tugas kimia bahan alam

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

http://plants.usda.gov/java/ClassificationServlet?source=display&classid=Plantae

http://plants.usda.gov/java/ClassificationServlet?source=display&classid=Magnoliophyta

http://plants.usda.gov/java/ClassificationServlet?source=display&classid=Magnoliopsida

http://plants.usda.gov/java/ClassificationServlet?source=display&classid=Asteridae

http://plants.usda.gov/java/ClassificationServlet?source=display&classid=Lamiales

http://plants.usda.gov/java/ClassificationServlet?source=display&classid=Verbenaceae

http://plants.usda.gov/java/ClassificationServlet?source=display&classid=CALLI2

http://plants.usda.gov/java/ClassificationServlet?source=display&classid=CALLI2

• 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

http://www.ncbi.nlm.nih.gov/pmc/articles/PMC2760847/table/T1/


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




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



Intermediol



Khusinol C. americana L. Leaf essential oil


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


Callicarpenal (5)C. americana L. Leaf essential oil



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



Calliterpenone-17-acetate (7)



C. macrophylla Vahl. Aerial parts


C. macrophylla Vahl. Seeds

Senyawa Spesies Bagian Tanaman3β,12(S )-Dihydroxycleroda-4(18),13-dien-15,16-olide (8)


3β,16ξ-Dihydroxycleroda-4(18),13-dien-15,16- olide (9)


12(S ),16ξ-Dihydroxycleroda-3,13-dien-15,16- olide (10)


2-Formyl-16ξ-hydroxy-3-A-norcleroda-2,13-dien-15,16-olide (11)


12(S )-Hydroxycleroda-3,13-dien-15,16-olide (12)


12(S )-Hydroxycleroda-3,13-dien-16,15-olide (13)


12(S )-Hydroxy-16ξ-methoxycleroda-3,13-dien-15,16-olide (14)


16ξ-Hydroxycleroda-3,13-dien-15,16-olide (15)


Senyawa Spesies Bagian Tanaman16ξ-Hydroxycleroda-3,11(E ),13-trien-15,16-olide (16)


6α-Hydroxynidorellol (17) C. pedunculata R.Br. Entire plant


3β-Hydroxyphyllocladan-17-oic acid (18)

C. furfuracea Leaves

Isopimaric acid (19) C. acuminata H.B.K. Leaves


Isopimarol (20) C. japonica Thunb. Leaf essential oil

16α,17-Isopropylideno-3-oxophyllocladane (21)


Maingayic acid (22) C. maingayi King & Gamble

Leaves

17-Norphyllocladane-3,16-dione (23)


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)


3β,16β-Phyllocladane-3,16,17-triol-17-acetate (30)


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)


4,16α,17-Trihydroxy-3,4-secophyllocladan-3-oic acid (34)


5β,16α-4,16,17-Trihydroxy-3,4-secophyllocladan-3-oic acid (35)


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


Bauerenol (83) C. arborea b Bark

Betulinic acid (84) C. arborea b Bark

C. bodinieri H.Lév. Entire plant


Corosolic acid (85)C. bodinieri H.Lév. Entire plant

C. pentandra Roxb. Leaves

2α,3α-Dihydroxyurs-12-en-28-oic acid (86)


C. formosana Rolfe Leaves




Senyawa Spesies Bagian TanamanEpilupeol (87) C. arborea b Leaves

Euscaphic acid (88)



Oleanolic acid (89) C. macrophylla Vahl. Seeds

Pomolic acid (90) C. pentandra Roxb. Leaves

2α,3α,24-Trihydroxyolean-12-en-28-oic acid (91)


Ursolic acid (92)

C. arborea b Leaves




C. pedunculata R.Br. Fruits





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


Apigenin-7-O -β-D-glucuronide (37)



Chrysoeriol-4′-O -β-D-glucoside (38)


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)


5,4′-Dihydroxy-3,7-dimethoxyflavone (42)


Senyawa Spesies Bagian Tanaman7,4′-Dihydroxy-3,5-dimethoxyflavone (43)


5,4′-Dihydroxy-3,7,3′-trimethoxyflavone (44)


5-Hydroxy-7,4′-dimethoxyflavone (45)


5-Hydroxy-3,6,7,4′-tetramethoxyflavone (46)


5-Hydroxy-3,7,3′,4′-tetramethoxyflavone (47)


5-Hydroxy-6,7,3′,4′-tetramethoxyflavone (48)

C. integerrima Champ. ex Benth.

Entire plant

5-Hydroxy-3,7,4′-trimethoxyflavone (49)



5-Hydroxy-6,7,4′-trimethoxyflavone (50)

C. acuminata H.B.K. Leaves



Luteolin (51)C. longifolia Lam. Leaves


Luteolin-4′-O -β-D-glucoside (52)


Luteolin-7-O -β-D-glucuronide (53)



Paeonidin (54)C. bodinieri H.Lév. Fruits

C. purpurea Juss. Fruits

3,5,7,3′,4′-Pentamethoxyflavone (55)


Petunidin (56) C. purpurea Juss. Fruits

5,7,3′,4′-Tetramethoxyflavone (57)


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)









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







Phytosterol

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