Oxyphyllol B

DIURETIC AND ANTI-DIURETIC BIOACTIVITY DIFFERENCES OF THE SEED AND SHELL EXTRACTS OF ALPINIA OXYPHYLLA FRUIT.[Pubmed:28487890]

Afr J Tradit Complement Altern Med. 2016 Aug 12;13(5):25-32.

BACKGROUND: Alpinia oxyphylla fruit (AOF, Yizhi in Chinese) is a well-known traditional Chinese medicine as an anti-diuretic agent and composed of two parts i.e. seed and shell. These two parts have different components, but the bioactivity differences of the two parts are not clear. This study aims to evaluate the different anti-diuretic effects of the seed and shell of AOF. MATERIALS AND METHODS: The potential bioactive components were analyzed by UPLC-Q-TOF-MS. The diuretic and anti-diuretic activity was determined with saline-loads rats. RESULTS: The results showed that the 200 mg/kg and 400mg/kg of SREAO displayed a short-time anti-diuretic activity 1h after administration and then a significant diuretic activity was being observed at 5-6 h in 400mg/kg group of SREAO. And the 400mg/kg doses of SREAO also showed a remarkable increase for electrolyte excretion of K(+). Three sesquiterpene compounds, namely oxyphyllol A (1), Oxyphyllol B (2), and nootkatone (3) were identified from the active SREAO fraction by UHPLC-ESI-Q-TOF/MS. CONCLUSION: The seed part of Alpinia oxyphylla possessed pronounced diuretic and anti-diuretic effect. The sesquiterpene components are the major constituents and possibly contributed the diuretic and anti-diuretic activity.

Collective total synthesis of englerin A and B, orientalol E and F, and oxyphyllol: application of the organocatalytic [4+3] cycloaddition reaction.[Pubmed:23292997]

Chemistry. 2013 Feb 11;19(7):2539-47.

The concise collective total synthesis of englerin A and B, orientalol E and F, and oxyphyllol has been accomplished in 10-15 steps, with the total synthesis of orientalol E and Oxyphyllol Being achieved for the first time. The success obtained was enabled by the realization of the [4+3] cycloaddition reaction of 9 and 10. Other features of the synthesis include 1) the intramolecular Heck reaction to access the azulene core, 2) the epoxidation-S(N)2' reduction sequence to access the allylic alcohol, 3) the efficient regioselective and stereoselective formal hydration of the bridging C=C bond in the synthesis of englerins, and 4) the late-stage chemo- and stereoselective C-H oxidation in the synthesis of orientalol E. The total synthesis of these natural products has enabled the structural revision of oxyphyllol and established the absolute stereochemical features of the organocatalytic [4+3] cycloaddition reaction. The identification of 5 as the natural product oxyphyllol, the success in converting 5 to orientalol E, along with the fact that englerins and oxyphyllol were isolated from plants of the same genus Phyllanthus gives support to our proposed biosynthetic pathways. This work may enable detailed biological evaluations of these natural products and their analogues and derivatives, especially of their potential in the fight against renal cell carcinoma (RCC).