Ypsiyunnosides A–E, Five New Cholestanol Glycosides from Ypsilandra yunnanensis

Abstract

Phytochemical investigation on the whole plants of Ypsilandra yunnanensis was carried out for the first time and led to the isolation of five new cholestanol glycosides, ypsiyunnosides A–E (1–5), and one known analogue. Their structures were determined mainly by detailed spectroscopic analysis, including extensive 1D and 2D NMR, MS and UV, as well as chemical methods. Among them, compound 1 possessed a rare 6/6/6/5/5 fused-rings cholestanol sketelon, which was identified as (23R,25R)-3β,16α,26-triol-16,23-cyclocholest-5,17(20)-dien-22-one. Their induced platelet aggregation activities and cytotoxicities were evaluated.Graphical AbstractFive new cholestanol glycosides, ypsiyunnosides A–E (1–5), were isolated from the whole plants of Ypsilandra yunnanensis. Compound 1 possessed a rare 6/6/6/5/5 fused-rings cholestanol sketelon. Their structures were elucidated by a combination of 1D and 2D NMR, MS and chemical analysis. Electronic supplementary materialThe online version of this article (doi:10.1007/s13659-016-0098-2) contains supplementary material, which is available to authorized users.

Furostanol Saponins from Trillium tschonoskii Promote the Expansion of Human Cord Blood Hematopoietic Stem and Progenitor Cells

“…By comparing the NMR data with reported values, several compounds of previously known structure were identified as 26- O -β- d -glucopyranosyl-(25 R )-Δ 5(6),16(20) -diene-16,22-dione­furostan-3β,26-diol-3- O -α- l -rhamnosyl-(1→2)-β- d -glucopyranoside ( 10 ), 26- O -β- d -glucopyranosyl-(25 R )-Δ 5(6),16(20) -diene-16,22-dione­furostan-3β,26-diol-3- O -α- l -rhamnosyl-(1→2)­[ O -α- l -rhamnosyl-(1→4)]-β- d -glucopyranoside ( 11 ), parispseudoside C ( 12 ), anguivioside XV ( 13 ), 3- O -α- l -rhamnosyl-(1→2)- O -β- d -glucopyranosyl­kryptogenin-26- O -β- d -glucopyranoside ( 14 ), furotrilliumoside ( 15 ), 26- O -β- d -glucopyranosyl-(22 S ,25 R )-furost-5-ene-3β,17α,22,26-tetraol-3- O -α- l -rhamnosyl-(1→2)- O -β- d -glucopyranoside ( 16 ), 26- O -β- d -glucopyranosyl-(22 S ,25 R )-furost-5-ene-3β,17α,22,26-tetraol-3- O -α- l -rhamnosyl-(1→2)-[ O -α- l -rhamnosyl-(1→4)]-β- d -glucopyranoside ( 17 ), saponin Th ( 18 ), ypsiyunnoside A ( 19 ), and trillikamtoside N ( 20 ) …”

“…By comparing the NMR data with reported values, several compounds of previously known structure were identified as 26-O-β-D-glucopyranosyl-(25R)-Δ 5(6),16 (20) -diene-16,22-dionefurostan-3β,26-diol-3-O-α-L-rhamnosyl-(1→2)-β-D-glucopyranoside (10), 25 26-O-β-D-glucopyranosyl-(25R)-Δ 5 (6), 16(20) 25 parispseudoside C (12), 26 anguivioside XV (13), 27 (14), 28 furotrilliumoside (15), 29 (17), 31 saponin Th (18), 32 ypsiyunnoside A (19), 33 and trillikamtoside N (20). 34 To evaluate the bioactivity of these compounds isolated from the rhizomes of T. tschonoskii, CD34 + cells from human CB were cultured for 4 days in medium containing 100 ng/mL of stem cell factor (SCF), thrombopoietin (TPO), and Fms-like tyrosine kinase 3 ligand (Flt3L) with and without compounds 1−20 (10 μM) (Figure 1A).…”

Four New Steroidal Saponins from the Roots of Dracaena cambodiana with NO Production Inhibition Activity in LPS Activated RAW 264.7 Cells

“…These suggested a steroidal aglycone bearing two glucose and two rhamnose moieties. [3,[8][9][10] The 13 C NMR and HSQC spectra of 1 revealed the presence of 51 carbon signals, including 27 of the steroidal aglycone and 24 of four hexose sugar moieties. [3,9,10] All the NMR data of 1 were assigned with the aid of HSQC, COSY, and HMBC spectra (Table 1, Figure 2).…”

Untiring Researches for Alternative Resources of Rhizoma Paridis

“…A total of two new sapogenins and 38 saponins (Fig. 2 ; Table 2 ) have been reported from the whole plants of Y. thibetica , Y. parviflora , and Y. yunnanensis up to 2017 by our research group, namely, isoypsilandrogenin ( 34 ), isoypsilandrosides A ( 35 ) and B ( 36 ), ypsilandrosides A ( 37 ) and B ( 38 ) [ 37 ], ypsilandrosides C–G ( 39 – 43 ) [ 38 ], ypsilandrosides H–L ( 44 – 48 ) [ 39 ], ypsilandrosides M–O ( 49 – 51 ) [ 40 ], ypsiparosides A–G ( 52 – 58 ) [ 41 ], ypsilanogenin ( 59 ), ypsilanogenin 3- O - β - d -glucopyranoside ( 60 ), 4′-acetylypsilanogenin 3- O - β - d -glucopyranoside ( 61 ) [ 42 ], ypsilandrosides P–R ( 62 – 64 ) [ 43 ], ypsilandrosides S ( 65 ) and T ( 66 ) [ 44 ], ypsiyunnosides A–E ( 67 – 71 ) [ 45 ], and ypsilactosides A ( 71 ) and B ( 72 ) [ 46 ]. These new saponins were usually the oxygenated derivatives at C-6, C-7, C-11, and C-12 of those known analogues and some of these isolates had unpredicted aglycones.…”