Four new oleanane-type triterpene glycosides, madlongisides A−D (1−4), were isolated from the seeds of Madhuca longifolia, and their structures were elucidated on the basis of extensive NMR experiments and chemical methods. Also obtained in this investigation were the known compounds mimusopside A, Mi-saponins A, B, and C, and 3-O-β-d-glucopyranosyl protobassic acid.
NCBI PubMed ID: 11141115Publication DOI: 10.1021/np000351rJournal NLM ID: 7906882Publisher: American Society of Pharmacognosy
Correspondence: yosikawa
ph.bunri-u.ac.jp
Institutions: Faculty of Pharmaceutical Sciences, Tokushima Bunri University, Tokushima, Japan, Medicinal Chemistry Division, Indian Institute of Chemical Biology, Jadavpur, India, Laboratory of Cell Biology, Osaka University of Pharmaceutical Sciences, Osaka, Japan
Methods: 13C NMR, 1H NMR, NMR-2D, TLC, enzymatic hydrolysis, acid hydrolysis, HPLC, optical rotation measurement, HR-FAB-MS
- Compound ID: 33419
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a-L-Arap-(1-28)-Subst
Subst = 2-oxo-uncargenin A = SMILES C[C@@]12CC[C@@]3({28}C(O)=O)CCC(C)(C)C[C@H]3C1=CC[C@H]4[C@@]2(C)C{3}[C@@H](O)[C@H]5[C@]4(C)CC({6}[C@H](O)[C@]5({23}CO)C)=O |
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Structure type: monomer
C35H54O10
Trivial name: madlongiside A
Compound class: glycoside, triterpenoid glycoside
- Compound ID: 33420
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b-D-Glcp-(1-3)-+
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a-L-Arap-(1-28)-Subst
Subst = 2-oxo-uncargenin A = SMILES C[C@@]12CC[C@@]3({28}C(O)=O)CCC(C)(C)C[C@H]3C1=CC[C@H]4[C@@]2(C)C{3}[C@@H](O)[C@H]5[C@]4(C)CC({6}[C@H](O)[C@]5({23}CO)C)=O |
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Structure type: oligomer
; 795 [M-H]-
C41H64O15
Trivial name: madlongiside B
Compound class: glycoside, triterpenoid glycoside
- Compound ID: 33421
Structure type: monomer
; 635 [M-H]-
C35H56O10
Trivial name: madlongiside C
Compound class: glycoside, triterpenoid glycoside
- Compound ID: 33422
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a-L-Rhap-(1-2)-a-L-Arap-(1-28)-Subst
Subst = protobassic acid28 |
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Structure type: oligomer
; 781 [M-H]-
C41H66O14
Trivial name: madlongiside D
Compound class: glycoside, triterpenoid glycoside
- Compound ID: 33423
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b-D-Glcp-(1-3)-+
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a-L-Rhap-(1-2)-a-L-Arap-(1-28)-Subst
Subst = protobassic acid28 |
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Structure type: oligomer
Trivial name: mimusopside A
Compound class: glycoside, triterpenoid glycoside
- Compound ID: 33424
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b-D-Glcp-(1-3)-+
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a-L-Rhap-(1-3)-b-D-Xylp-(1-4)-a-L-Rhap-(1-2)-a-L-Arap-(1-28)-Oleanolic |
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Structure type: oligomer
Trivial name: mi-saponin A
Compound class: glycoside, triterpenoid glycoside
- Compound ID: 33425
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b-D-Apif-(1-3)-+ b-D-Glcp-(1-3)-+
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a-L-Rhap-(1-3)-b-D-Xylp-(1-4)-a-L-Rhap-(1-2)-a-L-Arap-(1-28)-Subst
Subst = protobassic acid28 |
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Structure type: oligomer
Trivial name: mi-saponin B
Compound class: glycoside, triterpenoid glycoside
- Compound ID: 33426
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b-D-Glcp-(1-4)-+ b-D-Glcp-(1-3)-+
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a-L-Rhap-(1-3)-b-D-Xylp-(1-4)-a-L-Rhap-(1-2)-a-L-Arap-(1-28)-Subst
Subst = protobassic acid28 |
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Structure type: oligomer
Trivial name: mi-saponin C
Compound class: glycoside, triterpenoid glycoside
- Compound ID: 33427
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b-D-Glcp-(1-3)-Subst
Subst = protobassic acid = SMILES C[C@@]12CC[C@@]3(C(O)=O)CCC(C)(C)C[C@H]3C1=CC[C@H]4[C@@]2(C)C{6}[C@@H](O)[C@H]5[C@]4(C)C{2}[C@H](O){3}[C@H](O)[C@]5({23}CO)C |
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Structure type: monomer
Compound class: glycoside, triterpenoid glycoside
Found