Chemistry:Pogostone
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
- ↑ 1.0 1.1 1.2 1.3 1.4 Yi, Yu-Yang; He, Jing-Jin; Su, Jun-Quan; Kong, Song-Zhi; Su, Ji-Yan; Li, Yu-Cui; huang, Si-Han; Li, Chu-Wen et al. (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. https://linkinghub.elsevier.com/retrieve/pii/S0367326X12002985.
- ↑ Pharmacopoeia of the People's Republic of China. Vol. 3, 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
- ↑ Miyazawa, Mitsuo; Okuno, Yoshiharu; Nakamura, Sei-ichi; Kosaka, Hiroshi (2000-03-01). "Antimutagenic Activity of Flavonoids from Pogostemon cablin" (in en). Journal of Agricultural and Food Chemistry 48 (3): 642–647. doi:10.1021/jf990160y. ISSN 0021-8561. PMID 10725128. Bibcode: 2000JAFC...48..642M. https://pubs.acs.org/doi/10.1021/jf990160y.
- ↑ 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. https://europepmc.org/article/med/5796586.
- ↑ 5.0 5.1 5.2 5.3 5.4 5.5 5.6 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. doi:10.1016/j.molstruc.2013.10.054. ISSN 0022-2860. Bibcode: 2014JMoSt1058..189Z. https://linkinghub.elsevier.com/retrieve/pii/S0022286013009137.
- ↑ Li, Yu-Cui; Xian, Yan-Fang; Su, Zi-Ren; Ip, Siu-Po; Xie, Jian-Hui; Liao, Jin-Bin; Wu, Dian-Wei; Li, Chu-Wen et al. (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.
- ↑ Zhang, Guiying; Zhang, Yanping; Ma, Xianjie; Yang, Xin; Cai, Yuyan; Yin, Wenli (2021). "Pogostone inhibits the activity of CYP3A4, 2C9, and 2E1 in vitro" (in en). Pharmaceutical Biology 59 (1): 530–534. doi:10.1080/13880209.2021.1917630. ISSN 1388-0209. PMID 33915070.
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