Cytotoxic and anti-HIV-1 constituents from leaves and twigs of Gardenia tubifera

Reutrakul, Vichai; Krachangchaeng, Chongkon; Tuchinda, Patoomratana; Pohmakotr, Manat; Jaipetch, Thaworn; Yoosook, Chalobon; Kasisit, Jittra; Sophasan, Samaisukh; Sujarit, Kulawee; Santisuk, Thawatchai

doi:10.1016/j.tet.2003.12.010

Cited by 38 publications

(28 citation statements)

References 25 publications

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“…The structures of the known compounds were confirmed by comparison of their physical and spectral data with the published data, as genipin gentiobioside (4), geniposide (5), deacetylasperulosidic acid methyl ester (6), scandoside methyl ester (7), 6''-O-[(E)-p-coumaroyl]genipin gentiobioside (8), bartsioside (9), 6'-O-sinapoylgeniposide (10) [18].…”

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confidence: 65%

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Iridoid Glycosides from Gardenia jasminoidesEllis

Xiao-mei

Chou

Wang

2008

Helvetica Chimica Acta

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Three new iridoid glycosides, 4″‐O‐[(E)‐p‐coumaroyl]gentiobiosylgenipin (1), 6′‐O‐[(E)‐caffeoyl]deacetylasperulosidic acid methyl ester (2), and 6′‐O‐[(E)‐sinapoyl]gardoside (3), together with seven analogues, 4–10, were isolated from the BuOH extract of the fruits of Gardenia jasminoides Ellis. Their structures were determined by means of spectroscopic analyses, including HR‐ESI‐MS, IR, and 1H‐ and 13C‐NMR, and 2D experiments (COSY, HSQC, and HMBC), and comparison with known related compounds.

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confidence: 65%

“…719.21577). The molecular formula of 1 was the same as that of 6''-O-[(E)-p-coumaroyl]genipin gentiobioside (8), moreover, the NMR data were very similar. The IR spectrum revealed the absorption bands of OH (3411 cm À1 ) and C¼O (1697 cm À1 ) groups.…”

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confidence: 74%

Iridoid Glycosides from Gardenia jasminoidesEllis

Xiao-mei

Chou

Wang

2008

Helvetica Chimica Acta

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“…These include sootepin C (3), coronalonic acid (4), sootepin A (5), tubiferolide methyl ester (6), and coronalolide methyl ester (7). 10,13,14) Cytotoxic Activity As part of our ongoing efforts to investigate Thai natural products with potential for cancer therapy, compounds 1 and 2 were determined for their in vitro cytotoxicity toward five human tumor cell lines (BT474, CHAGO, KATO-3, SW620, and Hep-G2) and noncancerous CH liver cells. As shown in Table 2, sootependial (1) showed potent cytotoxicity against only Hep-G2 cell lines with an Anti-angiogenic Activity Angiogenesis, the formation of new blood vessels from the pre-existing vasculature, is also an important target for cancer therapy as the development of tumors is crucially angiogenesis-dependent.…”

Section: Resultsmentioning

confidence: 99%

Cytotoxic and Anti-angiogenic Properties of Minor 3,4-<i>seco</i>-Cycloartanes from <i>Gardenia sootepensis</i> Exudate

Pudhom

Nuanyai

Matsubara

2012

CHEMICAL & PHARMACEUTICAL BULLETIN

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Gardenia plants have long been used as traditional medicines in various countries including Thailand. In this study, two new 3,4-seco-cycloartane triterpenes, sootependial (1) and sootepenoic acid (2), were isolated from bud exudate of G. sootepensis, together with five known compounds. Their structures were elucidated on the basis of spectroscopic data. Sootependial (1) showed potent cytotoxicity selective to Hep-G2 cell lines and anti-angiogenic activity in ex vivo model (a rat aortic ring sprouting) assay. Furthermore, its angiogenic effect was found to occur mainly by suppressing endothelial cell proliferation and tubule formation, suggesting the potential of 1 as a lead compound for cancer treatment.

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“…Plants belonging to the genus Gardenia have proved to produce a variety of cycloartane triterpenoids, some of which display interesting biological activities (Grougnet et al, 2006;Reutrakul et al, 2004;Silva et al, 1999;Tuchinda et al, 2002Tuchinda et al, , 2004. Additionally, extracts of various species exhibiting anti-implantation and abortifacient effects (Lu et al, 1981), and antiulcer (Takase et al, 1989), antibacterial (Laurens et al, 1985), diuretic, analgesic, hypertensive and larvicidal activities (Hussian et al, 1991;Manson, 1939) have been reported.…”

Section: Introductionmentioning

confidence: 99%