Two New Lignan Glycosides from <i>Saussurea laniceps</i>

Zhou, Zhiliang; Yin, Sheng; Wang, Xiaoning; Fan, Cheng-Qi; Li, Hui; Yue, Jian‐Min

doi:10.1002/hlca.200790096

Cited by 25 publications

(20 citation statements)

References 24 publications

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“…The 1 H-NMR spectrum (l " Table 1) showed proton signals of two ABX systems of aromatic protons at δ H 6.83, 6.75, 6.70, 6.81, 6.70, and 6.70, two aromatic CH 3 O groups at δ H 3.73 (3H, s) and 3.76 (3H, s), indicating the presence of two trisubstituted benzene rings. Six oxygenated aliphatic protons at δ H 3.44, 3.49 (2H), 3.54, 3.95, and 4.51, together with two aliphatic protons at δ H 2.07 and 2.50 were evidence for the presence of a tetrahydrofuranoid lignan skeleton [8], which was supported by 13 C-NMR analysis. In the 13 C-NMR spectrum, apart from the twelve aromatic and three CH 3 O signals, there were six sp 3 C-atoms, including two oxymethines at δ C 83.3 and 85.7 and two oxymethylenes at δ C 61.5 and 69.1.…”

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confidence: 63%

“…We herein described the isolation and structure elucidation of four new lignans (1)(2)(3)(4) and the evaluation of the cytotoxic activity of all isolated compounds, along with their preliminary structure-activity relationships. Compound 5 was identified as lanicepside A by comparison with the literature [8]. Compound 1 was obtained as a sticky oil and possessed a molecular formula C 21 H 26 O 7 , as revealed from its HR-ESI-MS analysis (m/z 413.1574 [M + Na] + ).…”

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confidence: 96%

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Four New Cytotoxic Tetrahydrofuranoid Lignans fromSinopodophyllum emodi

Sun¹,

Li²,

Chen³

et al. 2012

Planta Med

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Four new tetrahydrofuranoid lignans, (-)-tanegool-7'-methyl ether ( 1), (+)-7'-methoxylariciresinol (2), sinolignan C (3), and epipinoresinol-4,4'-di- O- β- D-glucopyranoside (4), were isolated from the roots and rhizomes of SINOPODOPHYLLUM EMODI together with one known lignan (5). Their structures and stereochemistry were elucidated on the basis of spectroscopic and mass spectrometric evidence. The isolation of compounds 1- 5 represents the first report of tetrahydrofuran lignans from the genus SINOPODOPHYLLUM. The cytotoxic activities of all isolated compounds were evaluated against HeLa and KB cell lines, and compound 1 showed the most potent cytotoxicity with IC₅₀ values of 9.7 µM and 4.7 µM, respectively.

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confidence: 63%

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confidence: 96%

Four New Cytotoxic Tetrahydrofuranoid Lignans fromSinopodophyllum emodi

Sun¹,

Li²,

Chen³

et al. 2012

Planta Med

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“…xuelianlactone (1) (Dawa et al 2008b), xuelianlactone 8-O-β-D-glucopyranoside (2) (Dawa et al 2008b), mokko lactone (3) (Wang et al 2008), 3α,8α-dihydroxy-11βH-11,13-dihydrodehydrocostuslactone (4) (Wang et al 2008), 8α-hydroxy-11βH-11,13-dihydrodehydrocostuslactone (5) (Zhou et al 2007 (Wang et al 2005b), cynaropicrin (10) (Wang et al 2008) and lanicepomine A (11) (Wang et al 2010). An eudesmane-type sesquiterpene, 3α,7α,12-trihydroxyeudesm-4(15),11(13)-diene (12), has also been isolated (Wang et al 2005b).…”

Section: Sesquiterpene Constituentsmentioning

confidence: 99%

“…Fourteen flavonoids and their derivatives have been isolated from this species (Fig. 4), including 5,6,7trihydroxy-4'-methoxyflavone (14) (Zhou et al 2007), apigenin (15) (Dawa et al 2008b;Dawa et al 2010;Yi et al 2009a), apigenin 7-O-β-D-glucoside (16) (Dawa et al 2008b;Dawa et al 2010;Yi et al 2009a;Yi et al 2014)…”

Section: Flavonoidsmentioning

confidence: 99%

Review on Saussurea laniceps, a potent medicinal plant known as “snow lotus”: botany, phytochemistry and bioactivities

Chen

Zhu

et al. 2016

Phytochem Rev

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Saussurea laniceps (Compositae), commonly known as "cotton-headed snow lotus", is the most effective "snow lotus" used in both Tibetan and Chinese folk medicine. It performs outstandingly in treating rheumatoid arthritis, which mainly is credited for its anti-inflammatory and anti-nociceptive efficacy, as explained by modern pharmacological studies. Extracts of the herb, including umbelliferone and scopoletin, exert such effects in various in vivo and in vitro studies. Besides the two chemicals above, more than 100 organic compounds have been found in S. laniceps, and 58 of them are presented here in molecular structure, including cynaropicrin, mokko lactone, apigenin, acacetin, and luteolin, all contributing to different bioactivities, such as analgesic, antioxidant, immunomodulatory, anti-microbial and anticancer effects. We provide a natural product library of S. laniceps, giving inspirations for structure modification and bioactivity-oriented screening, enabling sustainable use of this valuable plant. The ethnomedical applications and pharmacological discoveries are compared and crosslinked, revealing modern evidence for traditional usages. Despite that S. laniceps is a representative "snow lotus" herb, its material medica records and clinical applications are complicated; there is considerable confusion with the different snow lotuses in the academic community and on the market. This review also aims at clearing such confusion, and improving quality assessment and control of the herb. To better utilize the valuable plant, further comparison among the chemical constitutions, pharmacological activities and therapeutic mechanisms of different snow lotuses are needed.

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“…Among them, approximately 60 were new compounds, and 6 had new carbon skeletons ( Figure 6). In particular, 48 of these compounds showed significant biological activities in a variety of bioassays and provided a scientific foundation for the use of a number of traditional Chinese herbs [103][104][105][106][107][108][109][110][111][112][113][114] .…”

Section: Miscellaneousmentioning

confidence: 99%

Discovery of structurally diverse and bioactive compounds from plant resources in China

Shi

Yue

2012

Acta Pharmacol Sin

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This review describes the major discoveries of structurally diverse and/or biologically significant compounds from plant resources in China, mainly from the traditional Chinese medicines (TCMs) since the establishment of our research group in 1999. In the past decade, a large array of biologically significant and novel structures has been identified from plant resources (or TCM) in our laboratory. The structural modification of several biologically important compounds led to more than 400 derivatives, some of which exhibited significantly improved activities and provided opportunities to elucidate the structure-activity relationship of the related compound class. These findings are important for drug discovery and help us understand the biological basis for the traditional applications of these plants in TCM.

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Two New Lignan Glycosides from Saussurea laniceps

Cited by 25 publications

References 24 publications

Four New Cytotoxic Tetrahydrofuranoid Lignans fromSinopodophyllum emodi

Four New Cytotoxic Tetrahydrofuranoid Lignans fromSinopodophyllum emodi

Review on Saussurea laniceps, a potent medicinal plant known as “snow lotus”: botany, phytochemistry and bioactivities

Discovery of structurally diverse and bioactive compounds from plant resources in China

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