1-Oxomiltirone

1-Oxomiltirone is a naturally occurring C20-norabietane diterpenoid with significant biological potential, first identified as a novel natural product from the roots of the Iranian medicinal plant Perovskia abrotanoides — a recognized new source of bioactive tanshinones. It can also be isolated from sage leaves, expanding its known natural reservoirs.
Chemically, this compound is classified as a quinoid diterpene, belonging to the miltirone series of abietane-type diterpenes — a class of molecules widely studied for their diverse pharmacological activities. Its structural uniqueness lies in a phenanthrene-derived skeleton with specific substitutions, which underpins its biological functions.
Beyond natural isolation, 1-oxomiltirone has been successfully synthesized in the laboratory. A key synthetic route involves using a versatile intermediate (compound 6) via high-yield Suzuki coupling and subsequent cyclization, followed by demethylation and oxidation steps — a method that achieves a notable yield of 64% and confirms structural consistency with natural isolates through ¹H and ¹³C NMR spectra. This dual availability (natural extraction and synthetic production) has accelerated its application in biomedical research.

Well-Characterized Chemical Identity: Possesses a clear C20-norabietane diterpenoid structure, with its molecular properties and purity verifiable through standard analytical techniques like NMR and HRMS, ensuring reliability for experimental use.
Dual Source Availability: Can be obtained both from natural plant sources (e.g., Perovskia abrotanoides roots, sage leaves) and via efficient synthetic routes, supporting consistent supply for large-scale or high-purity research needs.
Targeted Biological Activity Profile: Exhibits selective bioactivity, particularly in modulating inflammatory responses and interacting with specific microbial and cellular targets, distinguishing it from non-quinoid diterpenoid analogs.
Classical Quinoid Diterpene Traits: Belongs to the miltirone series, sharing structural motifs with other bioactive abietane diterpenes that enable comparative pharmacological studies.

Inflammatory Disease Research: Used to investigate the molecular mechanisms of NO-mediated inflammation, supporting studies on conditions like sepsis, autoimmune disorders, and chronic inflammatory responses.
Anti-Microbial Pharmacology: Applied in screening assays for gram-positive bacterial infections, aiding the development of new natural product-derived antibiotics.
Cancer Biology Studies: As part of the anti-tumor miltirone series, it contributes to research on diterpenoid-induced cytotoxicity in cancer cell lines (e.g., A549, BxPC-3, HL-60).
Natural Product Chemistry: Serves as a reference standard for isolating and identifying related norabietane diterpenes from medicinal plants like Perovskia abrotanoides and sage.
Synthetic Methodology Validation: Used to optimize and validate diterpenoid synthesis techniques, particularly Suzuki coupling and oxidative cyclization strategies.

Researchers interested in 1-oxomiltirone often explore other bioactive norabietane and abietane diterpenes within the same chemical class and research fields. Key related products include cryptotanshinone (a well-studied quinoid diterpene with norabietane skeleton), 1β-hydroxy cryptotanshinone (a hydroxylated tanshinone analog), 1-oxo cryptotanshinone (another oxo-substituted tanshinone), and miltirone (the parent compound of the miltirone series with anti-tumor activity). These compounds share applications in inflammation, oncology, and microbial research, providing complementary tools for comparative studies. If you are interested in related products, you can directly contact us or inquire about customized product services.