Microphyllandiolide, a New Diterpene with an Unprecedented Skeleton from <i>Salvia microphylla</i>

Microphyllandiolide (<b>1</b>), an unprecedented rearranged clerodane-type diterpene with a 9/3 bicyclic ring system, was isolated from the aerial parts of <i>Salvia microphylla</i> Kunth. Its structure was elucidated by analysis of its spectroscopic data and confirmed by single crystal X-ray diffraction analysis. A possible biogenesis for microphyllandiolide (<b>1</b>) is proposed

Microphyllandiolide, a New Diterpene with an Unprecedented Skeleton from <i>Salvia microphylla</i>

Microphyllandiolide (<b>1</b>), an unprecedented rearranged clerodane-type diterpene with a 9/3 bicyclic ring system, was isolated from the aerial parts of <i>Salvia microphylla</i> Kunth. Its structure was elucidated by analysis of its spectroscopic data and confirmed by single crystal X-ray diffraction analysis. A possible biogenesis for microphyllandiolide (<b>1</b>) is proposed

<i>neo-</i>Clerodane Diterpenes from <i>Salvia herbacea</i>

Chemical investigation of the aerial parts of <i>Salvia herbacea</i> led to the isolation of eight new <i>neo</i>-clerodane diterpenes (<b>1</b>–<b>8</b>), named tehuanins A–H, and three known compounds. The structures of these compounds were determined by analysis of their spectroscopic data. Three of the new diterpenes possess a 1,8-epoxy group (<b>1</b>–<b>3</b>). This unusual structural feature was confirmed by X-ray diffraction of <b>1</b>. The structure of the previously isolated 1α,10α-epoxysalviarin was revised. The absolute configuration of <b>6</b> was established by X-ray diffraction analysis of its bromo derivative <b>6a</b>. Cytotoxic and anti-inflammatory activities of these diterpenes were examined. None of the compounds were considered to be cytotoxic; however, compound <b>7</b> exhibited anti-inflammatory activity comparable to that of indomethacin

<i>neo-</i>Clerodane Diterpenes from <i>Salvia herbacea</i>

Chemical investigation of the aerial parts of <i>Salvia herbacea</i> led to the isolation of eight new <i>neo</i>-clerodane diterpenes (<b>1</b>–<b>8</b>), named tehuanins A–H, and three known compounds. The structures of these compounds were determined by analysis of their spectroscopic data. Three of the new diterpenes possess a 1,8-epoxy group (<b>1</b>–<b>3</b>). This unusual structural feature was confirmed by X-ray diffraction of <b>1</b>. The structure of the previously isolated 1α,10α-epoxysalviarin was revised. The absolute configuration of <b>6</b> was established by X-ray diffraction analysis of its bromo derivative <b>6a</b>. Cytotoxic and anti-inflammatory activities of these diterpenes were examined. None of the compounds were considered to be cytotoxic; however, compound <b>7</b> exhibited anti-inflammatory activity comparable to that of indomethacin

5,10-<i>seco</i>-<i>neo</i>-Clerodanes and <i>neo</i>-Clerodanes from <i>Salvia microphylla</i>

Two new 5,10-<i>seco</i>-<i>neo</i>-clerodanes, salvimicrophyllins A and B (<b>1</b> and <b>2</b>), and two new <i>neo</i>-clerodanes, salvimicrophyllins C and D (<b>3</b> and <b>4</b>), were isolated from the leaves and flowers of <i>Salvia microphylla</i>. The structures of these compounds were elucidated mainly by analysis of their NMR spectroscopic and mass spectrometric data. The relative configurations of the salvimicrophyllins were determined by analysis of NOESY spectra and ECD curves, and the relative configuration of compound <b>2</b> was confirmed by single-crystal X-ray diffraction crystallography

<i>neo-</i>Clerodane Diterpenes from <i>Salvia herbacea</i>

Chemical investigation of the aerial parts of <i>Salvia herbacea</i> led to the isolation of eight new <i>neo</i>-clerodane diterpenes (<b>1</b>–<b>8</b>), named tehuanins A–H, and three known compounds. The structures of these compounds were determined by analysis of their spectroscopic data. Three of the new diterpenes possess a 1,8-epoxy group (<b>1</b>–<b>3</b>). This unusual structural feature was confirmed by X-ray diffraction of <b>1</b>. The structure of the previously isolated 1α,10α-epoxysalviarin was revised. The absolute configuration of <b>6</b> was established by X-ray diffraction analysis of its bromo derivative <b>6a</b>. Cytotoxic and anti-inflammatory activities of these diterpenes were examined. None of the compounds were considered to be cytotoxic; however, compound <b>7</b> exhibited anti-inflammatory activity comparable to that of indomethacin

<i>neo-</i>Clerodane Diterpenes from <i>Salvia herbacea</i>

Chemical investigation of the aerial parts of <i>Salvia herbacea</i> led to the isolation of eight new <i>neo</i>-clerodane diterpenes (<b>1</b>–<b>8</b>), named tehuanins A–H, and three known compounds. The structures of these compounds were determined by analysis of their spectroscopic data. Three of the new diterpenes possess a 1,8-epoxy group (<b>1</b>–<b>3</b>). This unusual structural feature was confirmed by X-ray diffraction of <b>1</b>. The structure of the previously isolated 1α,10α-epoxysalviarin was revised. The absolute configuration of <b>6</b> was established by X-ray diffraction analysis of its bromo derivative <b>6a</b>. Cytotoxic and anti-inflammatory activities of these diterpenes were examined. None of the compounds were considered to be cytotoxic; however, compound <b>7</b> exhibited anti-inflammatory activity comparable to that of indomethacin

Hydroxyclerodanes from <i>Salvia shannoni</i>

Six new hydroxyclerodanes (<b>1</b>–<b>6</b>), named sepulturins A–F, and four known diterpenes were isolated from the leaves of <i>Salvia shannoni</i>. The structures of these compounds were established by extensive analysis of their NMR and MS spectroscopic data. The relative configurations of compounds <b>1</b> and <b>2</b> were determined by NOESY experiments and were confirmed by single-crystal X-ray diffraction studies. All of the isolated diterpenes possess tertiary OH groups. The structure of infuscatin (<b>7</b>), a clerodane previously isolated from <i>S</i>. <i>infuscata</i>, was revised. Cytotoxic, antiprotozoal, and anti-inflammatory activities of these compounds were evaluated

Hydroxyclerodanes from <i>Salvia shannoni</i>

Six new hydroxyclerodanes (<b>1</b>–<b>6</b>), named sepulturins A–F, and four known diterpenes were isolated from the leaves of <i>Salvia shannoni</i>. The structures of these compounds were established by extensive analysis of their NMR and MS spectroscopic data. The relative configurations of compounds <b>1</b> and <b>2</b> were determined by NOESY experiments and were confirmed by single-crystal X-ray diffraction studies. All of the isolated diterpenes possess tertiary OH groups. The structure of infuscatin (<b>7</b>), a clerodane previously isolated from <i>S</i>. <i>infuscata</i>, was revised. Cytotoxic, antiprotozoal, and anti-inflammatory activities of these compounds were evaluated

Hydroxyclerodanes from <i>Salvia shannoni</i>

Six new hydroxyclerodanes (<b>1</b>–<b>6</b>), named sepulturins A–F, and four known diterpenes were isolated from the leaves of <i>Salvia shannoni</i>. The structures of these compounds were established by extensive analysis of their NMR and MS spectroscopic data. The relative configurations of compounds <b>1</b> and <b>2</b> were determined by NOESY experiments and were confirmed by single-crystal X-ray diffraction studies. All of the isolated diterpenes possess tertiary OH groups. The structure of infuscatin (<b>7</b>), a clerodane previously isolated from <i>S</i>. <i>infuscata</i>, was revised. Cytotoxic, antiprotozoal, and anti-inflammatory activities of these compounds were evaluated