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Minor Prenylated Flavonoids from the Twigs of Macaranga adenantha and Their Cytotoxic Activity.

Yang DS, Wang SM, Peng WB, Yang YP, Liu KC, Li XL, Xiao WL - Nat Prod Bioprospect (2015)

Bottom Line: Three new minor prenylated flavonoids, named macadenanthins A-C (1-3), together with three known ones (4-6), were isolated from the twigs of Macaranga adenantha.Their structures were elucidated on the basis of extensive spectroscopic analysis including NMR, UV and MS.The prenyl moieties in compounds 1-3 were further modified by cyclization and hydroxylation.

View Article: PubMed Central - PubMed

Affiliation: Key Laboratory of Economic Plants and Biotechnology, Germplasm Bank of Wild Species in Southwest China, Institute of Tibetan Plateau Research at Kunming, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming, 650201, People's Republic of China.

ABSTRACT

Three new minor prenylated flavonoids, named macadenanthins A-C (1-3), together with three known ones (4-6), were isolated from the twigs of Macaranga adenantha. Their structures were elucidated on the basis of extensive spectroscopic analysis including NMR, UV and MS. The prenyl moieties in compounds 1-3 were further modified by cyclization and hydroxylation. The new compounds were tested for their cytotoxicity against four cancer cell lines (MCF-7, Hep G2, Hela and P388) and showed IC50 values in the range of 13.76-22.27 μM.

No MeSH data available.


Related in: MedlinePlus

Structures of compounds 1–6
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Fig1: Structures of compounds 1–6

Mentions: Macaranga adenantha Gagnep (Euphorbiaceae) is an arbor distributed in the tropical rainforests, previous studies showed that it contained triterpenoids, steroids and phenolic compounds [3–5]. As part of our program to discover new anticancer prenylated aromatic products from the genus Macaranga [6–8], a phytochemical investigation on this plant led to the isolation and characterization of three minor new prenylated flavonoids, named macadenanthins A–C (1–3), along with three known ones, including glyasperin A (4) [9], broussoflavonol F (5) [10], and macarangin (6) [11]. The new compounds 1–3 were evaluated for their cytotoxicity against a small panel of cancer cell lines. Described herein are the isolation, structure elucidation and cytotoxicity of these compounds (Fig. 1).Fig. 1


Minor Prenylated Flavonoids from the Twigs of Macaranga adenantha and Their Cytotoxic Activity.

Yang DS, Wang SM, Peng WB, Yang YP, Liu KC, Li XL, Xiao WL - Nat Prod Bioprospect (2015)

Structures of compounds 1–6
© Copyright Policy - OpenAccess
Related In: Results  -  Collection

Show All Figures
getmorefigures.php?uid=PMC4402582&req=5

Fig1: Structures of compounds 1–6
Mentions: Macaranga adenantha Gagnep (Euphorbiaceae) is an arbor distributed in the tropical rainforests, previous studies showed that it contained triterpenoids, steroids and phenolic compounds [3–5]. As part of our program to discover new anticancer prenylated aromatic products from the genus Macaranga [6–8], a phytochemical investigation on this plant led to the isolation and characterization of three minor new prenylated flavonoids, named macadenanthins A–C (1–3), along with three known ones, including glyasperin A (4) [9], broussoflavonol F (5) [10], and macarangin (6) [11]. The new compounds 1–3 were evaluated for their cytotoxicity against a small panel of cancer cell lines. Described herein are the isolation, structure elucidation and cytotoxicity of these compounds (Fig. 1).Fig. 1

Bottom Line: Three new minor prenylated flavonoids, named macadenanthins A-C (1-3), together with three known ones (4-6), were isolated from the twigs of Macaranga adenantha.Their structures were elucidated on the basis of extensive spectroscopic analysis including NMR, UV and MS.The prenyl moieties in compounds 1-3 were further modified by cyclization and hydroxylation.

View Article: PubMed Central - PubMed

Affiliation: Key Laboratory of Economic Plants and Biotechnology, Germplasm Bank of Wild Species in Southwest China, Institute of Tibetan Plateau Research at Kunming, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming, 650201, People's Republic of China.

ABSTRACT

Three new minor prenylated flavonoids, named macadenanthins A-C (1-3), together with three known ones (4-6), were isolated from the twigs of Macaranga adenantha. Their structures were elucidated on the basis of extensive spectroscopic analysis including NMR, UV and MS. The prenyl moieties in compounds 1-3 were further modified by cyclization and hydroxylation. The new compounds were tested for their cytotoxicity against four cancer cell lines (MCF-7, Hep G2, Hela and P388) and showed IC50 values in the range of 13.76-22.27 μM.

No MeSH data available.


Related in: MedlinePlus