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ARS Home » Southeast Area » Oxford, Mississippi » Natural Products Utilization Research » Research » Publications at this Location » Publication #384862

Research Project: Biobased Pesticide Discovery and Product Optimization and Enhancement from Medicinal and Aromatic Crops

Location: Natural Products Utilization Research

Title: (E)-2,6,10-Trimethyldodec-8-en-2-ol: An undescribed sesquiterpenoid from copaiba oil

item HAWWAL, MOHAMMED - University Of Mississippi
item ALI, ZULFIQAR - University Of Mississippi
item Wang, Mei
item ZHAO, JIANPING - University Of Mississippi
item LEE, JOSEPH - University Of Mississippi
item FANTOUKH, OMER - University Of Mississippi
item KHAN, IKHLAS - University Of Mississippi

Submitted to: Molecules
Publication Type: Peer Reviewed Journal
Publication Acceptance Date: 6/19/2021
Publication Date: 6/23/2021
Citation: Hawwal, M.F., Ali, Z., Wang, M., Zhao, J., Lee, J., Fantoukh, O.I., Khan, I.A. 2021. (E)-2,6,10-Trimethyldodec-8-en-2-ol: An undescribed sesquiterpenoid from copaiba oil. Molecules. 2021, 26, 4456.

Interpretive Summary: Copaiba oil is an exudate secretion that results from the trees’ detoxification process. South America, particularly Brazil, has diverse Copaifera species and is considered the largest global exporter of copaiba oil. Copaiba oil has been used in folk medicine for centuries as a wound-healing agent. This use was likely inspired by animals. The indigenous people observed injured animals rubbing their bodies on the stem of Copaifera trees. The indigenous people of the Amazon region also used the Copaifera tree to treat several other conditions such as urinary tract infections, sore throats, stomach ulcers, and infectious diseases. Copaifera trees play a vital role as an alternative remedy in the Amazon region of Brazil, and it is no surprise that phytotherapeutic and cosmetic products using copaiba oil have found their way not only into the Brazilian market but also to the international markets. In this study, the copaiba oil was investigated as part of a continuing effort to isolate and identify chemical markers for use in quality studies of dietary supplements and botanical drug products under development in the United States. In this regard, eight sesquiterpenes, including one new, were isolated and characterized by analyzing their 1D- and 2D NMR and GC/Q-ToF mass data.

Technical Abstract: The use of copaiba oil has been reported since the 16th century in Amazon traditional medicine, especially as an anti-inflammatory ingredient and for wound healing. The use of copaiba oil continues today, and it is sold in various parts of the world, including the United States. One new and seven known sesquiterpenes/sesquiterpenoids were isolated and identified from the copaiba oil. The new compound was identified as (E)-2,6,10-trimethyldodec-8-en-2-ol. Structure elucidation was achieved by 1D- and 2D NMR and GC/Q-ToF mass spectral data analyses.