Structures of rengyosides A, B and C, three glucosides of Forsythia suspensa fruits

Seya, Kazuhiko; Endo, Katsuya; Hara, Hiroshi

doi:10.1016/s0031-9422(00)97772-0

Cited by 34 publications

(24 citation statements)

References 14 publications

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“…The fraction eluted with MeOH was repeatedly chromatographed on columns of silica gel, . Fifteen were identified as known compounds; verbascoside (1), isoverbascoside (2), leucosceptoside A (3) (Miyase et al, 1982), luteoside A (6), luteoside B (7) (Kernan et al, 1998), 2 00 -O-apiosylverbascoside (8) (Kanchanapoom et al, 2001), decaffeoylverbacoside (9) (Karasawa et al, 1986), seguinoside K (10) (Zhong et al, 1999) (Achenbach et al, 1992) (Binns et al, 1987), (6S,9R)-roseoside (17) (Otsuka et al, 1995) rengyoside B (18) (Seya et al, 1989) and stegioside III (19) (Nass and Rimpler, 1996) by comparison of physical data with literature values and from spectroscopic evidence.…”

Section: Resultsmentioning

confidence: 99%

Phenolic glycosides from Barnettia kerrii

2002

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Section: Resultsmentioning

confidence: 99%

Phenolic glycosides from Barnettia kerrii

2002

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“…Salidroside was isolated from the fruits of Forsythia suspensa according to the method of Seya et al (1989). Salidroside was isolated from the fruits of Forsythia suspensa according to the method of Seya et al (1989).…”

Section: Chemicalsmentioning

confidence: 99%

Formation of benzoquinol moiety in cornoside by salidroside mono-oxygenase, a cytochrome P450 enzyme, from Abeliophyllum distichum cell suspension cultures

Yamamoto

Hori

Kuwajima

et al. 2003

Planta

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A microsomal fraction prepared from Abeliophyllum distichum Nakai (Oleaceae) cell suspension cultures oxidized salidroside, a glucoside of 4-hydroxyphenylethyl alcohol, to cornoside possessing a unique benzoquinol ring. The enzyme named salidroside monooxygenase required NADPH as the only cofactor, and molecular oxygen. The reaction was strongly inhibited by CO as well as several cytochrome P450 inhibitors, such as cytochrome c and miconazole, indicating the involvement of a cytochrome P450 enzyme. Salidroside mono-oxygenase accepted salidroside as the only substrate, but did not oxidize 4-hydroxyphenylethyl alcohol, the salidroside aglucone, and 4-hydroxybenzoic acid. The optimum pH of the reaction was 7.5, and apparent K m values for salidroside and NADPH were 44 lM and 33 lM, respectively. The benzoquinol ring formation mechanism is discussed in comparison to the mechanism for ipso substitution of 4-hydroxybenzoate by active oxygen species followed by elimination leading to hydroquinone.

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“…The fruit of F. suspensa is also called “Lianqiao” in Chinese and has been used for the treatment of various infectious diseases . The natural products that have been reported in F. suspensa include phenylethanoid glycosides, lignans, flavonoids, C 6 ‐C 2 glucoside conjugates (CCGCs), and triterpenes . Extensive scientific evidence has shown that some CCGCs are chemically unstable, thereby hindering their isolation and purification .…”

Section: Introductionmentioning

confidence: 99%

“…The natural products that have been reported in F. suspensa include phenylethanoid glycosides, lignans, flavonoids, C 6 ‐C 2 glucoside conjugates (CCGCs), and triterpenes . Extensive scientific evidence has shown that some CCGCs are chemically unstable, thereby hindering their isolation and purification . Various methods involving targeting acetylated fractions followed by isolation and purification have been previously applied to obtain purified compounds for NMR assays …”

Section: Introductionmentioning

confidence: 99%

UPLC‐QTOF‐MS^E‐based diagnostic product ion filtering to unveil unstable C₆‐C₂ glucoside conjugates in Forsythia suspensa

et al. 2017

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Forsythia suspensa contains C -C glucoside conjugates (CCGCs) that are chemically unstable, thereby hindering their isolation and purification. In the present study, ultra-performance liquid chromatography-quadrupole time-of-flight mass spectrometry (UPLC-QTOF) was utilized to screen and identify unstable CCGCs in the fruits and leaves of F. suspensa without any tedious isolation and purified process based on independent information acquisition (also called MS ) and individual MS/MS experiments. Diagnostic product ion filtering (DPIF) was further applied to mine unknown analogs in MS high energy levels based on characteristic m/z of key substructures. A modified nomenclature for CCGCs is hereby proposed to facilitate discussions. Possible fragmentation pathways of major types of known CCGCs were proposed and used for deducing their structures. A total of 8 potentially new CCGCs were discovered and initially identified. The accuracy of their identification was further verified by structural elucidation of 3 unstable CCGCs isolated from the fruits of F. suspensa using 1D and 2D-NMR spectroscopy. The established UPLC-QTOF-MS -based DPIF technique facilitates the rapid discovery and direct identification of unstable CCGCs in fruits and leaves of F. suspensa.

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Structures of rengyosides A, B and C, three glucosides of Forsythia suspensa fruits

Cited by 34 publications

References 14 publications

Phenolic glycosides from Barnettia kerrii

Phenolic glycosides from Barnettia kerrii

Formation of benzoquinol moiety in cornoside by salidroside mono-oxygenase, a cytochrome P450 enzyme, from Abeliophyllum distichum cell suspension cultures

UPLC‐QTOF‐MS^E‐based diagnostic product ion filtering to unveil unstable C₆‐C₂ glucoside conjugates in Forsythia suspensa

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Structures of rengyosides A, B and C, three glucosides of Forsythia suspensa fruits

Cited by 34 publications

References 14 publications

Phenolic glycosides from Barnettia kerrii

Phenolic glycosides from Barnettia kerrii

Formation of benzoquinol moiety in cornoside by salidroside mono-oxygenase, a cytochrome P450 enzyme, from Abeliophyllum distichum cell suspension cultures

UPLC‐QTOF‐MSE‐based diagnostic product ion filtering to unveil unstable C6‐C2 glucoside conjugates in Forsythia suspensa

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UPLC‐QTOF‐MS^E‐based diagnostic product ion filtering to unveil unstable C₆‐C₂ glucoside conjugates in Forsythia suspensa