Phytochemical studies on Stemona aphylla: isolation of a new stemofoline alkaloid and six new stemofurans.

@article{Sastraruji2011PhytochemicalSO,
  title={Phytochemical studies on Stemona aphylla: isolation of a new stemofoline alkaloid and six new stemofurans.},
  author={Thanapat Sastraruji and Sukanda Chaiyong and Araya Jatisatienr and Stephen G. Pyne and Alison Thavary Ung and Wilford Lie},
  journal={Journal of natural products},
  year={2011},
  volume={74 1},
  pages={
          60-4
        }
}
A new stemofoline alkaloid, (2'S)-hydroxy-(11S,12R)-dihydrostemofoline (3), new stemofurans M-R (8-13), and known compounds stemofoline (1), (2'S)-hydroxystemofoline (2), stemofuran E (4), stemofuran F (5), stemofuran J (6), and stilbostemin F (7) have been isolated from the root extracts of Stemona aphylla. The structures and relative configurations of these new compounds have been determined by spectroscopic data interpretation and from semisynthetic studies. These natural and semisynthetic… 

Figures and Tables from this paper

Structural classification and biological activities of Stemona alkaloids
  • H. Greger
  • Biology, Chemistry
    Phytochemistry Reviews
  • 2019
TLDR
Comparing the diverse bioactivities of Stemona alkaloids stemofoline-type derivatives are the most versatile compounds representing promising lead structures for further development as commercial agents in agriculture and medicine.
The diversity of Stemona stilbenoids as a result of storage and fungal infection.
  • H. Greger
  • Biology, Chemistry
    Journal of natural products
  • 2012
TLDR
A leucotriene biosynthesis inhibition assay using 15 stilbenoids showed interesting structure-activity relationships, with more potent effects of some compounds than the commercial 5-lipoxygenase inhibitor zileuton being observed.
Two new polyketides from the roots of Stemona tuberosa.
Stemona Alkaloids: Biosynthesis, Classification, and Biogenetic Relationships
TLDR
The biosynthesis, structural classification, and the intrinsic, biogenetic relationships of Stemona alkaloids are summarized in this review.
Stilbenoids from the roots of Stemona tuberosa
TLDR
Two new stilbenoids, stemobenoids A and B, together with three known compounds were obtained from the roots of Stemona tuberosa, and displayed potent quinone reductase inducing activity in Hepa 1c1c7 cells.
Response of Stemona alkaloid production in Stemona sp. to chitosan and yeast extract elicitors
TLDR
It was found that 1', 2'-didehydrostemofoline and stemofoline production was 2.65 fold and 2.95 fold higher than the control, respectively.
...
...

References

SHOWING 1-7 OF 7 REFERENCES
02 (s, 1H, H-1′′), 6.70 (br s, 1H, H-5), 6.36 (br s, 1H, H-3), 3.90 (s, 3H, 5′-OCH 3 ), 3.82 (s, 3H, 4-O-CH 3 ), 3.72 (s, 3H, 3′-O-CH 3 ), 2.41 (s, 3H, 2′-CH 3 ), 2.16 (s, 3H, 4′-CH 3 )
  • HRESIMS m/z 315.1237 [MH] + , calcd for C 18 H 19 O 5 315.1232. Stemofuran R (13): dark brown, amorphous solid; 1 H NMR δ 8.95 (br s, 1H, 2-OH), 7.16 (s, 1H, H-6′)
04 (s, 3H, H-16), 2.02-1.96 (m, 1H, H-6a), 1.90-1.84 (m, 1H, H-6b), 1.83 (d, J ) 12.5 Hz, 1H, H-1b), 1.74 (dd, J ) 11.5, 3.0 Hz
  • 3.62 (dt, J ) 9.0, 6.5 Hz, 1H, H-2′), 3.55 (br s, 1H, H-9a), 3.25 (ddd, J ) 14.5, 9.5, 5.0 Hz, 1H, H-5a), 3.03 (ddd, J ) 13.5, 9.0, 4.5 Hz
89 (s, 3H, 4-O-CH 3 ), 3.79 (s, 3H, 5′-O-CH 3 ), 2.34 (s, 3H, 2′-CH 3 ), 2.15 (s, 3H, 3-CH 3 ); 13 C NMR δ 159.2 (C-5′)
  • 104.7 (C-6′), 103.7 (C-1′′), 102.2 (C-4′), 87.1 (C-5)
01 (s, 1H, H-6′), 6.69 (br s, 1H, H-5), 6.67 (s, 1H, H-4′), 6.35 (d, J ) 1.5 Hz, 1H, H-3), 3.87 (s, 3H, 3′-OCH 3 ), 3.87 (s, 3H, 5′-OCH 3 ), 3.82 (s, 3H, 4-OCH 3 )
  • dark brown gum; 1 H NMR δ 8.96 (br s, 1H, 2-OH), 7.25 (s, 1H, H-1′′), 7.01 (s, 1H, H-2′)
Phytochemical studies on Stemona aphylla : isolation of a new stemofoline alkaloid and six new stemofurans
  • Journal of Natural Products
  • 2011
H-5b), 2.49-2.41 (m, 1H, H-10), 2.36 (d, J ) 6.0 Hz
  • 1.98 (d, J ) 12.0 Hz, 1H, H-1a), 1.89 (s, 3H, H-16), 1.88-1.81 (m, 1H, H-6a), 1.73-1.66 (m, 1H, H-6b), 1.67 (d, J ) 12.0 Hz, 1H, H-1b), 1.60 (d, J ) 14.5 Hz, 1H, H-1′a), 1.55 (d, J ) 11.5 Hz, 1H, H-9), 1.52 (d, J ) 10.5 Hz, 1H, H-1′b)
C-10), 36.2 (C-1′), 33.5 (C-1), 30.5 (C-3′)
  • 71.1 (C-2′), 60.8 (C-9a)