Structurally diverse diterpenoids from cones of Taxodium ascendens inhibit colorectal cancer proliferation via regulating mitophagy.

Taxascendins A - D (1-4), four unprecedented hetero-oligomeric terpenoids, and taxascendins E - K (5-11), seven new diterpenoids with five distinct and highly modified abietane-types frameworks, along with sixteen known analogues (10-27) were obtained from Taxodium ascendens. Their structures were determined by extensive spectroscopy, single-crystal X-ray diffraction, and quantum chemical calculations. Bioactivity screening indicated that the isolated compounds exhibited inhibitory activity in colorectal cancer cells.

Yatein-induced DNA damage of breast cancer cells by interfering with DNA topoisomerase IIα.

DNA topoisomerase IIα (TOP2A) plays a key role in resolving DNA topological stress during replication, transcription, and chromosome segregation. Yatein, a biogenic precursor of deoxypodophyllotoxin possesses antitumor effects. Herein, we explored its antitumor effect in breast cancer.

Labdane-type diterpenoids from Hypoestes phyllostachya inhibit pancreatic cancer stem cells.

Ten previously undescribed labdane diterpenoids, hypochins A-J (1-10), were isolated from the aerial parts of Hypoestes phyllostachya with white spots. Their structures and absolute configurations were elucidated through comprehensive spectroscopic characterization, including IR, HRMS, NMR, electronic circular dichroism analysis, single-crystal X-ray diffraction, and biosynthetic considerations. Notably, compound 10 represents a rare labdane diterpenoid incorporating 16,15;19,6-dilactone units.

Cassane diterpenoids with hepatic gluconeogenesis inhibitory activity from the seeds of Caesalpinia decapetala (Roth) Alston.

A chemical investigation of the seeds of Caesalpinia decapetala (Roth) Alston led to the isolation of fifteen cassane diterpenoids, including ten previously undescribed compounds (1-10) and five known analogues (11-15). The structures of 1-10 were determined using H, C, and 2D NMR, HRESIMS, and IR data. Their absolute configurations were confirmed by comparing experimental electronic circular dichroism data with calculated values, coupled with single-crystal X-ray diffraction analysis.

Clerodane furanoditerpenoids from the tuberous roots of Tinospora sagittata (Oliv.) Gagnep. and their α-glucosidase inhibitory activity.

Four previously undescribed clerodane-type furanoditerpenoids, tinosagins A-D (1-4), were isolated from the tuberous roots of Tinospora sagittata (Oliv.) Gagnep., together with 11 known compounds (5-15).

Clerodane Diterpenoids and Ecdysteroids From the Fruits of Tinospora sagittata (Oliv.) Gagnep.

A new clerodane-type diterpenoid, tinosaginoside A (1), and two new ecdysteroids, tinosagisterones A and B (8 and 9), were isolated from the fruits of Tinospora sagittata (Oliv.) Gagnep., as well as and nine previously reported compounds (2-7 and 10-12).

Nicotabacins A-P, New Cembrane-Type Diterpenes Isolated from L. and Their Antifungal Activities.

Sixteen previously undescribed cembrane-type diterpenoids, named nicotabacins A-P (-), were isolated from L., together with 12 known analogs (-). The structures of - were determined by extensive spectral analysis, single-crystal X-ray diffraction analysis, and ECD calculations.

Highly oxygenated sesquiterpenoids with neurotrophic and neuroprotective activities from the fruits of Illicium henryi Diels.

Illihenrolides A (1) and B (2), and illihenrin A (3), three highly oxygenated sesquiterpenoids were isolated from the fruits of Illicium henryi Diels, together with eight known analogs. The structures of 1-3 were elucidated using HRESIMS data and extensive H, C, and 2D NMR (HH COSY, HSQC, HMBC and ROESY) analyses. In addition, the absolute configurations of 1 and 2 were determined by single crystal X-ray diffraction experiment and electronic circular dichroism calculations.

Magnodelins A and B, Two New Tetrahydrofuran Lignans From the Fruits of Magnolia delavayi Franch. and Structural Revision of Magnostellin B and Magnone A.

Two previously undescribed tetrahydrofuran lignans, named magnodelins A and B (1 and 2), were isolated from the fruits of Magnolia delavayi Franch., together with two known lignans magnostellin B (3) and magnone A (4). The assignments of their structures were elucidated by extensive spectral analysis, electronic circular dichroism experiments, and single-crystal X-ray diffraction analysis.

Diverse Sesquiterpenoids From Michelia alba and Their Cytotoxic and Nitric Oxide Inhibitory Activities.

Two previously undescribed sesquiterpenoids, including one germacrane sesquiterpenoid (1) and one guaiane sesquiterpenoid (2), were isolated and characterized from the branches and leaves of Michelia alba DC., along with 11 known sesquiterpenoids (3-13). The structures of the new compounds were elucidated using comprehensive high-resolution electrospray ionization mass spectroscopy, infrared, ultraviolet, and nuclear magnetic resonance analyses, with the absolute configurations being determined through single-crystal X-ray diffraction analysis and electronic circular dichroism calculations.

Activation of SIK1 by phanginin A regulates skeletal muscle glucose uptake by phosphorylating HADC4/5/7 and enhancing GLUT4 expression and translocation.

Salt-inducible kinase 1 (SIK1) participates in various physiological processes, yet its involvement in regulating skeletal muscle glucose uptake remains unclear. Previously, we showed that phanginin A, a natural compound isolated from Caesalpinia sappan Linn, activated SIK1 to suppress gluconeogenesis in hepatocytes. Here, we aimed to elucidate the effects of SIK1 on skeletal muscle glucose uptake by using phanginin A.

Cassan Diterpenoids With Ca3.1 T-type Calcium Channel Inhibitory Activity From the Seeds of Caesalpinia decapetala (Roth) Alston.

Phytochemical investigation of the 80% ethanol extract from the seeds of Caesalpinia decapetala (Roth) Alston led to the identification of nine compounds, which included three new cassane-type diterpenoids, caesalpideplins A-C (1-3), and six known analogs (4-9). The structures of 1-3 were determined using a comprehensive analytical method that involved detailed infrared, high-resolution electrospray ionization mass spectrometry studies, as well as proton, carbon-13, and two-dimensional nuclear magnetic resonance analyses. The absolute configuration of 1 was established through X-ray single crystal diffraction analysis, while the absolute configurations of 2 and 3 were determined by comparing their calculated and experimental electronic circular dichroism data.

Clerodane diterpenoids from the vine stems of Fibraurea recisa Pierre and their hepatic gluconeogenesis inhibitory activity.

Fibraurea recisa Pierre is a vine plant and its vine stems are used as a traditional Chinese medicine to treat heat toxin, constipation, diarrhea, sore throat, eye inflammation, carbuncles, and skin ulcers. The alkaloid chemical composition of this plant has been extensively studied; however, investigations into non-alkaloid components remain limited. In this study, phytochemical studies of the vine stems of F.

Labdane-type diterpenoids with cytotoxic and anti-inflammatory activities from the aerial parts of Hypoestes purpurea (L.) R. Br.

Two new ent-labdane diterpenoids, hypoestesins A-B (1-2) and five new labdane diterpenoids, hypopurolides H-L (3-7), were isolated from the aerial parts of Hypoestes purpurea. All of the structures were fully determined based on extensive analysis of H, C, 2D NMR, and HRESIMS data. The absolute configurations of 1-3 was established through comparing the experimental and calculated ECD curves and the structure of 5 was confirmed by single crystal X-ray diffraction experiment.

Structurally diverse diterpenoids from the seeds of Caesalpinia minax Hance and their bioactivities.

Eight previously undescribed diterpenoids, caesamins A-H (1-8), were separated and identified from the seeds of Caesalpinia minax Hance. Their structures were characterized by extensive spectroscopic data and X-ray crystallographic analysis. Structurally, caesamin A (1) is the first cassane-type diterpenoid with a C23 carbon skeleton containing an unusual isopropyl.

Anti-pancreatic cancer activity of cassane diterpenoids isolated from the seeds of Caesalpinia sappan mediated by autophagy activation via ROS/AMPK/mTORC1 pathway.

Three undescribed cassane diterpenoids, caesalpanins D-F (1-3), and seven known ones were isolated from the seeds of Caesalpinia sappan. Structures and absolute configurations of 1-3 were elucidated based on the extensive spectroscopic analysis, single-crystal X-ray diffraction analysis, and ECD calculations. Structurally, compound 1 was the first example of 18-norcassane diterpenoid and 2 was a rare 20-norcassane diterpenoid having an unusual five-membered oxygen bridge between C-10/C-18.

Eudesmane-type sesquiterpenoids from the aerial parts of Artemisia lavandulaefolia and their anti-pancreatic cancer activities.

Five undescribed eudesmane sesquiterpenoids, artemilavanins A-E, and one undescribed rearranged eudesmane sesquiterpenoid, artemilavanin F, were isolated from the 95% ethanol extract of the aerial parts of Artemisia lavandulaefolia DC., along with ten known compounds. The structures and configurations of undescribed compounds were mainly elucidated by spectroscopic analyses and single-crystal X-ray diffraction analysis.

Spirocyclohexadienone-Type Neolignans with Neuroprotective and Neurite Outgrowth Enhancing Activities from Magnolia liliiflora.

Three rare spirocyclohexadienone-type neolignans, magnoflorins A-C (1-3), and three known analogs (4-6), were isolated from the leaves of Magnolia liliiflora. Magnoflorin D (4) was obtained from natural resources for the first time. The chemical structures and absolute configurations of 1-4 were elucidated through detailed analysis of HR-ESI-MS, IR, H, C, and 2D NMR, and ECD experiments.

Four Highly Oxygenated Sesquiterpenoids from the Fruits of Illicium micranthum Dunn.

Four highly oxygenated sesquiterpenoids, illimicranolides A (1) and B (2), and illicinolides E (3) and F (4), were obtained from the fruits of Illicium micranthum Dunn, as well as one known analog, illicinolide B (5). The chemical structures of 1-4 were determined comprehensively by 1D ( H and C) and 2D (HMBC, HSQC, H- H COSY, and ROESY) NMR, and HR-ESI-MS data. Structurally, compound 1 was an unprecedented sesquiterpenoid with a 5/5/6/5-fused tetracyclic ring system and was the first seco-prezizaane sesquiterpenoid featuring a 11,8-γ-lactone ring.

Hupertimines A-E, Fawcettimine-Type Lycopodium Alkaloids from Huperzia serrata.

Five new fawcettimine-type Lycopodium alkaloids, hupertimines A-E (1-5), were discovered from the whole plant of Huperzia serrata, along with two known alkaloids, 8α-hydroxyphlegmariurine B (6) and 8β-hydroxyphlegmariurine B (7). The structures of 1-7 were identified through HR-MS, IR, H, C, and 2D NMR, and single-crystal X-ray diffraction analysis. Structurally, compound 1 was the fourth example of Lycopodium alkaloid with an ether linkage between C-5 and C-13 and 2 was the third example of Lycopodium alkaloid with a 5/5/5/5/6 pentacyclic ring system and featuring a 1-aza-7-oxabicyclo[2.

Spiroligustolides A and B: Two pairs of enantiomeric spiro-orthoester-containing phthalide dimers as Ca3.1 calcium channel inhibitors from Ligusticum Chuanxiong Hort.

Two pairs of unprecedented enantiomeric phthalide dimers, spiroligustolides A (1a/1b) and B (2a/2b), featuring a unique spiroorthoster linkage between two monomeric units to form a 5/6/5/6/6-fused ring system, were isolated from the roots of Ligusticum chuanxiong. The structures and relative configurations of 1 and 2 were determined by HR-ESI-MS, IR, and NMR spectroscopic data, coupled with single-crystal X-ray diffraction analysis, and the absolute configurations of 1a, 1b, 2a, and 2b were established by comparing the experimental and calculated electronic circular dichroism (ECD) data. Plausible biosynthetic pathway for 1 and 2 was proposed.

Design, synthesis and structural-activity relationship studies of phanginin A derivatives for regulating SIK1-cAMP/CREB signaling to suppress hepatic gluconeogenesis.

Persistent activation of hepatic gluconeogenesis is a main cause of fasting hyperglycemia in patients with type 2 diabetes (T2D), and the salt-induced kinase 1 (SIK1) acts as a key modulator in regulating hepatic gluconeogenesis. Recently, we first reported phanginin A (PA, 1), a natural cassane diterpenoid isolated from the seeds of Caesalpinia sappan, exhibited potent anti-diabetic effect through activation of SIK1 and increasing PDE4 activity to inhibit hepatic gluconeogenesis pathway by suppressing the cAMP/PKA/CREB pathway in the liver. In present study, we designed and prepared 25 PA derivatives and their structure-activity relationship (SAR) for gluconeogenesis inhibitory activity were established.

seco-Prezizanne Sesquiterpenes and Prenylated C6-C3 Compounds from the Fruits of Illicium lanceolatum A. C. Smith.

Two new seco-prezizaane-type sesquiterpenes, 2β-hydroxy-6-deoxyneoanisatin (1) and 3,4-anhydro-2-oxo-1α-hydroxy-6-deoxyneoanisatin (2), and two new prenylated C -C compounds, illilanceofunones A (3) and B (4), were obtained from the fruits of Illicium lanceolatum, along with four known prenylated C -C compounds (5-8). Their structures were proposed through HR-ESI-MS, H, C, and 2D NMR data interpretation. Moreover, the absolute configuration of 1 and 2 were further assigned by single-crystal X-ray diffraction analysis and electronic circular dichroism (ECD) calculations, respectively.

Monoterpene Indole Alkaloids with Ca3.1 T-Type Calcium Channel Inhibitory Activity from .

is a well-known traditional herbal medicine for the treatment of cancer, hypertension, scald, and sore in China. Phytochemical investigation on the twigs and leaves of this species led to the isolation of two new monoterpene indole alkaloids, catharanosines A () and B (), and six known analogues (-). Structures of and were established by H-, C- and 2D-NMR, and HREIMS data.

Cassane diterpenoids from the seeds of Caesalpinia bonduc and their nitric oxide production and α-glucosidase inhibitory activities.

Ten previously undescribed cassane diterpenoids, cassabonducins A-J, and eleven known compounds were isolated from the seeds of Caesalpinia bonduc. The structures of the undescribed compounds were elucidated by extensive analysis of spectroscopic data (IR, HRESIMS, and H, C and 2D NMR) and their absolute configurations were determined by the ECD data and single-crystal X-ray diffraction analysis. ε-Caesalpin-Ⅶ was obtained from natural resources for the first time.