Three Secoiridoid Glucosides Esterified with a Linear Monoterpene Unit and a Dimeric Secoiridoid Glucoside from <i>Jasminum polyanthum</i>

Tanahashi, Takao; Takenaka, Yasuhiro; Nagakura, Naotaka

doi:10.1021/np9700376

Cited by 15 publications

(2 citation statements)

References 13 publications

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“…Compounds (187) to (189) have 188 (Fig. (3)) [133,134,83]. Similar to (182), secoiridoid is connected to C-8 of the aglycone via ester linkage in both compounds (187) and (188).…”

Section: Teucrioside-3''''-o-methylether (40) and Teucrioside-3''''4mentioning

confidence: 83%

Naturally Occurring Phenylethanoid Glycosides: Potential Leads for New Therapeutics

Fu¹,

Pang²,

Wong

2008

CMC

136

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ABATRACTNatural products have long been regarded as excellent sources for drug discovery given their structure diversity and wide variety of biological activities. Phenylethanoid glycosides are naturally occurring compounds of plant origin and are structurally characterized with a hydroxyphenylethyl moiety to which a glucopyranose is linked through a glycosidic bond. To date several hundred compounds of this type have been isolated from medicinal plants and further pharmacological studies in vitro or in vivo have shown that these compounds possess a broad array of biological activities including antibacterial, antitumor, antiviral, anti-inflammatory, neuro-protective, antioxidant, hepatoprotective, immunomodulatory, and tyrosinase inhibitory actions. Given their extensive activity profile, structure-activity relationships analyses of these compounds have been performed in a number of studies to reveal potential leads for future drug design. This article will summarize the major developments in phenylethanoid glycosides-based research in the past decade. The progresses made in phytochemistry and biological activity studies of these compounds will be reviewed. Particular attention will be given to the novel structures identified to date and the prominent therapeutic values associated with these molecules.

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“…Compounds (187) to (189) have 188 (Fig. (3)) [133,134,83]. Similar to (182), secoiridoid is connected to C-8 of the aglycone via ester linkage in both compounds (187) and (188).…”

Section: Teucrioside-3''''-o-methylether (40) and Teucrioside-3''''4mentioning

confidence: 83%

Naturally Occurring Phenylethanoid Glycosides: Potential Leads for New Therapeutics

Fu¹,

Pang²,

Wong

2008

CMC

136

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“…10 The 1 H NMR spectrum of compound (1) ( [12][13][14][15] (gardenamide class), and some were obtained as metabolites produced by human 16 and rat intestinal bacteria. 17 Comparison with the published data of known iridoid alkaloids, such as (6) (Figure 1), and hemiacetal-secoiridoids 11,18 like (7) ( Figure 1) and compound (1) 11,18 showed that (1) it was neither a hemiacetal nor a nitrogen-containing iridoid (N-2) but that it was compatible with a C-1(N)O-2 substitution. This was also supported by the presence of the 1 H-1 H COSY correlation between H-1/NH, rather than the H-1/NH, H-3/NH correlations expected in the iridoid alkaloids, 17 and by UV and IR data indicating the presence of the chromophore -OOCC=CHO.…”

Section: Resultsmentioning

confidence: 86%

Iridoids from Hymenodictyon floribundum

Borges

Diakanawma

Mendonça

2010

J. Braz. Chem. Soc.

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Das cascas do tronco e das folhas do Hymenodictyon floribundum B. L. Rob foram isolados dois novos iridoides, floribundano A (1) e floribundano B (2), e três compostos conhecidos, lupenona (3), escopoletina (4) e 4,5-di-hidroblumenol A (5). As estruturas de todos os compostos foram estabelecidas com base nos seus dados espectroscópicos.Two new iridoids floribundane A (1) and floribundane B (2) and the known compounds lupenone (3), scopoletin (4) and 4,5-dihydroblumenol A (5) were isolated from trunk bark and leaves of Hymenodictyon floribundum B.L. Rob. The structures of all compounds were established from their spectroscopic data. Keywords: Hymenodictyon floribundum, monoterpenes, secoiridoids, nitrogen-containing iridoid, C-9 iridoid IntroductionThe Hymenodictyon genus comprises 22 species. Of these, 11 are endemic to Madagascar, 4 to Asia and 7 to Tropical Africa. 1 Hymenodictyon floribundum B.L. Rob. (Rubiaceae), endemic to Tropical Africa, is a small tree that grows in the mountains of the Huíla province and its traditional name is NDambi Yov`olwi, (omu)Lia-tyimeme. Its trunk bark is used in Angola folk medicine to treat fever. 2 A previous study has shown that the trunk bark of this tree contains scopoletin, hymeselsin, scopolin and 3-O-β-D-glucopyranosyl-β-sitosterol. 3 An exhaustive literature review revealed that, with the exception of an ongoing study examining the trunk bark and dried leaves of Hymendictyon floribundum (in the context of other medicinal plants of Angola), 4 other parts of the tree have not yet to be studied.In the aforementioned study, powdered trunk barks and dried leaves were extracted by maceration with methanol. The methanol extract was partitioned with hexane and chloroform. The hexane extract from trunk barks yielded lupenone (3) 5 and the chloroform extract yielded scopoletin (4). 6 The chloroform extract from dried leaves yielded floribundane A (1), 4,5-dihydroblumenol A (5) 7,8 and floribundane B (2). Results and DiscussionFloribundane A (1) was obtained as a colourless oil with [α] 2 D 0 = +25.31º. The HR-TOF-EI-MS showed a molecular ion peak at m/z 223.0843 [M] + (in agreement with the molecular formula C 11 H 13 NO 4 ) implying 6 degrees of unsaturation. The UV maximum at 234 nm and the IR absorptions at 1724, 1633 and 1268 cm -1 suggested the presence of the chromophore -OOCC=CHO. 9 The IR also showed the presence of a lactam ring: NH band (3403 cm -1 ), and the amide band I (1690 cm -1 ) with an absence of the amide II band. 10 The 1 H NMR spectrum of compound (1) ( 16 and rat intestinal bacteria. 17 Comparison with the published data of known iridoid alkaloids, such as (6) (Figure 1), and hemiacetal-secoiridoids 11,18 like (7) ( Figure 1) and compound (1) 11,18 showed that (1) it was neither a hemiacetal nor a nitrogen-containing iridoid (N-2) but that it was compatible with a C-1(N)O-2 substitution. This was also supported by the presence of the 1 H-1 H COSY correlation between H-1/NH, rather than the H-1/NH, H-3/NH correlations expected in the iridoid alkaloids, 17 ...

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Occurrence and Biological Activities of Seco‐Iridoids from Jasminum L.

Frezza,

Nicolosi,

Brasili

et al. 2024

Chemistry & Biodiversity

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In this paper, the first complete review on the seco‐iridoids from the genus Jasminum L. was presented. In particular, their occurrence in the genus was detailed together with their biological activities. The literature survey has clearly pointed out that only a few Jasminum species have been studied for their seco‐iridoid content evidencing oleoside derivatives as main compounds. In addition, the biological studies performed on them are very scarce focusing mainly on antioxidant and anti‐inflammatory assays with modest effectiveness. All these results greatly underline the need for further in‐depth analyses on these compounds under both the aspects.

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Three Secoiridoid Glucosides Esterified with a Linear Monoterpene Unit and a Dimeric Secoiridoid Glucoside from Jasminum polyanthum

Cited by 15 publications

References 13 publications

Naturally Occurring Phenylethanoid Glycosides: Potential Leads for New Therapeutics

Naturally Occurring Phenylethanoid Glycosides: Potential Leads for New Therapeutics

Iridoids from Hymenodictyon floribundum

Occurrence and Biological Activities of Seco‐Iridoids from Jasminum L.

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