Two novel biphenyl dimers from the heartwood of Caesalpinia sappan

Shu, Shi-Hui; Deng, An‐Jun; Li, Zhihong; Qin, Hai‐Lin

doi:10.1016/j.fitote.2011.03.010

Cited by 18 publications

(6 citation statements)

References 11 publications

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“…The carbon signals of δ C 38.7 and 67.2 at the positions of C13 and C16 were also shifted to δ C 41.5 and 64.6 at the positions of C13′ and C16′ in the other partial structure, respectively. In contrast, although biphenyl dimer caesappanin B has been isolated from C. sappan, no any differences are observed in chemical shifts of respective dimers of this compound, which has the same stereochemistry at its chiral centers (Shu et al 2011). These findings suggest that 1 might represent different stereochemistry at the each chiral center.…”

Section: Resultsmentioning

confidence: 77%

Phytochemical investigation of the active constituents from <i>Caesalpinia sappan</i> on stimulation of osteoblastic cells

Subehan

Rifai

Mufidah

et al. 2014

Plant Biotechnology

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Heartwood of Caesalpinia sappan L. has been traditionally used to many diseases such as homoptysis, syphilis, eye disease, dysentery, depurative and prevention of osteoporosis. Our previous in vitro screening of Indonesian plants revealed that an ethanolic extract of the heartwood of C. sappan exhibits a proliferation stimulating activity against primary osteoblastic cells. In our continued interest to this plant, we further fractionated the extract and isolated active constituents on the basis of the stimulating activity in the osteoblastic cells. The fractionation and isolation were carried out with various chromatography methods and the structure of isolated compounds was elucidated based on NMR, IR, UV and MS spectroscopic data. From an active fraction, a new biphenyl dimer, namely caesappanin C (1), along with two known compounds, protosappanin A (2) and sappanchalcone (3), were isolated. Among them, the new compound 1 exhibited the strongest activity and significantly increased the cell viability up to 276±5%. The other two compounds 2 and 3 also stimulated the cell proliferation and increased the cell viability up to 233±8% and 187±4%, respectively.

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Section: Resultsmentioning

confidence: 77%

Phytochemical investigation of the active constituents from <i>Caesalpinia sappan</i> on stimulation of osteoblastic cells

Subehan

Rifai

Mufidah

et al. 2014

Plant Biotechnology

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“…2. Phanginin L [68] Caesappanin A [70] Sappan chalcone [71] Butein [71] Phanginin I [72] 11-oxo-phanginin A [73] Caesalsappanin O [73] Caesalsappanin P [73] Caesalsappanin Q [73] Phanginin U [73] Norcaesalpinin J [74] Caesalppan D [75]…”

Section: Discussionmentioning

confidence: 99%

“…Caesappanin A showed cytotoxicity against HCT-8, BGC-823, A549 and A2780 with IC50 between 1.67 μM and 4.88 μM. [70].…”

Section: Caesalpinia Sappan Lmentioning

confidence: 93%

A review of the genus Caesalpinia L.: emphasis on the cassane and norcassane compounds and cytotoxicity effects

et al. 2020

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“…Figure 3: Basic chemical structures of the diferent types of homoisofavonoids found in nature. [6]; cytotoxicity against human cancer cell lines [7,8]; antidiabetic activity [9]; and antimicrobial activity [10][11][12][13][14][15]; among others [16,17]. Each year, fungal infections afect more than a billion people worldwide, with candidiasis representing about 75% to 88% of these infections.…”

Section: Caesalpin-type (Iv)mentioning

confidence: 99%

Chemistry and Antifungal Activity of Homoisoflavonoids

Ferreira,

de Sousa

2023

Journal of Chemistry

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This review deals with the antifungal profile of a subclass of natural products known as homoisoflavonoids. These molecules belong to the larger flavonoids class, yet they are less common for presenting an extra carbon in their basic chemical structures. Homoisoflavonoids are important bioactive molecules because they exhibit promising antimutagenic, antiproliferative, antioxidant, anti-inflammatory, and antimicrobial activity. This review lists the principal experimental studies addressing homoisoflavonoid antifungal activity with the aim of discussing the role of these molecules in obtaining new antifungal agents. The vast majority of research consists of antimicrobial screenings. It was noted that sappanin-type homoisoflavonoids commonly exhibit antifungal activity, but their overall antifungal profile is still very little known. Studies evaluating mechanisms of action are needed to better understand the antifungal potential of homoisoflavonoids.

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Two novel biphenyl dimers from the heartwood of Caesalpinia sappan

Cited by 18 publications

References 11 publications

Phytochemical investigation of the active constituents from <i>Caesalpinia sappan</i> on stimulation of osteoblastic cells

Phytochemical investigation of the active constituents from <i>Caesalpinia sappan</i> on stimulation of osteoblastic cells

A review of the genus Caesalpinia L.: emphasis on the cassane and norcassane compounds and cytotoxicity effects

Chemistry and Antifungal Activity of Homoisoflavonoids

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