Structure Elucidation and Absolute Configuration of Megastigmane Derivatives from Cissus quadrangularis Linn

Cissus a genus of approximately 350 species of a woody climber (Family: Vitaceae) includes Cissus quadrangularis Linn (Veldt grape, winged treebine) which is often used as a medicinal plant. Commonly known as “bone setter”, the plant can be found in the warmer regions of India, Ceylon, East Africa, Malaysia and Thailand [1]. C.’quadrangularis is used as a common food supplement in southern India, while the stem is traditionally used for the treatment of gastritis, bone fractures, skin infections, constipation, eye diseases, piles, anemia, asthma, irregular menstruation, burns and wounds [2,3]. The fresh stem and leaves of C. quadrangularis is used for the treatment of hemorrhoids, menstrual disorders, scurvy and flatulence [4–8]. Phytochemical analysis of C. quadrangularis resulted in the identification of several classes of compounds e.g., flavonoids, triterpenoids and stilbene derivatives. As part of our continuing program to identity chemical and/or biomarkers of dietary supplements, we isolated four new megastigmane derivatives (1–4), and thirteen known compounds (5–17), trans-3-Oxo-ionol (5), corchoinoside C (6), resveratrol (7), pallidol (8), quadrangularin A (9), quadrangularin B (10), quadrangularin C (11), parthenocissin A (12), quercetin 3-O-α-L-rhaminoside (13), quercetin 3-O-β-D-glucopyranoside (14), isoengelitin (15), (+)-isolariciresinol 3-O-β-D-glucopyranoside (16) and avaculin (17) from Cissus quadrangularis Linn. Acknowledgements: The work was supported by the United States Department of Agriculture, Agricultural Research Service Specific Cooperative Agreement Number 58-6408-06-067. Thanks to Mr. Frank Wiggers for NMR work, Dr. Barathi Avula for HRESIMS and Dr. Vaishali C Joshi for plant identification at the National Center for Natural Products Research. References: [1] Pongboonrod S, (1995), Printing Thailand, 428–9. [2] Asolkar LV, et al. (1992), CSIR Publication, New Delhi 61. [3] Kritikar KR, Basu BD, (2000), Allahabad India, 841–843. [4] Udupa KN, Prasad G, (1964), Indian J Med Res. 52: 480–487 [5] Udupa KN, Prasad GC, (1964), Indian J Med Res. 52: 26–35 [6] Udupa KN, Prasad G, (1963) Indian J Med Res. 51: 667–676. [7] Singh LM, Udupa KN, (1962) Indian J Med Sci. 16: 926–931 [8] Udupa KN, et al. (1961) Indian J Med Sci. 15: 551–557