Kuguacin

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: C₃₀H₄₂O₅; 47 mg/kg, needles, melts at 275–276 °C ^[1]^:1
Kuguacin G: C₃₀H₄₄O₆; 23 mg/kg, needles, melts at 250–252 °C ^[1]^:2
Kuguacin H: C₃₀H₄₄O₅; 27 mg/kg, needles, melts at 226–228 °C ^[1]^:3
Kuguacin I: C₃₁H₄₆O₄; 20 mg/kg, needles, melts at 235–237 °C ^[1]^:4
Kuguacin J: C₃₀H₄₆O₃; 243 mg/kg, powder, melts at 166–169 °C ^[1]^:5
Kuguacin K: C₂₅H₃₄O₆; 130 mg/kg, powder, melts at 275–277 °C ^[1]^:6
Kuguacin L: C₂₅H₃₆O₄; 30 mg/kg, needles, melts at 320–321 °C ^[1]^:7
Kuguacin M: C₂₂H₂₈O₄; 7 mg/kg, needles, melts at 332–333 °C ^[1]^:8
Kuguacin N: C₃₀H₄₆O₄; 247 mg/kg, powder, melts at 140–143 °C ^[1]^:9
Kuguacin O: C₃₀H₄₂O₄; 20 mg/kg, needles, melts at 267–269 °C ^[1]^:10
Kuguacin P: C₂₇H₄₀O₄; 293 mg/kg, prisms, melts at 229–231 °C ^[1]^:11
Kuguacin Q: C₂₉H₄₄O₅; 11 mg/kg, needles, melts at 219–221 °C ^[1]^:12
Kuguacin R: C₃₀H₄₈O₄; 1357 mg/kg ^[1]^:13
Kuguacin S: C₃₀H₄₄O₄; 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

^ ^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
^ ^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
^ 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.
^ 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
^ 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.
^ ^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.