TUGAS KIMIA ORGANIK BAHAN ALAM FITRIANY EKA SAPUTRI (3325080199) SRI AMBAR WATY (3325083236) Genus Callicarpa Family : Verbenaceae
TUGAS KIMIA ORGANIK BAHAN ALAM
FITRIANY EKA SAPUTRI
(3325080199)
SRI AMBAR WATY
(3325083236)
Genus Callicarpa
Family : Verbenaceae
Callicarpa
Kingdom Plantae – Plants
Division Magnoliophyta - Flowering plants
Class Magnoliopsida - Dicotyledons
Subclass Asteridae
Order Lamiales
Family Verbenaceae - Verbena Family
Genus Callicarpa L. – beautyberry
• Terdapat 40 – 150 jenis spesies
• Tersebar di beberapa tempat, diantaranya
Asia, Australia dan Amerika
• Pada umumnya, tanaman Jenis ini
digunakan sebagai penangkal nyamuk,
khususnya nyamuk Aidest
• Genus ini telah banyak digunakan
sebagai pengobatan tradisional
• Aktivitas biologis, seperti anti bakteri, anti
fungi, anti hama, cytotoxic, and phytotoxic
activities
Spesies dari Callicarpa
Callicarpa acuminataCallicarpa americanaCallicarpa amplaCallicarpa bodinieriCallicarpa canaCallicarpa japonicaCallicarpa cathayanaCallicarpa dichotomaCallicarpa erioclonaCallicarpa formosana Callicarpa kwangtungensis
Callicarpa lanataCallicarpa longifoliaCallicarpa macrophyllaCallicarpa maingayiCallicarpa mollisCallicarpa nudifloraCallicarpa pedunculataCallicarpa pentandraCallicarpa reevesiiCallicarpa rubellaCallicarpa shikokianaCallicarpa tomentosa
Senyawa-Senyawa yang Terkadung di dalam Genus Callicarpa:
• Flavonoid• Lignans• Terpenoid• Phenylpropanoids• Phytosterols
Spesies Bagian Tanaman Asal Negara Penggunaan
C. americana L.
Bark United States Fever
Leaves United States Dropsy
Roots United States Skin cancer
Roots United States Dysentery
Roots and berries United States Colic
Roots and branches United States Fever, malaria,
rheumatism
C. arborea Roxb.
Bark India Skin disease
Bark Nepal Fever
Bark juice Nepal Indigestion
C. bodinieri H.Lév. Leaves China Wounds
Penggunaan Tanaman Callicarpa
SpesiesBagian
Tanaman Asal Negara Penggunaan
C. cana L. Not stated Papua New Guinea Antifertility
C. candicans (Burm. f.) Hochr.
Leaves Palau Islands, Philippines Fish poison
Leaves Malaysia Emmenagogue
C. cathayana Chang Leaves China Wounds
C. flavida Elmer Bark Philippines Toothache
C. formosana Rolfe
Entire plant Taiwan Hepatitis
Not stated TaiwanOral infections, intestinal and stomach disorders
Leaves China Wounds
C. giraldii Hesse ex Rehder Leaves China Wounds
SpesiesBagian
Tanaman Asal Negara Penggunaan
C. giraldii Hesse ex Rehder var. lyi (Levl.) C.Y.Wu Leaves China Wounds
C. integerrima Champ. ex Benth. Leaves China Wounds
C. japonica Thunb.Leaves China Wounds
Leaves Japan Fish poison
C. kochiana Makino Leaves China Wounds
C. lanata L. (C. tomentosa Murr.)a
Leaves India Anthelmintic
Fresh roots Bangladesh Fever, malaria
C. lingii Merr. Leaves China Wounds
C. longifolia Lam.Leaves China Wounds
Not stated Papua New Guinea Antifertility
Spesies Bagian Tanaman Asal Negara Penggunaan
C. macrophylla Vahl.
Fruit juice Nepal Fever
Leaves China Wounds
Leaves (smoked) India Headache
Not stated China Fever
Fresh roots India Fever, mouth ulcers, cough
Roots Nepal Oral infection
Root juice Nepal Indigestion
Seeds Infections, rheumatism
C. pedunculata R.Br. Not stated Papua New Guinea Antifertility
C. purpurea Juss. (C. dichotoma Raeusch.)a Leaves China Wounds
C. reevesii Wall. (C. nudiflora Hook. et Arn.)a Leaves China Wounds
Spesies Bagian Tanaman Asal Negara Penggunaan
C. rubella Lindl.
Bark India Tumors of the large intestine
Leaves China Wounds
Entire plant China Burns
Callicarpa sp.b Leaves Papua New Guinea Shoulder pain
Callicarpa sp. b Not stated Papua New Guinea Body pain
Callicarpa sp. Leaves Papua New Guinea Antifertility
Callicarpa sp. Leaves Papua New Guinea Antifertility
Callicarpa sp. Leaves and twigs Papua New Guinea Antifertility
Kandungan Senyawa Metabolit Sekunder pada Genus Callicarpa
Senyawa Spesies Bagian Tanaman
Nopinone C. americana L. Leaf essential oil
α-Pinene C. americana L. Leaf essential oil
β-Pinene C. americana L. Leaf essential oil
Monoterpene
Nopinone
Senyawa Spesies Bagian TanamanBicyclogermacrene C. japonica Thunb. Leaf essential oil
α-Cadinol C. americana L. Leaf essential oilCamphor (juniper camphor) C. japonica Thunb. Leaf essential oil
Caryophyllene oxide C. americana L. Leaf essential oil
Curcuphenol C. japonica Thunb. Leaf essential oil
β-Elemene C. japonica Thunb. Leaf essential oil
γ-Elemene C. japonica Thunb. Leaf essential oil
δ-Elemene C. japonica Thunb. Leaf essential oil
7-epi -α-Eudesmol C. americana L. Leaf essential oilGermacrene B C. japonica Thunb. Leaf essential oil
Germacrene D C. japonica Thunb. Leaf essential oil
Seskuiterpene
Senyawa Spesies Bagian TanamanGlobulol C. japonica Thunb. Leaf essential oil
α-Guaiene C. japonica Thunb. Leaf essential oil
α-Humulene
C. americana L. Leaf essential oil
C. japonica Thunb. Leaf essential oil
Humulene epoxide II
C. americana L. Leaf essential oil
C. japonica Thunb. Leaf essential oil
Intermediol
C. americana L. Leaf essential oil
C. japonica Thunb. Leaf essential oil
Khusinol C. americana L. Leaf essential oil
Senyawa Spesies Bagian Tanaman
Ledol C. japonica Thunb. Leaf essential oil
Selin-11-en-4-α-ol C. japonica Thunb. Leaf essential oil
α-Selinene C. americana L. Leaf essential oil
7-epi -α-Selinene C. americana L. Leaf essential oil
Seychellene C. japonica Thunb. Leaf essential oil
Spathulenol C. japonica Thunb. Leaf essential oil
Valencene C. americana L. Leaf essential oil
Viridiflorol C. japonica Thunb. Leaf essential oil
DiterpeneSenyawa Spesies Bagian Tanaman
Abieta-8,11,13,15-tetraen-18-oic acid (1)
C. pedunculata R.Br. Entire plant
C. pedunculata R.Br. Leaves
Akhdarenol (2) C. acuminata H.B.K. Leaves
Callicarpone (3) C. candicans (Burm. f.) Hochr. Leaves
Calliphyllin (4)C. macrophylla Vahl. Leaves
C. pedunculata R.Br. Leaves
Callicarpenal (5)C. americana L. Leaf essential oil
C. japonica Thunb. Leaf essential oil
Senyawa Spesies Bagian Tanaman
Calliterpenone (6)
C. americana L. Fruits, leaves, and twigs
C. furfuracea Ridl. Leaves
C. longifolia Lam. Leaves
C. macrophylla Vahl. Aerial parts
C. macrophylla Vahl. Leaves
C. macrophylla Vahl. Seeds
C. pedunculata R.Br. Entire plant
C. pedunculata R.Br. Leaves
Calliterpenone-17-acetate (7)
C. furfuracea Ridl. Leaves
C. longifolia Lam. Leaves
C. macrophylla Vahl. Aerial parts
C. macrophylla Vahl. Leaves
C. macrophylla Vahl. Seeds
Senyawa Spesies Bagian Tanaman3β,12(S )-Dihydroxycleroda-4(18),13-dien-15,16-olide (8)
C. americana L. Fruits, leaves, and twigs
3β,16ξ-Dihydroxycleroda-4(18),13-dien-15,16- olide (9)
C. americana L. Fruits, leaves, and twigs
12(S ),16ξ-Dihydroxycleroda-3,13-dien-15,16- olide (10)
C. americana L. Fruits, leaves, and twigs
2-Formyl-16ξ-hydroxy-3-A-norcleroda-2,13-dien-15,16-olide (11)
C. americana L. Fruits, leaves, and twigs
12(S )-Hydroxycleroda-3,13-dien-15,16-olide (12)
C. americana L. Fruits, leaves, and twigs
12(S )-Hydroxycleroda-3,13-dien-16,15-olide (13)
C. americana L. Fruits, leaves, and twigs
12(S )-Hydroxy-16ξ-methoxycleroda-3,13-dien-15,16-olide (14)
C. americana L. Fruits, leaves, and twigs
16ξ-Hydroxycleroda-3,13-dien-15,16-olide (15)
C. americana L. Fruits, leaves, and twigs
Senyawa Spesies Bagian Tanaman16ξ-Hydroxycleroda-3,11(E ),13-trien-15,16-olide (16)
C. americana L. Fruits, leaves, and twigs
6α-Hydroxynidorellol (17) C. pedunculata R.Br. Entire plant
C. pedunculata R.Br. Leaves
3β-Hydroxyphyllocladan-17-oic acid (18)
C. furfuracea Leaves
Isopimaric acid (19) C. acuminata H.B.K. Leaves
C. pedunculata R.Br. Entire plant
Isopimarol (20) C. japonica Thunb. Leaf essential oil
16α,17-Isopropylideno-3-oxophyllocladane (21)
C. macrophylla Vahl. Leaves
Maingayic acid (22) C. maingayi King & Gamble
Leaves
17-Norphyllocladane-3,16-dione (23)
C. furfuracea Ridl. Leaves
Pentandralactone (24) C. pentandra Roxb. Leaves
Pentandranoic acid A (25) C. pentandra Roxb. Leaves
Senyawa Spesies Bagian TanamanPentandranoic acid B (26) C. pentandra Roxb. Leaves
Pentandranoic acid C (27) C. pentandra Roxb. Leaves
Phylloclad-15-en-3,17-dione (28) C. furfuracea Ridl. Leaves
3β,16β-Phyllocladane-3,16,17-triol (29)
C. furfuracea Ridl. Leaves
3β,16β-Phyllocladane-3,16,17-triol-17-acetate (30)
C. furfuracea Ridl. Leaves
Phytol (31) C. japonica Thunb. Leaves and twigs
Sandaracopimaradien-19-ol (32) C. acuminata H.B.K. Leaves
16α,17,19-Trihydroxyphyllocladan-3-one (33)
C. furfuracea Ridl. Leaves
4,16α,17-Trihydroxy-3,4-secophyllocladan-3-oic acid (34)
C. furfuracea Ridl. Leaves
5β,16α-4,16,17-Trihydroxy-3,4-secophyllocladan-3-oic acid (35)
C. furfuracea Ridl. Leaves
Triterpenoids Senyawa Spesies Bagian Tanaman
α-Amyrin (81)C. acuminata H.B.K. Leaves
C. bodinieri H.Lév. Leaves
β-Amyrin (82)C. pedunculata R.Br. Fruits
C. pedunculata R.Br. Entire plant
Bauerenol (83) C. arborea b Bark
Betulinic acid (84) C. arborea b Bark
C. bodinieri H.Lév. Entire plant
C. macrophylla Vahl. Leaves
Corosolic acid (85)C. bodinieri H.Lév. Entire plant
C. pentandra Roxb. Leaves
2α,3α-Dihydroxyurs-12-en-28-oic acid (86)
C. bodinieri H.Lév. Entire plant
C. formosana Rolfe Leaves
C. pentandra Roxb. Leaves
Senyawa Spesies Bagian TanamanEpilupeol (87) C. arborea b Leaves
Euscaphic acid (88)
C. americana L. Fruits, leaves, and twigs
C. bodinieri H.Lév. Entire plant
Oleanolic acid (89) C. macrophylla Vahl. Seeds
Pomolic acid (90) C. pentandra Roxb. Leaves
2α,3α,24-Trihydroxyolean-12-en-28-oic acid (91)
C. bodinieri H.Lév. Entire plant
Ursolic acid (92)
C. arborea b Leaves
C. bodinieri H.Lév. Entire plant
C. formosana Rolfe Leaves
C. longifolia Lam. Leaves
C. pedunculata R.Br. Fruits
C. pedunculata R.Br. Entire plant
C. pentandra Roxb. Leaves
HOOC
OH
H
Calliphyllin
HOOC
H
H
Isopimaric acid
HOH2C
OH
H
Isopimarol
R3
OR2
OR1
6 R1 = H, R2 = H, R3 = O7 R1 = Ac, R2 = H, R3 = O21 R1 = R2 = CH(Me)2, R3 = O29 R1 = H, R2 = H, R3 = H, OH30 R1 = Ac, R2 = H, R3 = H, OH
O
O
HOH
H
HO
3,12(S )-Dihydroxycleroda-4(18),13-dien-15,16-olide
O
O
HH
OH
HO
3,12(S )-Dihydroxycleroda-4(18),13-dien-15,16-olide
O
O
HOH
OH
12(S ),16?-Dihydroxycleroda-3,13-dien-15,16- olide
O
O
HOH
H
12(S )-Hydroxycleroda-3,13-dien-15,16-olide
O
O
HOH
OCH3
12(S ),16?-Dihydroxycleroda-3,13-dien-15,16- olide
O
O
HH
OH
16?-Hydroxycleroda-3,13-dien-15,16- olide
HOOC
CH2
Abieta-8,11,13,15-tetraen-18-oic acid
H
OH
HH
Akhdarenol
H
Callicarpone
O
OO
OH
O
H
Callicarpenal
O
OH
OCH2COOH
Calliterpenone-17-acetate
FlavonoidsSenyawa Spesies Bagian Tanaman
Apigenin (36)C. longifolia Lam. Leaves
C. macrophylla Vahl. Leaves
Apigenin-7-O -β-D-glucuronide (37)
C. longifolia Lam. Leaves
C. macrophylla Vahl. Leaves
Chrysoeriol-4′-O -β-D-glucoside (38)
C. bodinieri H.Lév. Entire plant
Cyanidin (39)C. bodinieri H.Lév. Fruits
C. purpurea Juss. Fruits
Cynaroside (40) C. bodinieri H.Lév. Entire plant
5,4′-Dihydroxy-7-methoxyflavone (Genkwanin) (41)
C. americana L. Fruits, leaves, and twigs
5,4′-Dihydroxy-3,7-dimethoxyflavone (42)
C. macrophylla Vahl. Leaves
Senyawa Spesies Bagian Tanaman7,4′-Dihydroxy-3,5-dimethoxyflavone (43)
C. pedunculata R.Br. Entire plant
5,4′-Dihydroxy-3,7,3′-trimethoxyflavone (44)
C. macrophylla Vahl. Leaves
5-Hydroxy-7,4′-dimethoxyflavone (45)
C. americana L. Fruits, leaves, and twigs
5-Hydroxy-3,6,7,4′-tetramethoxyflavone (46)
C. bodinieri H.Lév. Leaves
5-Hydroxy-3,7,3′,4′-tetramethoxyflavone (47)
C. formosana Rolfe Leaves
5-Hydroxy-6,7,3′,4′-tetramethoxyflavone (48)
C. integerrima Champ. ex Benth.
Entire plant
5-Hydroxy-3,7,4′-trimethoxyflavone (49)
C. formosana Rolfe Leaves
C. pedunculata R.Br. Entire plant
5-Hydroxy-6,7,4′-trimethoxyflavone (50)
C. acuminata H.B.K. Leaves
C. americana L. Fruits, leaves, and twigs
Senyawa Spesies Bagian Tanaman
Luteolin (51)C. longifolia Lam. Leaves
C. macrophylla Vahl. Leaves
Luteolin-4′-O -β-D-glucoside (52)
C. bodinieri H.Lév. Entire plant
Luteolin-7-O -β-D-glucuronide (53)
C. longifolia Lam. Leaves
C. macrophylla Vahl. Leaves
Paeonidin (54)C. bodinieri H.Lév. Fruits
C. purpurea Juss. Fruits
3,5,7,3′,4′-Pentamethoxyflavone (55)
C. formosana Rolfe Leaves
Petunidin (56) C. purpurea Juss. Fruits
5,7,3′,4′-Tetramethoxyflavone (57)
C. formosana Rolfe Leaves
5,6,7-Trimethoxyflavone (58) C. japonica Thunb. Not stated
O
R4
R2
OR3
O
R1
OR5
O
OR2 O
R3
R1
O
O
O46 R1 = R2 = H; R3 = OCH348 R1 = OCH3; R2 = R3 = H50 R1 = R2 = R3 = H
OHO
OH
OH
OR
OH
39 R = H54 R = CH3
OHO
OH
OH
O
OH
OH
OO
O
O O
Phenylethanoids and Phenyl Propanoids (including Lignans)
Senyawa Jenis Tumbuhan Bagian
2′-Acetylverbascoside (2′-acetylacteoside) (64)
C. purpurea Juss. (C. dichotoma Raeusch.)a Leaves and twigs
Brandioside (65) C. purpurea Juss. (C. dichotoma Raeusch.)a Leaves and twigs
Calceolarioside A (66) C. bodinieri H.Lév. Leaves
Cistanoside H (67) C. purpurea Juss. (C. dichotoma Raeusch.)a Leaves and twigs
Echinacoside (68) C. purpurea Juss. (C. dichotoma Raeusch.)a Leaves and twigs
Eugenol (69) C. japonica Thunb. Leaf essential oil
Forsythoside B (70) C. purpurea Juss. (C. dichotoma Raeusch.)a Leaves and twigs
Isoverbascoside (isoacteoside) (71)
C. bodinieri H.Lév. Leaves
C. purpurea Juss. (C. dichotoma Raeusch.)a Leaves and twigs
Senyawa Jenis Tumbuhan Bagian
Poliumoside (72) C. purpurea Juss. (C. dichotoma Raeusch.)a Leaves and twigs
E -Tubuloside E (73) C. purpurea Juss. (C. dichotoma Raeusch.)a Leaves and twigs
Z -Tubuloside E (74) C. purpurea Juss. (C. dichotoma Raeusch.)a Leaves and twigs
Verbascoside (acteoside) (75) C. bodinieri H.Lév. Leaves
C. tomentosa b Leaves
C. purpurea Juss. (C. dichotoma Raeusch.)a Leaves and twigs
Phytosterol
TERIMA KASIH