, Jian-Hui; Liao, Jin-Bin; Wu, Dian-Wei; Li, Chu-Wen; Chen, Jian-Nan; Lin, Zhi-Xiu; Lai, Xiao-Ping (2014-11-18). "Pogostone suppresses proinflammatory mediator production and protects against endotoxic shock in mice". Journal of Ethnopharmacology. 157: 212–221. doi:10.1016/j.jep.2014.09.023. ISSN 1872-7573. PMID 25256685.
  7. ^ Zhang, Guiying; Zhang, Yanping; Ma, Xianjie; Yang, Xin; Cai, Yuyan; Yin, Wenli (2021). "Pogostone inhibits the activity of CYP3A4, 2C9, and 2E1 in vitro". Pharmaceutical Biology. 59 (1): 530–534. doi:10.1080/13880209.2021.1917630. ISSN 1388-0209. PMC 8871619. PMID 33915070.

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