Isodon flexicaulis

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- Isodon flexicaulis (C.Y.Wu & H.W.Li) H.Hara is a perennial herb of the Lamiaceae, typically found in montane regions of southwestern China. Phytochemical investigations of the aerial parts have consistently reported a suite of ent‑kaurane diterpenoids, a group of 20‑carbon, bicyclic terpenes derived from the geranylgeranyl diphosphate pathway. The most frequently cited constituent is a compound referred to as flexicaulin A, which possesses a keto‑functionalized kaurane skeleton. The ent‑kaurane scaffold confers a non‑polar character; the diterpenoids are readily soluble in common organic solvents such as hexane, petroleum ether, and ethyl acetate, and they display limited polarity under standard reverse‑phase conditions. This solubility profile enables efficient extraction with 80 % aqueous ethanol followed by liquid–liquid partition between water and a mixture of petroleum ether/ethyl acetate, a protocol described in the primary literature (e.g., Sun et al.). Subsequent purification by silica‑gel column chromatography, typically using a hexane–ethyl acetate gradient, isolates the diterpenoids in a pure form. The isolated compounds exhibit characteristic spectroscopic signatures: a downfield ¹H NMR resonance for a C‑20 methyl (δ ≈ 1.2 ppm), a carbonyl carbon signal in the ¹³C NMR spectrum (δ ≈ 210 ppm), and an IR absorption near 1710 cm⁻¹ corresponding to the ketone carbonyl. For several of the compounds, single‑crystal X‑ray diffraction has been employed to confirm the relative and absolute stereochemistry of the kaurane framework. The ent‑kaurane diterpenoids are chemically stable under ambient laboratory conditions (room temperature, pH 3–8) and show resistance to mild oxidation, making them suitable for long‑term storage as reference standards. The documented isolation and structural elucidation of these diterpenoids constitute the primary non‑medicinal utilization of I. flexicaulis, providing a source of well‑characterized kaurane derivatives for natural‑product chemistry, chemotaxonomic investigations, and as substrates for synthetic transformations within the broader field of terpene research. These findings establish I. flexicaulis as a reliable source of ent‑kaurane diterpenoids for ongoing research into terpene chemistry.

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