Four New Styryllactones form Goniothalamus leiocarpus

Mu, Quanquan; Tang, Weidong; Li, Chaoming; Yang, Lü; Sun, Han‐Dong; Zheng, Huilan; Hao, Xiaojiang; Zheng, Qi‐Tai; Wu, Nan; Lou, Liguang; Xu, Bin

doi:10.3987/com-99-8679

Cited by 45 publications

(37 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…5) Literature surveys indicated that two major types of bioactive compounds, styryllactones and acetogenins, have been found from Goniothalamus species. In this study, we report herein the isolation and structure elucidation of two new compounds, goniothalesacetate (1) and goniothaesdiol A (2), together with eight known compounds, include three styryllactones, goniodiol-7-monoacetate, 4) goniodiol-8-monoacetate, 4) leiocarpin C, 6) and five alkaloids, liriodenine, 3) griffithazanone A, 7) 4-methyl-2,9,10-(2H)-1-azaanthracencetrione, 7) velutinam 8) and aristolactam BII. 8) Compound 1 was isolated as yellow oil.…”

mentioning

confidence: 99%

New Constituents from Stems of Goniothalamus amuyon

Lan

Chang

Yang

et al. 2006

CHEMICAL & PHARMACEUTICAL BULLETIN

View full text Add to dashboard Cite

show abstract

mentioning

confidence: 99%

New Constituents from Stems of Goniothalamus amuyon

Lan

Chang

Yang

et al. 2006

CHEMICAL & PHARMACEUTICAL BULLETIN

View full text Add to dashboard Cite

show abstract

“…The similarity of 1 H-and 13 C-NMR spectra of 1 to those of known pyrano-pyrones leiocapin A (3), deoxygoniopypyrone A (4), and (Ϫ)-8-epi-9-deoxygoniopypyrone (5) (Tables 1, 2) showed that 1 had a pyrano-pyrone type skeleton. 12,[16][17][18] The presence of a saturated pyrone ring in 1 was suggested by an IR carbonyl absorption band at 1737 cm Ϫ1 and a slight upfield-shifted carbonyl signal at d C 169.1 ppm (C-3) in the 13 C-NMR spectrum. The heteronuclear single quantum coherence (HSQC) spectrum of 1 showed the direct 1 H- 13 Tables 1 and 2 showed that compound 1 has 1 H-and 13 C-NMR parameters similar to those of compound 5.…”

mentioning

confidence: 99%

New Pyrano-Pyrone from Goniothalamus tamirensis Enhances the Proliferation and Differentiation of Osteoblastic MC3T3-E1 Cells

Tài

Huyền

Hương

et al. 2010

CHEMICAL & PHARMACEUTICAL BULLETIN

View full text Add to dashboard Cite

The genus Goniothalamus comprises about 160 species of shrubs and trees growing in tropical and subtropical Asia. 1) Many of these species are used for timber, as fiber sources, as mosquito repellant, and most interestingly in folk medicine in several countries. 2,3) Phytochemical studies of Goniothalamus species have led to the isolation and characterization of a large number of styryl-lactones. These can be classified into several main subtypes: styryl-pyrones, furano-pyrones, furano-furones, and pyrano-pyrones. 4) Styryl-lactones possess significant cytotoxic activity against several human tumor cell lines such as A-549 (lung carcinoma), HT-29 (colon adenocarcinoma), MCF-7 (breast carcinoma), RPMI (melanoma), U251 (brain carcinoma), 3,5) and to induce apoptosis in HL-60 leukemic cell. 6) Some of styryl-lactones have been synthesized via total synthesis. 3,7-10) Goniopypyrone, the first pyrano-pyrone compound, was first isolated in 1990 from G. giganteus. 11,12) It was high bioactive, showing ED 50 values of ca. 0.67 mg/ml in the cytotoxicity of human tumor cell lines (A-549, MCF-7, HT-29), high toxicity to the brine shrimp (BS), and significant inhibition of the formation of crown gall tumors on potato discs (PD). Typically, up to date, pyrano-pyrone compounds are found in some Goniothalamus species.The formation of bone involves a complex series of events, including the proliferation and differentiation of osteoprogenitor cells. Eventually, this results in the formation of a mineralized extracellular matrix. Most effective osteoporosis therapies reduce bone loss but do not restore lost bone mass and strength. Therefore, it is desirable to discover bone-building (anabolic) agents that stimulate new bone formation and correct the imbalance of microarchitecture characteristic of established osteoporosis. 13) As new bone formation is primarily a function of the osteoblasts, agents that regulate bone formation act either by increasing the proliferation of cells in the osteoblastic lineage or inducing osteoblast differentiation. 13,14) Early intervention is now possible with the help of some effective medications, which may reduce the risk of first and recurrent fractures.In our investigation of phytochemistry of the leaves of G. tamirensis, 9-deoxygoniopypyrone (2) and a new pyranopyrone, (ϩ)-8-epi-9-deoxygoniopypyrone (1), were isolated and identified using spectral methods. To investigate whether these compounds could stimulate the function of osteoblasts, their effects on cell growth, collagen content, alkaline phosphatase (ALP) activity, and calcium deposition were assessed in the pre-osteoblastic target cell line, MC3T3-E1, which is a well-characterized in vitro model of osteoblast differentiation. 15) Results and DiscussionCompound 1 Science and Technology; 18 Hoang Quoc Viet St., Caugiay, Hanoi, Vietnam: and c Faculty of Chemistry, Hanoi University of Science; 19 Le Thanh Tong St., Hoankiem, Hanoi, Vietnam. Received November 24, 2009; accepted January 8, 2010; published online January 19, 2010 The n...

show abstract

“…of NaClO 2 (0.3 g, 3.3 mmol) and NaH 2 PO 4 (0.51 g, 3.3 mmol) in H 2 O (1 ml), was added, and the mixture was stirred at r.t. for 3 h. The solvent was evaporated, the residue was dissolved in AcOEt (5 ml) and washed with H 2 O (5 ml) and brine (5 ml), and dried (Na 2 SO 4 ). Evaporation of the solvent under reduced pressure and purification of the residue by CC (SiO 2 ; 12% AcOEt/hexane) gave 11 (0.34 g, 86% over two steps 2 Cl 2 (3.5 ml), 1H-imidazole (0.25 g, 3.67 mmol) was added at 08, and the mixture was stirred for 5 min; then, TBS-Cl (0.30 g, 2.04 mmol) was added, and the mixture was stirred for 0.5 h at r.t. The mixture was diluted with CH 2 Cl 2 (4 ml), and the org.…”

Section: Experimental Partmentioning

confidence: 99%

“…Styryl lactones are natural products that exhibit significant biological activities such as antitumor, antifungal, and antibiotic properties [1]. Compound 1 was isolated from the stem bark of the tropical plant Goniothalamus leiocarpus [2]. Recently, two syntheses of 1 were reported [3].…”

mentioning

confidence: 99%

“…The primary alcohol 10 was oxidized to the corresponding aldehyde under Swern oxidation conditions, which was further oxidized [8] to the acid 11 (86% over two steps). The latter was subsequently esterified to afford 5 (85%) using CH 2 The known methanol derivative 8 was protected (Scheme 3) as its silyl ether 6. Based on our earlier results, this protection was warranted to enable a facile crossmetathesis reaction.…”

mentioning

confidence: 99%

See 1 more Smart Citation