<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

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

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

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

Jalapinoside, a Macrocyclic Bisdesmoside from the Resin Glycosides of <i>Ipomea purga</i>, as a Modulator of Multidrug Resistance in Human Cancer Cells

The first macrocyclic bisdesmoside resin glycoside, jalapinoside (<b>4</b>), was purified by preparative-scale recycling HPLC from the MeOH-soluble extracts of <i>Ipomoea purga</i> roots, the officinal jalap. Purgic acid C (<b>3</b>), a new glycosidic acid of ipurolic acid, was identified as 3-<i>O</i>-β-d-quinovopyranoside, 11-<i>O</i>-β-d-quinovopyranosyl-(1→2)-<i>O</i>-β-d-glucopyranosyl-(1→3)-<i>O</i>-[β-d-fucopyranosyl-(1→4)]-<i>O</i>-α-l-rhamnopyranosyl-(1→2)-<i>O</i>-β-d-glucopyranosyl-(1→2)-<i>O</i>-β-d-quinovopyranoside (3<i>S</i>,11<i>S</i>)-dihydroxytetradecanoic acid. The acylating residues of this core were acetic, (+)-(2<i>S</i>)-methylbutanoic, and dodecanoic acids. The site of lactonization was defined as C-3 of the second saccharide moiety. Reversal of multidrug resistance by this noncytotoxic compound was evaluated in vinblastine-resistant human breast carcinoma cells

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

Teotihuacanin, a Diterpene with an Unusual Spiro-10/6 System from <i>Salvia amarissima</i> with Potent Modulatory Activity of Multidrug Resistance in Cancer Cells

Teotihuacanin (<b>1</b>), an unusual rearranged clerodane diterpene with a new carbon skeleton containing a spiro-10/6 bicyclic system, was isolated from the leaves and flowers of <i>Salvia amarissima</i>. Its structure was determined through spectroscopic analyses. Its absolute configuration was established by single-crystal X-ray diffraction. Compound <b>1</b> showed potent modulatory activity of multidrug resistance in vinblastine-resistant MCF-7 cancer cell line (reversal fold, RF_MCF‑7/Vin+ > 10703) at 25 μg/mL