Nardosinone

Nardosinone

Names
IUPAC name (3aR,9R,9aR,9bS)-1,1,9,9a-Tetramethyl-1,3a,4,7,8,9,9a,9b-octahydro-5H-naphtho[2,1-c][1,2]dioxol-5-one
Identifiers
CAS Number	23720-80-1
ChemSpider	147074
Jmol interactive 3D	Image
PubChem	168136
InChI InChI=1S/C15H22O3/c1-9-6-5-7-10-11(16)8-12-13(15(9,10)4)14(2,3)18-17-12/h7,9,12-13H,5-6,8H2,1-4H3/t9-,12-,13+,15+/m1/s1 Key: KXGHHSIMRWPVQM-JWFUOXDNSA-N InChI=1/C15H22O3/c1-9-6-5-7-10-11(16)8-12-13(15(9,10)4)14(2,3)18-17-12/h7,9,12-13H,5-6,8H2,1-4H3/t9-,12-,13+,15+/m1/s1 Key: KXGHHSIMRWPVQM-JWFUOXDNBH
SMILES O=C2/C1=C/CC[C@@H](C)[C@@]1([C@@H]3C(OO[C@@H]3C2)(C)C)C
Properties
Chemical formula	C15H22O3
Molar mass	250.34 g·mol^−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Nardosinone is a sesquiterpene and chemical constituent of Nardostachys jatamansi.^[1] In in vitro studies, the compound has demonstrated concentration-dependent enhancement of bucladesine and staurosporine-induced neurite outgrowth.^[2] Nardosinone has similarly been demonstrated to enhance NGF-mediated neurite outgrowth and synaptogenesis from PC12D cells.^[3]

Additionally, nardosinone has demonstrated cytotoxic activity against cultured P-388 lymphocytic leukemia cells.^[4]

References

1. Schulte KE, Glauch G, Rücker G (1965). "Nardosinon, ein neuer Inhaltsstoff von Nardostachys chinensis Batalin" [Nardosinone, a new constituent of Nardostachys chinensis Batalin]. Tetrahedron Letters (in German) 6 (35): 3083–3084. doi:10.1016/S0040-4039(01)89226-1. PMID 5828044.
2. Li P, Matsunaga K, Yamakuni T, Ohizumi Y (2003). "Nardosinone, the first enhancer of neurite outgrowth-promoting activity of staurosporine and dibutyryl cyclic AMP in PC12D cells". Developmental Brain Research 145 (2): 177–183. doi:10.1016/S0165-3806(03)00239-6. PMID 14604758.
3. Li P, Matsunaga K, Yamamoto K, Yoshikawa R, Kawashima K, Ohizumi Y (1999). "Nardosinone, a novel enhancer of nerve growth factor in neurite outgrowth from PC12D cells". Neuroscience Letters 273 (1): 53–56. doi:10.1016/S0304-3940(99)00629-1. PMID 10505650.
4. Itokawa H, Masuyama K, Morita H, Takeya K (1993). "Cytotoxic sesquiterpenes from Nardostachys chinensis". Chemical & Pharmaceutical Bulletin 41 (6): 1183–1184. doi:10.1248/cpb.41.1183. PMID 8370115.