Vicoside A, a 28-nortriterpenoid glucoside from Vicoa indica

Vasanth, Saradha; Kundu, Amit; Panda, Sauris; Patra, Amarendra

doi:10.1016/s0031-9422(00)98251-7

Cited by 9 publications

(11 citation statements)

References 7 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The presence of a singlet at 73.5 (C-17) coupled with the absence of a singlet at 28.0 for the Me-28 agreed with mass spectral data and confirmed placement of the -OCHO at C-17. With the exception of the glucose residue, the 1H-and 13Cnmr spectra of 1 exhibited resonances closely similar to vicoside A [2] previously isolated from the same plant (4). 'H-nmr signals for H-23, H-2, and H-16 observed at 3.32, 4.25 (m), and 4.00 (dd, J= 11.5 and 5 Hz), respectively, were in conformity with those of the aglycone part of the saponified product of vicoside A hexacetate {3} (4).…”

supporting

confidence: 58%

See 1 more Smart Citation

Further Oleanane Triterpenoids from Vicoa indica

Vasanth¹,

Kundu²,

Patra³

1992

J. Nat. Prod.

Self Cite

View full text Add to dashboard Cite

i%BsTRACT.-vicosigenin El], a new 28-nortriterpenoid, and vicoside B 141, a new triterpenoid glucoside, were isolated from V i m indica. Their structures were elucidated by spectral methods. Previous investigations on Vicoa indica DC. (Asteraceae), a tribal female antifertility drug in India, led to the isolation of four sesquiterpenoid lactones ( 1,2), a monoterpene diol (3), and a 28-noroleanane glucoside, vicoside A E21 (4). The present work describes the isolation and characterization of a new 28-nortriterpenoid, vicosigenin (11, and a new triterpenoid glucoside, vicoside B (41, from the same plant.Chromatography of the CHCI, extract of the aerial parts of V. indica afforded vicosigenin El]. Compound 1 was assumed to have molecular formula C30H4806 from its DEPT spectrum. Its ir spectrum showed hydroxyl and ester bands at 3425 and 1735 cm-', respectively. The 'H-and l3C-nmr spectra of 1 exhibited signals for six tertiary methyl groups, a trisubstituted double bond, three secondary and one primary hydroxyl groups, and a formate group (see Experimental). The mass spectrum of 1 did not exhibit the molecular ion peak and gave the highest mass peak at m h 458 {M -HCOZH}+. The facile loss of formic acid from the molecule suggested that the formate group in 1 must be at C-17, as it is well known that substituents at C-17 are readily lost (5). Furthermore, fragment peaks at mlz 239 and 218 (base peak) were due to retro-'CSMDRIA Communication NO. 304. 'Present address: Regional Research Institute (Ayurveda) (CCRAS) 14, Jagannath Dutta Lane, Calcutta 7oooO9.Diels-Alder cleavage from m/z 458. This indicated that three hydroxyl groups were in the rings NB and one hydroxyl group was in the DIE portion of a 28-norolean-12-ene skeleton (4). The presenceofasingletat673.5 (C-17)coupled with the absence of a singlet at 6 28.0 for the Me-28 agreed with mass spectral data and confirmed placement of the -OCHO at C-17. With the exception of the glucose residue, the 'H-and 13C-nmr spectra of 1 exhibited resonances closely similar to vicoside A (21 previously isolated from the same plant (4). 'H-nmr signals for H-23, H-2, and H-16 observed at 6 3.32, 4.25 (m), and 4.00 (dd,J= 11.5 and 5 Hz), respectively, were in conformity with those of the aglycone part of the saponified product of vicoside A hexacetate (37 (4). The 13C-nmr data also confirmed the above assignments. Thus, the structure ofvico-1 R,=R2=R3=H, R,=OCHO 2 R,=P-D-GIc, R2=R3=H, R,=OCHO 3 R, = P-D-GIC(AC),, R,= R, = Ac, R,=OCHO 4 R,=P-D-GIc, R,=R,=H, R,=CHO 5 R,=P-D-GIc(Ac)~, R~= R~= A c , R,=CHO

show abstract

supporting

confidence: 58%

“…tifertility drug in India, led to the isolation of four sesquiterpenoid lactones (1,2), a monoterpene diol (3), and a 28noroleanane glucoside, vicoside A [2] (4). The present work describes the isolation and characterization of a new 28nortriterpenoid, vicosigenin [1], and a new tri terpenoid glucoside, vicoside B [4], from the same plant.…”

mentioning

confidence: 99%

Further Oleanane Triterpenoids from Vicoa indica

Vasanth¹,

Kundu²,

Patra³

1992

J. Nat. Prod.

Self Cite

View full text Add to dashboard Cite

show abstract

“…Various constituents reported in VI are germacranolide (Sawaikar et al, 1998), vicogenin (Balakrishna et al, 1995) and vicoside A (Vasanth et al, 1991). It is reported to have antifungal (Rai and Vasanth, 1995), antipyretic and anti-inflammatory (Alam et al, 1992a) activities.…”

Section: Vicoa Indica DC (Family: Asteraceae)mentioning

confidence: 99%

Potential antifertility agents from plants: A comprehensive review

Kumar

Prakash

2012

Journal of Ethnopharmacology

123

View full text Add to dashboard Cite

“…l~~ 1 74) is called javanicinoside C while javanicinoside B has structure (196). These authors should give more thought to their nomenclature.…”

Section: Quassinoidsmentioning

confidence: 99%

“…150 Another degraded limonoid, calodendrolide (1 72), has been synthesized. 151 (196). These authors should give more thought to their nomenclature.…”

Section: An Insect Antifeedant From Croton J ~T R O P H O I D E S ' ~~mentioning

confidence: 99%