6-Hydroxysalvinolone

Abstract

The title compound {systematic name: 5,6,10-trihydr­oxy-7-iso­propyl-1,1,4a-trimethyl-2,3,4,4a-tetra­hydro­phenanthren-9(1H)-one}, C20H26O4, is a diterpenoid which was isolated from the roots of Premna obtusifolia. The mol­ecule has three fused six-membered rings; the cyclo­hexane ring is in a twisted-boat conformation and the cyclo­hexene ring adopts a sofa form. Intra­molecular O—H⋯O hydrogen bonds generate two S(5) ring motifs. In the crystal, mol­ecules are linked into infinite one-dimensional chains along the [001] direction by O—H⋯O hydrogen bonds and weak C—H⋯O inter­actions.

Redetermination and absolute configuration of 6-hydroxysalvinolone

“…Fig. 1 shows the molecular structure of (I); the ring conformations, bond lengths and angles are almost identical to those previously described (Salae et al, 2009).…”

“…For background to diterpenes, see: Fraga et al (2005); Hueso-Rodríguez et al (1983) and Topcu & Ulubelen (1996). For the previous determination, see : Salae et al (2009). For bondlength data, see: Allen et al (1987).…”

“…The title diterpenoid compound (I) known as 6-hydroxysalvinolone (Topcu & Ulubelen, 1996) or 14-deoxycoleon U (Fraga et al, 2005;Hueso-Rodríguez et al, 1983), was isolated from the roots of Premna obtusifolia, a Thai manglove plant which was collected from Satun province in the Southern part of Thailand. Its crystal structure has been reported (Salae et al, 2009) but the absolute configuration could not be determined due to no large anomalous dispersion using a data set collected with Mo radiation. Data on the same sample was recollected using Cu radiation with our newlyinstalled Bruker Apex-Duo CCD diffractometer and the absolute configuration at atom C10 (or the 4a position) was determined as (R)-methyl making use of the large anomalous scattering of Cu Kα X-radiation with the Flack parameter being refined to 0.06 17.…”

“…The crystal structure of the title compound [systematic name: 5,6,10-trihydroxy-7-isopropyl-1,1,4a-trimethyl-2,3,4,4a-tetra hydrophenanthren-9(1H)-one], C 20 H 26 O 4 , has been reported previously [Salae et al (2009). Acta Cryst.…”

Cytotoxic and apoptogenic properties of three isolated diterpenoids from Salvia chorassanica through bioassay-guided fractionation

“…6-hydroxysalvinolone (MW = 330.40) is a diterpenoid which was first isolated from the roots of Premna obtusifolia (Salae et al, 2009).…”