Polyprenylated Benzoylphloroglucinols Isolated from Species and Their Cytotoxic Effects on Cancer Cell Lines.

Polyprenylated benzoylphloroglucinols (PPBPs) make up a group of complex natural products with anticancer potentials that are mainly distributed in plants. As part of our intensive exploration on new bioactive substances from this genus, we report two undescribed PPBPs, picrorhizones I () and J (), along with four known analogues (-) from the stem bark of and . The new structures were elucidated on the basis of spectroscopic analysis, particularly 1D and 2D NMR and HRESIMS, whereas the absolute configurations were determined by a combination of ECD and NMR calculations coupled with a DP4+ probability analysis.

Cytotoxic prenylated xanthone derivatives from the twigs of .

A new prenylated xanthone, kaennacowanol D (), was isolated from the twigs of together with 22 known analogs. The structure of the new metabolite was elucidated by extensive spectroscopic analysis, particularly using HRMS and NMR. Kaennacowanol D is the first example of a natural xanthone containing a levulinyl group incorporated at the terminal prenyl unit ester bond.

Schomburginones A‒J, geranylated benzophenones from the leaves of Garcinia schomburgkiana and their cytotoxic and anti-inflammatory activities.

Ten undescribed benzophenones, schomburginones A-J, together with 14 known analogs were isolated from the leaves of Garcinia schomburgkiana, an edible plant native to the Indochina region. The structures of the undescribed compounds were elucidated by NMR combined with HRMS spectroscopy, while their absolute configurations were determined using ECD and single-crystal X-ray diffraction analysis. The isolated metabolites represent benzophenone derivatives containing a modified monoterpene unit, including tri- and tetracyclic skeletons, which are rarely found in genus Garcinia.

Garcowacinols A-J, cytotoxic polyprenylated benzoylphloroglucinol derivatives from the twigs of Garcinia cowa.

Ten undescribed polyprenylated benzoylphloroglucinol derivatives named garcowacinols A‒J (1-10) and four known analogues (11-14) were isolated from the twigs of Garcinia cowa. Their structures were determined by spectroscopic data analysis (1D and 2D NMR and HRESIMS), and their absolute configurations were established based on NOESY and ECD data. All isolated compounds were evaluated for their cytotoxicity against five types of human cancer cells (KB, HeLa S3, MCF-7, Hep G2, and HT-29) as well as Vero cells by MTT colorimetric assay.

Cytotoxic Polyprenylated Benzoylphloroglucinol Derivatives from the Branches of Garcinia schomburgkiana.

Five undescribed polyprenylated benzoylphloroglucinol derivatives (1:  - 5: ), named garschomcinols A - E, and five known analogues (6:  - 10: ) were isolated from the branches of . Their structures were determined on the basis of 1D and 2D NMR and HRESIMS analyses. The absolute configuration of the bicyclo [3.

Cytotoxic and Anti-Inflammatory Activities of Dihydroisocoumarin and Xanthone Derivatives from .

, a woody plant native to Sulawesi and Maluku Islands, Indonesia, has been traditionally used as a wound healing ointment. In our continuous search for bioactive compounds from this plant, 15 phenolic compounds were isolated from its stem bark, including a previously undescribed dihydroisocoumarin, 2'-hydroxyannulatomarin, and two undescribed furanoxanthones, gerontoxanthone C hydrate and 3'-hydroxycalothorexanthone. The structures of the new metabolites were elucidated on the basis of spectroscopic analysis, including 1D and 2D NMR and HRESIMS.

Four new xanthones and their cytotoxicity from the stems of Garcinia schomburgkiana.

Four new xanthones, named schomburgones C-F (1‒4), along with six known xanthones (5‒10) were isolated from the stems of Garcinia schomburgkiana. Their structures were determined by spectroscopic analysis especially 1D and 2D NMR spectroscopies. The isolated compounds were evaluated for their cytotoxicity against five human cancer cell lines.

Picrorhizones A-H, Polyprenylated Benzoylphloroglucinols from the Stem Bark of .

Eight new polyprenylated benzoylphloroglucinol derivatives (-) and four known analogues (-) were isolated from the stem bark of . Their structures were determined by spectroscopic data analysis (1D and 2D NMR and HRESIMS), and the absolute configurations were established by single-crystal X-ray diffraction combined with experimental and calculated ECD data. The new metabolites represent rare examples of benzoylphloroglucinols bearing a cyclobutyl-containing side chain.

Velucarpin D, a new pterocarpan from the stems of and its cytotoxicity.

A new pterocarpan, named velucarpin D (), along with nine known pterocarpans () were isolated from the stems of . Their structures were determined by spectroscopic analysis. All isolated compounds were evaluated for their cytotoxicity against five human cancer cell lines (KB, HeLa S-3, MCF-7, Hep G2, and HT-29).

Tetrandraxanthones A-I, Prenylated and Geranylated Xanthones from the Stem Bark of Garcinia tetrandra.

Nine new xanthones, tetrandraxanthones A-I (1-9), and 22 known xanthones (10-31) were isolated from Garcinia tetrandra stem bark. The structures of 1-9 were characterized through detailed spectroscopic analysis, including HRESIMS and 2D NMR data. Among the compounds tested for their cytotoxicity, 26 showed significant cytotoxic effects against five human cancer cell lines, including MCF-7, HT-29, KB, Hep G2, and HeLa S3, with IC values in the range of 1.

Veluflavanones A-P, Cytotoxic Geranylated Flavanones from Dalbergia velutina Stems.

Sixteen new geranylated flavanones, named veluflavanones A-P (1-16), and a known analogue (17), were isolated from Dalbergia velutina. The chemical structures of 1-17, as well as their absolute configurations, were determined by spectroscopic analysis and experimental ECD data. All isolated compounds were tested for their cytotoxicity against five human cancer cell lines.

Two new xanthones and cytotoxicity from the bark of Garcinia schomburgkiana.

Two new xanthone derivatives, named schomburgones A (1) and B (2), along with eight known compounds, including xanthones (3-8) and anthraquinones (9-10) were isolated from the bark of Garcinia schomburgkiana. Their structures were determined by spectroscopic analysis especially 1D and 2D NMR spectroscopies. All isolated compounds were evaluated for their cytotoxicity against five cancer cell lines (KB, HeLa S-3, HT-29, MCF-7 and HepG-2).

Xanthones and biphenyls from the stems of Garcinia cylindrocarpa and their cytotoxicity.

Six new compounds including four new xanthones, cylindroxanthones D-G (1-4), and two new biphenyls, cylindrobiphenyls A and B (5 and 6), were isolated from the stems of Garcinia cylindrocarpa together with 28 known compounds (7-34). The structures of the new compounds were established on the basis of extensive 1D and 2D NMR and HRESIMS spectroscopic analysis. Their cytotoxicity was evaluated against five human cancer cell lines including KB, HeLa S-3, MCF-7, Hep G2, and HT-29.

Erythrosaponins A-J, triterpene saponins from the roots and stem bark of Gardenia erythroclada.

Ten undescribed triterpene saponins, named erythrosaponins A-J, along with one known analogue were isolated from the roots and stem bark of Gardenia erythroclada. Their structures were determined on the basis of extensive 1D and 2D NMR analyses. Absolute structure of erythrosaponin A was unequivocally affirmed by single-crystal X-ray crystallography.

Calaxanthones A-C, three new xanthones from the roots of and the cytotoxicity.

Three new xanthones, named calaxanthones AC (-), along with 17 known xanthones (-) were isolated from the roots of . Their structures were determined by spectroscopic analysis. All isolated compounds were evaluated for their cytotoxicity against five cancer cell lines (KB, HeLa S-3, HT-29, MCF-7 and HepG-2).

Catomentosaponin, a new triterpene saponin from the roots of Catunaregam tomentosa.

A new triterpene saponin, catomentosaponin (1) and 11 known analogues (2-12) were isolated from the roots of Catunaregam tomentosa. The structures of 1-12 were determined on the basis of extensive NMR and MS data analysis. The sugar residues were identified by co-TLC and HPLC analysis after hydrolysis.

Cytotoxicities of two new isoflavanes from the roots of Dalbergia velutina.

Two new isoflavanes, dalvelutinanes A (1) and B (2), along with three known isoflavanes (3-5) were isolated from the roots of Dalbergia velutina. Their chemical structures, including their absolute configurations, were determined by spectroscopic analysis (1D and 2D NMR, HRESIMS, and CD). All isolated compounds were evaluated for their in vitro cytotoxicities against five human cancer cell lines (KB, HeLa-S3, MCF-7, HepG-2, and HT-29).

Dalvelutinoside, a new isoflavone glycoside from the methanol extract of Dalbergia velutina roots.

A new isoflavone glycoside, dalvelutinoside (1), together with one known isoflavone (2) and five known isoflavone glycosides (3-7) were isolated from the methanol extract of the roots of Dalbergia velutina. Their structures were determined by spectroscopic analysis. All isolated compounds were evaluated for their cytotoxicity against KB and HeLa cell lines.

Velucarpins A-C, three new pterocarpans and their cytotoxicity from the roots of Dalbergia velutina.

Three new pterocarpans, named velucarpins A-C (1-3), along with three known pterocarpans (4-6) were isolated from the roots of Dalbergia velutina. Their structures were determined by spectroscopic analysis. All isolated compounds were evaluated for their cytotoxicity against KB and HeLa cell lines.

Kaennacowanols A-C, three new xanthones and their cytotoxicity from the roots of Garcinia cowa.

Three new xanthones, named kaennacowanols A-C (1-3), along with nineteen known xanthones were isolated from the roots of Garcinia cowa Roxb. Their structures were determined by spectroscopic analysis. All isolated compounds were evaluated for their cytotoxicity against KB and HeLa cell lines.

A new taraxerol derivative from the roots of Microcos tomentosa.

A new 3beta-O-vanilloyl-taraxerol, microcisin (1) and eight known compounds, 3beta-taraxerol acetate (2), 3beta-taraxerol (3), cholest-4-en-3-one (4), cholest-4-en-6beta-ol-3-one (5), beta-sitosterol (6), 7-hydroxycadalene (7), mellein (8) and vanillin (9), were isolated from the roots of Microcos tomentosa. The structures were determined by extensive analysis of their spectroscopic data. All isolated compounds were evaluated for their cytotoxicity against KB and HeLa cells.

A new cytotoxic phenolic derivative from the roots of Antidesma acidum.

A new phenolic derivative, acidumonate (1), together with a synthetically known compound, 4-((E)-3,3-dimethylpenta-1,4-dienyl)-phenol (2), and sixteen known natural products, antidesmol (3), mellein (4), sitosterol (5), stigmasterol (6), 5-cholesten-3beta-ol (7), 4-cholesten-3-one (8), 3-(1,1-dimethylallyl)-scopoletin (9), (-)- 5,7-dihydroxy-2-eicosyl-chromone (10), 2,5-dimethoxy-1,4-benzoquinone (11), barbatumol A (12), N-trans-feruloyltyramine (13), syringic aldehyde (14), p-hydroxybenzoic acid (15), taxifolin (16), (+)-catechin (17) and gallocatechin (18), were isolated from the roots of Antidesma acidum. The structural assignment of the new compound was based on spectroscopic methods. All isolated compounds were evaluated for their cytotoxicity (KB and HeLa cells).

Tabebuialdehydes A-C, cyclopentene dialdehyde derivatives from the roots of Tabebuia rosea.

Two new cyclopentene dialdehydes, tabebuialdehydes A and B (1 and 2) and a new dihydrocyclopenta[c]furan monoaldehyde, tabebuialdehyde C (3), along with ten known compounds were isolated from the roots of Tabebuia rosea. The structures of all isolated compounds were elucidated through their physical properties and by the use of spectroscopic methods, as well as comparisons with previous literature data. Moreover, all isolated compounds were evaluated for their cytotoxicity (KB and HeLa cell lines).