Fortunoids A–C, Three Sesquiterpenoid Dimers with Different Carbon Skeletons from <i>Chloranthus fortunei</i>

Three dimeric sesquiterpenoids (<b>1</b>–<b>3</b>), fortunoid A (<b>1</b>) possessing a new carbon skeleton of rearranged lindenane dimer and fortunoids B (<b>2</b>) and C (<b>3</b>) representing the first example of the dimers of a lindenane and a eudesmane sesquiterpene, were isolated from <i>Chloranthus fortunei</i>. Their structures with absolute configurations were established by spectroscopic data and electric circular dichroism analysis. Their biosynthetic origins were also proposed. Compounds <b>1</b> and <b>2</b> showed moderate antimalarial activities

Cipacinoids A–D, Four Limonoids with Spirocyclic Skeletons from <i>Cipadessa cinerascens</i>

Four limonoids, cipacinoids A–D (<b>1</b>–<b>4</b>), with spirocyclic skeletons were isolated from <i>Cipadessa cinerascens</i>. It is particularly notable that compounds <b>1</b>–<b>3</b> had a 17<i>S</i>-configuration for the first time in the limonoid family. Their structures with absolute configurations were assigned by spectroscopic data, X-ray crystallography, and CD analysis. Compound <b>1</b> showed moderate protein tyrosine phosphatase 1B (PTP1B) inhibition

Cipacinoids A–D, Four Limonoids with Spirocyclic Skeletons from <i>Cipadessa cinerascens</i>

Four limonoids, cipacinoids A–D (<b>1</b>–<b>4</b>), with spirocyclic skeletons were isolated from <i>Cipadessa cinerascens</i>. It is particularly notable that compounds <b>1</b>–<b>3</b> had a 17<i>S</i>-configuration for the first time in the limonoid family. Their structures with absolute configurations were assigned by spectroscopic data, X-ray crystallography, and CD analysis. Compound <b>1</b> showed moderate protein tyrosine phosphatase 1B (PTP1B) inhibition

Cipacinoids A–D, Four Limonoids with Spirocyclic Skeletons from <i>Cipadessa cinerascens</i>

Four limonoids, cipacinoids A–D (<b>1</b>–<b>4</b>), with spirocyclic skeletons were isolated from <i>Cipadessa cinerascens</i>. It is particularly notable that compounds <b>1</b>–<b>3</b> had a 17<i>S</i>-configuration for the first time in the limonoid family. Their structures with absolute configurations were assigned by spectroscopic data, X-ray crystallography, and CD analysis. Compound <b>1</b> showed moderate protein tyrosine phosphatase 1B (PTP1B) inhibition

17-<i>nor</i>-Cephalotane-Type Diterpenoids from <i>Cephalotaxus fortunei</i>

Seventeen new 17-nor-cephalotane-type diterpenoids, fortalpinoids A–Q (1–17), were isolated from the seeds of Cephalotaxus fortunei var. alpine. Compound 12 represents the first 17-nor-cephalotane-type diterpenoid featuring an 8-oxabicyclo[3.2.1]­oct-2-ene moiety. The absolute configuration of fortunolide A (18) was determined for the first time, and the structure of cephinoid Q was revised to 14-epi-cephafortoid A (24) by X-ray crystallographic data analysis. Some of the compounds showed significant cytotoxicity against A549 and HL-60 cells, and the structure–activity relationship of this compound class is discussed

Laeviganoids A–T, <i>ent</i>-Clerodane-Type Diterpenoids from <i>Croton laevigatus</i>

Laeviganoids A–T (1–20), 20 new ent-clerodane-type diterpenoids featuring a 2-furanone (1–3) or a furan (4–20) ring, as well as six analogues (21–26), were isolated from the roots of Croton laevigatus. Their structures were determined by spectroscopic data analysis, experimental electronic circular dichroism measurements, and X-ray crystallographic studies. Compounds 4–6, 16, 21–24, and 26 could influence the anti-inflammatory protumoral phenotype of macrophages. Among these compounds, 21 and 26 are the most potent, as evidenced by consistently downregulating the classic anti-inflammatory cytokine IL-10 and upregulating the classic pro-inflammatory cytokine TNF-α on the secretion level in RAW 264.7 cells

Laeviganoids A–T, <i>ent</i>-Clerodane-Type Diterpenoids from <i>Croton laevigatus</i>

Laeviganoids A–T (1–20), 20 new ent-clerodane-type diterpenoids featuring a 2-furanone (1–3) or a furan (4–20) ring, as well as six analogues (21–26), were isolated from the roots of Croton laevigatus. Their structures were determined by spectroscopic data analysis, experimental electronic circular dichroism measurements, and X-ray crystallographic studies. Compounds 4–6, 16, 21–24, and 26 could influence the anti-inflammatory protumoral phenotype of macrophages. Among these compounds, 21 and 26 are the most potent, as evidenced by consistently downregulating the classic anti-inflammatory cytokine IL-10 and upregulating the classic pro-inflammatory cytokine TNF-α on the secretion level in RAW 264.7 cells

Ciliatonoids A and B, Two Limonoids from <i>Toona ciliata</i>

Three new ring B-<i>seco</i> limonoids, ciliatonoids A–C (<b>1</b>–<b>3</b>), were isolated from <i>Toona ciliate</i> and structurally characterized by spectroscopic data, X-ray crystallography, and electronic circular dichroism analysis. Ciliatonoids A and B feature an unprecedented limonoid architecture, while ciliatonoid C belongs to a rare class of limonoids. Biological evaluation showed that compound <b>3</b> exhibited modest activities against the tested tumor cell lines

Suadimins A–C, Unprecedented Dimeric Quinoline Alkaloids with Antimycobacterial Activity from <i>Melodinus suaveolens</i>

The suadimins A–C (1–3) from Melodinus suaveolens are the first example of monoterpenoid quinoline alkaloid dimers featuring an unprecedented carbon skeleton. Their structures and absolute configurations were established on the basis of extensive spectroscopic analyses, electric circular dichroism (ECD), and X-ray crystallography. Suadimin A showed significant antimycobacterial activity in vitro with an MIC90 of 6.76 μM against the H37Rv strain of M. tuberculosis.</i

Laeviganoids A–T, <i>ent</i>-Clerodane-Type Diterpenoids from <i>Croton laevigatus</i>

Laeviganoids A–T (1–20), 20 new ent-clerodane-type diterpenoids featuring a 2-furanone (1–3) or a furan (4–20) ring, as well as six analogues (21–26), were isolated from the roots of Croton laevigatus. Their structures were determined by spectroscopic data analysis, experimental electronic circular dichroism measurements, and X-ray crystallographic studies. Compounds 4–6, 16, 21–24, and 26 could influence the anti-inflammatory protumoral phenotype of macrophages. Among these compounds, 21 and 26 are the most potent, as evidenced by consistently downregulating the classic anti-inflammatory cytokine IL-10 and upregulating the classic pro-inflammatory cytokine TNF-α on the secretion level in RAW 264.7 cells