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