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Kuguacin

Summary

A kuguacin is one of several chemical compounds isolated from the bitter melon vine (Momordica charantia, kǔguā in Chinese) by J.-C. Chen and others.[1]

Kuguacins are cucurbitacins, formally derived from the triterpene hydrocarbon cucurbitane. They include:

  • Kuguacin A[2]
  • Kuguacin B[2]
  • Kuguacin C[2]
  • Kuguacin D[2]
  • Kuguacin E[2]
  • Kuguacin F: C
    30    H
    42    O
    5    ; 47 mg/kg, needles, melts at 275–276 °C [1]: 1 
  • Kuguacin G: C
    30    H
    44    O
    6    ; 23 mg/kg, needles, melts at 250–252 °C [1]: 2 
  • Kuguacin H: C
    30    H
    44    O
    5    ; 27 mg/kg, needles, melts at 226–228 °C [1]: 3 
  • Kuguacin I: C
    31    H
    46    O
    4    ; 20 mg/kg, needles, melts at 235–237 °C [1]: 4 
  • Kuguacin J: C
    30    H
    46    O
    3    ; 243 mg/kg, powder, melts at 166–169 °C [1]: 5 
  • Kuguacin K: C
    25    H
    34    O
    6    ; 130 mg/kg, powder, melts at 275–277 °C [1]: 6 
  • Kuguacin L: C
    25    H
    36    O
    4    ; 30 mg/kg, needles, melts at 320–321 °C [1]: 7 
  • Kuguacin M: C
    22    H
    28    O
    4    ; 7 mg/kg, needles, melts at 332–333 °C [1]: 8 
  • Kuguacin N: C
    30    H
    46    O
    4    ; 247 mg/kg, powder, melts at 140–143 °C [1]: 9 
  • Kuguacin O: C
    30    H
    42    O
    4    ; 20 mg/kg, needles, melts at 267–269 °C [1]: 10 
  • Kuguacin P: C
    27    H
    40    O
    4    ; 293 mg/kg, prisms, melts at 229–231 °C [1]: 11 
  • Kuguacin Q: C
    29    H
    44    O
    5    ; 11 mg/kg, needles, melts at 219–221 °C [1]: 12 
  • Kuguacin R: C
    30    H
    48    O
    4    ; 1357 mg/kg [1]: 13 
  • Kuguacin S: C
    30    H
    44    O
    4    ; 17 mg/kg, powder, melts at 174–177 °C [1]: 14 

Kuguacins F-S can be extracted with ethanol from the stems and leaves of M. charantia. Kuguacins I, J, and Q are artifacts of the extraction process. Kuguacin R is obtained as mixture of two epimers. In this process one also obtains momordicine I,[3] kuguacin E, 5β,19-epoxycucurbita-6,23-diene-3β,19,25-triol,[4] karavilagenin D,[5] 3β,7β,25-trihydroxycucurbita-5,(23E)-dien-19-al,[6] and 3β,7β-dihydroxy-25-methoxycucurbita-5,(23E)-dien-19-al[6] In vitro tests showed weak anti-HIV activity for kuguacins F-S, especially kuguacin Q and kuguacin S.[1]

References edit

  1. ^ a b c d e f g h i j k l m n o p Jian-Chao Chen, Wu-Qing Liu, Lu Lu, Ming-Hua Qiu, Yong-Tang Zheng, Liu-Meng Yang, Xian-Min Zhang, Lin Zhou and Zhong-Rong Li (2009), "Kuguacins F–S, cucurbitane triterpenoids from Momordica charantia". Phytochemistry, volume 70, issue 1, pages 133-140 doi:10.1016/j.phytochem.2008.10.011
  2. ^ a b c d e J. C. Chen, R. R. Tian, M. H. Qiu, L. Lu, Y. T. Zheng, Z. Q. Zhang (2008), "Trinorcucurbitane and cucurbitane triterpenoids from the roots of Momordica charantia." Phytochemistry, volume 69, pages 1043–1048
  3. ^ M. Yasuda, M. Iwamoto, H. Okabe, T. Yamauchi (1984), "Structures of momordicines I, II and III, the bitter principles in the leaves and vines of Momordica charantia L. Chem. Pharm. Bull., volume 32, pages 2044–2047.
  4. ^ Dulcie A. Mulholland, Vikash Sewram, Roy Osborne, Karl H. Pegel and Joseph D. Connolly (1997), "Cucurbitane triterpenoids from the leaves of Momordica foetida." Phytochemistry, volume 45, issue 2, pages 391-395. doi:10.1016/S0031-9422(96)00814-X
  5. ^ H. Matsuda, S. Nakamura, T. Murakami, M. Yoshikawa (2007). "Structures of new cucurbitane-type triterpenes and glycosides, karavilagenins D and E, and karavilosides VI, VII, VIII, IX, X, and XI, from the fruit of Momordica charantia." Heterocycles,volume 71, pages 331–341.
  6. ^ a b Majekodunmi Fatope, Yoshio Takeda, Hiroyasu Yamashita, Hikaru Okabe, and Tatsuo Yamauchi (1990), "New cucurbitane triterpenoids from Momordica charantia." Journal of Natural Products, volume 53, issue 6, pages 1491-1497.